JP3344522B2 - Method for producing flavor imparting agent - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a flavor imparting agent useful as a flavor for various foods and drinks.
More specifically, the present invention provides a flavor mixture while refluxing a mixture of animal and vegetable fats and oils and water under heating conditions in the presence of oxygen, and forming the resulting flavor in a saturated fatty acid triglyceride solution. The present invention relates to a method for producing a flavoring agent to be collected.

[0002]

2. Description of the Related Art Heretofore, several proposals have been made on a method for producing a flavor mixture containing a saturated or unsaturated aliphatic aldehyde and other oxidation products by oxidizing fats and oils. For example, a flavoring composition comprising subjecting a fat or oil to an oxidation reaction in the presence of oxygen at a temperature in the range of 300 ° C. to 475 ° C. and collecting the resulting volatile flavor mixture in a cold trap. Manufacturing method (Japanese Unexamined Patent Publication No.
735) or an antioxidant (for example, butylated hydroxytoluene, butylated hydroxyaniso-
, Fatty acids or fatty acid derivatives (animal and vegetable oils and fats) in the temperature range of 65 ° C to 180 ° C in the presence of aldehydes and other compounds. There has been proposed a method for producing a flavor mixture containing (Japanese Patent Laid-Open No. 4-229151).

[0003]

However, the flavor imparting agent produced according to the above-mentioned conventional proposal has a temperature of 300.degree.
Because the oxidation reaction proceeds at a high temperature of ~ 475 ° C,
Polymers that cannot be avoided in the high temperature reaction of fats or oils produce by-products. The unpleasant odor of this by-product accompanies the volatile flavor mixture formed. For this reason, the flavor of the flavor composition collected in the cold trap is not always satisfactory. Further, there is a problem that it is difficult to collect the entire amount of the generated flavor components, and this method is not always an excellent method (Japanese Patent Laid-Open No. 11735/1990). On the other hand, the proposal of Japanese Patent Application Laid-Open No.
This is a method of producing a flavor mixture by controlling the oxidation reaction of an oil or fat at a low temperature in the presence of an antioxidant. However, the flavor of the resulting flavor mixture is monotonous, and it is difficult to obtain a rich and varied flavor. This method has the advantage that by-products of the polymer can be avoided, but on the other hand, it is inevitable that the type of flavor produced by oxidation is limited by controlling the oxidation reaction, and the flavor is complicated. The method of obtaining the mixture is not always satisfactory.

[0004]

Means for Solving the Problems The present inventors have made intensive studies to solve the above problems. As a result, the oxidation reaction of animal and vegetable fats and oils is carried out under mild conditions in the presence of water, and the resulting flavored mixture containing saturated or unsaturated aliphatic aldehydes and other oxidation products is converted to fatty acids. By dissolving and collecting in a trap filled with triglycerides, it is possible to control the generation of by-products (polymers) due to oxidation, and there is no accompanying generation of an unpleasant odor. Further, substantially all of the produced flavor mixture can be dissolved and collected in the fatty acid triglyceride solution. That is, according to the present invention, the flavor mixture collected in the fatty acid triglyceride solution by the production method of the present invention has a complex, variety-rich flavor, and is excellent as a flavor imparting agent for foods and drinks. That headline was completed. Hereinafter, the production method of the present invention will be described in detail.

According to the present invention, an oxidation reaction is performed by refluxing a mixture of animal and vegetable fats and water in a vessel equipped with a reflux condenser, a stirrer, and an oxygen inlet under heating conditions while blowing oxygen. Filled with a fatty acid triglyceride solution in which a flavor mixture containing a saturated or unsaturated aliphatic aldehyde and other oxidation products which is propagated and vaporized by the exhausted oxygen is connected from the top of the reflux unit by an inlet tube. By dissolving and collecting in a trap, a method for easily producing a rich and varied flavor imparting agent is provided. If desired, several traps filled with a fatty acid triglyceride solution may be connected. If a cooled trap is used, the flavor can be collected efficiently. The flavor mixture dissolved and collected in the fatty acid triglyceride solution can be used as a flavor imparting agent for various foods and drinks without separating the flavor mixture from the solution. If desired, a flavor mixture can be collected from the solution by a suitable separation means such as distillation, and used as a flavor imparting agent.

[0006] The reflux temperature is appropriately selected depending on the kind of animal and vegetable fats and oils to be used. Usually generally about 10
The oxidation reaction is performed in the range of about 0 ° to 130 ° C. Preferably, the range is about 100 ° C to 110 ° C.
The reflux time also depends on the type of animal or vegetable fat used.
This is performed for about 20 to 150 hours. In determining the reaction time, the optimum range in which the flavor mixture is formed can be determined by measuring the POV (peroxide value) of the animal and vegetable fats and oils during the reaction. The POV value at the time of this oxidation differs depending on the kind of animal and vegetable fats and oils to be used, but is preferably, for example, in a range exceeding about 30 meq / Kg.

The animal and vegetable oils and fats of the present invention include, for example, animal oils such as chicken oil, lard, tallow, milk fat, sheep oil, egg fat, sardine oil, salmon oil, mackerel oil, whale oil and cod oil: sunflower oil , Corn oil, olive oil, coconut oil, sesame oil, palm oil, palm kernel oil, safflower oil, soybean oil, avocado oil, almond oil, rapeseed oil, rice bran oil, coconut oil,
Vegetable oils such as wheat germ oil, camellia oil, peanut oil, cottonseed oil, castor oil, cocoa butter and the like can be mentioned. Among them, animal and vegetable fats and oils containing a large amount of unsaturated fatty acids or branched chain fatty acids are particularly preferably used. The amount of water used for these animal and vegetable fats and oils depends on the type of animal and vegetable fats and oils used, but is usually used in a range of about 0.05 to 5 times the weight of the animal and vegetable fats and oils.

Further, the following flavors are used in the water to be used.
Precursors can be added to further enhance flavor. Examples of the flavor precursor include monosaccharides such as ribose, xylose, arabinose, glucose and fructose: disaccharides such as sucrose and lactose: glycine Amino acids such as, alanine, valine, threonine, histidine, lysine, glutamines, leucine, isoleucine, serine, cysteine, cystine, arginine, aspartic acid, proline: organic acids such as acetic acid, lactic acid, malic acid, citric acid, etc. Acids: Nucleic acids such as inosinic acid, guanylic acid or salts thereof: α- such as diacetyl, pyruvaldehyde, pyruvate, etc.
Dicarbonyl compounds: α, such as hydroxyacetone, dihydroxyacetone, and acetylmethylcarbinol;
β-hydroxycarbonyl compounds: other extracts of animals and plants: and the like. These additional components also
Not only one kind but also plural kinds can be used. The amount of these flavor precursors to be added is not particularly limited and is appropriately selected.

It is advantageous to use air as oxygen present during the oxidation reaction. The air is preferably passed at a rate of 1 to 200 ml / min, particularly preferably 5 to 50 ml / min per 100 g of animal and vegetable fats and oils, for example with stirring. The resulting flavor mixture, which is propagated to the exhausted air and volatilizes, passes through a trap filled with a fatty acid triglyceride solution, which is connected by an inlet pipe from the top of a condenser mounted on the container. Thus, the flavor mixture is efficiently collected in the solution. If desired, the trap may be cooled with a suitable refrigerant, in which case the flavor mixture can be collected efficiently. A trap cooled with dry ice-acetone may be connected to the trap to collect flavor components not collected by the trap. The flavor components collected by these several types of traps can be used alone or in combination as various food and drink flavor imparting agents, and as materials for various flavor-mixed flavor compositions.

[0010] If desired, the residual oil liquid in the container is subjected to, for example, steam distillation to collect flavor components (oxidation products) present in the residual oil liquid, and as it is as a flavor imparting agent. And the flavor is obtained from the flavor obtained above.
An appropriate amount can be added to a saturated fatty acid triglyceride solution containing the mixture to be used as a flavor imparting agent for various foods and drinks. Distilled flavor components present in the residual oil liquid collected by steam distillation are collected in a cooling trap,
Alternatively, it is collected in the trap by any means such as a trap filled with a saturated fatty acid triglyceride solution.

The fatty acid triglycerides used for collecting the produced flavor mixture include, for example, those having 6 to 6 carbon atoms.
And triglycerides of 16 fatty acids. Particularly, fatty acid triglycerides having 8 to 12 carbon atoms are particularly preferable, and vegetable oil containing these fatty acid triglycerides can be used at all.

The flavor of the flavor-imparting agent of the present invention depends on the type of animal and vegetable fats and oils used, and different flavor-imparting agents can be obtained. For example, when using chicken oil as a raw material, boiled chicken-like flavor, when using tallow, beef tallow meat-like flavor, when using tallow as a raw material, fried pork-like flavor, when using sheep fat, boiled In the case of using lamb meat-like flavor, or olive oil, a flavor having a pickled oil-like flavor of the olive fruit, or in the case of palm oil, a flavor having a fried food-like flavor is obtained.

The flavoring agent of the present invention thus produced can be used as a flavoring agent for various foods and drinks as a fatty acid triglyceride solution. It can also be used in the form of a powder after treatment with various coating agents. To obtain a powder, it is admixed with a commonly used coating agent and, for example, means such as spray drying and freeze drying may be used. Examples of the coating agent include gum arabic, gum tragacanth, cyclodextrin, dextrin, gelatin, and modified starch. Further, the flavor imparting agent of the present invention can be used in a wide variety of fields as an excellent and unique flavor imparting agent in any form such as paste and emulsion. Further, the flavor imparting agent of the present invention can be used by being mixed with various known flavor materials, and can also be used by being appropriately mixed with other prepared flavor compositions for foods. Can also. further,
In flavor production, it can also be used as a material for known sugar-amino reactions.

The flavor-imparting agents of the present invention include, for example, soups, seasonings, processed foods such as livestock, poultry, fish and shellfish, sprinkles, instant foods and snack foods,
It is extremely useful as a flavoring agent for foods, dairy products, confectioneries, frozen desserts, and a wide variety of other foods and beverages. The amount of the flavor imparting agent of the present invention is
Depending on the type of the imparting agent and the method of use, for example, when used as a material for a food preparation flavor composition, about 0.0
About 2 to 40% by weight is generally used.

Next, embodiments of the present invention will be described in more detail with reference to examples. In each of the following examples, parts and% mean parts by weight and% by weight, respectively, unless otherwise specified.

[0016]

【Example】

Example 1 Trap 1 (filled with 120 g of fatty acid triglyceride having 8 and 10 carbon atoms as a main component) connected to a reflux condenser, a stirrer, an oxygen inflow port, and an introduction pipe from the top of the reflux condenser, and a trap connected to trap 1 2 (dry ice-acetone cooled) and chicken oil 2400
g, 240 g of water, and 480 ml / min.
100 ° to 10 ° while blowing air from the oxygen inlet
The oxidation reaction was performed at 5 ° C. Flavor components propagated and volatilized in the evacuated air were collected in trap 1.
Further, flavor components not collected in trap 1 were collected in trap 2. The reaction time was terminated when the POV of the chicken oil exceeded 115 meq / Kg. The flavor components obtained in traps 1 and 2 are mixed and flavored.
A bar imparting agent was produced. The resulting flavor imparting agent is
It had an excellent boiled chicken-like flavor with a variety of persistence and richness.

Example 2 According to Example 1, tallow, lard, sheep butter, olive oil, palm oil, peanut oil, milk fat, egg yolk fat, corn oil, a A flavoring agent was prepared using mond oil. The results are shown in Table 1.

Table 1 Characteristics of POV Value Flavor during Oxidation of Raw Material Tallow 135 meq / Kg Boiled tallow meat-like flavor with excellent durability. Pork fat 75meq / Kg Fried pork-like flavor with excellent durability. Sheep fat 50meq / Kg Heated sheep-like flavor with excellent durability and mellowness. Olive oil 250meq / Kg Oil-like flavor of olive fruit with excellent durability and richness. Palm oil 100meq / Kg Fried food-like flavor with persistence and richness. Peanut oil 80meq / Kg Peanut butter-like flavor with excellent richness and richness. Milk fat 115meq / Kg Excellent sustained, rich sweet creamy flavor. Egg yolk oil 80meq / Kg A long-lasting and rich yolk-like flavor. Corn oil 200meq / Kg Corn-like flavor with a long lasting and rich oily feel. Almond oil 150meq / Kg Fried door-mond-like flavor with excellent persistence and richness.

REFERENCE EXAMPLE 1 The flavor imparting agent obtained in Example 1 was added to the following chicken flavor compounded flavor composition formulation in an amount of 10 parts to prepare a chicken flavor compounded flavor composition. It had a harmonious chicken flavor with a remarkably rounded and full-bodied taste as compared with the flavor composition formulation to which the flavor imparting agent of the present invention was not added. Chicken flavor compounded flavor composition prescription compound name part hexanal 7 trans-2-decenal 2 2,4-decadienal 46 dimethylsulfide 1% ethanol solution 10 linalool 2 terpineol 3 1-octen-3-ol 3 maltol 10% ethanol solution 10 diacetyl 1% ethanol solution 5 acetoin 1% ethanol solution 5 ethanol 907 1000

Reference Example 2 In Example 2, 20 parts of a flavor-imparting agent obtained by using beef tallow as a raw material was added to the following formulation of a meat flavor-mixed flavor composition. A bar mix perfume composition was prepared. It has a remarkably roasted feeling and body taste, and has a harmonious roasted meat flavor as compared with the flavor composition composition to which the flavor imparting agent of the present invention is not added. I was Meat flavor compounded perfume composition formulation Compound name part Dimethylsulfide 10% ethanol solution 8 2,5-Dimethyl-4-hydroxy-3- (2H) -furanone 10% ethanol solution 50 Full Furyl mercaptan 0.1% ethanol solution 3 2,4-decadienal 3 γ-octalactone 2 γ-decalactone 2 methional 5 diacetyl 10% ethanol solution 20 2-methylthiophene 2 dipropyl disulphide 10 4-methyl-5- (β-hydroxymethyl) thiazol 25 ethanol 870 1000

REFERENCE EXAMPLE 3 In Example 2, 20 parts of a flavor imparting agent obtained by using corn oil as a raw material was added to the following sweet corn blended perfume composition formulation to obtain a sweetener. A tocoone-mixed fragrance composition was produced. This product has a richer and harmonious corn-like flavor than that of the flavor composition composition to which the flavor imparting agent of the present invention is not added. Had. Formulation of sweetened sucrose perfume composition Compound name part Dimethylsulfide 1% ethanol solution 10 Methanol 5 Furfural 12 Maltol 10% Ethanol solution 300 Vanillin 300 Diacetyl 1% Ethanol Solution 50 Propyl acetate 5 Hexanal 2 Ethyl caproate 10 δ-Decalactone 10% Ethanol solution 10 Ionone 10% Ethanol solution 20 Ethanol 276 1000

[0022]

The flavor-imparting agent produced by the production method of the present invention has no unpleasant odor of a polymer produced as a result of oxidation of fats and oils, and includes saturated or unsaturated aliphatic aldehydes. , And other various oxidation products,
It has a rich and versatile flavor that cannot be obtained by conventional methods, has excellent persistence, and is extremely useful as a flavor material for various foods and drinks.

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Claims (1)

(57) [Claims] 1. A flavor is generated while refluxing a mixture of animal and vegetable fats and oils and water under a heating condition of 100 to 130 ° C. in the presence of oxygen, and is propagated to the exhausted oxygen to be volatilized.
A method for producing a flavor imparting agent, comprising collecting a flavor mixture in a fatty acid triglyceride solution.