JP5871609B2 - High concentration menthol-containing powder flavor preparation - Google Patents

Description

  The present invention is a powdered fragrance preparation containing menthol, which has high storage stability even if it contains a high concentration of menthol, can quickly express the menthol flavor, and the fragrance and flavor are sustained. The present invention relates to a powder fragrance preparation containing high concentration menthol.

Menthol is often used for chewing gum, tablet confectionery, candy, etc., and the scent and flavor spread when you put it in your mouth, the scent you feel when you chew, and the scent and taste you feel when swallowed are products. It is one of the important factors for differentiating.
Powdered fragrances are widely used for flavoring foods and the like, and affect the scent felt when put in the mouth and the scent felt after chewing.
A general method for producing a powdered fragrance is to add a fragrance to an emulsifier such as gum arabic or esterified starch, and then spray-dry the resulting emulsified mixture to produce a powdered fragrance. The resulting powdery fragrance has a slow onset of fragrance and flavor, and is not satisfactory particularly with respect to the scent that is felt at the moment when it is put in the mouth.
In addition, chewing gum and the like have a problem that the fragrance is not easily detached from the gum base, the onset of the fragrance and flavor is delayed, and the fragrance and flavor are not sustained and become weak immediately and difficult to feel.

As a solution for promoting the expression of the aroma and flavor, one or more selected from arabic gum, soybean polysaccharide, esterified starch, lecithin, quilla extract, sucrose fatty acid ester, and glycerin fatty acid ester as perfumes An immediate-release fragrance powder formulation has been proposed in which an emulsifier and a sugar alcohol such as lactitol are added and mixed and emulsified to form a powder formulation (Patent Document 1).
On the other hand, as a solution for promoting the persistence of aroma and flavor, a fragrance is added to an aqueous solution of an emulsifier such as sucrose fatty acid ester, glycerin fatty acid ester, sorbitan fatty acid ester, and lecithin, and emulsification is performed under high pressure. It has been proposed to prepare finely emulsified oil droplets, add an aqueous solution of excipients to this, stir and mix, and spray dry to obtain a sustained-flavored powder flavor (Patent Document 2).
Also, an oil-soluble component such as oil-soluble fragrance and medium-chain triglyceride mixed or dissolved in a ratio of 100: 1 to 1: 1 is finely dispersed or emulsified in an emulsifier solution such as gum arabic, An emulsified fragrance composition obtained by setting the average particle size of the emulsified particles of the oil phase component to less than 0.1 μm, which is transparently dissolved in water, and has improved flavor expression such as taste and top note has also been proposed. (Patent Document 3).
Furthermore, using one or more emulsifiers selected from sucrose fatty acid ester, glycerin fatty acid ester and lecithin, polyoxyethylene sorbitan fatty acid ester, and gati gum as an oily fragrance, the aroma and flavor can be quickly produced. In addition, an oily fragrance-containing powder formulation that is expressed in the above and has long lasting aroma and flavor has been proposed (Patent Document 4).

JP-A-11-140482 JP 2001-152179 A JP 2006-257246 A JP 2011-074306 PR

However, when adding a large amount of menthol to a chewing gum or the like, it is necessary to increase the amount of the menthol-containing powder fragrance preparation itself. The expression of the fragrance will worsen. Therefore, it is conceivable to increase the amount of menthol added to the powdered fragrance formulation, but in the above-mentioned powdered fragrance formulation, it is possible to add menthol content up to 20% by mass, but when adding more menthol, The storage stability of the menthol-containing powder flavor preparation itself is lost.
Therefore, a high-concentration menthol-containing powder perfume preparation that contains a high concentration of menthol, has good storage stability, rapidly expresses the aroma and flavor, and maintains the aroma and flavor has been demanded.

  As a result of diligent research, the present inventors have added specific amounts of (1) lecithin and / or organic acid monoglyceride, (2) triglyceride and (3) gati gum emulsifier and excipients to 20 to 45% by mass of menthol. The high-concentration menthol-containing powder fragrance preparation obtained by emulsifying the added and mixed solution and then drying is highly storage-stable and can quickly express the flavor of menthol. As a result, the inventors have found that the flavor lasts, and have completed the present invention.

That is, the present invention is as follows.
Item 1. A high-concentration menthol-containing powder flavor preparation obtained by subjecting 20 to 45% by mass of menthol to an emulsification treatment of a solution obtained by adding and mixing the following emulsifiers (1) to (3) and excipients: Manufacturing method of
(1) 0.5 to 50% by mass of lecithin and / or organic acid monoglyceride with respect to the amount of menthol,
(2) 0.5 to 50% by mass of triglyceride with respect to the amount of menthol,
(3) Gati gum is 10 to 100% by mass with respect to the amount of menthol.
Item 2. High concentration menthol-containing powder obtained by emulsifying a solution obtained by adding and mixing the following emulsifiers and excipients (1) to (3) with respect to 20 to 45% by mass of menthol. A method for improving the storage stability of a fragrance preparation.
(1) 0.5 to 50% by mass of lecithin and / or organic acid monoglyceride with respect to the amount of menthol,
(2) 0.5 to 50% by mass of triglyceride with respect to the amount of menthol,
(3) Gati gum is 10 to 100% by mass with respect to the amount of menthol.

  ADVANTAGE OF THE INVENTION According to this invention, even if it contains a high concentration menthol, the storage stability is high, the flavor of menthol can be rapidly expressed, and the fragrance and flavor maintain a high concentration menthol-containing powder fragrance formulation Can be provided.

  Menthol of the present invention is an organic compound of cyclic monoterpene and alcohol. The menthol used in the present invention is preferably l-menthol or dl-menthol, which has a particularly cool and cool flavor, but a mixture of these with other isomers may also be used. Further, l-menthol is contained in Japanese mint oil by 65 to 85% and Western mint oil by 50 to 70%, and these essential oils can also be used.

  The menthol content in the high-concentration menthol-containing powder fragrance formulation of the present invention is 20 to 45% by mass, and if it is 20% by mass or less, there is a problem with the storage stability of the menthol-containing powder fragrance formulation even if a known emulsifier is used. When the amount is 45% by mass or more, even if the emulsifier of the present application is used, a problem arises in the storage stability of the powder fragrance preparation containing high concentration menthol.

  The lecithin used in the present invention is a phosphoric acid derivative adduct of glycerin difatty acid ester (diglyceride), and is widely distributed in animals and plants, especially egg yolk lecithin contained in egg yolk, and soybean lecithin contained in soybean. Can be mentioned. Moreover, the fractionated lecithin which took out the active ingredient from these lecithins, the enzyme-processed lecithin which processed lecithin with the enzyme, and an enzyme-decomposed lecithin can also be used. The lecithin used in the present invention is commercially available, and examples thereof include SLP-white (manufactured by Sakai Oil Co., Ltd.).

  The addition amount of lecithin in the present invention is 0.5 to 50% by mass, preferably 2 to 10% by mass, based on the amount of menthol used. When the addition amount is 0.5% by mass or less, the storage stability of the high-concentration menthol-containing powder fragrance preparation is insufficiently improved, and when it is 50% by mass or more, the viscosity of the emulsified solution before drying increases so much that it is pulverized. Since it becomes difficult, it is not preferable.

  The organic acid monoglyceride used in the present invention is obtained by further esterifying an organic acid to the hydroxy group of the monoglyceride, and is also referred to as a monoglyceride derivative. And diacetyltartaric acid monoglyceride (TMG or DATEM) and lactic acid monoglyceride (LMG). A preferable HLB is 5 to 12, and 7 to 10 is particularly preferable. The organic acid monoglyceride used in the present invention is commercially available, and examples thereof include glyceryl succinate monostearate (Sunsoft NO.681NU) (manufactured by Taiyo Kagaku Co., Ltd.).

  The addition amount of the organic acid monoglyceride in the present invention is 0.5 to 50% by mass, preferably 2 to 10% by mass, based on the amount of menthol used. When the addition amount of the organic acid monoglyceride is 0.5% by mass or less, the storage stability of the high-concentration menthol-containing powder flavor preparation is insufficient, and when it is 50% by mass or more, the viscosity of the emulsified solution before drying increases. Therefore, powdering becomes difficult, and the powder properties are poor and fluidity is poor.

  The triglyceride used in the present invention is acylglycerol (glyceride) in which three molecules of fatty acid are ester-bonded to one molecule of glycerol (glycerin), and is one of neutral fats. The triglyceride used in the present invention is commercially available, and examples thereof include ODOO (manufactured by Nisshin Oillio Group Co., Ltd.) and tri (capryl / capric acid) glycerin.

  The addition amount of the triglyceride in this invention is 0.5-50 mass% with respect to the menthol amount to be used, Preferably it is 2-10 mass%. When the amount of triglyceride added is 0.5% by mass or less, the storage stability of the high-concentration menthol-containing powder flavor preparation is insufficient, and when it is 50% by mass or more, the viscosity of the emulsified solution before drying increases excessively. Therefore, powdering becomes difficult, and the powder has poor physical properties and lacks fluidity.

  Gati gum used in the present invention is mainly composed of a polysaccharide obtained by drying the trunk secretion of Anogeissus Latifolia WALL. Known as a thickening stabilizer (food additive) It is gum. The gati gum used in the present invention is commercially available, and examples thereof include gati gum SD manufactured by San-Ei Gen FFI Co., Ltd.

  The addition amount of gati gum in this invention is 10-100 mass% with respect to the menthol amount to be used, Preferably it is 20-50 mass%. When the addition amount of gati gum is 10% by mass or less, the storage stability of the high-concentration menthol-containing powder flavor preparation is insufficient, and when it is 100% by mass or more, the viscosity of the emulsified solution before drying increases excessively. This makes powdering difficult.

  Excipients used in the present invention include monosaccharides such as water-soluble dextrin, glucose, fructose and galactose, disaccharides such as lactose, maltose and trehalose, sugar alcohols such as mannitol, sorbitol, xylitol and erythritol, oligosaccharides and malto-oligosaccharides. , Isomaltooligosaccharide, nigerooligo and the like, palatit, gelatin, gelatin hydrolyzate and the like.

  The high-concentration menthol-containing powder fragrance preparation of the present invention is obtained by emulsifying a mixed solution of the above menthol, emulsifier and excipient by a conventional method, and drying the emulsion by a method such as spray drying or vacuum drying. Can be obtained.

  Other food raw materials and the like can be added to the high-concentration menthol-containing powder fragrance preparation of the present invention within a range not impeding the effects of the present invention. For example, surfactants such as propylene glycol fatty acid ester, sorbitan fatty acid ester, soybean polysaccharide, esterified modified starch, quilla extract, gum arabic, modified gum arabic, xanthan gum, locust bean gum, caraya gum, pullulan, arabinogalactan , Tragacanth gum, carrageenan (copper, iota, lambda), tamarind seed gum, alginic acid, agar, tara gum, gellan gum (native, deacyl), thickening polysaccharides and gelling agents such as pectin, synthetic and natural food coloring , Various food flavors other than menthol, ascorbic acids such as L-ascorbic acid and sodium L-ascorbate; ascorbic acid s such as L-ascorbic acid stearate, L-ascorbic acid palmitate Rus, extracted tocopherol, dl-α-tocopherol, dl-γ-tocopherol, mixed tocopherol, rosemary extract, bayberry extract, rutin extract, rutin enzyme degradation product, enzyme-treated rutin, enzyme-treated isoquercitrin, tea Extracts and antioxidants such as tocotrienol, acidulants such as lactic acid, citric acid, acetic acid and alcorbic acid, various amino acids and various vitamins may be added.

The high-concentration menthol-containing powder fragrance preparation of the present invention can be used for confectionery such as chewing gum, tablet confectionery, candy, and drop, but is particularly preferably used for chewing gum.
Although there is no restriction | limiting in particular in the addition amount to these confectionery, when it becomes 10 mass% or more, menthol is too strong to eat and is unsuitable.

  EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated, this invention is not limited to these Examples. Unless otherwise specified, “%” means “mass%” and “part” means “part by mass”. In addition, the lecithin of an Example is SLP-white (manufactured by Teisei Oil Co., Ltd.), the organic acid monoglyceride is Sunsoft NO. 681NU (manufactured by Taiyo Kagaku Co., Ltd.), triglyceride is ODOO (manufactured by Nissin Oilio Group Co., Ltd.), Gatigam is Gatigam SD (manufactured by Saneigen FFI Corporation), gum arabic Spray Gum 1206 (manufactured by HENELIE INDUSTRIES CO LTD), sucrose fatty acid ester is DK ester F160 (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), polyglycerin fatty acid ester is NIKKOL Decaglyn 1-50SV (Nikko Chemicals Co., Ltd.) The special dextrin NS300 (manufactured by Sanei Saccharification Co., Ltd.) was used as the dextrin.

Experimental example 1
<Preparation method>
Menthol, lecithin, organic acid monoglyceride, and triglyceride, which are oil phase components in the amounts described in Table 1, are uniformly mixed. Then, the oil phase component uniformly mixed was added to the emulsifier solution prepared by dissolving the aqueous phase component gati gum or gum arabic, sucrose fatty acid ester, polyglyceric acid fatty acid ester and dextrin in water, and the mixture was stirred and mixed. . Next, the mixture was treated twice at a pressure of 2.942 kPa (300 kg / cm ² ) using a high-pressure homogenizer 15MP-8TA manufactured by APV Gaulin, and the resulting emulsion was spray-dried (inlet temperature: APV Nordic Hydro). 140 ° C., outlet temperature 80 ° C.) and spray-dried to obtain a menthol-containing powder fragrance formulation (Examples 1 to 7, Comparative Examples 1 to 6).

Experimental method <Menthol survival rate>
0.2 g of the obtained menthol-containing powder fragrance preparation was accurately weighed into a 100 ml volumetric flask, dissolved by adding 50 ml of pure water, and then subjected to ultrasonic treatment for 3 minutes with an ultrasonic processor SU-2TH manufactured by Shibata Kagaku Co., Ltd. went. Next, 25 ml of acetone was added and sonication was performed again for 3 minutes, 5 ml of an internal standard solution 1% 1-octanol: acetone solution was added, and the volume was adjusted to 100 ml with acetone. This liquid was filtered through a 0.5 μm filter, and the filtrate was used as a test solution.

Separately, 0.8 g of l-menthol was accurately weighed into a 100 ml volumetric flask and made up to 100 ml with acetone. 3 ml, 5 ml, 8 ml, and 12 ml of this solution were accurately weighed in a 100 ml volumetric flask, respectively, 50 ml of pure water, 25 ml of acetone, and 5 ml of an internal standard solution were added in the same manner as the test solution preparation method, and quantified to 100 ml with acetone. This solution was filtered through a 0.5 μm filter, and the filtrate was used as a calibration solution.
These test solutions and calibration solutions were tested by gas chromatography, and menthol was quantified using an internal standard method. The residual rate of menthol was determined by (residual amount of menthol obtained / amount of menthol used) × 100.

<Surface oil ratio of menthol>
2 g of the obtained menthol-containing powder fragrance preparation was accurately weighed into a 100 ml beaker, 50 ml of acetone was added, and the mixture was stirred for 5 minutes with a stirrer and then allowed to stand. After leaving still for 5 minutes, the supernatant liquid was filtered with the filter paper 2 made from ADVANTEC, and the filtrate was put into a 100 ml volumetric flask. Again, 25 ml of acetone was added to the sample remaining in the beaker, stirred for 5 minutes with a stirrer, and allowed to stand. After leaving still for 5 minutes, the supernatant liquid was filtered with the filter paper 2 made from ADVANTEC, and the filtrate was put into a 100 ml volumetric flask. 5 ml of an internal standard solution 1% 1-octanol: acetone solution was added to the filtrate placed in a 100 ml volumetric flask, and the volume was adjusted to 100 ml with acetone. This liquid was filtered through a 0.5 μm filter, and the filtrate was used as a test solution.
These test solutions were tested by gas chromatography, and menthol was quantified using an internal standard method. The surface oil ratio of menthol was determined by (surface oil amount of menthol / residual amount of menthol) × 100.

<Sublimation test>
In a 100 ml colorless transparent glass tube, the menthol-containing powdered fragrance preparation obtained so that the menthol concentration was 1000 ppm was accurately weighed, and the glass tube was sealed and stored in a 60 ° C. incubator for 3 hours. Then, it cooled to room temperature 20 degreeC and confirmed the crystal | crystallization of the menthol deposited in the glass tube.

<Expression of flavor>
The menthol-containing chewing gum was prepared by adding each menthol-containing powder flavor preparation obtained to a chewing gum base so that the menthol concentration was 2000 ppm. The expression of the flavor from the prepared menthol-containing chewing gum was evaluated by a sensory evaluation in four stages described in the lower part of Table 5 by eight panelists.

From the results of Tables 3 and 4, the powder preparations (Examples 1 to 7) which are the products of the present invention have a specific amount of (1) lecithin and / or organic acid monoglyceride with respect to menthol 20 to 45%, (2) By using triglyceride and (3) gati gum, the residual rate of menthol was as high as about 90%, and the menthol content on the powder surface was as low as about 1%. Therefore, menthol crystal formation was not confirmed even in the sublimation test, and it was found that the storage stability of the product of the present invention was high.
The gum arabic preparations (Comparative Examples 1 and 2) produced by a general production method have a menthol residual rate of 80% or less, and the menthol content on the powder surface is 5 to 10% regardless of the amount of menthol added. It was high. Therefore, in both sublimation tests, menthol crystal formation was confirmed.

  In the powder preparation using the surfactants of sucrose fatty acid ester and polyglycerin fatty acid ester (Comparative Example 3), the menthol content on the powder surface was as high as 40% or more. Therefore, in the sublimation test, many menthol crystals were confirmed.

  In addition, even when the menthol and emulsifier used in the present invention deviated from the specific amount of the present invention (Comparative Examples 4, 5, and 6), the menthol content on the powder surface was high. Therefore, in the sublimation test, menthol crystal formation was confirmed even in Comparative Example 6 in which the menthol content on the powder surface was a little over 3%.

From the results shown in Table 5, the flavor expression was superior to the conventional powder menthol formulation, and it had good flavor expression. The powder preparations (Examples 1 to 7) prepared according to the present invention can quickly express the flavor of menthol as compared to the gum arabic preparation (Comparative Example 1) produced by a general manufacturing method, and the flavor. It was excellent in sustainability. In addition, the menthol flavor is superior in sustainability compared to a powder formulation using a surfactant of sucrose fatty acid ester and polyglycerin fatty acid ester (Comparative Example 3), and the flavor expression from chewing gum is balanced. It had good expression.

ADVANTAGE OF THE INVENTION According to this invention, even if it contains a high concentration menthol, the storage stability is high, the flavor of menthol can be rapidly expressed, and the fragrance and flavor maintain a high concentration menthol-containing powder fragrance formulation By adding the powdered fragrance preparation thus prepared, a confectionery such as chewing gum containing a high concentration of menthol can be provided.

Claims (2)

A high-concentration menthol-containing powder flavor preparation obtained by subjecting 20 to 45% by mass of menthol to an emulsification treatment of a solution obtained by adding and mixing the following emulsifiers (1) to (3) and excipients: Manufacturing method of
(1) 0.5 to 50% by mass of lecithin and / or organic acid monoglyceride with respect to the amount of menthol,
(2) 0.5 to 50% by mass of triglyceride with respect to the amount of menthol,
(3) Gati gum is 10 to 100% by mass with respect to the amount of menthol. High concentration menthol-containing powder obtained by emulsifying a solution obtained by adding and mixing the following emulsifiers and excipients (1) to (3) with respect to 20 to 45% by mass of menthol. A method for improving the storage stability of a fragrance preparation.
(1) 0.5 to 50% by mass of lecithin and / or organic acid monoglyceride with respect to the amount of menthol,
(2) 0.5 to 50% by mass of triglyceride with respect to the amount of menthol,
(3) Gati gum is 10 to 100% by mass with respect to the amount of menthol.