JP6429643B2 - Umami enhancer containing methional and lower fatty acid ester - Google Patents

Description

  The present invention relates to an umami enhancer, liquid seasoning or food / beverage product containing methional and a specific lower fatty acid ester, and a method for producing the same.

  Conventionally, sodium glutamate, sodium inosinate, sodium guanylate and the like have been known as umami ingredients and are blended in umami seasonings and the like. In recent years, umami has been regarded as an important component of the taste of food, and demand for foods and beverages such as seasonings with enhanced umami has increased, and the development of liquid seasonings with a high umami enhancement effect is desired in small quantities. ing.

  As a method of enhancing the umami of seasonings, methods of adding yeast extract, protein hydrolyzate, seafood extract, livestock meat extract, etc. to seasonings are known. However, there is a problem that the amount of use is limited and sufficient umami cannot be imparted.

  Methional (also called 3-methylthio-propionaldehyde or 3-methylthiopropanal) is known to have a potato-like scent. Present in food. It is also known that methional enhances the umami taste of glutamic acid at a specific concentration (see, for example, Patent Document 1) and enhances the salty taste of salt (see, for example, Patent Document 2).

  However, the flavor-enhancing effect of known methional is limited to the enhancement of the flavor inherent to certain coexisting flavor components such as the umami of the umami component and the salty component of the salty component, and is independent of the flavor exhibited by the certain flavor component There is no report on how it affects the flavor of sushi.

  Certain lower fatty acid esters are widely known to exhibit fruit-like scents, and some are actually used as perfumes. However, it is not known that lower fatty acid esters contribute to the enhancement of umami in combination with methional.

JP 2014-18146 A JP 2011-83262 A

  Methional is often not yet known for flavor enhancement. In addition, in the food industry, as described above, there is still a demand for a seasoning having a high umami enhancing effect in a small amount. Then, this invention makes it a subject to provide the novel umami enhancer which shows a remarkable effect in a small quantity, the seasoning containing the said umami enhancer, and its manufacturing method.

  As described above, methional is known to have a potato-like scent, and lower fatty acids have a fruit-like scent. The present inventors have surprisingly found that a combination of methional and a specific lower fatty acid ester other than acetate ester exhibits the same taste as sodium glutamate, and has completed the present invention.

That is, this application includes the following inventions.
[1]
Methional,
The following general formula (I):
R ₁ —COO—R ₂ (I)
(In the formula, R ₁ is a hydrocarbon group having 1 to 10 carbon atoms, R ₂ is a hydrocarbon group having 1 to 5 carbon atoms,
(However, when R ₁ is a hydrocarbon group having 1 carbon atom, R ₂ is not a hydrocarbon group having 1 or 2 carbon atoms.)
The umami enhancer containing the compound or its salt represented by these.
[2] The umami enhancer 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-4-methylpentanoate, ethyl-2-methylpentanoate, ethyl-3-methylbutanoate and ethyl-2-methylbutanoate. The umami enhancer according to [1] or [2], which is one or more compounds selected from the group consisting of ate.
[4] The umami enhancer according to any one of [1] to [3], further including sodium chloride.
[5] A food or drink containing the umami enhancer according to any one of [1] to [4].
[6] The food or drink according to [5], which is a liquid seasoning.
[7] The food or drink according to [6], wherein the liquid seasoning is a soy sauce-like seasoning.
[8] A method for producing a food or drink according to any one of [5] to [7], comprising a step of blending the umami enhancer according to any one of [1] to [4]. .

Methional and the lower fatty acid ester represented by the general formula (I) have the same taste as sodium glutamate. Therefore, the umami enhancer of the present invention containing methional and a lower fatty acid ester can be suitably blended in foods and drinks that require enhancement of umami, particularly liquid seasonings. Here, WO2013 / 118741 discloses a combination of methional and isovaleric acid as a lower fatty acid (corresponding to a compound in which R ₁ is an isopropyl group having 4 carbon atoms and R ₂ is hydrogen). In the presence of 1-octen-3-ol and / or 1-octen-3-one, the fragrance and / or flavor inherently possessed by the brewed fermented food or seafood extract can be imparted to foods and drinks without any unusual flavor. It is stated. However, the present inventors have confirmed that isovaleric acid in combination with methional does not have an umami enhancing effect as compared with the lower fatty acid ester used in the present invention.

(Umami enhancer)
In the umami enhancer according to the present invention, methional and a lower fatty acid ester represented by the following general formula (I) or a salt thereof are contained as active ingredients.
R ₁ —COO—R ₂ (I)
(In the formula, R ₁ is a hydrocarbon group having 1 to 10 carbon atoms, R ₂ is a hydrocarbon group having 1 to 5 carbon atoms,
(However, when R ₁ is a hydrocarbon group having 1 carbon atom, R ₂ is not a hydrocarbon group having 1 or 2 carbon atoms.)

In a preferred embodiment, in the above general formula, 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. As used herein, “hydrocarbon group” means a substituted or unsubstituted monovalent hydrocarbon group. The hydrocarbon group is preferably a monovalent group composed only of a chain structure.

  Although not intended to be limiting, examples of the hydrocarbon group having 1 to 5 carbon atoms include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, Examples thereof include alkyl groups such as sec-butyl group, t-butyl group and pentyl group; alkenyl groups such as ethenyl group, propenyl group, butenyl group and pentenyl group; and alkynyl groups such as ethynyl group, propynyl group and butynyl group.

  The hydrocarbon group is, for example, a halogen atom such as a fluorine atom, chlorine atom, bromine atom, iodine atom, hydroxy group, carboxy group, amino group, cyano group, nitro group, alkoxy group, alkoxycarbonyl group, alkoxycarbonyloxy group , An acyl group, an acyloxy group, and the like.

  In a more preferred embodiment, the compound represented by the above general formula is ethyl-2-methylpropanoate, ethyl-4-methylpentanoate, ethyl-2-methylpentanoate, ethyl-3-methylbutanoate. And ethyl-2-methylbutanoate.

  As used herein, “umami” means umami of the same quality as sodium glutamate.

  The “umami enhancing effect” in the present specification means the production of umami in the absence of other umami ingredients, or the additive or synergistic enhancement of umami in combination with other umami ingredients. Among the above lower fatty acid esters, a combination of methional and ethyl-2-methylbutanoate is particularly preferable as an active ingredient of the umami enhancer of the present invention because of its high umami enhancer action.

The umami enhancer of the present invention can contain, as an active ingredient, a combination of methional and one or more lower fatty acid esters alone or in combination with other known umami ingredients. The lower fatty acid ester may be present in the form of a salt.
Other umami components include amino acids, yeast extracts, nucleic acids, organic acids, protein hydrolysates, and the like. Among these, amino acid glutamate, yeast extract, and nucleic acid are particularly preferred for the purpose of imparting soy sauce umami to the soy sauce-like seasoning. These umami components can be added alone or in combination.

  The form of the umami enhancer is not particularly limited, and may be, for example, a dry powder, a paste, or a solution. Various additives that can be used for foods and drinks such as seasonings, spices, inorganic salts, acids, amino acids, nucleic acids, saccharides, etc. can be added to the umami enhancing agent as long as the desired umami taste is not impaired. . As described above, other umami ingredients known as active ingredients, such as sodium glutamate, may be added to the umami enhancer.

  Although the compounding quantity to the food / beverage products of the umami enhancer which concerns on this invention is determined suitably, for example, methional is 10-50,000 ppb in a food / beverage product, Preferably it is 20-5,000 ppb, More preferably, it is 30-3. 500 ppb, lower fatty acid ester is added to a concentration of 10 to 40,000 ppb, preferably 15 to 25,000 ppb, more preferably 20 to 20,000 ppb.

  As methional and lower fatty acid ester, commercially available products may be used, or they may be synthesized or produced by known methods. As an example, the methional may be a synthetic product, an extracted product, a fermented product or a processed product thereof, a heating reaction of various materials, or a methionine produced by fermentation of methionine using yeast. Moreover, it is also possible to increase to a desired density | concentration without adding methional in food-drinks by adding methionine and sugar to a seasoning as needed, and heating, or changing fermentation conditions.

(Food and drink containing methional and lower fatty acid ester)
In the food and drink containing the umami enhancer according to the present invention, methional is 10 to 50,000 ppb, preferably 20 to 5,000 ppb, more preferably 30 to 3,500 ppb, and the lower fatty acid ester is 10 to 40,000 ppb, preferably Is contained at a concentration of 15 to 25,000 ppb, more preferably 20 to 20,000 ppb. However, these blending amounts are appropriately changed in consideration of the flavor resulting from the food and drink before adding the umami enhancer, the desired degree of umami enhancement, and the like.

The umami enhancer of the present invention can be used without particular limitation for various foods and beverages that require umami enhancement. Various foods or beverages, such as 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. Various soy sauces, various low salt soy sauces, various soy sauces, various sauces, yeast extracts, livestock meat extracts, seafood extracts, seasonings such as protein hydrolysates, and seasonings containing nucleic acids (such as inosine monophosphate and guanosine monophosphate) By adding the umami enhancer of the present invention to the food, it is possible to further enhance the umami inherent to those foods or drinks or supplement the umami of foods and drinks with insufficient umami.
The umami enhancer of the present invention is assumed to be used in liquid seasonings such as soy sauce, ponzu, soy sauce, sauce and dressing, particularly in soy sauce-like seasonings exhibiting a soy sauce flavor.

  Even if the umami enhancer of the present invention is not directly added to the food or drink, it can be volatilized to impart umami to the food or drink, or to further enhance the umami contained in the food or drink. For example, such an effect is obtained by impregnating the umami enhancer of the present invention into a base material (for example, a seal or cotton), sticking it to a container for food and drink, and volatilizing an active ingredient from the base material. Can be achieved. The method for volatilizing is not particularly limited, and sodium chloride may be included in the base material, and the active ingredient may be volatilized due to the salting out effect, or the active ingredient may be physically volatilized using an aroma diffuser or the like.

  The umami enhancer of the present invention exhibits umami alone, but is appropriately added to food and drink in combination with other umami ingredients. Examples of the umami component include amino acids, yeast extracts, nucleic acids, organic acids, and protein hydrolysates. Among these, amino acid glutamate, yeast extract, and nucleic acid are particularly preferred for the purpose of imparting soy sauce umami to the soy sauce-like seasoning. These umami components can be added alone or in combination.

(Manufacturing method of umami enhancer-containing food and drink)
In the method for producing a food or drink containing the umami enhancer according to the present invention, methional and a lower fatty acid ester are blended at an arbitrary timing.

  The blending amount of the umami enhancer in the food or drink is appropriately determined. For example, methional in the food or drink is 10 to 50,000 ppb, preferably 20 to 5,000 ppb, more preferably 30 to 3,500 ppb, and a lower fatty acid ester. Is added to a concentration of 10 to 40,000 ppb, preferably 15 to 25,000 ppb, more preferably 20 to 20,000 ppb.

  The umami enhancer 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 in the fermentation process instead of adding methional. More specifically, by adding methionine or sugar and heating or changing the fermentation conditions, it is possible to increase the concentration to a desired level without adding methional to the food or drink.

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

  In this experiment, sensory evaluation was carried out using three specialized panelists who were fully trained unless otherwise specified. In addition, unless otherwise specified, reagents made by Tokyo Chemical Industry Co., Ltd. were used.

(Sensory evaluation 1)
-Confirmation of umami enhancing effect by aroma of methional and lower fatty acid ester The sample was prepared by adding lower fatty acid and lower fatty acid ester to an aqueous solution of 343 ppb of methional (manufactured by Sigma Aldrich Japan). Furthermore, 16% (w / v) sodium chloride and 3% ethanol (v / v) were added to each sample in order to salt out the active ingredient. Table 1 shows the compositions of the samples of Examples 1 to 5 and Comparative Examples 1 and 2.

  In sensory evaluation, cotton was affixed inside 280 ml of a cup with a black lid, and 7 ml of a sample was included in the cotton. 120 ml of water was put into the cup, and the paneler ingested the water in the cup covered with the lid scented with the sample and the non-scented lid, respectively, to select a sample with strong taste. In addition, when there was no difference in the strength of umami, it was answered that there was no difference. In addition, five 1 mm holes were made in the lid so that the panelists could sense the smell of scent stimulation.

Compare the taste of the two samples, and if three panelists answered that the flavored sample was stronger ◎ If two people (the other panel says no difference) ○, etc. In each case, the results are shown in Table 1 with x.

  As a result of sensory evaluation, sodium chloride, ethanol and methional were mixed with ethyl-2-methylpropanoate or ethyl-4-methylpentanoate, ethyl-2-methylpentanoate, ethyl-3-methylbutanoate, ethyl-2 -It was confirmed that samples 2 to 6 to which methylbutanoate was added had a delicious taste.

  On the other hand, it was confirmed that isovaleric acid and ethyl acetate do not exhibit umami even when combined with methional.

  In addition, two panelists commented that ethyl-2-methylbutanoate had the strongest umami enhancement and the strongest lingering taste on the tongue, and among the lower fatty acid esters, ethyl-2-methylbutanoate was particularly strong. It was confirmed that the effect of was strongest.

(Sensory evaluation 2)
-Confirmation of umami enhancing effect by flavor of methional and lower fatty acid ester Sodium chloride 1.6% (w / v), ethanol 0.3% (v / v) aqueous solution, sodium chloride 1.6% (w / v), An aqueous solution was prepared by adding 343 ppb methional and 20 ppb ethyl-2-methylpropanoate to an aqueous solution of ethanol 0.3% (v / v).

  As a result of comparing the umami strength of the two aqueous solutions by sensory evaluation, all three panelists answered that the aqueous solution added with methional and ethyl-2-methylpropanoate had stronger umami strength. Therefore, it was confirmed that methional and ethyl-2-methylpropanoate enhance umami as a flavor.

(Sensory evaluation 3)
-Confirmation of the optimal addition density | concentration of methional The sample prepared the methyl-2-methylpropanoate 20ppb aqueous solution so that methional might become 3.43-34,300ppb. Furthermore, 16% (w / v) sodium chloride and 3% ethanol (v / v) were added to each sample in order to salt out the active ingredient. Table 2 shows the compositions of the samples of Examples 6 to 9 and Comparative Example 3.

  In the sensory evaluation, as in the procedure of sensory evaluation 1, cotton was affixed to the inside of a 280 ml cup with a black lid, and 7 ml of the sample was included in the cotton. 120 ml of water was put into the cup, and the paneler ingested the water in the cup covered with the lid scented with the sample and the non-scented lid, respectively, to select a sample with strong taste.

  In addition, when there was no difference in the strength of umami, it was answered that there was no difference. In addition, five 1 mm holes were made in the lid so that the panelists could sense the smell of scent stimulation.

Compare the taste of the two samples, and if three panelists answered that the flavored sample was stronger ◎ If two people (the other panel says no difference) ○, etc. In all cases, the results were shown as x.

  As a result of sensory evaluation, it was confirmed that the mixed fragrance exhibited umami when the concentration of methional was 34.3 ppb or more.

  In addition, the panelists evaluated that methional concentrations were 3,430 ppb and 34,300 ppb, and that umami was particularly strong, but 3,430 ppb replied that a more preferable umami enhancing effect was obtained. From these results, it was found that the umami was enhanced when the concentration of methional was 10 to 50,000 ppb.

(Sensory evaluation 4)
-Confirmation of the optimal addition density | concentration of a lower fatty acid ester The sample prepared the methional in 343 ppb aqueous solution, and ethyl-2-methylpropanoate was 2-200,000 ppb. Furthermore, 16% (w / v) sodium chloride and 3% ethanol (v / v) were added to each sample in order to salt out the active ingredient. Table 3 shows the compositions of the samples of Examples 10 to 13 and Comparative Examples 4 to 5.

  In the sensory evaluation, as in the procedures of sensory evaluations 1 and 3, cotton was attached to the inside of 280 ml of a cup with a black lid, and 7 ml of a sample was included in the cotton. 120 ml of water was put into a cup, and a sample covered with a sample and a sample covered with a non-scented lid were presented to the panel as a pair, and a sample with strong taste was selected. In addition, when there was no difference in the strength of umami, it was answered that there was no difference. In addition, five 1 mm holes were made in the lid so that the panelists could sense the smell of scent stimulation.

Compare the taste of the two samples, and if three panelists answered that the flavored sample was stronger ◎ If two people (the other panel says no difference) ○, etc. In each case, the results are shown in Table 4.

  As a result of sensory evaluation, it was confirmed that these mixed aromas had a delicious taste when the concentration of ethyl-2-methylpropanoate was 20 to 20,000 ppb. The panelists evaluated that the concentration of ethyl-2-methylpropanoate was particularly strong at 200 ppb and 2,000 ppb.

  From these results, it was found that the umami was enhanced when the addition concentration of ethyl-2-methylpropanoate was 10 to 40,000 ppb.

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

Claims (4)

Methional,
Selected from the group consisting of ethyl-2-methylpropanoate, ethyl-4-methylpentanoate, ethyl-2-methylpentanoate, ethyl-3-methylbutanoate and ethyl-2-methylbutanoate One or more compounds or salts thereof,
An umami enhancer comprising sodium chloride. A method of manufacturing a food or drink, comprising the step of blending the taste enhancer according to claim 1, the manufacturing method. The manufacturing method of Claim 2 whose food / beverage products are liquid seasonings. The manufacturing method of Claim 3 whose liquid seasoning is a soy sauce-like seasoning.