JP3523127B2 - Fermented food and beverage flavor enhancer - Google Patents

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a flavor enhancer and a flavor enhancer for fermented foods and drinks (excluding dairy products) such as rice bran pickles and seasonings for bran pickles, or miso, soy sauce and sake. Regarding the blended fermented food and drink, more specifically, optically active or racemic cis-6-dodecene-4-olide (hereinafter, simply referred to as cis-6-dodecene-4-olide)
Alone or with cis-6-dodecene-4-olide,
2,6-dimethyl-5-heptene-4-olide, 3,7
-Decadiene-5-olide, 2 or 4-methyl-2-prenyl-4-olid, cis-3-methyl-4-decanolide, cis-3-decene-5-olide, cis-7-decene-4-olide , Fermented food and drink flavor enhancer to be blended in combination with one or more selected from the group of 2-decene-5-olide (hereinafter, these may be collectively referred to as "other lactones") TECHNICAL FIELD The present invention relates to a flavor enhancer for a fermented food or drink, which can be added to the fermented food or drink to enhance a persistent sweet fermentation sensation and to give a fermented food or drink with high palatability.

[0002]

2. Description of the Prior Art Cis-6-dodecene-4-olide is one of yeasts, Sporobolomyces odorus (Sporobol).
omyces odorus) as a volatile component having a fruity aroma in a culture solution [S. Tahara et al Agr
ic.Biol.Chem., 37 (12), 2855-2861,1973]. It was also reported that it was obtained as a lactone having a fruity aroma such as peach from a culture solution of Fusarium Poae, which is one of the molds [J. Sarri.
S. et al. Agric. Biol. Chem., 49 (11), 3227-3230, 1985].

The natural product-derived cis-6-dodecene-4-olide is an optically active substance rich in the (R) form, and is commercially available, for example, "Natural cis-6-
Dodecen-4-Olide "(Aldrich products and SA
(FISIS product), the (R) body is 85% to 88%,
It is a mixture of optical isomers in which the (S) form is 12 to 15%.

It can also be obtained as a racemate by chemical synthesis [Pirkle WH, Adams PE
(1979) J. Org. Chem. , 44: 216
9].

On the other hand, 2,6-dimethyl-5-heptene-
4-Olide is a perfume substance having an aroma such as green floral, spice-like, celery-like, roast-like, fruit-like, black tea / green tea-like (JP-A-4-91084), and 3,7-decadiene. -5-Olido has a scent of milk-like, butter-like, fruit-like, peach-like, apricot-like, pineapple-like, floral-like, jasmine-like, etc. with a green sensation (Japanese Patent Laid-Open No. Hei 4).
-91087), and 2 or 4-methyl-2-prenyl-4-olide has a fresh citrus aroma (JP-A-8-73450),
In addition, among cis-3-methyl-4-decanolide, (3S, 4S) -cis-3-methyl-4-decanolide, which is an optically active substance, is a ripe fruit-like, waxy, milk-like aroma, and the same optically active substance. (3R, 4R) -cis-3-methyl-
In 4-decanolide, the top note has an oily odor and the middle note has a green lactone odor (Japanese Patent Application No. 10-
263913), and also cis-3-decene-5
-Olido is milky, buttery, with a green touch
It has an aroma such as fruit, peach, apricot, pineapple, floral, jasmine and the like (Japanese Patent Laid-Open No. 4-59594), and also has cis-
7-decene-4-olide has a jasmine-like aroma,
In addition, (R)-of the optically active substance of 2-decene-5-olide
(-)-2-decene-5-olid is Fatty,
It is known as butter-like and milk-like aroma (Japanese Patent Laid-Open No. 2-59564).

[0006] Further, when producing the bran pickles, the method for producing the bran pickles with enhanced flavor by adding γ-octalactone, γ-nonalactone, γ-undecalactone and γ-dodecalactone JP-A-59-39242) is proposed, and it is described that 4-heptanolide, 4-octanolide, and 4-nonanolide are found as a peculiar scent of Shinzuke Sakuan [Kikuda Kuboda et al. Journal, 31 (8), 520-524, 1984].

[0007]

As described above, some lactones have been found as flavor components of bran pickles, and although they have been used, they impart a long-lasting sweet fermentation sensation and further At present, there is no flavor enhancer for fermented foods or drinks that can enhance palatability.

[0008]

Therefore, as a result of intensive studies by the present inventors, the optically active or racemic cis-6 was obtained.
The present invention has been completed by finding that the above problems can be solved by adding an effective amount of a flavor enhancer containing -dodecene-4-olide to a fermented food or drink. In addition, cis-6-dodecene-4-olide and 2,6-dimethyl-
5-heptene-4-olide, 3,7-decadiene-5-
Olide, 2 or 4-methyl-2-prenyl-4-olide, cis-3-methyl-4-decanolide, cis-3-decene-5-olide, cis-7-decene-4-olide, 2
-By blending an effective amount of the fermented food and drink flavor enhancer using one or more selected from the group of decene-5-olide, cis-6-dodecene-4-olide is more effective than when used alone. It was also found that a sufficient effect can be obtained by using a small amount of the flavor enhancer for fermented food and drink due to the synergistic effect.

Therefore, the object of the present invention is fermented foods and drinks, such as pickled bran floor, bran pickling seasoning liquid, lightly pickled seasoning liquid, sake lees pickled seasoning liquid, miso, soy sauce, salted fish, fish soy sauce, sake, distilled liquor Another object of the present invention is to provide a fermented food and drink flavor enhancer capable of enhancing the fermentation odor originally generated and improving the fermentation aroma thereof by adding an effective amount thereof to wine, vinegar and bread.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION One embodiment of the present invention is cis-
It is a flavor enhancer for fermented food and drink containing 6-dodecene-4-olide. The cis-6-dodecene-4-olide may be a natural optically active substance obtained by fermentation culture as described above, or an optically active substance or a racemic substance obtained by chemical synthesis, which are commercially available. Can be easily obtained.

The form of the product of the present invention is, for example, as a water-soluble preparation in which glycerin or propylene glycol is dissolved in 0.001% to 20% by weight or an emulsifier is used so that it can be easily added to fermented food and drink. Then, an emulsion of cis-6-dodecene-4-olide may be prepared by an emulsification method that is usually used. Further, an excipient such as dextrin or modified starch may be added to the above water-soluble preparation or emulsion and dried to prepare a powder preparation.

At that time, for example, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, 2-methylbutyric acid, caproic acid, myristic acid, palmitin, depending on the aroma and flavor of the fermented food and drink. Acids, lower to higher fatty acids such as stearic acid and linoleic acid; keto acids such as pyruvic acid and levulinic acid; acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, 2-methylbutyric acid, caproic acid, myristin Acids, palmitic acid, stearic acid, stearic acid, linoleic acid and other lower-to-higher fatty acid ethyl esters; pyruvic acid, levulinic acid and other keto acid ethyl esters, lactic acid ethyl esters, succinic acid diethyl esters and other esters; propanal, butanal , Pentanal,
Hexanal, heptanal, octanal, nonenal, 2-butanone, 2-pentanone, diacetyl, acetoin, benzaldehyde, phenylacetaldehyde, cinnamic aldehyde, methional, decadienal and other aliphatic and aromatic carbonyl compounds; eugenol, vanillin and other phenolic compounds; Furfural, 5-methylfurfural, 3-hydroxy-4,5
-Dimethyl-2 (5H) -furanone, 4-hydroxy-
Furan compounds such as 2,5-dimethyl-3 (2H) -furanone may also be added.

The effective amount of the flavor enhancer for fermented food or drink of the present invention to be added to the fermented food or drink is generally determined depending on the use of the fermented food or drink (difference between final product and raw material) or production method. However, 0.00001% by weight of cis-6-dodecene-4-olide is based on the fermented food and drink.
It is desirable to mix it so as to be ˜5% by weight.

Another aspect of the invention is cis-6-dodecene-4-olide and 2,6-dimethyl-5-heptene-4.
-Olido, 3,7-decadiene-5-olid, 2 or 4
-Methyl-2-prenyl-4-olide, cis-3-methyl-4-decanolide, cis-3-decene-5-olide,
It is a fermented food and drink flavor enhancer comprising one or more selected from the group of cis-7-decene-4-olide and 2-decene-5-olide (“other lactones”).

"Other lactones" used in the present invention
May be an optically active substance isolated from a natural product, or an optically active substance or a racemic substance obtained by chemical synthesis. Similar to the case of cis-6-dodecene-4-olide alone, cis-6-dodecene-4-olide was mixed with glycerin or propylene glycol to give 0.00
A water-soluble preparation in which 1% by weight to 20% by weight is dissolved, or an emulsion may be prepared by an emulsifying method which is usually performed using an emulsifier. Further, an excipient such as dextrin or modified starch may be added to the above water-soluble preparation or emulsion and dried to prepare a powder preparation.

Further, the combination ratio of cis-6-dodecene-4-olide and "other lactones" is different depending on the scent, so it is determined according to the characteristics of the fermented food and drink to which the product of the present invention is added. , Usually cis-6-dodecene-4-
Oride: “Other lactones” = 1: 10 to 10: 1.

Further, as in the case of using cis-6-dodecene-4-olide alone, a fatty acid, a carbonyl compound or the like can be added. The fermented food and beverage flavor enhancer of this embodiment is cis-6-based on the synergistic effect of the blended lactone.
A smaller amount than dodecene-4-olide alone is effective, and in the case of the above seasoning liquid for shallow pickling, cis-6 is used.
-Dodecene-4-1 / 2 to 1/10 of the case of using alone
Is sufficient.

The fermented food and drink flavor enhancer of the product of the present invention can be used not only for the above-mentioned fermented food and drink, but also for other various foods and drinks. For example, processed meat and fish meat products such as ham, sausage, fish sausage, and kamaboko; milk and milk processed products such as milk powder, condensed milk, cheese, butter, yogurt, and cream; confectionery such as cakes, buns, chocolate, and biscuits; fruit juice It can be used for a wide range of foods and drinks such as beverages, soft drinks, lactic acid bacteria beverages, alcoholic beverages, etc. to modulate or enhance the aroma and flavor.

Hereinafter, several embodiments of the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto.

[0020]

EXAMPLE 1 A seasoning liquid flavor enhancer for lightly pickled vegetables (invention product 1) having the following formulation containing cis-6-dodecene-4-olide (using a product of Aldrich, hereinafter the same) was prepared.

[0021] As a comparative example, from the above formulation, cis-6-dodecene-4-
Seasoning liquid flavor enhancer (comparative product 1) for lightly pickled pickles excluding olido,
Also, a seasoning liquid flavor enhancer for lightly pickled vegetables (Comparative Product 2) was prepared in which γ-dodecalactone was mixed in place of cis-6-dodecene-4-olide. This invention product 1, comparative product 1 and comparative product 2 were blended with a commercially available pickling seasoning solution at 0.2%, and then the seasoning solution was used to make a lightly pickled cucumber, which was prepared by 10 well-trained panelists. A sensory evaluation of the lightly pickled cucumber was performed. The sensory evaluation results are shown in Table 1.

[0022]

[Table 1] Table 1 Sensory evaluation results

The numerical values of the sensory evaluation results in Table 1 represent the number of persons who were judged to have the best flavor or the longest sustainability. From the above results, it can be seen that the product 1 of the present invention is superior in the flavor of pickled vegetables and the persistence of flavor as compared with the comparative product.

Examples 2 to 8 Seasoning liquid flavor enhancers for lightly pickled vegetables (invention products 2 to 8) of the following formulation were prepared using cis-6-dodecene-4-olide and "other lactones" in combination.

[0025] In the above formulation, cis-6-dodecene-4-olid mix is (invention product 2) cis-6-dodecene-4-olid 50% 2,6-dimethyl-5-heptene-4-olid 50% (present Invention product 3) cis-6-dodecene-4-olide 50% 3,7-decadiene-5-olid 50% (Invention product 4) cis-6-dodecene-4-olide 70% 2-methyl-2-prenyl -4-Olido 30% (Invention Product 5) cis-6-Dodecene-4-Olide 80% (3R, 4R) -cis-3-Methyl-4-decanolide 20% (Invention Product 6) cis-6- Dodecene-4-olid 40% Cis-3-decene-5-olid 60% (Invention product 7) Cis-6-dodecene-4-olid 30% Cis-7-decene-4-olid 70% (Invention product 8) cis-6-dodecene-4-olide 9 % (R) - (-) - representing a 10% 2-decene-5-olide.

As in Example 1, the products 2 to 8 of the present invention were mixed with a commercially available pickled seasoning solution in an amount of 0.1%, and then the seasoning solution was used to make a lightly pickled cucumber. A sensory evaluation of lightly pickled cucumber by 10 people was performed. As a comparative product, the lightly pickled cucumbers of Comparative Products 1 and 2 prepared in Example 1 were used as they were. Table 2 shows the results of sensory evaluation
It was shown to.

[0027]

[Table 2] Table 2 Sensory evaluation results

The numerical values of the sensory evaluation results in Table 2 represent the number of persons who were judged to have a better flavor or longer lasting than Comparative Product 1 or 2. From the above results, it can be seen that each of the products 2 to 8 of the present invention is superior in the flavor of pickled vegetables and the persistence of flavor, as compared with the comparative products 1 and 2.

Example 9 A 1% PG solution of cis-6-dodecene-4-olide was added to commercially available miso in an amount of 0.1% to prepare a flavor-enhancing miso containing the product of the present invention. Compared with the additive-free product, the aroma and flavor of sweet miso was emphasized, and the miso tasted better.

Example 10 Mixture of cis-6-dodecene-4-olide: 3,7-decadiene-5-olide = 1: 9 0.1% glycerin solution was added to commercially available sake at 0.001%, Sake with the product of the present invention was prepared. Compared with the additive-free product, refined sake was obtained which is reminiscent of a high-grade product with a fruity aroma and flavor.

Example 11 Mixture of cis-6-dodecene-4-olide: 3,7-decadiene-5-olide = 1: 9 A 0.1% glycerin solution was added to a commercially available vinegar in an amount of 0.001%, Vinegar containing the product of the present invention was prepared. Compared with the additive-free product, vinegar was obtained in which the pungent odor was diluted and a sweet mild aroma was felt.

[0032]

EFFECTS OF THE INVENTION By adding the fermented food and drink flavor enhancer of the present invention to a fermented food and drink, it is possible to impart a persistent sweet fermentation sensation and further enhance palatability.

─────────────────────────────────────────────────── ─── Continued Front Page (51) Int.Cl. ⁷ Identification Code FI A23L 1/238 104 C12G 3/06 C12G 3/06 A23L 1/226 G // A23L 1/226 A23B 4/02 C (56) Reference: Japanese Unexamined Patent Publication No. 8-126467 (JP, A) Journal of Agricultural and Food Chemistry, Vol. 45 (1997), p. 3027-3032 (58) Fields surveyed (Int.Cl. ⁷ , DB name) A23L 1/22 -1/23 A23B 7/10 C11B 9/00 CA (STN) REGISTRY (STN)

Claims (4)

(57) [Claims] 1. A flavor enhancer for fermented food and drink, which comprises an optically active or racemic form of cis-6-dodecene-4-olide. 2. An optically active or racemic cis-6-dodecene-4-olide, 2,6-dimethyl-5-heptene-4-olide, 3,7-decadiene-5-olide, and 2.
Or 4-methyl-2-prenyl-4-olide, cis-3
-Methyl-4-decanolide, cis-3-decene-5-olide, cis-7-decene-4-olide, 2-decene-5
-A fermented food and drink flavor enhancer, characterized in that it is used in combination with one or more selected from the group of orido. 3. A fermented food / beverage product (excluding dairy products), which comprises an effective amount of the fermented food / beverage flavor enhancer according to claim 1 or 2. 4. The fermented food and drink is bran pickles for pickles, seasoning liquid for bran pickles, seasoning liquid for light pickles, seasoning liquid for sake lees, miso, soy sauce, salted fish, fish sauce, sake, distilled liquor, wine, vinegar and bread. The fermented food and drink according to claim 3.