Classifications

• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
  • A23L2/52—Adding ingredients
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
  • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
  • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
  • A23L33/17—Amino acids, peptides or proteins
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
  • A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
  • A23L5/27—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption

Definitions

• the present invention relates to an amino acid degradation odor inhibitor, an amino acid-containing food and drink, and a degradation odor prevention method. More specifically, the present invention relates to an amino acid degradation odor inhibitor containing a predetermined short molecular ester compound as an active ingredient, an amino acid-containing food / beverage product containing the amino acid degradation odor inhibitor in an effective amount, and a degradation odor prevention method.
• Amino acids have been added to food and drinks and pharmaceuticals, for example, for the purpose of strengthening nutritional components.
• amino acids have functions such as recovery from fatigue, strength strengthening, growth support, increased immunity, promotion of beautiful skin, and regulation of lipid metabolism.
• the development of foods and drinks containing amino acids is being promoted.
• Patent Document 1 discloses a method for producing an amino acid-containing food in which the pH is adjusted with an acidulant and then the flavor is adjusted with a non-reducing sugar and a sweetener.
• Patent Document 2 discloses a method of masking a deteriorated odor by adding a stevia extract to a branched amino acid or a peptide containing a branched amino acid.
• JP 2007-185169 A (Patent Document 3 below) specifies a non-reducing sugar by adjusting the threonine content to a weight content ratio of 10 times or more with respect to the methionine content of the amino acid-containing food. A method of blending in quantities is disclosed.
• Patent Document 4 discloses a method of blending an amino acid having a bitter taste with a herb-based or fruit-based fragrance.
• Patent Document 5 discloses a method of blending a fruit-based flavor, chocolate flavor, milk flavor, tea flavor or vanilla flavor with a main raw material containing amino acids.
• JP-A-2005-82488 discloses an oral composition containing an amino acid and carboxyl or methyl salicylate.
• An object of the present invention is to provide an amino acid degradation odor inhibitor that can effectively prevent the degradation odor of amino acids.
• Another object of the present invention is to provide an amino acid-containing food or drink that can effectively prevent the degradation odor of amino acids.
• an object of the present invention is to provide a method for preventing deterioration odor that can effectively prevent deterioration odor of amino acids.
• the present invention is basically based on the knowledge that the use of a predetermined low molecular ester compound can effectively prevent the deterioration odor of amino acids.
• the 1st side surface of this invention is related with the degradation odor prevention agent of the amino acid which contains the ester compound (ester compound of this invention) shown by following formula (I) as an active ingredient.
• formula (I) When R 1 is a methyl group, R 2 is a C 4 -C 7 alkenyl group, When R 1 is an ethyl group, R 2 is a C 2 -C 3 alkyl group or a C 4 -C 7 alkenyl group.
• the deterioration odor of amino acids could be effectively prevented by blending a predetermined low molecular ester compound. That is, the above ester compound can be used effectively in order to prevent the deterioration odor of amino acids.
• ester compounds of the present invention are those represented by the formula (I):
• R 1 is a methyl group
• R 2 is a cis C 5 -C 7 alkenyl group
• R 1 is an ethyl group
• R 2 is a C 2 to C 3 alkyl group, or a cis C 5 to C 7 alkenyl group.
• the compounds that were proved to prevent the degradation odor of amino acids by the examples described later are “ethyl butyrate, ethyl propionate, methyl 2-hexenoate, ethyl 2-hexenoate, methyl 3-hexenoate, ethyl 3-hexenoate, methyl 2-octenoate, ethyl 2-octenoate, methyl 3-octenoate, and ethyl 3-octenoate ”. Therefore, one type of ester compound selected from the group consisting of these ester compounds or a mixture of two or more types is surely effective as a deodorizing agent for amino acids.
• ester compound of the present invention can effectively prevent deterioration odor derived from methionine, isoleucine, leucine, phenylalanine and tryptophan.
• the second aspect of the present invention relates to an amino acid-containing food or drink containing an amino acid.
• the amino acid is contained in the amino acid-containing food or drink at 1% by weight or more.
• this amino acid containing food-drinks contain the ester compound of this invention in 0.1 ppm or more and 200 ppm or less.
• a preferred embodiment of the second aspect of the present invention relates to an amino acid-containing beverage or an amino acid-containing jelly beverage.
• the third aspect of the present invention relates to a method for preventing the deterioration odor of an amino acid-containing food or drink comprising the step of adding the ester compound of the present invention.
• the ester compound of this invention may be added in the manufacturing process of amino acid containing food / beverage products, and an ester compound may be added to the manufactured amino acid containing food / beverage products.
• ester compound of the present invention by containing the ester compound of the present invention as an active ingredient, it is possible to provide an amino acid degradation odor inhibitor that can effectively prevent the degradation odor of amino acids.
• an amino acid-containing food or drink that can effectively prevent an amino acid degradation odor can be provided by containing an effective amount of an amino acid degradation odor inhibitor as an active ingredient.
• the ester compound of the present invention by adding an effective amount of the ester compound of the present invention, it is possible to provide a method for preventing deterioration odor that can effectively prevent deterioration odor of amino acids.
• the 1st side surface of this invention is related with the degradation odor prevention agent of the amino acid which contains the ester compound (ester compound of this invention) shown by following formula (I) as an active ingredient.
• formula (I) When R 1 is a methyl group, R 2 is a C 4 -C 7 alkenyl group, When R 1 is an ethyl group, R 2 is a C 2 -C 3 alkyl group or a C 4 -C 7 alkenyl group.
• the ester compounds included in the above formula (I) are all low molecular weight ester compounds. These low molecular ester compounds are known and are commercially available. Therefore, the ester compound of the present invention can be purchased commercially.
• the C 4 to C 7 alkenyl group means an alkenyl group having 4 to 7 carbon atoms.
• C 4 -C 7 alkenyl groups also include dialkenyl groups with two double bonds. However, as demonstrated in the examples, (mono) alkenyl groups containing one double bond as the C 4 -C 7 alkenyl group are preferred.
• the C 4 ⁇ C 7 alkenyl group, C 4 ⁇ C 7 alkenyl groups branched also included. However, as demonstrated in Example, C 4 ⁇ C 7 alkenyl group, C 4 ⁇ C 7 alkenyl group is preferably linear. Since an alkenyl group has a double bond, a cis isomer and a trans isomer exist.
• the cis isomer is preferred.
• the C 4 to C 7 alkenyl group in the ester compound of the present invention is preferably a C 5 to C 7 alkenyl group.
• the C 2 -C 3 alkyl group means an alkyl group having 2 or 3 carbon atoms.
• a specific C 2 -C 3 alkyl group is an ethyl group or a propyl group.
• ester compounds of the present invention include: “ethyl butyrate, ethyl propionate, methyl 2-hexenoate, ethyl 2-hexenoate, methyl 3-hexenoate, ethyl 3-hexenoate, methyl 2-octenoate, ethyl 2-octenoate, methyl 3-octenoate , And ethyl 3-octenoate ”.
• An amino acid degradation odor preventive agent means an agent for preventing a degradation odor peculiar to amino acids that occurs during sterilization, storage, or aging of amino acids in foods containing amino acids.
• the amino acid degradation odor inhibitor of the present invention contains the ester of the present invention as an active ingredient for preventing the degradation odor of amino acids.
• the degradation odor preventing agent for amino acids of the present invention may be the ester of the present invention, or a composition containing a known diluent or carrier.
• the amino acid degradation odor preventive agent of the present invention may contain known components in addition to the diluent and the carrier.
• known dosage forms can be appropriately employed as the dosage form of the amino acid degradation odor preventing agent of the present invention. Examples of dosage forms are liquids, tablets, powders, granules, pastes, emulsions, and jellys.
• diluents are water, ethanol, propylene glycol, glycerin, and surfactants.
• carriers are gum arabic, dextrin, glucose, cyclodextrin, and sucrose.
• the degradation odor preventing agent for amino acids of the present invention can be effectively used to prevent the degradation odor of amino acids in an amino acid-containing food or drink containing amino acids and saccharides.
• the ester compound of the present invention can effectively prevent the deterioration odor derived from methionine, isoleucine, leucine, phenylalanine and tryptophan. These amino acids are thought to cause a particularly deteriorated odor. For this reason, the deterioration odor preventing agent for amino acids of the present invention can be effectively used to prevent the deterioration odor of amino acids in an amino acid-containing food or drink containing these amino acids.
• the second aspect of the present invention relates to an amino acid-containing food or drink containing an amino acid.
• An amino acid-containing food or drink means a food or drink containing an amino acid in a predetermined amount or more.
• the example of an amino acid containing food / beverage is food / beverage which added the amino acid component and raised content of an amino acid.
• Specific examples of amino acid-containing foods and beverages are beverages, jelly beverages, jelly, and foods.
• a preferred amino acid-containing food or drink is an amino acid-containing beverage or an amino acid-containing jelly beverage.
• the amino acid in the amino acid-containing food or drink may be a free amino acid or an amino acid salt. Examples of amino acid salts are sodium, hydrochloride, and acetate.
• the amino acid-containing food or drink according to the present invention contains 1% by weight or more of amino acids.
• a deteriorated odor derived from the amino acid is particularly likely to occur.
• the amino acid-containing food / beverage product of the present invention when the amino acid is contained in the amino acid-containing food / beverage product by 1.5% by weight or more, the amino acid-containing food / beverage product enjoys the beneficial function of the amino acid and prevents the amino acid from deteriorating This is particularly preferable because it can be performed.
• the amino acid-containing food of the present invention when the total amount of methionine, isoleucine, leucine, phenylalanine and tryptophan is contained in 1% by weight or more (preferably 1.5% by weight or more) of the amino acid-containing food or drink, the amino acid-containing food of the present invention is effective. In addition, the degradation odor of amino acids can be prevented.
• the amino acid-containing food or drink of the present invention contains the ester compound of the present invention at 0.1 ppm or more and 200 ppm or less. If the ester compound of the present invention is less than 0.1 ppm, the deterioration odor of the amino acid-containing food or drink cannot be sufficiently suppressed. On the other hand, when the ester compound of the present invention is blended in excess of 200 ppm, the aroma of the ester compound becomes too strong and adversely affects the flavor of the amino acid-containing food or drink.
• the preferable content of the ester compound of this invention is 1 ppm or more and 100 ppm or less in the amino acid containing food / beverage products of this invention.
• blending the ester compound of this invention with an amino acid containing food / beverage products is not specifically limited.
• An example of a method of blending the ester compound of the present invention with an amino acid-containing food or drink is a method of adding the ester compound of the present invention when mixing raw materials; and, after mixing and sterilizing the raw materials, The method of adding is mention
• a fragrance may be blended within a range that does not adversely affect the flavor of the amino acid-containing food or drink.
• Amino acid-containing foods and drinks are sugars, sweeteners, acidulants, colorants, preservatives, fungicides, antioxidants, thickening stabilizers, emulsifiers, and gels that are commonly used in foods and drinks as needed.
• An agent may be blended.
• the third aspect of the present invention relates to a method for preventing the deterioration odor of an amino acid-containing food or drink comprising the step of adding the ester compound of the present invention.
• the ester compound of the present invention or the amino acid-containing food / drink preventive agent of the present invention may be added to thereby prevent the deterioration odor of the amino acid-containing food / beverage product.
• the deterioration odor of an amino acid containing food / beverage product may be prevented by adding the ester compound of this invention, or the degradation odor inhibitor of the amino acid of this invention.
• Example 1 Examination of masking effect of perfume component by functional group Examination method 1.6% by weight of amino acid balance composition shown in Table 1, 0.7% by weight of citric acid, 1.0% by weight of trehalose and sucrose An aqueous solution (simulated liquid) in which 3.0% by weight was dissolved was prepared. After storing the simulated solution at 55 ° C. for 7 days, 0.5 ppm of various functional group-based perfume ingredients (acid part, alcohol part, ester part 1 and 2, lactone part, sulfur-containing compound part) shown below. Beverages were prepared by adding them at respective concentrations of 5 ppm and 50 ppm. Sensory evaluation was conducted by five panelists who were well trained in each beverage, and the masking effect of each part was compared. Table 2 shows the average evaluation of five panelists. The evaluation criteria are shown below.
• Perfume ingredients by functional group Acetic acid, propionic acid, butyric acid, hexanoic acid, isovaleric acid, octanoic acid and decanoic acid are mixed and dissolved in equal amounts in 70% ethanol aqueous solution. It added to the drink so that it might become a concentration.
• Alcohol part In 70% ethanol aqueous solution, hexanol, cis-3-hexenol, octanol, decanol, linalool, geraniol, menthol and ⁇ -phenylethyl alcohol are mixed and dissolved in equal amounts, and the total amount of these alcohols is the above concentration. It added to the drink so that it might become.
• Ester part 1 Ethyl acetate, ethyl butyrate, ethyl propionate, ethyl valerate, propyl acetate, butyl acetate and isoamyl acetate are mixed and dissolved in an equal amount in a 70% aqueous ethanol solution. So that it was added to the beverage.
• Ester part 2 In 70% ethanol aqueous solution, ethyl hexanoate, methyl 2-hexenoate, ethyl 2-hexenoate, methyl 3-hexenoate, ethyl 3-hexenoate, ethyl heptanoate, ethyl octanoate, methyl 2-octenoate, ethyl 2-octenoate, methyl 3-octenoate, ethyl 3-octenoate, ethyl nonanoate, ethyl decanoate, hexyl acetate, isoamyl butyrate, octyl acetate, methyl 2-decenoate, ethyl 2-decenoate and methyl 3-nonanoate are mixed and dissolved in equal amounts, and their ester compounds Was added to the beverage so that the total amount of Lactone part: ⁇ -hexalactone, ⁇ -o
• Example 2 Examination of the masking effect of each ester compound The masking effect of each ester compound of the ester parts 1 and 2 examined in Example 1 was added to the simulated solution in the same manner as in Example 1, and the respective beverages were thoroughly used. Sensory evaluation was performed by five trained panelists, and the masking effects of each ester compound were compared. Table 3 shows the average evaluation of five panelists. The evaluation criteria are the same as in Example 1.
• Example 3 Examination of Addition Concentration of Ester Compound Masking flavor A shown in Table 4 was prepared using the five ester compounds having a masking effect in Example 2.
• this masking flavor A was added in a total amount of 5 ester compounds (Comparative product 1), 0.05 ppm (Comparative product 2), 0.1 ppm (Invention product 1). , 10 ppm (Invention product 2), 100 ppm (Invention product 3), 200 ppm (Invention product 4), and 300 ppm (Comparative product 3).
• Each beverage was subjected to sensory evaluation by five well-trained panelists, and the deterioration odor derived from amino acids and the flavor of masking flavor A were evaluated according to the following evaluation criteria. Table 5 shows the average evaluation results of five panelists.
• Evaluation criteria (degraded odor derived from amino acids) X: Deterioration odor derived from amino acids is strongly felt. ⁇ : A slight deterioration odor derived from amino acids is felt, but it is hardly noticed. A: Deterioration odor derived from amino acids is not felt at all. (Mask flavor A flavor) X: The flavor of the masking flavor A is too strong. ⁇ : The flavor of masking flavor A is slightly strong, but it is hardly anxious. A: The flavor of the masking flavor A is hardly a concern.
• Example 4 Comparison between cis and trans isomers Next, it was verified whether there was a difference in the ability to prevent the degradation odor of amino acids between cis and trans isomers in ester compounds having an alkenyl group. Evaluation was performed in the same manner as in Example 2 using the following compounds. The results are shown in Table 6.
• the present invention can be used in the field of the food industry.

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• Proteomics, Peptides & Aminoacids (AREA)
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• Coloring Foods And Improving Nutritive Qualities (AREA)
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• 2009
  • 2009-11-27 JP JP2010540391A patent/JP5825787B2/ja active Active
  • 2009-11-27 WO PCT/JP2009/006440 patent/WO2010061632A1/ja active Application Filing
  • 2009-11-27 CN CN2009801382528A patent/CN102164509A/zh active Pending
• 2014
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