JP2016140321A - Soy sauce-like seasoning or soy sauce flavor improver containing low molecular weight ester - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel flavor improver.SOLUTION: A soy sauce-like seasoning or soy sauce flavor improver of the present invention contains a compound represented by the general formula (I) defined by R-COO-R, where Ris a C1-10 hydrocarbon group and Ris a C1-5 hydrocarbon group.SELECTED DRAWING: None

Description

  The present invention relates to a flavor improving agent capable of improving the flavor of soy sauce-like seasonings or soy sauce with improved flavor containing low molecular weight esters.

  Conventionally, sodium glutamate, sodium inosinate, sodium guanylate and the like have been known as taste ingredients and are blended in seasonings and the like. In recent years, the role of fragrance is regarded as important as an element constituting the deliciousness of food, and it is evaluated not only as a taste but also as a “flavor” including a fragrance in taste. The demand for foods and beverages such as seasonings with enhanced “flavor” is increasing, and there is a demand for the development of seasonings with a small amount and high flavor improvement effect.

  As a method for enhancing the flavor of the seasoning, methods of adding yeast extract, seafood extract, livestock meat extract, etc. to the seasoning are known, but all are added in a large amount, and the flavor of the original seasoning changes. Therefore, there is a problem that the amount of use is limited and a sufficient flavor cannot be imparted (see, for example, Patent Documents 1 and 2).

International Publication Number WO2010 / 058527 JP 2007-097488

  This invention makes it a subject to provide the flavor improving agent which can improve the flavor of the soy sauce-like seasoning or soy sauce which improved the novel flavor, and its manufacturing method.

  The present inventors have surprisingly found a flavor improving agent that can improve the flavor of a seasoning containing soy sauce (hereinafter referred to as “soy sauce-like seasoning”) or soy sauce, in which a specific low molecular weight ester is contained, The present invention has been completed

That is, this application includes the following inventions.
[1] The following general formula (I):
R ₁ —COO—R ₂ (I)
(Wherein R ₁ is a hydrocarbon group having 1 to 10 carbon atoms, and R ₂ is a hydrocarbon group having 1 to 5 carbon atoms)
A flavor improver for soy sauce-like seasonings or soy sauce, comprising a compound represented by:
[2] The flavor improver according to [1], wherein R ₁ is a hydrocarbon group having 2 to 6 carbon atoms, and R ₂ is a hydrocarbon group having 1 to 3 carbon atoms.
[3] The compound is ethyl-2-methylpropanoate, ethyl-2-methylbutanoate, ethyl-3-methylbutanoate, ethyl-2-methylpentanoate and ethyl-4-methylpentanoate. The flavor improving agent according to [1] or [2], which is one or more compounds selected from the group consisting of ate.
[4] The flavor improvement according to any one of [1] to [3], wherein the compound is ethyl-2-methylbutanoate, ethyl-3-methylbutanoate, and ethyl-4-methylpentanoate. Agent.
[5] Ethyl-2-methylbutanoate, ethyl-3-methylbutanoate and ethyl-4-methylpentanoate are blended in a weight ratio of 1-20: 1 to 40: 1. [4] The flavor improving agent as described in 1 ..
[6] The flavor improving agent according to any one of [1] to [5] for imparting a fruit-like flavor.
[7] A soy sauce-like seasoning or soy sauce containing the flavor improving agent according to any one of [1] to [6].

  By containing the low molecular weight ester represented by the general formula (I) in the soy sauce-like seasoning or soy sauce, the fragrant scent possessed by the normal soy sauce-like seasoning or soy sauce is suppressed and becomes gentle, A natural fresh feeling that combines sweetness and fruitiness is added. In addition, the overall flavor becomes richer and more “mellow” and “taste depth / spread” is increased, and it is improved to a high-quality flavor that is extremely natural and natural, and greatly contributes to improving palatability. The effect is brought about. As a result, it is possible to provide a product that more suits the consumer's preference and to expand the range of cooking.

  The flavor improving agent of the present invention containing such low-molecular esters can be suitably blended in foods and beverages that require enhanced flavor, particularly liquid seasonings.

(Flavor improver)
The flavor improving agent according to the present invention has the following general formula (I):
R ₁ —COO—R ₂ (I)
(Wherein R ₁ is a hydrocarbon group having 1 to 10 carbon atoms, and R ₂ is a hydrocarbon group having 1 to 5 carbon atoms), ethyl-2-methylpropanoate represented by -Low molecular esters such as methylbutanoate, ethyl-3-methylbutanoate, ethyl-2-methylpentanoate, and ethyl-4-methylpentanoate are included as active ingredients. The low molecular weight esters are appropriately selected according to the flavor to be improved. For example, when improving the flavor and freshness in soy sauce-like seasonings or soy sauce, ethyl-2-methylbutanoate, ethyl-3-methylbutanoate And ethyl-4-methylpentanoate can be selected. These blending ratios can be changed as appropriate according to the strength of the desired flavor. For example, ethyl-2-methylbutanoate, ethyl-3-methylbutanoate and ethyl-4-methylpentanoate are 1-20: 1-40: 1, preferably 3-15: 10-30: 1. More preferably, the fresh soy sauce peculiar to raw soy sauce is imparted by blending it with ordinary concentrated soy sauce at a weight ratio of 6: 17: 1.

  The “flavor” in the present specification means a sense that combines taste and scent that are felt when eating food. For example, the soy sauce-like seasoning or the flavor of soy sauce is intended to mean the fragrant scent they normally have. Moreover, this invention can also play the role which reinforces the flavor which is not contained in the foodstuff which the flavor improvement is intended, or was lost. For example, in normal concentrated soy sauce, fruit-like fragrance is lost by heat treatment (fired) during production, but the present invention can be applied to concentrated soy sauce to impart a fruit-like scent. In other words, the “flavor improving effect” in this specification means not only partial or complete modification of the flavor existing in the food from the beginning, but also enhancement of the flavor that needs to be reinforced in the food. Means.

  The flavor improving agent of the present invention can contain, as an active ingredient, one or more low molecular esters alone or in combination with other known flavor / flavoring ingredients. Moreover, low molecular ester may exist in the form of a salt. Examples of other flavor / flavor components include yeast extract, seafood extract, livestock meat extract, amino acid, nucleic acid, organic acid, protein hydrolyzate, and the like. Among these, for the purpose of imparting a flavor to the soy sauce-like seasoning or soy sauce, amino acid glutamate, nucleic acid, yeast extract and the like are particularly preferable. These flavor and taste components can be added alone or in combination.

  The form in particular of a flavor improving agent is not restrict | limited, For example, forms, such as a dry powder, a paste, a solution, may be sufficient. As long as the desired flavor is not impaired, various additives usable for food and drink such as seasonings, spices, inorganic salts, acids, amino acids, nucleic acids, saccharides and the like can be added to the flavor improver as necessary. As above-mentioned, you may mix | blend other taste ingredients known as an active ingredient, for example, sodium glutamate, with a flavor enhancer.

  Although the compounding quantity to the food / beverage products of the flavor improving agent concerning this invention is determined suitably, for example, low molecular ester becomes the density | concentration of 10-500 ppb, Preferably it is 10-250 ppb, More preferably, it is 50-100 ppb. Can be formulated as follows.

  Low molecular weight esters may be commercially available, or may be synthesized or produced by a known method. For example, as the low molecular weight esters, synthetic products, extracted products, fermented products and processed products thereof, those produced by using a heat reaction of various materials and yeast fermentation may be used.

(Food and drink containing low molecular weight esters)
In the food and drink containing the flavor improving agent according to the present invention, for example, soy sauce-like seasoning or soy sauce, the low molecular esters are 10 to 500 ppb, preferably 10 to 250 ppb, more preferably 50 to 100 ppb. Can be blended. However, these blending amounts take into consideration the flavor attributed to the food / beverage product before the addition of the flavor improving agent, the salt content present in the food / beverage product from the beginning, the degree of the desired flavor improving effect, etc. As appropriate.

  The flavor improving agent of the present invention can be used without particular limitation for various foods and beverages that require enhanced flavor. For example, various foods or beverages, meat, seafood, vegetables, algae, mushrooms, fruits, nuts, etc. or cooked foods using them, rice, noodles, breads, vegetables, pickles, tempura, boiled eggs , Snacks, cereals, fried foods, cheese, meat products, soups (cup soups, instant noodle soups, etc.), processed foods such as roux, seafood, meat products such as salmon, chikuwa, fried fish, ham, sausage, etc. Contains various soy sauces such as concentrated soy sauce, various low-salt soy sauces, various soy sauces, various sauces, yeast extract, livestock meat extract, seafood extract, protein hydrolysate, etc., and nucleic acids (sodium inosinate, sodium guanylate, etc.) By adding the flavor improving agent of the present invention to the seasoning, it is possible to enhance the flavor unique to those foods or beverages or supplement the flavor of foods and beverages with insufficient flavors. .

  The flavor improver of the present invention is not limited, but used in soy sauce-like seasonings or soy sauces, for example, liquid seasonings such as dark soy sauce, ponzu, soy sauce, sauce, dressing, etc., especially soy sauce-like seasonings or soy sauce that exhibits a soy sauce flavor It is assumed that

  Although the flavor improving agent of this invention exhibits a flavor independently, it is added to food-drinks suitably in combination with another flavor and taste component. Examples of the flavor / flavoring component include yeast extract, seafood extract, livestock meat extract, amino acid, nucleic acid, organic acid, protein hydrolyzate, and the like. Among these, for the purpose of giving the soy sauce flavor to the soy sauce-like seasoning, amino acid glutamate, yeast extract, and nucleic acid are particularly preferable. These flavor and taste components can be added alone or in combination.

(Manufacturing method of flavor improver-containing food and drink)
In the manufacturing method of the food / beverage products containing the flavor improving agent which concerns on this invention, flavor improvement is carried out so that low molecular ester may be contained in food / beverage products 10-500 ppb, Preferably it is 10-250 ppb, More preferably, it is 50-100 ppb. Agent is added.

  The flavor improver is preferably added directly to the food or drink. However, when the target food or drink is a fermented product, the active ingredient may be increased to a desired concentration during the fermentation process instead of adding the flavor improving agent.

  Hereinafter, the present invention will be described more specifically with reference to specific examples. In addition, this invention is not limited by this.

Experimental example 1
(Analysis of components characteristically contained in raw soy sauce)
1) Sample solution 20 ml of raw soy sauce or soaking sauce was put in a glass vial and sealed with a septum and an aluminum cap to obtain a sample solution.

2) Aroma collection conditions After using a commercially available headspace (HS) -SPME analysis CAR (Carboxen) / PDMS fiber for 10 minutes at 40 ° C and allowing the SPME unit to penetrate the septum. Then, the fiber was exposed to the head space (HS), extraction was performed for 30 minutes, and aroma was collected.

3) GC-O analysis of headspace (HS) volatile components The SPME unit adsorbing HS volatile components is passed through the GC inlet septum, and the fiber is exposed for 5 minutes in the GC inlet set at 230 ° C. The aromatic components were heated and desorbed, GC-O analysis was performed, and the fragrance of each component was confirmed.

4) GC-MS analysis and quantification Also in the GC-MS analysis, the HS volatile component was heated and desorbed under the same conditions as the GC-O analysis. In the GC-MS analysis, the compound was identified based on the GC retention time and the mass spectrum standard material or the agreement with literature values.
Detailed analysis conditions are
Column: DB-WAX (60 m × 0.25 mm (id), 0.25 μm (film thickness))
Even Temp: 40 ° C. (10 min hold), 3 ° C./min, 220 ° C. (30 min hold)
Ion source temperature: 200 ° C
Ionization voltage: 70 eV
Library: Wiley database (338323 compounds) was used.

  The concentration of low molecular esters (ethyl ester) in soy sauce was analyzed in the SIM mode of GC-MS by adding an internal standard substance. A calibration curve was created and quantified by comparing the characteristic ions of the internal standard substance and the ionic strength of the target component. All analyzes were performed in triplicate.

  Most of the commercially available concentrated soy sauce was burned, and most of the low molecular weight esters of concentrated soy sauce from multiple manufacturers were less than 3 ppb. On the other hand, many low molecular weight esters of raw soy sauce contained 20 ppb or more.

5) Evaluation and classification of soy sauce fragrance by GC-O analysis The characteristics of the fragrance perceived from each fragrance concentrate by GC-O analysis were reported in Reference 1 reported by Shimoda et al. (Mitsuya Shimoda, Yuji Tsukamoto, Yuko Ito, Using a panel of 3 people, using Tomonori Yoshinaga, Kameda Ya, Yutaka Samejima (1989), creation and evaluation of evaluation terms for basic odor characteristics of food, Journal of Japan Society for Food Science and Technology, 36, 17-25) evaluated.
Since there are more than 100 types of aroma components that can be detected from each sample, references 2 to 5 (Reference 2: Kaneko, S., Kumazawa, K) are used to clarify the qualitative characteristics of the fragrances of raw and soy sauce. and Nishimura, O. (2012), Comparison of key aroma compounds in five different types of Japanese soy sauces by aroma extract dilution analysis (AEDA), J. Agric. Food Chem., 60, 3831-3836; Reference 3: Steinhaus , P. and Schieberle, P. (2007), Characterization of the key aroma compounds in soy sauce using approaches of molecular sensory science, J. Agric. Food Chem., 55, 6262-6269; Reference 4: Miho Imamura, Hiroe Sato (2008), Selection of descriptive analysis-type panels for soy sauce and soy sauce-related seasonings, Journal of Japan Society for Food Science and Technology, 55, 468-480; Reference 5: Ohata, M., Tominaga, T., Dubourdieu, D ., Kubota, K. and Sugawara, E. (2009), Quantification and Odor contribution of 2-furanmethanethiol in different types of fermented soy-bean paste miso, J. Agric. Food Chem., 57, 2481-2485), referring to the evaluation term of the scent of soy sauce, the scent of the aroma component detected by GC-O analysis is "sweet", "unpleasant" , “Savory”, “shapply (reminiscent of salty taste)”, “fruit-like”, and “smoked-like”.

  From the above results, ethyl-2-methylpropanoate, ethyl-2-methylbutanoate, ethyl-3-methylbutanoate, ethyl-2-methylpentanoate, ethyl-4-methylpentanoate, etc. It has been clarified that all of the low molecular esters exhibit a favorable flavor.

Experimental example 2
(Sensory evaluation test of soy sauce with low molecular esters)
The sensory evaluation test produced three low molecular esters (ethyl-2-methylbutanoate, ethyl-3-methylbutanoate, and ethyl-4-methylpentanoate) that had a high content in soy sauce. Prepare liquids blended in the ratios contained in the soy sauce (6: 17: 1, respectively), and add the above three low molecular weight esters to the concentrated soy sauce (produced by Kikkoman Co., Ltd.) that has been subjected to normal heating. It added and implemented so that a density | concentration might be 5 ppb-500 ppb. Three panelists trained in the sensory test of flavor from within Kikkoman Corporation evaluated the concentration range, strength and preference of low-molecular-weight esters of various concentrations.

The results are shown in Table 1.

  When low molecular weight esters were added to commercially available concentrated soy sauce, the effect of addition was confirmed in the range of 10 ppb to 500 ppb. Also, by adding low molecular weight esters, the fragrant scent of normal soy sauce is suppressed, it becomes a gentle scent, and at the same time, a natural fresh feeling with sweetness and fruitiness is given. Was confirmed. As a result, there were many people who felt that the flavor became rich overall, and that “mellow” and “depth and spread of taste” increased.

  Thus, by adding low molecular weight esters, a natural fresh feeling was imparted and a mild flavor was obtained, and the effect of greatly contributing to improvement in palatability was brought about.

  The flavor improving agent of this invention can be suitably mix | blended with the food-drinks in which the enhancement of flavor is required, especially a liquid seasoning.

Claims (7)

The following general formula (I):
R ₁ —COO—R ₂ (I)
(Wherein R ₁ is a hydrocarbon group having 1 to 10 carbon atoms, and R ₂ is a hydrocarbon group having 1 to 5 carbon atoms)
A flavor improver for soy sauce-like seasonings or soy sauce, comprising a compound represented by: R ₁ is a hydrocarbon group having 2 to 6 carbon atoms, R ₂ is a hydrocarbon group having 1 to 3 carbon atoms, flavor improving agent according to claim 1.   Said compound consists of ethyl-2-methylpropanoate, ethyl-2-methylbutanoate, ethyl-3-methylbutanoate, ethyl-2-methylpentanoate and ethyl-4-methylpentanoate The flavor improving agent of Claim 1 or 2 which is 1 type, or 2 or more types of compounds selected from the group.   The flavor improving agent according to any one of claims 1 to 3, wherein the compound is ethyl-2-methylbutanoate, ethyl-3-methylbutanoate, and ethyl-4-methylpentanoate.   5. The compound according to claim 4, wherein ethyl-2-methylbutanoate, ethyl-3-methylbutanoate and ethyl-4-methylpentanoate are blended in a weight ratio of 1-20: 1 to 40: 1. Flavor improver.   The flavor improving agent of any one of Claims 1-5 for providing fruit-like flavor.   A soy sauce-like seasoning or soy sauce containing the flavor improving agent according to any one of claims 1 to 6.