JP2003052330A - Flavor composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a flavor composition capable of imparting flavor and body to a milk-associated product and enhancing them to a necessary and sufficient level, and further to provide the milk-associated product obtained by formulating the flavor composition. SOLUTION: This flavor composition for milk, a milk product, a drink containing the milk or the milk product, or a substitute for the milk product contains 3-methylnonane-2,4-dione. The milk, the milk product, the drink containing the milk or the milk product, or the substitute for the milk product is obtained by formulating 0.001 ppt to 100 ppb of the 3-methylnonane-2,4-dione therewith.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a flavor composition for milk, a dairy product, a food or drink containing a milk or a dairy product or a dairy product substitute, and a milk or a dairy product to which the flavor composition is added. , Foods and drinks containing milk or dairy products, or dairy substitutes.

[0002]

2. Description of the Related Art Milk and dairy products are foods that are rich in protein, fat, vitamins, minerals, etc. and are nutritionally balanced, and are widely consumed all over the world. In addition to the nutritional enhancement of foods and drinks, it is widely practiced to add milk, fresh cream, fermented milk, powdered milk and the like to various foods and drinks for the purpose of making the flavor mellow. Furthermore, various dairy product substitutes such as margarine and fat spread that do not use milk fat as a raw material have been developed, and the demand for them is increasing with the increasing health consciousness of consumers (hereinafter, “milk, dairy products,
Milk or food or drink containing dairy products or dairy substitutes "
Are collectively referred to as "dairy-related products"). In general, dairy products have a unique and desirable flavor, a “koku” (deep and rich taste), and a voluminous feeling, which is considered to contribute greatly to the taste of dairy products.

However, milk fat is deeply involved in the flavor and "koku" of milk-related products, and when the milk fat content in the product is suppressed for the purpose of calorie reduction and cost reduction, the flavor and "koku" are reduced. , Etc. are lacking. In such a case, a flavoring material capable of supplementing or enhancing such a flavor at a necessary and sufficient level has not been known so far. That is, flavors for dairy-related products need to be in harmony with milk without impairing the original balance of flavors of milk, but conventional δ-decalactone and the like as flavoring materials are all flavors unique to milk. The effect of imparting "Koku" or "Koku" is insufficient. For example, when added in an amount that does not impair the original flavor of milk, "Koku" lacks a sense of volume, while "Koku"
When adding a sufficient amount to give a voluminous feel, the balance with the original flavor of milk is lost and there is a trade-off that it deviates from the natural flavor of milk. In other words, δ
-If a lactone flavoring agent such as decalactone is used to give the product a "koku" or volume feeling, it is necessary to add a sufficient amount of lactones to give a "koku" or volume feeling to the product. There was a tendency for the balance to be disturbed, resulting in an unnatural flavor with a strong lactone odor.

[0004]

DISCLOSURE OF THE INVENTION The present invention provides a flavor composition capable of imparting and enhancing the flavor and "bodily" of a milk-related product at a necessary and sufficient level, and a milk-related product containing the flavor composition. The purpose is to provide.

[0005]

Means for Solving the Problems As a result of intensive studies conducted by the present inventors in order to solve the above problems, surprisingly, it is known as a green odor flavoring agent contained in vegetables, tea, etc. 3 -Methylnonane-2,4-dione was found to be able to replenish and enhance the "body" and volume feeling peculiar to milk to milk and milk-related products without disturbing the balance of aroma and flavor of milk, and further 3- The inventors have found that the combined use of methylnonane-2,4-dione and a specific lactone and / or ester further improves the effect, and completed the present invention.

That is, the present invention relates to 3-methylnonane-
A flavor composition for milk, a dairy product, a food or drink containing milk or a dairy product, or a dairy product substitute characterized by containing 2,4-dione, and further, in the flavor composition. 3-methylnonane-2,4-dione was added at 1 ppt to 100
It is characterized by containing ppm.

The present invention also relates to 3-methylnonane-2,4
-The flavor composition according to claim 1 or 2, further comprising at least one flavor selected from the group consisting of the following lactones and esters together with dione. (Lactones) γ-hexalactone, γ-heptalactone, γ-octalactone, γ-nonalactone, γ-decalactone, cis-7-deceno-γ-lactone, γ-undecalactone, γ-dodecalactone, cis- 6-dodeceno-γ-lactone, δ-heptalactone, δ-octalactone, δ-nonalactone, δ-decalactone, 2-deceno-δ-lactone, δ-undecalactone, δ-dodecalactone, δ-tridecalactone , (Esters) 5-hydroxyoctanoic acid and 1 to 1 carbon atoms
4, an ester with an alcohol of any one of 5, an ester of 5-hydroxynonanoic acid and an alcohol of any of 1 to 4 carbon atoms, a 5-hydroxydecanoic acid with an carbon number of 1 to 4
With any of the alcohols, an ester of 5-hydroxyundecanoic acid with any of the alcohols having 1 to 4 carbon atoms, and 5-hydroxydodecanoic acid with 1 carbon atom
~ Ester with alcohol of any one of 4

Further, the dairy product substitute is coffee whitener, margarine or fat spread, and milk or dairy product containing 3-methylnonane-2,4-dione in an amount of 0.01 ppt to 100 ppb. , Foods and drinks containing milk or dairy products, or dairy products substitutes.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below. [1] 3-Methylnonane-2,4-dione The 3-methylnonane-2,4-dione used in the present invention is, for example, a bad odor (returning odor) produced when soybean oil is oxidized.
Causative ingredient (Fat Sci. Technol., 1989, 91, 225-23
0), the causative component of the offensive odor of dried spinach and parsley (Z. Lebensum. Unters. Forsch. A, 1998, 206, 108-1
13, 114-120), aroma component of green tea (Flavour Fragrance
J., 1993, 8, 173-), Aroma components of processed trout and anchovy products (J. Agric. Food Chem., 1993, 41, 2076-2081
, J. Agric. Food Chem., 1995, 43, 453-458) and the like, which have been conventionally known as compounds having a green odor. In the above conventional report example, 3
-It is described that methylnonane-2,4-dione is an aroma / flavor component. However, there is no description or suggestion that this substance may be added to a dairy-related product, or may be imparted or enhanced with a flavor or "body" peculiar to a dairy-related product by mixing.

3-Methylnonane-2,4-dione can be obtained by a conventional synthetic method known in the art, for example, by treating nonane-2,4-dione with sodium ethylate and then methylation with iodomethane. . Also,
For example, a commercial product manufactured by RCTreatt of England is available.

[2] Milk-related products to be blended In the present invention, milk-related products to which the 3-methylnonane-2,4-dione is blended, that is, milk, dairy products, foods and drinks containing milk or dairy products , Or dairy substitutes,
It is as follows. As the milk, for example, raw milk, milk, special milk, partially skimmed milk, processed milk, etc. stipulated in "Ministerial Ordinance Concerning Ingredient Standards for Milk and Milk Products" (December 27, 1952, Ministry of Health and Welfare Ordinance No. 52) Can be mentioned. As dairy products, for example, cream, butter, butter oil, fermented milk such as yogurt, lactic acid bacteria beverages, milk beverages, cheese, ice cream, concentrated milk, skimmed concentrated milk, condensed milk, whole milk powder, which are stipulated in the Ministerial Ordinance, Examples thereof include skim milk powder, sweetened milk powder, concentrated whey, whey powder and the like.

Examples of milk or dairy products-containing food and drink include, for example, coffee drinks, tea drinks, fruit juice drinks, carbonated drinks, frozen desserts, Japanese and Western confectioneries to which the above-mentioned milk, creams, butter, cheese, condensed milk, powdered milk and the like are added. Examples thereof include breads, breads, soups, curries, stews, various instant foods and drinks, various snack foods, and seasonings such as dressings.

Examples of the dairy product substitute include butter substitutes such as margarine and fat spread produced by emulsifying fats and oils, and cream substitutes such as coffee whiteners added to coffee and tea. Can be mentioned.

3-Methylnonane-2,4-dione is a milk
Especially if it does not spoil the balance of traditional flavors
It can be added to dairy products without limit, but it has an extremely strong aroma.
Therefore, the content in milk-related products is preferably 0.01 ppt
To 100 ppb, more preferably 1 ppt to 1 ppb
To mix. Therefore, 3-methylnonane-2,4
-If dione is included in the flavor composition, milk-related products
Assuming that 0.1% of the flavor composition is added to the product,
Including 3-methylnonane-2,4-dione in the flavor composition
Content is 10ppt-100ppm, more preferably 1ppb-1p
It may be contained in the range of pm. This specification
"Ppb" is an abbreviation for part per billion, and is 1 ppb
= 10 ^-9And "ppm" is an abbreviation for part per million
And 1ppm = 10^-6, And "ppt" is part p
Abbreviation for er trillion, 1 ppt = 10^-12Is.

[3] Flavor-enhancing ingredient The present invention further enhances the original flavor of milk by using 3-methylnonane-2,4-dione in combination with a specific lactone and / or ester, and milk-related products. The flavor of can be further improved. Lactones are particularly preferable, and saturated or unsaturated γ- and δ having 6 to 13 carbon atoms.
-Lactones can be mentioned. Preferably 8 carbon atoms
Examples thereof include saturated and unsaturated γ- and δ-lactones having 12 to 12 carbon atoms, and more preferably saturated and unsaturated γ- and δ-lactones having 10 or 12 carbon atoms. Specific examples of the lactone used in combination include γ-hexalactone, γ-heptalactone, γ-octalactone, γ-nonalactone, γ-decalactone, cis-7-
Deceno-γ-lactone, γ-undecalactone, γ-dodecalactone, cis-6-dodeceno-γ-lactone, δ
-Heptalactone, delta-octalactone, delta-nonalactone, delta-decalactone, 2-deceno-delta-lactone,
Examples thereof include δ-undecalactone, δ-dodecalactone and δ-tridecalactone, and preferably γ-octalactone, γ-nonalactone, γ-decalactone, cis-7-deceno-γ-lactone and γ-un Decalactone, γ-dodecalactone, cis-6-dodeceno-γ-lactone, δ-heptalactone, δ-octalactone, δ
-Nonalactone, δ-decalactone, 2-deceno-δ-
Lactone, δ-undecalactone, δ-dodecalactone, and most preferably γ-decalactone and cis-
7-deceno-γ-lactone, γ-dodecalactone, cis-6-dodeceno-γ-lactone, δ-decalactone, 2
Examples include -deceno-δ-lactone and δ-dodecalactone.

Examples of the esters include esters of hydroxycarboxylic acids having 6 to 13 carbon atoms as precursors of these lactones. Preferred are esters of saturated and unsaturated hydroxycarboxylic acids having 8 to 12 carbon atoms, more preferably 1 carbon atoms.
Mention may be made of 0 or 12 esters of saturated, unsaturated hydroxycarboxylic acids. Specifically, an ester of 5-hydroxyoctanoic acid and any alcohol having 1 to 4 carbon atoms, 5-hydroxynonanoic acid and 1 to 4 carbon atoms
, An ester of any of the alcohols, an ester of 5-hydroxydecanoic acid and any of the alcohols having 1 to 4 carbons, 5-hydroxyundecanoic acid and the number of carbons of 1 to 4
It is possible to use an ester with an alcohol of any of 4 and an ester of 5-hydroxydodecanoic acid with an alcohol of any of 1 to 4 carbon atoms. Preferred are esters of 5-hydroxydecanoic acid with alcohols having 1 to 4 carbon atoms and esters of 5-hydroxydodecanoic acid with alcohols having 1 to 4 carbon atoms. 3-
The compounding ratio of methylnonane-2,4-dione and lactones and / or esters is not particularly limited, but the former: the latter is preferably 1:10 to 1: 100,000, and 1: 100.
To 1: 20,000 is more preferable, and 1: 200 to 1: 5.
000 is most preferred.

A flavor composition containing 3-methylnonane-2,4-dione or 3-methylnonane-2,4-dione and lactones and / or esters is appropriately prepared according to the milk-related product to be blended. It can be used after being converted.
For example, it can be added to milk or dairy products as a diluent using ethanol, propylene glycol, or the like as a solvent, or as a flavor composition in which other flavor components are further mixed.

[4] Additional component There is no particular limitation on the additional flavor component to be blended with 3-methylnonane-2,4-dione, and known flavor components are appropriately mixed and used according to the purpose. To be Examples thereof include diacetyl, short chain fatty acids, methyl ketones, fresh cream with lipase, and a flavor composition obtained by extracting butter oil with an organic solvent.

Further, limonene, myrcene, α used for the purpose of imparting flavors such as fruits and coffee to dairy products.
Hydrocarbons such as -pinene, β-pinene, α-terpinene, γ-terpinene, caryophyllene, hexanol, heptanol, octanol, nonanol, decanol,
cis-3-hexenol, cis-6-nonenol,
Alcohols such as cis-3,6-nonadienol, citronellol, geraniol, nerol, linalool, α-terpineol, γ-terpineol, terpinen-4-ol, menthol, thymol and eugenol,
Hexanal, cis-3-hexenal, trans
2-aldehydes such as 2-hexenal, heptanal, octanal, nonanal, decanal, undecanal, 10-undecenal, 2,6-nonadienal, citral, citronellal, vanillin, ethylvanillin, and their acetals, carvone, pregon, mentone, Camphor, nootkatone, acetoin, p-
Methyl acetophenone, p-methoxy acetophenone,
Ketones such as raspberry ketone, anisylacetone, zingerone, acetylfuran, maltol, ethylmaltol, cycloten, dimethylhydroxyfuranone, acetylpyrazine and their ketals, ethyl acetate, propyl acetate, butyl acetate, isoamyl acetate, hexyl acetate, Heptyl acetate, geranyl acetate, linalyl acetate, ethyl propionate, isoamyl propionate, hexyl propionate, geranyl propionate, citronellyl propionate, ethyl butyrate, isoamyl butyrate, geranyl butyrate, butyl pentano Ester such as ate, methyl butyrate, methyl anthranilate, mentofuran, theaspirane, cineol,
Flavor of sulfur oxides such as ethers such as rose oxide, anethole, methoxypyrazine, thiazole, propyl mercaptan, allyl mercaptan, furfuryl mercaptan, dimethyl sulfide, dimethyl disulfide, diallyl sulfide, diallyl disulfide, methional, furfuryl disulfide, etc. It is also possible to mix the ingredients in such an amount that the balance of the flavor of the milk-related product is not disturbed.

[0020]

EXAMPLES The present invention will now be described in detail with reference to examples, but the present invention is not limited thereto.

[Reference Example] Fat Science Technology, Vol.9
Nonane-2,4 according to the method described in 1,225 (1989).
After reacting -dione with equimolar sodium ethylate in ethanol at 70 ° C, equimolar methyl iodide was added and refluxed for 3 hours to synthesize 3-methylnonane-2,4-dione.

[Example 1] For a commercially available sterilized lactic acid bacterium beverage,
3-Methylnonane-2,4-dione was added to 100 ppb, 1 ppb
Alternatively, it was added at 10 ppt. As a comparative control, using a sterilized lactic acid bacterium beverage to which 3-methylnonane-2,4-dione was not added, it was judged by sensory evaluation whether or not the "bodily" or volume feeling of the dairy product was felt.

The sensory evaluation was conducted by a panel of 10 persons, which was 5
It was done by scoring stages and describing comments. That is, the degree of "milky, voluminous" that is felt when 3-methylnonane-2,4-dione is not added is 2
3 points if you feel the richness and volume of milk more strongly
The points were scored as 4 points when they felt more strongly, 1 point when they felt less strongly, and 0 points when they did not feel at all, and the average value of the scores of 10 people was calculated. In addition, I freely commented on the impression of each beverage. The score of each beverage is shown in Table 1. Among the comments from the evaluators, the most common opinions are also listed.

[0024]

[Table 1]

As described above, it was found that 3-methylnonane-2,4-dione gives a voluminous feel to a lactic acid bacterium beverage at an appropriate addition concentration.

Example 2 A milk drink base was prepared by dissolving 50 parts by weight of skim milk and 50 parts by weight of sucrose in 900 parts by weight of distilled water. A fragrance product was prepared by adding δ-decalactone to the milk beverage base at 100 ppb, 1 ppm and 10 ppm. These perfumes were divided into two, and 3-methylnonane-2,4-dione was added to one so that the concentration was 1 ppb. For these perfumes, lactones,
A sensory evaluation was conducted by a panel of 10 people using a milk beverage base to which neither 3-methylnonane-2,4-dione was added as a comparative control product. The sensory evaluation was performed on a 5-point scale, and the degree of "milky, voluminous" that was felt when no lactone was added was set to 2 points.
The average score was calculated by scoring the points as 4 points if they felt more strongly, 1 point if they did not feel much, and 0 points if they did not feel at all. I also freely commented on my impressions. The evaluation results are shown in Table 2.

[0027]

[Table 2]

As described above, the addition of δ-decalactone to the milk beverage increased the "bodiedness" but gave an artificial aroma. However, the addition of 3-methylnonane-2,4-dione provided a natural flavor.

[Example 3] Table 3 was added to the milk drink base of Example 2.
A beverage was prepared by adding the lactones shown in 1 to 100 ppb. These beverages were divided into two groups, and 3-methylnonane-2,4-dione was added to one of the groups so that the concentration was 0.5 ppb. These beverages were sensory-evaluated in the same manner as in Example 2. The results are shown in Table 3.

[0030]

[Table 3]

As shown in Table 3, lactone and 3-methylnonane
The combined use of 2,4-dione was able to further enhance the milk fat feeling.

Example 4 Milk flavors were prepared according to the blending ratios shown in Table 4a.

[0033]

[Table 4]

Subsequently, a milk beverage was prepared by adding the above-mentioned milk flavor to the milk beverage base of Example 2 at the concentrations shown in Table 4b. In addition, as Comparative Example 4, 3 from the formulation of Table 4a.
-Milknonane-2,4-dione-free milk flavor was prepared, and a milk drink added at the concentration shown in Table 4b was prepared. These were sensory-evaluated in the same manner as in Example 1. The evaluation results are shown in Table 4b.

[0035]

[Table 5]

As described above, 3-methylnonane-2,4-
By adding dione, it was possible to prepare a flavor composition for dairy drinks, which has a volume feeling and a natural aroma like dairy products.

[0037]

The flavor composition containing 3-methylnonane-2,4-dione according to the present invention has a flavor and "fat" peculiar to milk-related products without impairing the aroma and balance of milk.
Can be added and enhanced at a necessary and sufficient level. Furthermore, 3
By using -methylnonane-2,4-dione in combination with a specific lactone and / or ester, the effect is further improved.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) A23C 11/00 A23C 11/00 A23D 7/00 500 A23D 7/00 500 A23L 1/22 A23L 1/22 C (72) Inventor Hideki Masuda 19-35-702, Nihonbashi Hakozakicho, Chuo-ku, Tokyo F-term (reference) 4B001 AC05 AC17 EC01 4B026 DC01 DL02 DX05 4B047 LB08 LE01 LE02 LE05 LF05 LG05 LG20 LG51

Claims (5)

[Claims] 1. A flavoring composition for milk, a dairy product, a food or drink containing milk or a dairy product, or a dairy product substitute, which comprises 3-methylnonane-2,4-dione. 2. 1-p of 3-methylnonane-2,4-dione
pt-100ppm is contained, The flavor composition of Claim 1 characterized by the above-mentioned. 3. A compound containing at least one flavor selected from the group consisting of the following lactones and esters together with 3-methylnonane-2,4-dione: 1. The flavor composition described. (Lactones) γ-hexalactone, γ-heptalactone, γ-octalactone, γ-nonalactone, γ-decalactone, cis-7-deceno-γ-lactone, γ-undecalactone, γ-dodecalactone, cis- 6-dodeceno-γ-lactone, δ-heptalactone, δ-octalactone, δ-nonalactone, δ-decalactone, 2-deceno-δ-lactone, δ-undecalactone, δ-dodecalactone, δ-tridecalactone (Esters) 5-ester of 5-hydroxyoctanoic acid and alcohols having 1 to 4 carbon atoms, 5-ester of 5-hydroxynonanoic acid and alcohols having 1 to 4 carbon atoms, 5-hydroxy Ester of decanoic acid and alcohol having 1 to 4 carbon atoms, 5-hydroxyundecanoic acid and 1 to 4 carbon atoms Esters of any of the alcohols, esters of any of the alcohols having 1 to 4 carbon atoms 5-hydroxy dodecanoic acid 4. The dairy substitute is coffee whitener,
Margarine or fat spread.
The flavor composition according to any one of 1. 5. The amount of 3-methylnonane-2,4-dione is 0.
Milk, dairy products, foods and drinks containing milk or dairy products, or dairy product substitutes, which are blended with 01 ppt to 100 ppb.