AU2003236474B2 - Food products having enhanced cocoa polyphenol content and processes for producing same - Google Patents

Description

pool Section 29 Regulation 3.2(2)

AUSTRALIA

Patents Act 1990 COMPLETE SPECIFICATION STANDARD PATENT Application Number: Lodged: Invention Title: FOOD PRODUCTS HAVING ENHANCED COCOA POLYPHENOL CONTENT AND PROCESS FOR PRODUCING SAME The following statement is a full description of this invention, including the best method of performing it known to us: TITLE OF THE INVENTION FOOD PRODUCTS HAVING ENHANCED COCOA POLYPHENOL CONTENT AND PROCESSES FOR PRODUCING SAME BACKGROUND OF THE INVENTION FIELD OF THE INVENTION The invention relates to food products having a conserved or enhanced content of cocoa polyphenols and processes for producing the same. The food products prepared by the processes of this invention include edible food products, confectionery products and standard of identity and non-standard of identity chocolate products, and the like, having conserved concentrations of cocoa polyphenols therein.

RELATED .BACKGROUND ART Polyphenolic compounds are bioactive substances that are derived from plant materials and are closely associated with the sensory and nutritional quality of products derived from these plant materials. The term cocoa polyphenol" includes the polyphenolic products, including proanthocyanidins, and more particularly procyanidins, extracted from cocoa beans and derivatives thereof.

More specifically, the term cocoa polyphenol" includes monomers of the formula A (where n is 1) or oligomers of the formula A.

(where n is an integer from 2 to 18, and higher), wherein A has the 0 H

OH

Y

HO 8 Z R formula: OH X and R is 3- 3-()-O-saccharide, 3- (p)-O-saccharide, or bonding between adjacent monomers takes place at positions 4, 6 or 8; a bond to a monomer in position 4 has alpha or beta stereochemistry; X, Y and Z are selected from the group consisting of A, hydrogen, and a saccharide moiety, with the provisos that as to at least one terminal monomer, bonding of the adjacent monomer thereto is at position 4 and optionally Y Z hydrogen; and wherein the saccharide moiety is a mono- or di-saccharide moiety and may be optionally substituted with a phenolic moiety and R' may be an aryl or heteroaryl moiety optionally substituted with at least one hydroxyl group; and salts, derivatives and oxidation products thereof.

Advantageously, the saccharide moiety is derived from the group consisting of glucose, galactose, xylose, rhamnose and arabinose. The saccharide moiety and any or all of R, X, Y, and Z may optionally be substituted at any position with a phenolic moiety via an ester bond. The phenolic moiety is selected from the group consisting of caffeic, cinnamic, coumaric, ferulic, gallic, hydroxybenzoic and sinapic acids.

Many plant polyphenols have antioxidant activity and have an inhibitory effect on mutagenesis and carcinogenesis. Cocoa polyphenol extracts, particularly procyanidins, have recently been shown to possess significant biological utility. Particularly, WO 97/36497 discloses that these extracts also function to reduce periodontal disease, Artherosclerosis and hypertension, inhibit LDL oxidation and DNA topoisomerase II, modulate cyclo-oxygenase, lipoxygenase, nitric oxide or NO-synthase, apoptosis, platelet aggregation, and possess anti-inflammatory, antigingivitis and antiperiodontis activity. Moreover, WO 97/36497 (published December 24, 1997) discloses that oligomers 5-12 possess the highest anticancer activity of the polyphenolic compounds isolated from cocoa.

Thus, consumption of these higher oligomers in cocoa products may provide significant health benefits. Accordingly, food products, such as confectioneries and cocoa-containing products (cocoa powders, chocolate liquors, or extracts thereof) having a high cocoa polyphenol concentration, especially a high concentration of cocoa polyphenol oligomers 5-12, would be especially desirable.

The cocoa polyphenol extracts, or compounds further separated therefrom, have generally been prepared, on a laboratory scale, by reducing cocoa beans to a powder, defatting the powder, and extracting and purifying the active compound(s) from the defatted powder. The powder is generally prepared by freeze-drying the cocoa beans and pulp, de-pulping and de-shelling the freeze-dried beans and grinding the de-shelled beans or nibs. The extraction of active compound(s) has been accomplished by solvent extraction techniques, and the extracts have been purified by gel permeation chromatography, preparative high performance liquid chromatography (HPLC) techniques, or by a combination of such methods, as disclosed in Romanczyk et al., U.S. Patent No. 5,554,645.

Under-fermented and unfermented cocoa raw materials contain substantial amounts of cocoa polyphenols, compared to fermented cocoa. r Fermentation and drying bring about complex changes in the cocoa bean, most notably, the formation of components required for the development of the characteristic flavor and color of cocoa.

Fermentation, however, also significantly decreases the concentrations of polyphenolic compounds in the fermented cocoa beans, relative to the concentrations of polyphenolic compounds in unfermented or under-fermented beans. Traditional cocoa bean processing, including such steps as roasting or de-fatting of the cocoa beans, also reduces the cocoa polyphenol concentration in the cocoa powder or chocolate liquors produced thereby. Moreover, these processes reduce the concentrations of higher oligomeric polyphenols (oligomers 5-12) more rapidly than lower oligomers or monomers. Accordingly, it was highly desirable to develop methods of conserving or retaining the higher oligomers that not only possessed more significant biological activity than lower oligomers, but also appeared to be more sensitive to processing conditions than the lower oligomers.

Accordingly, it would be highly desirable to develop processing techniques to prepare food products and confectioneries, particularly cocoa-containing confectioneries, that will conserve the cocoa polyphenol concentration of cocoa powders, chocolate liquors, or extracts thereof, in the finished, shelf-ready product.

SUMMARY OF THE INVENTION According to a first embodiment of the invention there is provided a process for conserving. cocoa polyphenols during the processing of one or more cocoa ingredient(s) containing cocoa polyphenols including cocoa procyanidins into a product comprising carbohydrate ingredient(s), (ii) milk ingredients(s), or (iii) carbohydrate ingredients(s) and milk ingredient(s) and (iv) the polyphenolcontaining cocoa ingredient(s) which are selected from the group consisting of chocolate liquor, partially defatted cocoa solids, fully defatted cocoa solids, cocoa extract, synthetic cocoa procyanidins, and mixtures thereof, which process comprises the steps of: pretreating the carbohydrate ingredients(s), the milk ingredient(s), or the carbohydrate ingredient(s) and milk ingredient(s) with one or more pretreatment ingredients selected from the group consisting of an antioxidant, an emulsifier, a fat, a flavorant, and mixtures thereof to form a first mixture; adding the cocoa polyphenol-containing cocoa ingredient(s) to the first mixture to form a second mixture; and processing the second mixture into the cocoa-containing product.

According to a second embodiment of the invention there is provided a food product prepared by the process of the first embodiment wherein the cocoa ingredient is chocolate liquor or mixtures thereof with partially defatted or fully defatted cocoa solids.

According to a third embodiment of the invention there is provided a diet supplement prepared by the process of the first embodiment.

21-Feb-2007 05:49 PM WATERMARK 61398196010 3/4 0 SAccording to a fourth embodiment of the invention there is provided a food product including one or more cocoa ingredients which contain cocoa polyphenols in combination with a carbohydrate ingredient and/or a milk

C

ingredient which are pre-treated with an antioxidant, an emulsifier, a fat, a flavorant, or a mixture thereof before the addition of the cocoa ingredient(s).

According to a fifth embodiment of the invention there is provided a food product comprising one or more cocoa ingredients which conta n cocoa ND polyphenols in combination with a carbohydrate ingredient and/or a milk Singredient which are pre-treated with an antioxidant, an emulsifier, a fat, a O 10 flavorant, or a mixture thereof before the addition of the cocoa ingredient(s).

Ci As employed above and throughout this disclosure (including the claims), the following terms, unless otherwise indicated, shall be understood to have the following meanings: "comprises/comprising" when used in this specification is taken to specify the presence of stated features, integers, steps or components but loes not preclude the presence of addition of one or more other features, intege-s, steps, components or groups thereof.

The present inventors recognized that the cocoa polyphenol concentration of chocolate decreased during manufacture. The concentration of polyphenols in finished chocolates was approximately 20% to 60% lower than that calculated based on the cocoa polyphenol concentration of the cocoa powder or chocolate liquor used to prepare the chocolate. It was determined that the dec eases in cocoa polyphenol concentration occurred during the batching stages, the initial mixing of the ingredients used to make chocolate and after milling or refining. Conventional processing techniques do not provide food products, especially chocolate-containing confectioneries, that adequately retain the cocoa polyphenol concentrations, and particularly the concentrations of cocoa procyanidin oligomers 5-12, of the cocoa raw materials.

The invention relates to novel food products, and their p cess of production, containing a conserved or enhanced concentration of polyphenols.

The invention also provides processes for producing confectionery products, COMS ID No: SBMI-06335147 Received by IP Australia: Time 17:51 Date 2007-02 21 The invention relates to novel food products, and their process of production, containing a conserved or enhanced concentration of polyphenols. The invention also provides processes for producing confectionery products, having conserved concentrations of polyphenols, and preferably cocoa polyphenols, and more preferably cocoa polyphenol oligomers.

The process of this invention avoids the significant and detrimental losses of polyphenols that occur during conventional manufacture. This invention provides novel food products prepared from polyphenol-containing ingredients that may be cocoa ingredients, extracts of a cocoa material (beans, liquor, or powder, etc.) or may be a synthesized derivative thereof, or may be synthesized polyphenol compounds or a mixture of polyphenol compounds or derivative thereof. Mixing ingredients in a specific order provides a product having a significant amount of the cocoa polyphenol concentration, present in the raw materials, conserved in the finished product. Additionally, the production steps of milling/refining and conching may also be controlled and modified to provide the confectioneries of the present invention having conserved concentrations of cocoa polyphenols. Thus, the invention relates to processes of obtaining food products and confectioneries having a conserved concentration of cocoa polyphenols relative to the starting ingredients. The invention avoids the significant and detrimental losses of cocoa polyphenols that occur during conventional manufacture.

q ft BRIEF DESCRIPTION OF THE DRAWINGS Figures 1 illustrate the change in the surface of the cut bean half during the fermentation of the cocoa bean; Fig. 1 depicts the cut bean of an unfermented cocoa bean; Figs. 1 depict the cocoa bean as it is fermented, with Fig. 1 illustrating the fully fermented cocoa bean.

DESCRIPTION OF THE INVENTION It has now been determined that the retention of polyphenols, and particularly higher oligomeric (5-12) polyphenols, in food products is dependent upon the order of addition of ingredients during batch processing. Polyphenols are known to complex with proteins, alkaloids, metal cations and carbohydrates.

Without being bound to theory, it is believed that the processes of this invention prevent or reduce the adverse interactions between the polyphenolcontaining ingredients and the protein-containing and/or carbohydrate-containing ingredients used therein. The processes of the present invention provide finished, shelf-ready food products with conserved concentration of the cocoa polyphenols present in the polyphenol-containing ingredients used to prepare the food products.

More preferably, the processes of the present invention provide finished, shelf-ready confectionery products with conserved concentration of cocoa polyphenol oligomers 5-12. The concentration of cocoa polyphenol pentamer (polyphenol oligomer in the resulting products of the present invention, was used as an indicator of the effectiveness of cocoa polyphenol conservation in the processes of the invention.

The process of preparing a food product according to this invention comprises: mixing at least one ingredient of the product with at least one polyphenol-conserving pre-treatment ingredient to form a mix, combining the mix with at least one ingredient containing cocoa polyphenol, and forming the polyphenol-containing food product, wherein the product contains at least about 10% by weight more polyphenol than a product prepared without using the pre-treatment process according to step Additional ingredients desired in the resulting food product may be added at any point in the process.

As used herein, the term food product" includes any edible product, including foods, confectioneries, and diet supplements, particularly cocoa-containing foods, confectioneries, and diet supplements. Confectioneries refer to any sweetened foods, particularly candy, chocolate, icings and the like.

The term cocoa polyphenol" includes the procyanidins present in cocoa beans or a cocoa ingredient used in the production of confectionery products, chocolate confectioneries and chocolate products, extracts of cocoa beans or a cocoa ingredient comprising procyanidins, and synthesized derivatives thereof, and includes synthesized cocoa polyphenol compounds or synthesized mixtures of polyphenol compounds, and derivatives thereof. The term 11cocoa ingredientm refers to a cocoa solids -containing material derived from -shell-free cocoa nib and includes chocolate liquor and partially or fully defatted cocoa solids cake or powder), alkalized cocoa powder or alkalized chocolate liquor and the like.

The term chocolate liquor" refers to the dark brown fluid liquor" formed by grinding a cocoa nib. The fluidity is due to the breakdown of the cell walls and the release of the cocoa butter during the. processing resulting in a suspension of ground particles of cocoa solids suspended in cocoa butter. Pref erred chocolate liquors include those from underfermented beans because the beans have a higher cocoa polyphenol content.

Partially defatted cocoa solids having a high cocoa polyphenol (CP) content, including a high cocoa procyanidin content, can be obtained by processing the cocoa beans directly to cocoa solids without a bean or nib roasting step. This method conserves the cocoa polyphenols because it omits the traditional roasting step.

The method consists essentially of the steps of: heating the cocoa beans to an internal bean temperature just sufficient to reduce the moisture content to about 3k by weight and to loosen the cocoa shell; winnowing the cocoa nibs from the cocoa shells; (C) screw pressing the cocoa nibs; and recovering the cocoa butter and partially defatted cocoa solids which contain cocoa polyphenols including cocoa procyanidins.

.Optionally, the cocoa beans are cleaned prior to the heating step, in an air fluidized bed density separator. The winnowing can also be carried out in the air fluidized bed density separator. Preferably, the cocoa beans are heated to an internal bean temperature of about 100*C to about 1100C, more preferably less than about 1050C, typically using a infra red heating apparatus for about 3 to 4 minutes.

If desired, the cocoa solids can be alkalized and/or milled to a cocoa powder.

The internal bean temperature (IBT) can be measured by filling an insulated container such as a thermos bottle with beans (approximately 80 100 beans). The insulated container is then appropriately sealed in order to maintain the temperature of the S sample therein. A thermometer is inserted into the bean-filled insulated container and the temperature of the thermometer is equilibrated with respect to the beans in the thermos. The temperature reading is the SET temperature of the beans. IBT can also be considered the equilibrium mass temperature of the beans.

Cocoa beans can be divided into four categories based on their color: predominately brown (fully fermented), purple/brown, purple, and slaty (unfermented). Preferably, the cocoa solids are prepared from underfermented cocoa beans which have a higher cocoa polyphenol content than fermented beans. Underfermented beans include slaty cocoa beans, purple cocoa beans, mixtures of slaty and purple cocoa beans, mixtures of purple and brown cocoa beans, or mixture of slaty, purple, and brown cocoa beans. More preferably, the cocoa beans are slaty and/or purple cocoa beans The cocoa polyphenols, including the cocoa procyanidins, may be solvent extracted from the partially defatted cocoa solids. The cocoa procyanidin oligomers identified in the extract include the dimer to the nonamer.

The partially defatted cocoa solids and/or cocoa polyphenol extracts can be used in therapeutic compositions, optionally with a carrier or a diluent. The therapeutic compositions are useful as antineoplastic compositions, antioxidants, antimicrobial agents, nitric oxide (NO) or NO-synthase modulators, cyclo-oxygenase modulators, lipoxygenase modulators, and in vivo glucose modulators.

As discussed above, the cocoa polyphenol (CP) content, including the cocoa procyanidin content, of roasted cocoa nibs, chocolate liquor, and partially defatted or nonfat cocoa solids is higher when they are prepared cocoa beans or blends thereof which are underfermented, beans having a fermentation factor of 275 or less.

The "fermentation factor" is determined using a grading system for characterizing the fermentation of the cocoa beans. Slaty is designated 1, purple is 2, purple/brown is 3, and brown is 4. The percentage of beans falling within each category is multiplied by the weighted number. Thus, the "fermentation factor" for a sample of 100t brown beans would be 100 x 4 or 400, whereas for a 100% sample of purple beans it would be 100 x 2 or 200. A sample of 501 slaty beans and 50% purple beans would have a fermentation factor of 150 E (50 x 1) (50 x 2) High CP chocolate liquor and/or high CP cocoa solids can be prepared by: roasting the selected cocoa beans (fermentation factor of 275 or less) to an internal bean temperature of 950C to 1600C winnowing the cocoa nibs from the roasted cocoa beans; (c) milling the cocoa nibs into the chocolate liquor; and optionally recovering cocoa butter and partially defatted cocoa solids from the chocolate liquor. Alternatively, the chocolate liquor and/or cocoa solids can be prepared by: heating the selected cocoa beans (fermentation factor of 275 or less) to an internal bean temperature of 95-135DC to reduce the moisture content to about 3% by weight and to loosen the cocoa shell from the cocoa nibs; winnowing the cocoa nibs from the cocoa shells; roasting the cocoa nibs to an internal nib temperature of 950C to 160C; milling the roasted nibs into the chocolate liquor; and optionally recovering cocoa butter and partially defatted cocoa solids from the chocolate liquor. Chocolate liquor and partially defatted cocoa solids containing at least 50,000 xg of total cocoa procyanidins and/or at least 5,000 zg of cocoa procyanidin pentamer per gram of nonfat cocoa solids can be prepared by the above processes.

An extract containing cocoa polyphenols including cocoa procyanidins can be prepared by solvent extracting the partially defatted cocoa solids or nonfat cocoa solids prepared from the underfermented cocoa beans or cocoa nibs.

High CP food products may be prepared using the high CP roasted cocoa nibs, high CP chocolate liquors, and/or high CP partially defatted or nonfat cocoa solids. The food products include pet food, dry cocoa mixes, puddings, syrups, cookies, savory sauces, rice mixes, and rice cakes. Preferably, the food products are confectioneries, a dark chocolate or a milk chocolate. The extract can also be used to prepare foods having high cocoa polyphenol contents.

The health of a mammal can be improved by administering to the mammal a composition containing cocoa procyanidins or the above high CP cocoa components. In these compositions the total amount of the cocoa procyanidin oligomers is at least I zg or greater and the composition is administered daily over greater than 60 days.

Cocoa polyphenols may be structurally represented as bligomers of monomer A, having the formula where n is 2-18, wherein A has the formula:

OH

OH

Y

HO B

I

0 s 3 )#4X Z

R

OH X and R is 3- 3-(0)-O-saccharide, 3- -0-sacoharide I bonding between adjacent monomers takes place at positions 4, 6 or S; a bond to a monomer in position 4 has alpha or beta stereochemistry; X, Y and Z are selected from the group consisting of A, hydrogen, and a saccharide moiety, with the proviso that as to at least one terminal monomer, bonding of the adjacent monomer thereto is at position 4 and optionally Y Z hydrogen; and salts thereof; wherein the saccharide moiety is derived from a mono- or di-saccharide.

Synthesized derivatives of the cocoa polyphenols include compounds, according to the structure above, wherein R may be 3- (a)-O-saccharide, 3-(P)-O-eaccharide, or 3wherein the eaccharide moiety may be derived from a mono- or di-eaccharide selected from the group consisting of glucose, galactose, xylose, rhamnose and arabinose; the saccharide moiety of any or all of R, X, Y, and Z may be optionally substituted at any position with a phenolic moiety via an ester bond; the phenolic moiety may be selected from the group consisting of caffeic, cinnamic, coumaric, ferulic, gallic, hydroxybenzoic and sinapic acids; and R' is an aryl or heteroaryl moiety optionally substituted with at least one hydroxyl group. The substituted aryl or heteroaryl moiety of R' may preferably contain a substitution pattern corresponding to the substituted phenolic moieties of caffeic, cinnamic, coumaric, ferulic, gallic, hydroxybenzoic or sinapic acids.

The cocoapolyphenol oligomers may be prepared by protecting each phenolic hydroxyl group of a first and a second polyphenol monomer with a protecting group to produce a first and second protected polyphenol monomer; functionalizing the 4-position of the first protected polyphenol monomer to produce a functionalized protected polyphenol monomer having the formula: (OR)d O

R)

O(CH

2 )yOH 11 wherein: c is an integer from 1 to 3; d is an integer from 1 to 4; y is an integer from 2 to 6; R is a protecting group; and R" is H or OH; coupling the second protected polyphenol monomer with the functionalized protected polyphenol monomer to produce a protected polyphenol dimer as the polyphenol oligomer; optionally repeating the functionalization and coupling steps to form the polyphenol oligomer having n monomeric units, wherein n is an integer from 3 to 18; preferably 5-12; and removing the protecting groups from the phenolic hydroxyl groups.

The preferred protected polyphenol monomer is a brominated protected epicatechin or brominated protected catechin, more preferably an 8-bromo-epicatechin or an 8-bromo-catechin.

In the above process, the 4-position of the protected polyphenol monomer may be oxidatively functionalized using a quinone oxidizing agent in the presence of a diol, ethylene glycol where y is 2.

The above process may further comprise the step of forming a derivative of the polyphenol oligomer by esterifying the polyphenol oligomer at the 3-position of at least one monomeric unit to produce an esterified polyphenol oligomer. The ester group may be selected from the group consisting of -OC(O)-aryl, -OC(O) -substituted aryl, -OC(0)-styryl, and OC(0)-substituted styryl, where the substituted aryl or substituted styryl contains at least one substituent selected from the group consisting of halo, hydroxyl, nitro, cyano, amino, thiol, methylenedioxy, dihalomethylenedioxy, a C, C, alkyl, a C, C, alkoxy, a C 1 C, haloalkyl, a C, C, haloalkoxy, a C, C, cycloalkyl and a C, C, cycloalkoxy. Preferably the 3-position of at least one monomeric unit is converted to a derivative group derived from an acid selected from the group consisting of caffeic, cinnamic, coumaric, ferulic, gallic, hydroxybenzoic and sinapic acids.

The above process may further comprise the step of forming a derivative of the polyphenol oligomer by glycosylating the polyphenol oligomer at the 3-position of at least one monomeric unit to produce a glycosylated polyphenol oligomer. Preferably, the 3position of at least one monomeric unit is converted to a derivative group selected from the group consisting of -0-glycoside or an -0substituted glycoside wherein the substituted glycoside is substituted by -C(0)-aryl, -substituted aryl, -C(0)-styryl, or -substituted styryl. The substituted aryl or substituted styryl may contain substituents selected from the group consisting of halo, hydroxyl, nitro, cyano, amino, thiol, methylenedioxy, dihalomethylenedioxy, a C, C, alkyl, a C, C, alkoxy, a C, C, haloalkyl, a Ci C, haloalkoxy, a C, C, cycloalkyl and a C, C, cycloalkoxy. Preferably, the glycoside is selected from the group consisting of glucose, galactose, xylose, rhamnose, and arabinose.

The food products of this invention may contain one or more of the cocoa polyphenol monomers, oligomers 2-18, or derivatives thereof. Preferably, the food products of this invention contain mixtures of cocoa polyphenol oligomers 2-18, or derivatives thereof; more preferably, the food products contain mixtures of cocoa polyphenol oligomers 5-12, or derivatives thereof.

The term oligomer" as used herein, refers to any compound of the formula presented above, wherein n is 2 through 18, and preferably, wherein n is 5-12. When n is 2, the oligomer is termed a dimer" when n is 3, the oligomer is termed a trimer" when n is 4, the oligomer is termed a tetramer" when n is 5, the oligomer is termed a pentamer" and similar recitations may be designated for oligomers having n up to and including 18 and higher, such that when n is 18, the oligomer is termed an octadecamer" A pre-treatment ingredient" is any ingredient that may be used in food products, confectionery products and/or chocolate products that functions to conserve and/or retain the cocoa polyphenol concentration of any cocoa polyphenol-containing ingredient used therein. Preferably, the pre-treatment ingredient is any ingredient that may be used in food products, especially 20-Feb-2007 12:52 PM WATERMARK 61398196010 15/30 14

O

0 confectionery products and/or chocolate products, that functions to conserve Sand/or retain the concentration of cocoa polyphenol oligomers 5-12 of any |T ingredient containing such oligomers. The pre-treatment ingredient deronstrates San activity that prevents reaction, complexation, decomposition or adverse interaction of cocoa polyphenols with any of the other ingredients or pparatus used in the preparation of such products or with any polyphenol-reactive material generated from or by the other ingredients during the preparation of the products.

SAn example of a reactive material that may be generated from or by other c ingredients during the preparation of these food products is a free-radical reactive intermediate species. The pre-treatment ingredients may function to prevent the formation of polyphenol-reactive materials or interact with polyphenol-reactive materials, thereby preserving the cocoa polyphenol concentration of the cocoa polyphenol-containing ingredient in the products. Exemplary pre-treatment ingredients that may be used in the food products of this invention incl de water, fats, emulsifying agents, antioxidant compounds, flavoring agents, and the like.

The term "fat" as used herein, refers to triglycerides typically used in food products, especially confectionery products and chocolate products. Fats useful in this invention include the naturally occurring fats and oils such as cocoa butter, pressed cocoa butter, expeller cocoa butter, solvent extracted cocoa butter, refined cocoa butter, milk fat, anhydrous milk fat, fractionated milk fat, milk fat replacers, butterfat, fractionated butterfat, and other vegetable fat, as well as other modifications of these fats, including cocoa butter equivalents (CBE), cocoa butter substitutes (CBS), cocoa butter replacers (CBR), anti-blooming agents, such as behenoyl oleoyl behenate (BOB), reduced calorie fals and/or synthetically modified fats, including reduced calorie fats and non- aloric fat substitutes. A reduced calorie fat is a fat having all the properties of a typical fat but having fewer calories than typical fat. A non-caloric fat substitute, e.g. a sucrose polyester, COMS ID No: SBMI-06311629 Received by IP Australia: Time 12:59 Date 2007-02 likewise possesses all the typical fat characteristics, but is not absorbed after ingestion and thus is not metabolized.

To be suitable for use as a pro-treatment ingredient in this invention, the fat must not demonstrate an activity that promotes reaction, decomposition or adverse interaction of cocoa polyphenols.

Pats that are highly unsaturated are considered unsuitable for use as pre-treatment ingredients because these fats may generate freeradical species during processing. Accordingly, fats and fatty acids having relatively high levels of unsaturation, such as linoteic and linolenic acids, are considered unsuitable as polyphenol -conserving pre -treatment ingredients. Cocoa butter and fats obtained from genetically modified seed oils or modified seed oils having relatively low levels of unsaturation, e.g. high oleic sunflower oil or high oleic peanut oil would be especially preferred polyphenol -conserving pre -treatment ingredients.

A full-fat, chocolate has a total fat content greater than by weight, typically about 2S% to about 35% by weight based on the weight of the full fat chocolate. A 14reduced-fat" chocolate has a total fat content of less than 25%, preferably less than 23%, by weight, based an the weight of the reduced fat chocolate.

The amount of the second emulsifying agent to be added is that amount which is sufficient to provide the chocolate with the desired rheology, which depends on the particular end use, enrobing, extruding, or moulding. This determination is considered within the skill of one in the art.

Emulsif ying agents, or emulsifiers, are also used as ingredients in the food products of the present invention.

Emlsifying agents are well known to play a critical role in suspension rheology and are used throughout food manufacturing, especially confectionery and chocolate manufacturing, to enhance the rheology reduce viscosity and/or yield value) of solids suspensions. Soy lecithin is one of the oldest and most widely used emuilsifying agent. In chocolate, 'lecithin demonstrates a significant viscosity lowering effect when used at an optimum concentration of about 0.3% to about 0.7% by weight of the finished chocolate.

Exemplary emulsifying agents useful in the present invention may be any of those emulsifying agents typically used in the art and include lecithin derived from vegetable sources such as soybean, safflower, corn, etc., fractionated lecithins, mono- and diglycerides, di-acetyl tartaric acid esters of mono- and diglycerides (also referred to as DATEM), monosodium phosphate derivatives of mono- and di-glycerides of edible fats or oils, sorbitan monostearate, polyoxyethylene sorbitan monostearate, hydroxylated lecithin, lactylated fatty acid esters of glycerol and propylene glycol, polyglycerol esters of fatty acids, propylene glycol mono- and di-esters of fats and fatty acids, and especially any emulsifying agents that may become approved for the U.S. Food and Drug Administration-defined soft candy category. It is considered within the skill of one in the art to select an emulsifying agent for use in the preparation of a food product of the present invention. In addition, other emulsifying agents that may be used include polyglycerol polyricinoleate (PGPR), ammonium salts of phosphatidic acid YN), sucrose esters, oat extract, etc., and any emulsifying agent or combination, thereof, found to be suitable in chocolate or similar fat/solid system.

Selected combinations of emulsifying agents have been identified to provide confectioneries of the present invention, particularly reduced-fat confectioneries, having improved rheology over confectioneries prepared using conventional emulsifying agents.

Emulsifying agent combinations that are particularly useful in the present invention are combinations of lecithin, fractionated lecithin (sold by Lucas Meyers, Decatur, Illinois), sucrose polyerucate (ER-290 sold by Mitsubishi Kasei Corporation, Japan) sucrose polystearate (sold by Mitsubishi Kasei Corporation, Japan), ammonium phosphatide (YN sold by Palsgaard, Juledsminde, Denmark), mono-derivatives phosphate mono-di-glycerides/diacetyl tartaric acid esters of mono and di-glycerides (PMD/DAT4M), or fractionated lecithin, with sucrose polyerucate and/or polyglycerol polyricinoleate (PGPR ADMUL Wol sold by Quest International, Hoffman Estates, Illinois as BetrflowO).

Advantageously, the emulsifying agent combinations of polyglycerol polyricinoleate, sucrose polyerucate, and soy lecithin, offer significant improvement in the rheology of the chocolates of the present invention. Use of these preferred emulsifying agent combinations provides the chocolates of this invention having enhanced viscosity and yield value.

When a reduced fat chocolate is prepared, a combination of emulsifying agents are used, a base emulsifying agent and a second emulsifying agent. The base emulsifying agent is added in an amount of less than 1.0% by weight, as limited by current U.S. Food and Drug Agency Standards of Identity. The amount of the base emulsifying agent present in the reduced-fat chocolates is about 0.1% to about preferably about 0.2% to about and more preferably about 0.4% to about 0.6% by weight, based on the total weight of the chocolate. Optionally, the mixture of the fat and solid-containing chocolate ingredients may be conched prior to addition of the base emulsifying agent.

Sucrose polyerucate may be used as either the base emulsifying agent and/or as the second emulsifying agent. When used as the second emulsifying agent, the sucrose polyerucate is present in an amount of about 0.4% to about 0.6% by weight, based on the total weight of the reduced fat chocolate. Sucrose polyerucate is particularly useful because it reduces both the plastic viscosity and yield value even when used at concentrations greater than by weight. Sucrose polyerucate may be present in an amount of less than about e.g. about 0.1% to about preferably about 0.2% to about and more preferably about 0.4% to about 0.5% by weight, based on the total weight of the reduced fat chocolate.

Polyglycerol polyricinoleate (PGPR-Admul WOL from Quest Int'l.) is useful as the second emulsifying agent. Polyglycerol polyricinoleate, which is the partial polyglyceryl ester of interesterified castor oil fatty acids, has proven very useful in modifying the yield value of high-viscosity chocolates. The PGPR may be present in amount of about 0.05% to about preferably about 0.2% to about 0.35%, based on the total weight of the low fat chocolate.

The use of very small amounts of PGPR provides significant benefits. The combination of PGPR by weight) with lecithin by weight) reduces the yield value to zero. When the second emulsifying agent is polyglycerol polyricinoleate, it is present in an amount of about 0.2% to about 0.351 by weight, based on the total weight of the reduced fat chocolate.

When there is 20% total fat, the PGPR concentration can be as low as 0.05% by weight. When the reduced fat chocolate contains less than 23% by weight total fat, the PGPR, in combination with a base emulsifying agent, may be about 0.05V to about 0.5% by weight.

Preferably, POPR in combination with a base emulsifying agent may be present in an amount of about 0.2% to about 0.35% by weight, based on the total weight of the reduced fat chocolate The rheology of reduced-fat chocolates may be further improved by the use of a three component emulsifier combination. The addition of sucrose polyerucate (0.21 by weight) and PGPR by weight) reduced the yield value over 701 of a reduced fat chocolate containing 0.6% by weight lecithin and reduced the plastic viscosity over 45%, compared to the lecithin containing reduced fat chocolate.

The preferred emulsifying agent combinations include the combinations of lecithin-sucrose polyerucate, lecithin-polygrycerol polyricinoleate, sucrose polyerucate-polygly c erol polyricinoleate, and lecithin-sucrose polyerucate-polyglycerol polyricinoleate. Use of these preferred emulsifying agent combinations provides reducedfat chocolates having a total fat content below 23% by weight, viscosity values of less than 100 poise, and yield values of less than 150 dynes/cm.

As used herein, the term -antioxidant compoundN refers to compounds that prevent oxidation and function as a reducing agent or as an electron donor/receptor. According to their mode of action, antioxidants may be classified as free radical terminators, metal ion chelators, or as oxygen scavengers that react with oxygen.

Suitable antioxidant compound classes include tannins, including condensed tannins and hydrolyzable tannins, quinones, polyhydroxy compounds, phospholipids, tocol compounds or derivatives thereof. The antioxidants also include reducing agents including such diverse materials as organic acids, such as ascorbic acid, stannous chloride, and tocopherols (vitamin Sulfur dioxide, a preservative, can also function as an antioxidant. Di-lauryl thiodipropionate and thiodipropionic acid can function as preventive antioxidants by reacting with hydroperoxides.

As used herein, the term "flavouring agent" refers to flavoured compounds or compositions used in food products and confectionery, particularly in chocolates, to impart a desired taste and aroma. A flavoring agent that is suitable for use as a pre-treatment ingredient is a flavour compound or composition that demonstrates an activity that prevents reaction, complexation, decomposition or adverse interaction of cocoa polyphenols with any of the other ingredients used in the preparation of these products or with any polyphenol-reactive material generated from or by the other ingredients during the preparation of these produces. Exemplary flavouring agents suitable for use as pre-treatment ingredients include vanillin, spices, and naturally expressed citrus or spice oils, which contain flavanoids and phenol-based flavourants, e.g. eugenol, which may function as a free radical terminator and may thus prevent reaction of cocoa polyphenols with any free radical species generated during production.

The most popular chocolate or chocolate candy consumed in the United States is in the form of sweet chocolate or milk chocolate. Chocolate is essentially a mixture of solid-containing ingredients, including cocoa solids, suspended in fat. Milk chocolate is a confection which contains milk solids, milk fat, chocolate liquor, a nutritive carbohydrate sweetener, cocoa butter and may include a variety of other ingredients such as emulsifying agents, flavourings and other additives. brumb chocolate is a type of milk chocolate, containing the same ingredients, however, wet milk and carbohydrate sweetener ingredients are pre-combined then codried, at elevated temperatures, to form a milk crumb that is then used to prepare the milk chocolate. Sweet chocolate contains higher amounts of chocolate liquor, but lower amounts of milk solids than milk chocolate. Semisweet chocolate requires at least 35% by weight chocolate liquor and is otherwise similar in definition to sweet chocolate. Dark chocolate, generally containing only chocolate liquor, a nutritive carbohydrate sweetener and cocoa butter, is by definition either a sweet chocolate or a semisweet chocolate. Buttermilk chocolate and skim milk chocolate differ from milk chocolate in that the milk fat comes from various forms of sweet cream buttermilk and skim milk, respectively. Skim milk requires the total amount of milk fat to be limited to less than the minimum for milk chocolate.

Mixed dairy product chocolates differ from milk chocolate in that the milk solid includes any or all of the milk solids listed for milk chocolate, buttermilk chocolate or skim milk chocolate. White chocolate differs from milk chocolate in that it contains no non-fat cocoa solids. Non-standardized chocolates are those chocolates which have compositions which fall outside the specified ranges of the standardized chocolates. Chocolates are classified as "non-standardized" chocolates when a specified ingredient is replaced, either partially or completely, such as when the ingredient cocoa butter is replaced with vegetable oils or fats.

The reduced fat chocolates comprise a fat, solid-containing chocolate ingredients, and a combination of a base emulsifying agent and at least one other emulsifying agent. The chocolates are prepared by mixing the f at and chocolate ingredients, adding the base emulsifying agent to the mixture, and then adding at least one other emulsifying agent. when the emulsifying agent combination comprises more than two emulsifying agents, the third. emulsifying agent is typically added after the second emulsifying agent. Any emulsifying agents added after the base emulsifying agent may be added in any order. The use of combiniations of the emulsifying agents aids in dispersing the fat. The resulting confectioneries have the texture of a full-fat confectionery. The reduced fat chocolates are suitable for use in enrobing, extruding, or moulding operations. The chocolates have yield values Of less than 250 dynes/cmt, preferably less than 190 dynes/cmt, more preferably less thanl4Q dynes/cm 2 and viscosities of less than 150 poise, preferably less than 100 poise, more preferably, less than 75 poise.

Chocolate may take the form of solid pieces of chocolate, such as bars or novelty shapes, and may also be incorporated as an ingredient of other, more complex confections where chocolate is combined with and generally coats other foods such as caramel, peanut butter, nougat, fruit pieces, nuts, wafers, ice cream or the like. These foods are characterized as microbiologi call y shelfstable at 65Q- 95IF (18 290C), under normal atmospheric conditions.

The term I carbohydrate" refers to nutritive carbohydrate sweeteners, with varying degrees of sweetness intensity that are useful in the present invention, may be any of those typically used in the art and include, but are not limited to, sucrose, from cane or beet), dextrose, fructose, lactose, maltose, glucose syrup solids, corn syrup solids, invert sugar, hydrolyzed lactose, honey, maple sugar, brown sugar, molasses and the like.

The food products of the present invention may additionally contain other ingredients such as milk solids, cocoa solids (cocoa powder), sugar substitutes, natural and artificial flavors spices, coffee, salt, brown nut-meats, etc., as well as mixtures of these), proteins, and the like.

Sugar substitutes may be used to partially replace the nutritive carbohydrate sweetener, particularly in the production of reduced-calorie confectioneries and chocolates. As used herein, the term sugar substitute" includes high potency sweeteners, sugar alcohols (polyols) and bulking agents, or combinations thereof. The high potency sweeteners include aspartame, cyclamates, saccharin, acesulfams, neo-hesperidin dihydrochalcone, sucralose, alitame, stevia sweeteners, glycyrrhizin, thaumatin, and the like, and mixtures thereof. The preferred high potency sweeteners include aspartame, cyclamates, saccharin, and acesulfame-K. Examples of sugar alcohols may be any of those typically used in the art and include sorbitol, mannitol, xylitol, maltitol, isomalt, lactitol and the like. The food products of the present invention may also contain bulking agents, typically used in combination with high potency sweeteners. The term bulking agentsr as defined herein may be any of those typically used in the art and include polydextrose, cellulose and its derivatives, maltodextrin, gum arabic, and the like.

The term fermentation factor" is a numerical quantification of the level of fermentation of a batch of cocoa beans.

Fermentation factors range from 100 (under/unfermented) to 400 (fully fermented). To assess the degree of fermentation, cocoa beans are typically subjected to a standard cut test for assessing quality as defined in industry grade standards. The bean halves are laid out on a board for visual inspection of color as well as defects which can arise during bean fermentation, drying and/or storage. Beans can be divided into four fermentation categories according to their color and appearance: fully fermented, e.g., predominantly a brown hue; partially fermented, e.g., purple/brown; purple (under-fermented): and slaty (very under-fermented and/or unfermented beans). Purple/brown beans include all beans showing any blue, purple or violet color on the exposed surface, whether suffused or as a patch. Purple beans should include all beans showing a completely blue, purple or violet color over the whole exposed surface. This should also include, irrespective of color, any beans which are slaty, but not predominantly so (wherein predominantly, in this context, means more than half).

The S fermentation factora is determined using a grading system f or characterizing the fermentation of the cocoa beans.

Slaty, being under/unfermented, is designated as purple as 2, purple/brown as 3 and brown as 4. The percentage' of beans falling within each category is multiplied by the weighted number. Thus, the "fermentation factor" for a sample of 100% brown beans would be 100 x 4 or 400, whereas the fermentation factor for a sample of 100% purple beans would be 100 x 2 or 200. A sample of S0% slaty' beans and 50% purple beans would have a fermentation factor of 150 [(S0 x 1) (50 x Cut tests applicable to cocoa beans derived from the Trinitario and Forastero types may or may not be applicable to cocoa beans derived from the Criollo type, f or example, where bean color variation ranging from fully purple to light tan can be encountered. Accordingly, the cut test based on color would not be applicable to specific cocoa genotypes lacking the anthocyanin pigments responsible for the purple color, such as the Catango (or Catongo) type whose beans are light tan in color. Other exceptions include 'A cocoa beans' derived from other Theb. o o species, the Rerranla species and their inter- and intra-specific crosses. The beans from these species are tan,' in color. For these types of beans the level of fermentation may be determined using a modified standard cut test. Using the modified test, the surface of the bean (halved) is inspected for the degree of lines, fissures or cracks which form during fermentation, rather than the change of color.

Figs. 1 illustrate the change in the surf ace of the cut bean half during the fermentation of the cocoa bean. As can be seen from Figs. 1 the number of linesffissures and the extent to which they extend across the entire surface of the cut bean half increases as the bean is fermented. Fig. 1 depicts the cut bean half of an unfermented cocoa bean where the surface is relatively smooth. Figs. 1 Cb) (d depict the cocoa beans as it is fermented, with Fig. 1 illustrating the fully fermented cocoa bean. As the cocoa bean is fermented, the surface develops small branch-like lines or fissures. This modified test can also be used to approximate the fermentation factor wherein a cocoa bean corresponding to Fig. 1 i. designated as 100, Fig. 1 as 200, Fig. 1. as 300 and rig. i as 400. While the definitions of the aforementioned categories are a general guide, the assessment according to these categories is well within the skill of the ordinary skilled artisan well versed in chocolate and cocoa processing (see Wood et al., Cocoa,, 4th Ed. (1965), incorporated herein by reference, especially pages 511 to 513). The numerical index, 1-4 or 100-400, are qualitative terms that are used herein to reflect the relative fermentation of cocoa beans and therefore related to the relative concentration of cocoa polyphenols in cocoa beans. A value of I or 100 would reflect unfermented beans possessing the highest relative concentration of cocoa polyphenols, that is, the total amount or nearly the total amount of cocoa polyphenols produced by the cocoa plant in the cocoa bean. A value of 4 or 400 would reflect fully fermented beans possessing the relative lowest concentration of cocoa polyphenols, that is, the remaining amount of cocoa polyphenols that did not react, decompose, or otherwise transform under fermentation, roasting, alkalization or other processing procedures. The actual cocoa polyphenol concentration of any cocoa bean sample or cocoa ingredient may be determined using the high performance liquid chromatographic CHPLC) technique described in Romancryk, et al., U.S. Patent No. 5,554,645.

The term Isignificant amount 3 means an amount Which maintain the basic characteristics of the specified ingredients or composition or product.

The term '1 fair average quality cocoa beans" refers to cocoa beans that have been separated from the pulp material and dried and are relatively free of mold and infestation. Such beans are a commercial commodity and form the feedstock for the next step in the production processes, infra-red heating, roasting, pressing, etc. The term includes any such bean that has been genetically modified or produced.

The term "raw freshly harvested cocoa beans" refers to seeds or beans freshly harvested from the cocoa pod and which have not been subjected to processing other than separation from the pulp. The term includes any such bean that has been genetically modified or produced.

The process for providing a confectionery product having a conserved cocoa polyphenol concentration, comprises: mixing a carbohydrate ingredient with at least one pre-treatment ingredient to form a confectionery mix, combining the confectionery mix with at least one ingredient containing cocoa polyphenol, and forming the polyphenol-containing confectionery product, wherein the product contains at least about 10% by weight more polyphenol than a product prepared without using the pre-treatment process according to step The process of preparing a chocolate product having a conserved concentration of cocoa polyphenol; comprises: mixing at least one ingredient selected from the group consisting of milk ingredients and carbohydrate ingredients, with at least one pre-treatment ingredient to form a confectionery mix, combining the confectionery mix with at least one ingredient containing cocoa polyphenol, conching the combined ingredients, and forming the polyphenol-containing chocolate product, wherein the product contains at least about 10% by weight more polyphenol than a product prepared without using the pre-treatment process according to step Also disclosed are confectionery products, particularly chocolate products, having a conserved concentration of cocoa polyphenol, and particularly, cocoa polyphenol oligomers 5-12 which may be prepared using a split milling, or split refining process comprising: mixing at least one ingredient selected from the group consisting of milk ingredients and carbohydrate ingredients, with at least one pre-treatment ingredient to form a confectionery mix, combining the milled confectionery mix with at least one ingredient containing cocoa polyphenol and having a particle size equal to or less than that desired in the confectionery product or chocolate product, conching the combined ingredients, and forming the polyphenol-containing confectionery or chocolate product, wherein the product contains at least about 10% by weight more polyphenol than a product prepared without using the pre-treatment process according to step Also disclosed are chocolates having a strong chocolate flavor and conserved concentrations of cocoa polyphenols, and particularly, cocoa polyphenol oligomers 5-12 which may be prepared using a split conching process comprising: mixing at least one ingredient selected from the group consisting of milk ingredients and carbohydrate ingredients, with at least one pre-treatment ingredient to form a confectionery mix, conching the confectionery mix, combining at least one ingredient containing cocoa polyphenol with the conched confectionery mix, refining, then conching, the resulting mixture, and forming the polyphenol-containing chocolate product, wherein the product contains at least about 10% by weight more polyphenol than a product prepared without using the pre-treatment process according to step Another form of the split conching process, providing chocolates having a strong chocolate flavor and conserved concentrations of cocoa polyphenols, particularly, cocoa polyphenol oligomers 5-12, comprises: mixing at least one ingredient selected from the group consisting of milk ingredients and carbohydrate ingredients, with at least one pre-treatment ingredient to form a confectionery mix, conching the confectionery mix at a temperature of about 60°C to about 900C, cooling the conched confectionery mix to a temperature of about 350C to about 506C, combining at least one ingredient containing cocoa polyphenol with the cooled, conched confectionery mix, refining, then conching, the resulting mixture, and (0 forming the polyphenol-containing chocolate product, wherein the product contains at least about 10% by weight more polyphenol than a product prepared without using the pre-treatment process according to step Preferably the polyphenol-containing food products prepared by the processes of this invention contain about 15% by weight more cocoa polyphenol than a polyphenol-containing food product prepared without using the pre-treatment process according to step more preferably, the food product of this invention contains about 20% by weight more cocoa polyphenol than a food product prepared without using step The comparative polyphenol-conservation value of 15% and 20% refer to the difference between the conserved concentration of polyphenol in a test sample and the conserved concentration of the polyphenol in a control sample. The conserved concentration of polyphenol in a sample, expressed as percentage, is the concentration of polyphenol in the sample, relative to the concentration of polyphenol in a theoretical sample having 1001 conservation. The increased concentration of cocoa polyphenol retained, or conserved, in the food products of this invention may be measured by analysis of a single oligomer, such as cocoa polyphenol pentamer, as an indicator of improvement in retention.

Significantly, the use of the polyphenol pentamer as the analytical standard also provides an indication of the concentration of the process-sensitive polyphenol oligomers 5-12 retained, or conserved, in the food products of this invention.

The food products of this invention contain at least a carbohydrate-containing ingredient or a protein-containing ingredient, or a mixture thereof. According to the processes of this invention, at least one of these ingredients is mixed first with at least one pre-treatment ingredient. Preferably, if both a carbohydrate-containing ingredient and a protein-containing ingredient are present in the food product, both ingredients are mixed with at least one pre-treatment ingredient prior to mixing with the polyphenol-containing ingredient. Optionally, the carbohydrate -containing ingredient, protein- containing ingredient, or mixture thereof, may be milled or refined prior to mixing with at least one pre-treatmenit ingredient. Alternatively, the mixture of carbohydrate and/or protein- containing ingredients with the pretreatment ingredient(s) may be milled or refined after mixing.

Optionally, the protein- containing ingredient may be a milk ingredient. According to the process of the present invention, the process of preparing a milk chocolate, having a conserved concentration of cocoa polyphenol, comprises mixing both milk ingredients and carbohydrate ingredients with at least one pretreatment ingredient. Milk ingredients, as used herein, include any milk-based ingredient coimmonly used In food manufacturing, and part icularly, confectionery or chocolate manufacturing. Exemplary milk ingredients include liquid milk, milk proteins (casein, whey protein), condensed milk, sweetened condensed milk, evaporated milk, milk crumb, milk powder, re-constituted milk, malted milk, malted milk powder, cultured milk powders, and the like.

Preferably, in each of the above-described processes of this invention, the pre-treatment ingredient is selected from the group consisting of fat, an emulsifying agent, a cocoa ingredient, an antioxidant compound, a flavoring agent and mixtures thereof. The pre-treatment fat ingredient may be selected from any fat described hereinabove, but is preferably cocoa butter. The pre-treatment emulsifying agent ingredient may be -selected from any emulsifying agent described Lhereinabove, but is preferably lecithin, fractionated lecithin, or mixtures thereof. The pre-treatmnent cocoa ingredient may be any cocoa ingredient described hereinabove, but is preferably obtained from cocoa beans having a fermentation factor of 300 or greater. The pre-treatment antioxidant and flavoring agent ingredients may be any of the above-described antioxidant and flavoring agent ingredients.

Preferably, in each of the above-described processes of this invention, the pre-treatment ingredient is a mixture of fat and an at least one emulsifying agent.

More preferably, the pre-treatment ingredient is a mixture of lecithin and cocoa butter.

In each of the above-described processes of this invention, the polyphenolcontaining ingredient may be selected from the group consisting of a cocoa ingredient comprising procyanidins, an extract of cocoa beans or a cocoa ingredient comprising procyanidins, synthesized derivatives of the extracts of cocoa beans or a cocoa ingredient comprising procyanidins, synthesized cocoa polyphenol compounds, and synthesized derivatives of synthesized cocoa polyphenol compounds. The polyphenol-containing cocoa ingredient is preferably a cocoa solids-containing material derived from shell-free cocoa nib and includes chocolate liquor and partially or fully defatted cocoa solids cake or powder), and the like. Advantageously, the polyphenol-containing cocoa ingredient is obtained from cocoa beans having a fermentation factor less than 300; preferably, the cocoa ingredient is obtained from cocoa beans have a fermentation factor less than 275, more preferably, from cocoa beans have a fermentation factor less than 250, more preferably, from cocoa beans have a fermentation factor less than 225, even more preferably, from cocoa beans have a fermentation factor less than 200, more preferably, from cocoa beans have a fermentation factor less than 150, and most preferably, from cocoa beans have a fermentation factor less than 125.

The process for providing a dark chocolate having a conserved cocoa polyphenol concentration, comprises: mixing a carbohydrate nutritive sweetener with lecithin and cocoa butter to form a confectionery mix, combining the confectionery mix with a chocolate liquor obtained from cocoa beans having a fermentation factor less than 300, and forming the polyphenol-containing dark chocolate, wherein the chocolate contains at least about 10% by weight more polyphenol than a dark chocolate prepared without using the pre-treatment process according to step The process for providing milk chocolate having a conserved cocoa polyphenol concentration, comprises: mixing a milled or refined carbohydrate nutritive sweetener and a milled. or refined milk powder with lecithin and cocoa butter to form a confectionery mix, combining the confectionery mix with a chocolate liquor obtained from cocoa beans having a fermentation factor less than 300, and forming the polyphenol-containing milk chocolate, wherein the chocolate contains at least about 10% by weight more polyphenol than a milk chocolate prepared without using the pre-treatment process according to step It is preferred that at least two cocoa ingredients having varying concentrations of cocoa polyphenois are used to prepare the food products and confectionery products of this invention. For example, a first cocoa ingredient, derived from fermented cocoa beans having a fermentation factor of 300 or greater (having a low cocoa polyphenols concentration, but a high chocolate flavor/aroma content) may be used either as the pre-treatment ingredient, or in combination with other pre-treatment ingredients. A second cocoa ingredient, derived from under-fermented beans having a fermentation factor less than 300 (having a higher cocoa polyphenols concentration, but a lower chocolate flavor/aroma content) may be used as the polyphenol-containing cocoa ingredient. The use of such a cocoa-ingredient blend allows for the production of a chocolate having strong flavor/aroma characteristics as well as enhanced concentrations of cocoa polyphenols.

The ingredient containing cocoa polyphenol may be a combination of chocolate liquor and cocoa powder, wherein the liquor and powder are obtained from cocoa beans having a fermentation factor less than 300. Preferably, the chocolate liquor and cocoa powder are obtained from cocoa beans having a fermentation factor less than 275, more preferably, from cocoa beans having a fermentation factor less than 250, more preferably, from cocoa beans having a fermentation factor less than 225, even more preferably, from cocoa beans having a fermentation factor less than 200, more preferably, from cocoa beans having a fermentation factor less than 150, and most preferably, from cocoa beans having a fermentation factor less than 125.

Additionally, each of the above-described processes may further comprise the step of adding a second emulsifying agent, which may be added either during or after conching. The second emulsifying agent may be selected from any of the above-described emulsifying agents. Preferably, the second emulsifying agent may be lecithin, sucrose polyerucate, ammonium phosphatide, polyglycerol polyrincinoleate, phosphated mono- and di-glycerides/di-acetyl tartaric acid of mono-glycerides (PMD/DATEM), fractionated lecithin, or mixtures thereof.

Accordingly, a novel chocolate of the present invention, having a high cocoa polyphenol concentration, may be prepared according to any of the abovedescribed process further comprising the step of combining the confectionery mix with a chocolate liquor and a cocoa powder. The novel chocolate may be prepared by the process comprising the steps of: combining carbohydrate or carbohydrate and milk ingredients with a pre-treatment ingredient comprised of lecithin and optionally, at least one ingredient selected from the group consisting of a fat, a cocoa ingredient, an antioxidant compound and flavoring agent, (ii) using a combination of a chocolate liquor and a cocoa powder as the polyphenol-containing ingredient, and (iii) adding a second emulsifying agent either during or after conching, and (iv) forming the polyphenol-containing chocolate, wherein the chocolate contains at least about 10% by weight more cocoa polyphenol than a polyphenolcontaining chocolate prepared without using the pre-treatment process according to step Also described is a food product, and a process for preparing the product, having enhanced concentrations of cocoa polyphenols derived from a cocoa polyphenol-containing ingredient. Preferred cocoa polyphenol-containing ingredients may be selected from the group consisting of extracts of cocoa beans or a cocoa ingredient comprising procyanidins, synthesized derivatives, synthesized cocoa polyphenol compounds, and synthesized derivaties of synthesized cocoa polyphenol compounds. The polyphenol ingredient may be mixed with other product ingredients during the processing, but is preferably mixed with other ingredients at or near the end of processing, or added to the product after processing spraying onto the product).

Preferably the polyphenol-containing food products prepared by the processes of this invention contain about 15% by weight more cocoa polyphenol than a polyphenol-containing product prepared without using the pre-treatment process according to step more preferably, the food products of this invention contain about 20% by weight more cocoa polyphenol than a food product prepared without using step The percentage improvement of cocoa polyphenol concentration, as defined herein may be measured using a single oligomer, such as pentamer, as an indicator of improvement in retention.

Novel food products containing cocoa polyphenols, particularly enhanced concentrations of cocoa polypehnols, may be prepared by any of the abovedescribed processes. The novel products are distinguishable from conventional products either because the inventive products contain elevated concentrations of cocoa polyphenols relative to comparative conventional products chocolates, chocolate-flavored confections, etc.) and/or the inventive products contain cocoa polyphenois in contrast to comparative products which do not contain cocoa polyphenols rice cakes, edible foods without chocolate flavour/aroma, etc.).

This invention also discloses a food product containing a cocoa polyphenol ingredient. Preferably, the product comprises at least 1 pg cocoa polyphenols per gram product, preferably at least 2 gg, more preferably at least 5 gg, and most preferably at least 10 pg cocoa polyphenols per gram product. According to one preferred embodiment, the product comprises at least 25 jg cocoa polyphenols per gram product, preferably at least 50 jig, more preferably at least 100 jig, and most preferably at least 150 gg cocoa polyphenols per gram product.

Also disclosed is a chocolate comprising at least 3,600 lag cocoa polyphenol per gram chocolate, preferably at least 4,000 ig, advantageously at least 4,500 jag, more preferably at least 5,000 jig, and most preferably at least 5,500 jg cocoa polyphenols per gram chocolate. According to one preferred form, the .chocolate contains at least 6,000 ag cocoa polyphenols per gram chocolate, preferably at least 6,500 pg, more preferably at least 7,000 jg, and most preferably at least 8,000 gig cocoa polyphenols per gram chocolate.

Also disclosed is a chocolate comprising at least 100 jig cocoa polyphenol pentamer per gram of chocolate, preferably the chocolate contains at least 150 jg, preferably the chocolate contains at least 200 jig, preferably the chocolate contains at least 250 ig, preferably the chocolate contains at least 300 jg, more preferably, at least 325 jig, and most preferably, at least 350 gg cocoa polyphenol pentamer per gram chocolate. According to one preferred form, the chocolate contains at least 375 jg cocoa polyphenol pentamer per gram chocolate, preferably at least 400 g.g, more preferably at least 425 ig, and most preferably, at least 450 pg cocoa polyphenol pentamer per gram chocolate.

Also disclosed is a milk chocolate containing milk solids and comprising at least 1,000 jg cocoa polyphenols per gram chocolate, preferably at least 1,250 jig, more preferably at least 1,500 pig, and most preferably at least 2,000 jg cocoa polyphenols per gram chocolate. According to one preferred form, the milk chocolate contains at least 2,500 jig cocoa polyphenols per gram chocolate, preferably at least 3,000 jig, more preferably at least 4,000 jig, and most preferably at least 5,000 jg cocoa polyphenols per gram chocolate.

Also disclosed is a milk chocolate containing milk solids and comprising at least 85 jig cocoa polyphenol pentamer per gram chocolate, preferably at least jg, more preferably at least 100 jg, and most preferably at least 125 jg cocoa polyphenol pentamer per gram chocolate. According to one preferred form, the milk chocolate contains at least 150 gg cocoa polyphenol pentamer per gram polyphenol-containing chocolate liquor and cocoa polyphenol-containing cocoa powder, respectively, obtained from cocoa beans having a fermentation factor of less than 300.

EXAMPLE 1 Method of obtaining Cocoa Polyphenol Cocoa Solids from Cocoa Beans Commercial available cocoa beans having an initial moisture content of from about 7 to 8 percent by weight were pre-cleaned using an 11" X 56" Scalperator (manufactured by Carter Day international,, Minneapolis, MN, 'USA). Approximately 600 bags of cocoa beans (359,000 kg) were pre.-cleaned over a 6.5 hour time period. The beans were fed into the inlet hopper where the flow rate was regulated by a positive feed roll. The beans were fed onto the outside of a rota ting wire mesh scalping reel. The beans passed through the wire mesh reel and subsequently through an air aspiration chanter where light, dirt, dust and strings were aspirated out of the product stream. The beans that did not pass through the scalping reel were conveyed to the reject stream. This reject stream consisted of large clumps of beans, sticks, stones, etc. The amount of resultant reject was approximately 150 kg, or 0.38% of the starting material. The resulting pre-cleaned product weighed about 39,850 kg and was passed to the bean cleaning step.

The pre-cleaned bean products from the Scalperator were then further cleaned using a Cams international SV4-5 Air Fluidized Bed Density Separator (AFEDS, manufactured by Camas International, Pocotello, ID, USA) About 39,950 kg of cocoa bean products were fed into the ADS over a time period of about 6.5 hours. The apparatus removed substantially all heavy impurities such as stones, metal, glass, etc. from the bean as well as lighter unusable materials such as moldy and infested cocoa beans, resulting in a cleaned bean product which contained substantially only usable cocoa beans. The resulting heavy impurities removed weighed about 50 kg and the light unusable materials weighed about 151 kg. A total of about 39,649 kg of cleaned beans was obtained after both the precleaning and cleaning steps described hereinabove (99.1& yield after cleaning).

The cleaned cocoa beans were then passed through a infra-red heating apparatus. The apparatus used was the Micro Red 20 electric infra-red vibratory Micronizer (manufactured by Micronlizing Company Limited, The Micronizer was run at a rate of about 1,701 kilograms per hour. The depth of bean in the vibrating bed of the Micronizer was about 2 inches or about 2-3 beans deep. The surface temperature of the Microniler was set at about 1650C, thereby producing an internal bean temperature (1ST) of about 135C in a time ranging from 1 to 1.5 minutes. This treatment caused the shells to dry rapidly and separate from the cocoa nib. Since substantially all of the cocoa beans fed into the lMicronizer were whole beans and were substantially free of small broken pieces of bean or shell, no sparks or fires were observed during the infra-red heating step. The broken pieces separated by the vibrating screen prior to the Micronizer were re-introduced into. the product stream prior to the winnowing step.

The beans after the Micronizer had a moisture content of about 3.9t by weight. The beans emerged from the Micronizer at an lET of about 1350C and were immediately cooled to a temperature of about 900C in about three minutes to minimize additional moisture loss.

The total beans available after the heating step was about 36,137 kg.

The beans were then subjected to winnowing using a Jupiter Mitra Seita winnower (manufactured by Jupiter Mitra Seita, Jakarta, Indonesia). The winanowing step cracked the beans to loosen the shells and separated the lighter shells from the nibs while at the same time minimizing the amount of nib lost with the shell reject stream. The feed rate into the winnower was about 1,591 kg per hour. The resultant products included about 31,861 kg of usable nibs and 4,276 kg of reject shells. The overall yield of usable nibs from starting material was about 81.7%.

The resulting cocoa nibs were pressed using a Pupps 10-6 Pressor (manufactured by The Dupps Company, Germantown, Ohio, USA).

A steady, consistent feed of about 1,402 kg per hour of nibs was fed into two screw presses to extract butter. The press produced about 16,198 kg of cocoa butter which contained about 10% cocoa solids, and about 15,663 kg of cocoa solids which contained about butter.

The cocoa butter was further processed using a Sharples V3 000 decanting centrifuge (manufactured by Jenkins Centrifuge Rebuilders, N. Kansas City, NO, USA). Centrifugation reduced the solids content in the butter to about 1-2% solids and provided about 13,606 kg of butter and 2,592 kg of cocoa solids containing about 40 to butter. The butter containing 1-2% solids was further processed using a plate and frame filter (manufactured by Jupiter Mitra Seita) which removed the remaining solids from the butter and provided about 13,271 kg of clear cocoa butter and about 335 kg of cocoa S solids containing 40 -45% butter.

The cocoa solids removed from the centrifuge and the filter press contained about 40-45% fat and were pressed in a batch hydraulic press to produce 10% fat cocoa cake. This material produced about 1,186 kg of clear butter and 1,742 kg of cocoa solids.

The total clear butter yield from the incoming beans was 14,456 kg, or 37.1%. The total cocoa solids produced from the incoming beans was 17,405 kg, or 44.6t.

Analysis of the actual cocoa polyphenol content of the cocoa beans and cocoa-containing products produced therefrom, may be conducted using the high performance liquid chromatographic

(HPLC)

technique described in Romanczyk, et al., U.S. Patent No. 5,554,645.

A sample of cocoa powder, produced according to the above-described process from unfermented cocoa beans (fermentation factor 100), was analyzed according to the above-referenced method and shown to contain the following polyphenol concentrations: a total polyphenol concentration of 32,743 pg of polyphenol per gram of cocoa powder, a monomer concentration of 9,433 pg/g, a dimer concentration of 5,929 pg/g, trimer concentration of 5,356 pg/g, tetramer concentration of 4,027 g/g, pentamer concentration of 3,168 gq/g, hexamer concentration of 2,131 pg/g, heptamer concentration of 1,304 pIg/g, octamer concentration of 739 nonamer concentration of 439 pg/g.

EXAMPLE 2 Production of Chocolate Liquor Containing Cocoa Polyphenols Fair average quality (FAQ) cocoa beans having an initial moisture content 7.4% by weight and a fermentation factor level of 233 (31W slaty, 29% purple, 22% purple brown and 17% brown) were selected as the starting material. The cocoa beans were then passed through an infra-red heating apparatus. The apparatus used was an infra-red vibrating micronizer (manufactured by Micronizer Company Limited, The feed rate of beans through the infra-red heater and the infra-red heater bed angle were varied to control the amount of heat treatment the beans received. The amount of time the beans spent in the infra-red heater (residence time) was determined by the bed angle and the feed rate. The times used to prepare the example material are listed in the Table I below. At the outlet of the micronizer the IBT of the beans was measured, these values are also shown in Table 1.

A 1 kg sample of infra-red heated beans, collected off the infra-red heater at different IBTs, were cracked into smaller pieces. This is done to facilitate the separation of the nib from the shell. The laboratory piece of equipment used to remove the shell was the Limiprimita Cocoa Breaker made by the John Gordon Co.

LTD. of England. The cracked beans were next passed through a laboratory scale winnowing system, using a Catador CC-i manufactured by the John Gordon Co. LTD, England.

The cocoa nibs were next milled into a coarse liquor using a Melange made by Pascall Engineering Co. LTD, England. This device crushes and grinds the nibs into a chocolate liquor. The normal operating temperature for the liquor in the Melange in approximately 500C. This same process of taking nibs to a coarse liquor could be done on a larger production scale using other types of mills, such as a Carle Montanari Mill. The cocoa nibs were ground in the Melange for one hour. The concentration of cocoa polyphenols was measured for the samples relative to the infra-red heated temperatures. These values are contained in the Table 1 below.

TABLE 1 pg/g Residence g/g Of Total Of Total Time in Moisture in Pentamer in IBToC Polyphenols in Micronizer, Finished Defatted Defatted Seconds Liquor Liquor Liquor Liquor 107 42 3.9 3,098 39,690 126 82 1.87 1,487 28,815 148 156 1.15 695 23,937 EXAMPLE 3 CONTROL SAMPLE A standard chocolate batch process using a 10 lb. Sigma blade mixer (manufactured by Teledyne Read Co., York, Pennsylvania) was used to mix together the following ingredients.

Ingredient V Concentration (by weight) Sucrose Chocolate Liquor 7% CP Liquor 49% Fat Lecithin The ingredients were added into a 10 lb. Sigma blade mixer (manufactured by Teledyne Read Co., York, Pennsylvania), in order of chocolate liquor and CP liquor, sucrose, cocoa butter, and flavorings. The resulting batch of ingredients was mixed until homogeneous, at about 350C to about 90°C. TheCP liquor,._prepared according to Example 2, used to prepare the chocolate samples containeiTC150 ig-plyphenol pentamer per gram of CP liquor. The mixture was refined to a micrometer particle size of 20 microns, conched and standardized (adjustment of viscosity and/or fat content to obtain chocolate with desired properties). The samples were analyzed for cocoa polyphenol concentration using the high performance liquid chromatographic (HPLC) technique described in Romanczyk, et al., U.S. Patent No. 5,554,645 after mixing or after standardization.

EXAMPLE 4 Test chocolates were prepared using the same recipe and ingredients as Examples 3. The lecithin and fat were combined and mixed, using a 10 lb. Sigma blade mixer until homogeneous. The resulting fat/lecithin mixture was added to the granulated sucrose in a second 10 lb. Sigma mixer. The sucrose, fat and lecithin were mixed at about 35 0 C to about 900C until homogeneous. The remaining ingredients, including the chocolate liquor having a high cocoa polyphenol concentration, were added and mixed until homogeneous.

The resulting mixture was refined to a micrometer particle size of about 20 microns, conched, standardized and analyzed for cocoa polyphenol concentrations as in Example 3.

Table 2 lists the comparative results from a set of chocolates prepared according to the processes described in Examples 3 (Control) and 4 (Test). The chocolate liquor, used to prepare these chocolates, contained 1150 pg polyphenol pentamer per gram of chocolate liquor. Assuming 100% conservation of polyphenol concentration, the chocolates would contain 570 pg of polyphenol pentamer per gram of chocolate. Pentamer concentration of the Test samples was determined directly after initial batch mixing.

TABLE 2 Sample Pentamer Increased (Ag) conservation Control-l 361 Test-1 418 73.3% Control-2 360 Test-2 472 82.8% 19.6% Control-3 313 Test-3 385 67.5% 12.6% Each test sample showed at least about a 10% by weight increase in polyphenol concentration over the control sample.

IEXAMPLE A control and test chocolate were prepared using the same ingredients and in a manner substantially similar to Examples 3 and 4, except that the concentration of lecithin was increased to 0.75% by weight. Pentamer concentration of these chocolates was measured after standardization (finished chocolate). The chocolate sample prepared according to the above test process contained 545.5 pg pentamer per gram of chocolate (95.7% conservation of pentamer), whereas the chocolate prepared according to the control process contained 439.6 pg pentamer per gram of chocolate (77.1% conservation of pentamer). Accordingly, the test chocolate, prepared by the inventive process, retained 18.61 by weight more cocoa polyphenol pentamer than the control chocolate.

EXAMPLE 6 A control and test dark chocolate were prepared according to the processes described in Examples 3 and 4, using the ingredients within the concentration ranges set forth below. The selection of the appropriate ingredients and ingredient amounts within the given range to prepare a chocolate is readily performed by one skilled in the art, without undue experimentation.

Ingredient Concentration Range (by weight) Sucrose 35 -551 CP Liquor 30-65% Fat 1-35% Lecithin 0.2 The chocolate liquor used to prepare the chocolates in these Examples contained 7819 pg total procyanidins per gram of chocolate liquor and 1300 jIg pentamer per gram of chocolate liquor. The total procyanidin content represents the total cocoa polyphenol content of the liquor. Assuming 100% conservation of polyphenol concentration, the chocolates would contain 615 pg polyphenol pentamer per gram of chocolate. The test dark chocolate, prepared according to the process of Example 4, contained 502 pg pentamer (81.6% conservation) and 7091 pg total procyanidin (90.6% conservation) per gram of chocolate. The control dark chocolate, prepared according to the process of Example 3, contained 421 pg pentamer (68.5% conservation) and 6292 pg total procyanidin (80.5% conservation) per gram of chocolate. Accordingly, the test chocolate sample prepared using the inventive process retained 13.1% by weight more cocoa polyphenol pentamer and 10.2% by weight more total procyanidins than the control chocolate sample.

EXAMPLE 7 Dark chocolates were prepared according to the process described below, using the following general recipe: Ingredient k Concentration Range (by weight) Sucrose 3 5 5 5 Chocolate Liquor 15 3 0% CP Liquor 10-20% Fat 0-15 Lecithin 0.1-1. 0 The lecithin and fat were combined and mixed in a Buhler Paste Mixer (sold by Buhler Refiner Co., Minneapolis, Minnesota) until homogeneous. The resulting fat/lecithin mixture was added to the sucrose in Petzholdt conches, models PVW 2000 and PVW 3000 (manufactured by J.S. Petzholdt Inh. H. Pilz., Frankfurt, Germany) and mixed at about 35°C to about 90°C until homogeneous. The remaining ingredients, including the chocolate liquor and the CP liquor were added to the lecithin/fat/sucrose mixture and mixed until homogeneous. The resulting mixture was refined to a micrometer particle size of about 20 microns, conched, standardized and analyzed for cocoa polyphenol concentration as in Example 3.

The combined chocolate liquors used in this Example could provide a dark chocolate containing a total procyanidin concentration of 2933 pg and a pentamer concentration of 162 pg per gram of chocolate. Two samples of the dark chocolate were prepared according to the above process and were determined to contain 158 pg pentamer and 2845 pg total procyanidins and 140 pg pentamer and 2866 pg total procyanidins, respectively.

EXAMPLE 8 A dark chocolate was prepared according to the process described below, using the following general recipe: Ingredient concentration Range (by weight) Sucrose 15 3 5 CP Liquor 40-75% CP Cocoa Powder 1-10% Fat 1-10% Vanillin 0.01-0.05% Lecithin 0.1-1.0t Using a 10 lb. Sigma blade mixer, the lecithin and fat were combined and mixed until homogeneous. The resulting fat mixture was added to the granulated sucrose in a second 10 lb. sigma mixer. The sucrose, fat and lecithin were mixed at about 350C to about 90 0

C

until homogeneous. The remaining ingredients, including the CP liquor and CP cocoa powder, were added and mixed until homogeneous.

The resulting mixture was refined to a micrometer particle size of about 20 microns, conched, standardized and analyzed for cocoa polyphenol concentration as in Example 3. The chocolate liquor used to prepare the chocolates in this Example contained a total of 1000 pg pentamer per gram of chocolate liquor and the cocoa powder contained 1700 pg pentamer per gram of powder. Assuming 100% conservation of polyphenol concentration, the chocolates prepared according to the recipe above would contain of 768 pg polyphenol pentamer per gram of chocolate. This dark chocolate contained 732 gig pentamer per gram of chocolate, and thus retained over 95%, by weight, of the desired polyphenol pentamer present in the polyphenol pentamer-containing ingredients used to prepare the chocolate.

EXAMPLE 9 A milk chocolate was prepared according to the process described below, using the following general recipe: Concentration Range Ingredient (by weight) Sucrose 3 5 5 5 Milk Ingredient 12-25% CP Liquor 10-20% Fat 15-25% Emulsifier 0.1 I 0 At least 21% of the fat and at least 30% of the emulsifier were combined and mixed until homogeneous, and the resulting fat mixture was added to the sucrose and milk ingredients, and mixed.

The CP liquor was added to that mixture, and mixed until homogeneous. The resulting mixture was refined, conched, standardized by addition of the remaining fat and emulsifier, and analyzed for cocoa polyphenol concentration as in Example 3.

Assuming 100t conservation of polyphenol concentration, the chocolate liquor used to prepare this chocolate, would provide a milk chocolate containing 120 pg pentamer per gram of chocolate.

The milk chocolate, prepared according to the above process, contained 115 jg pentamer per gram of chocolate, and thus retained over 95%, by weight, of the desired polyphenol pentamer present in the polyphenol pentamer-containing ingredient used to prepare the chocolate.

Other variations and modifications, which will be obvious to those skilled in the art, are within the scope and teachings of this invention. This invention is not to be limited except as set forth in the following claims.

Claims (36)

1. A process for conserving cocoa polyphenols during the processing of one or more cocoa ingredient(s) containing cocoa polyphenols including cocoa procyanidins into a product comprising carbohydrate ingredient(s), (ii) milk ingredients(s), or (iii) carbohydrate ingredients(s) and milk ingredient(s) and (iv) the polyphenol-containing cocoa ingredient(s) which are selected from the group consisting of chocolate liquor, partially defatted cocoa solids, fully defatted cocoa solids, cocoa extract, synthetic cocoa procyanidins, and mixtures thereof, which process comprises the steps of: pretreating the carbohydrate ingredients(s), the milk ingredient(s), or the carbohydrate ingredient(s) and milk ingredient(s) with one or more pretreatment ingredients selected from the group consisting of an antioxidant, an emulsifier, a fat, a flavorant, and mixtures thereof to form a first mixture; adding the cocoa polyphenol-containing cocoa ingredient(s) to the first mixture to form a second mixture; and processing the second mixture into the cocoa-containing product.

2. The process of claim 1, wherein the cocoa ingredient(s) are prepared from cocoa beans having a fermentation factor of less than 300, from cocoa beans having a fermentation factor of 300 or greater, or from mixtures thereof.

3. The process of claim 2, wherein the cocoa ingredient(s) are prepared from cocoa beans having a fermentation factor of less than 300.

4. The process of claim 2, wherein the cocoa ingredient(s) are prepared from cocoa beans having a fermentation factor of 300 or greater. The process of any one of claims 1 to 4, wherein the carbohydrate ingredient(s) are carbohydrate sweetener(s), sugar substitute(s), or mixtures thereof.

6. The process of claim 5, wherein the carbohydrate sweetener is selected from the group consisting of sucrose, dextrose, fructose, lactose, invert sugar, hydrolyzed lactose, honey, maple sugar, brown sugar, molasses, and mixtures thereof.

7. The process of claim 6, wherein the carbohydrate sweetener is sucrose, lactose, or mixtures thereof.

8. The process of any one of claims 1 to 7, wherein the antioxidant is selected from the group consisting of tannins, quinones, polyhydroxy compounds, phospholipids, tocol compounds, and derivatives thereof.

9. The process of any one of claims 1 to 8, wherein the emulsifier is selected from the group consisting of lecithin, fractionated lecithin, hydroxylated lecithin, mono-glycerides, di-glycerides, sorbitan monstearate, polyoxyethylene sorbitan monostearate, lactylated fatty acid esters of glycerol, lactylated fatty acid esters of propylene glycol, polyglycerol esters of fatty acids, propylene glycol monoesters of fats, propylene glycol diesters of fats, propylene glycol monoesters of fatty acids, propylene glycol diesters of fatty acids, polyglycerol polyricinoleate, ammonium salts of phosphatidic acid, sucrose esters, oat extract and mixtures thereof. The process of any one of claims 1 to 9, wherein the fat is cocoa butter

11. The process of any one of claims 1 to 10, wherein the flavorant is vanillin, spices, naturally expressed citrus oils, or naturally expressed spice oils.

12. The process of any one of claims 1 to 11, wherein the pretreatment ingredient is a mixture of the emulsifier and the fat or a mixture of the antioxidant and the fat.

13. The process of claim 12, wherein the emulsifier is lecithin and the fat is cocoa butter.

14. The process of any one of claims 1 to 13, wherein the product further comprises alkalized cocoa. The process of any one of claims 1 to 14, further comprising the step of reducing the particle size of the carbohydrate ingredient(s) and/or the milk ingredient(s) prior to the pretreating step.

16. The process of any one of claims 1 to 14, further comprising the step of reducing the particle size of the cocoa ingredient(s) prior to adding the cocoa ingredient(s) to the first mixture.

17. The process of any one of claims 1 to 14, further comprising the step of reducing the particle size of the carbohydrate ingredient(s) and/or milk ingredient(s) prior to the pretreating step and further comprising the step of reducing the particle size of the cocoa ingredient(s) prior to adding the cocoa ingredient(s) to the first mixture.

18. A process for conserving cocoa polyphenols during the processing of one or more cocoa ingredient(s) containing cocoa polyphenols including cocoa procyanidins into a product comprising carbohydrate ingredient(s), (ii) milk ingredients(s), or (iii) carbohydrate ingredients(s) and milk ingredient(s) and (iv) the polyphenol-containing cocoa ingredient(s) which are selected from the group consisting of chocolate liquor, partially defatted cocoa solids, fully defatted cocoa solids, cocoa extract, synthetic cocoa procyanidins, and mixtures thereof, which process is substantially as herein described with reference to any one of Examples 4 to 9; excluding the control samples.

19. A food product prepared by the process of any one of claims 1 to 17, wherein the cocoa ingredient is chocolate liquor or mixtures thereof with partially defatted or fully defatted cocoa solids. The food product of claim 19, wherein the food product is a confectionery.

20-Feb-2007 12:53 PM WATERMARK 61398196010 16/30 48 O ci S21. The food product of claim 20, wherein the confectionery is a ser isweet or Ll sweet chocolate. 0

22. The food product of claim 20, wherein the confectionery s a milk chocolate, a buttermilk chocolate, a skim milk chocolate, or a mixed dairy chocolate. eD C 23. The food product of claim 20, wherein the confectionery is a food product Swith a chocolate coating.

24. The food product of claim 20, wherein the confectionery is a reduced fat chocolate confectionery.

25. A diet supplement prepared by the process of any one of claims 1 to 18.

26. A product prepared by the process of any one of claims I to 17, wherein the cocoa polyphenol-containing ingredient is the cocoa extract.

27. A product prepared by the process of any one of claims 1 to 17, wherein the cocoa polyphenol-containing ingredient is the synthetic cocoa procy nidin.

28. A food product including one or more cocoa ingredients which contain cocoa polyphenols in combination with a carbohydrate ingredient and/or a milk ingredient which are pre-treated with an antioxidant, an emulsifier, a fat, a flavorant, or a mixture thereof before the addition of the cocoa ingredien

29. The food product of claim 28 wherein the cocoa polyphenol is a cocoa procyanidin. The food product of claim 28 or 29, wherein the pre-treatment s with the emulsifier, the fat, or mixtures thereof. COMS ID No: SBMI-06311629 Received by IP Australia: Time 12:59 Date 200 7 02 20 20-Feb-2007 12:53 PM WATERMARK 61398196010 17/30 49 0 0 S31. The food product of claim 30, wherein the emulsifier is lecithin and the fat is cocoa butter. o 32. The food product of any one of claims 28 to 31, wherein t e cocoa ingredient is selected from the group consisting of chocolate liquor, partially defatted or fully defatted cocoa solids, cocoa extract, synthetic cocoa procyanidin or a derivative thereof, and mixtures thereof. C 33. The food product of claim 32, wherein the cocoa ingredient is the o chocolate liquor or a mixture of the chocolate liquor with the cocoa solids. 0

34. The food product of any one of claims 28 to 33, wherein at least one of the cocoa ingredients is prepared from cocoa beans having a fermentation factor of less than 300. The food product of any one of claims 28 to 34, wherein the food product is a chocolate.

36. The food product of claim 35, wherein the chocolate is a dark chocolate.

37. The food product of any one of claims 28 to 36, which contairs at least about 10% by weight more cocoa polyphenols, measured as to al cocoa procyanidins, than a food product prepared with a carbohydrate Ingredient and/or a milk ingredient that is not pre-treated.

38. The food product of claim 37, wherein the food product cont ins about 15% by weight more cocoa polyphenols.

39. The food product of claim 38, wherein the food product cont ins about by weight more cocoa polyphenols. The food product of any one of claims 28 to 39, wherein he cocoa ingredient is selected from the group consisting of chocolate liquor, partially COMS ID No: SBMI-06311629 Received by IP Australia: Time 12:59 Date 200 7 02 20 20-Feb-2007 12:53 PM WATERMARK 61398196010 18/30 O tN defatted or fully defatted cocoa solids, cocoa extract, a synthetic cocoa procyanidin or derivative thereof, and mixtures thereof. o 41. The food product of claim 40, wherein the cocoa ingredient is the chocolate liquor or a mixture thereof with the partially or the fully defatted cocoa solids. V 42. The food product of any one of claims 28 to 41, wherein at lest one of Ci the cocoa ingredients is prepared from cocoa beans having a fermentation factor o of less than 300. 0

43. The food product of any one of claims 28 to 42, wherein the food product is a chocolate.

44. The food product of claim 43, wherein the chocolate is a dark ch colate. The food product of claim 43, wherein the chocolate is a milk ch colate, a buttermilk chocolate, a skim milk chocolate, or a mixed dairy chocolate.

46. The food product of claim 43, wherein the chocolate is a rejuced fat chocolate.

47. A food product comprising one or more cocoa ingredients which contain cocoa polyphenols in combination with a carbohydrate ngredient and/or a milk ingredient which are pre-treated with an antioxidant, an emulsifier, a fat, a flavorant, or a mixture thereof before the addition of the cocoa ingredient(s), substantially as herein described with reference to any one of Examples 4 to 9, excluding the control examples.

48. A dry cocoa mix comprising non-alkalized, partially defatted co, a solids having a high cocoa polyphenol content prepared from cocoa beans having a fermentation factor of less than 300, cocoa solids having a high chocolate flavour/aroma content, milk solids, and a sweetener, wherein the milk solids and/or the sweetener are treated with a pre-treatment ingredient, prior to mixing COMS ID No: SBMI-06311629 Received by IP Australia: Time 12:59 Date 2007-0220 20-Feb-2007 12:54 PM WATERMARK 61398196010 19/30 51 0 0 with the non-alkalized, partially defatted cocoa solids during preparation of the dry cocoa mix, the pre-treatment ingredient being selected from the group consisting Sof an antioxidant, an emulsifier, a fat, a flavorant and mixtures thereof. 0

49. A dry cocoa mix according to claim 48, wherein the non-alkalized cocoa solids are prepared from cocoa beans having a fermentation factor of less than

200. Cl 50. A dry cocoa mix according to claim 48, wherein the non-alkalized cocoa o solids are prepared from cocoa beans having a fermentation factor of less than C 125. 51. A dry cocoa mix according to claim 48, wherein the non-alkalized cocoa solids are prepared from slaty cocoa beans and/or purple cocoa beans. 52. A dry cocoa mix according to claim 51, wherein the non-alkalized cocoa solids are prepared from slaty cocoa beans. 53. A dry cocoa mix according to claim 48, wherein the cocoa solids having a high chocolate flavour/aroma content are prepared from brown and/or purple brown cocoa beans. 54. A dry cocoa mix according to claim 53, wherein the cocoa solids having the high chocolate flavour/aroma content are prepared from brown cocoa beans. A dry cocoa mix according to claim 53, wherein the cocoa soli s having the high chocolate flavour/aroma content are alkalized cocoa solids. 56. A dry cocoa mix according to claim 48, wherein the selected ingredient is the flavorant. 57. A dry cocoa mix according to claim 56, wherein the flavorant i- a spice, coffee, salt, or brown nut meats. COMS ID No: SBMI-06311629 Received by IP Australia: Time 12:59 Date 2 007 -02 I 20-Feb-2007 12:54 PM WATERMARK 61398196010 20/30 52 O 0 C 58. A dry cocoa mix according to claim 56, wherein the flavorant is vanillin. 59. A dry cocoa mix according to claim 48, wherein the selected in redient is Sthe emulsifier. A dry cocoa mix according to claim 59, wherein the emulsifier is lecithin. 1 5 61. A dry cocoa mix according to claim 48, further comprising a nutritive C carbohydrate/sweetener or a sugar substitute. 0 S62. A dry cocoa mix according to claim 48, further comprising a protein. 63. A dry cocoa mix according to claim 61, wherein the nutritive carlohydrate sweetener is sucrose, dextrose, fructose, lactose, maltose, glucose syrup solids, corn syrup, invert sugar, hydrolysed lactose, honey, maple sugar, brown sugar, and/or molasses. 64. A dry cocoa mix according to claim 61, wherein the sugar substitute is a high potency sweetener, a polyol, and/or a bulking agent. A dry cocoa mix according to claim 64, wherein the high potency sweetener is aspartame, cyclamate, saccharin, acesulfame, neohespertdin, dehydrochalcone, sucralose, alitame, stevia, glycyrrhizin, and/or thaumatin. 66. A dry cocoa mix according to claim 64, wherein the polyol i. sorbitol, mannitol, xylitol, maltitol, isomalt, and/or lactitol. 67. A dry cocoa mix according to claim 66, wherein the bulking agent is polydextrose, cellulose, a cellulose derivative, maltodextrin, and/or gum Arabic. COMS ID No: SBMI-06311629 Received by IP Australia: Time 12:59 Date 2007-02 20-Feb-2007 12:55 PM WATERMARK 61398196010 21/30 53 O 0 68. A dry cocoa mix according to any one of claims 48 to 67, wherein the cocoa polyphenols are catechin, epicatechin or cocoa procyanidin oligomers 0 thereof. t MARS, INCORPORATED n WATERMARK PATENT TRADE MARK ATTORNEYS (c O O ci COMS ID No: SBMI-06311629 Received by IP Australia: Time 12:59 Date 2007 -0220