WO1995004476A1 - Procede de suppression du gout sucre - Google Patents

Procede de suppression du gout sucre Download PDF

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Publication number
WO1995004476A1
WO1995004476A1 PCT/JP1994/001269 JP9401269W WO9504476A1 WO 1995004476 A1 WO1995004476 A1 WO 1995004476A1 JP 9401269 W JP9401269 W JP 9401269W WO 9504476 A1 WO9504476 A1 WO 9504476A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
sweetness
sweet
weight
tasting
Prior art date
Application number
PCT/JP1994/001269
Other languages
English (en)
Japanese (ja)
Inventor
Takashi Oonishi
Hiroaki Koiso
Toshinaga Tamiya
Toshihiro Ishii
Original Assignee
San-Ei Gen F.F.I., Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by San-Ei Gen F.F.I., Inc. filed Critical San-Ei Gen F.F.I., Inc.
Priority to JP50632695A priority Critical patent/JP3514459B2/ja
Priority to AU72391/94A priority patent/AU7239194A/en
Publication of WO1995004476A1 publication Critical patent/WO1995004476A1/fr

Links

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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/204—Aromatic compounds
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives

Definitions

  • the present invention relates to a method for suppressing sweetness of a sweet-tasting functional substance.
  • the present invention suppresses the sweetness of a sweetening functional substance such as amino acid, protein or glycoside added to food, feed, pet food, pharmaceuticals, quasi-drugs, cosmetics, etc.
  • a sweetening functional substance such as amino acid, protein or glycoside added to food, feed, pet food, pharmaceuticals, quasi-drugs, cosmetics, etc.
  • it is useful for utilizing the inherent functional properties of the sweet-tasting functional substance.
  • Amino acids such as glycine, alanine, and vein, have antibacterial and other functional properties, but they have a limited amount of use due to their inherent sweetness, which significantly deteriorates the taste. Antibacterial properties could not be obtained-and its use was also limited.
  • glycosides such as glycyrrhizin have functionalities such as antioxidant properties, physical properties improving properties, and physiological activities, but have a characteristic long-lasting sweetness with a certain amount of delay, so that their usage and usage are limited. However, its functionality was not fully utilized.
  • proteins such as tumatin and neohesperidin dihydrochalcone have the effect of enhancing the flavor of peppermint, perilla, fruit flavors, etc., but have a characteristic intense sweetness. Therefore, the amount used was limited.
  • Riveteam also has antibacterial properties due to its bacteriolytic effect, but because of its inherent sweetness, its usage is limited and its antibacterial activity has not been fully utilized.
  • R is the same or different and is a hydrogen atom, a halogen atom, a hydroxy group, a lower alkyl group, a lower alkanoyl group or an alkoxy group, n is an integer of 0-4, and A is It is a lower alkylene group of a straight chain or a branching technique of 5.
  • Phenoxya represented by) It is characterized in that at least one kind of lucan is added to suppress the sweetness of a sweetening functional substance selected from the group consisting of amino acids, proteins and glycosides. A method for suppressing sweetness is provided.
  • halogen atom examples include fluorine, chlorine, bromine and iodine.
  • lower alkyl group examples include a linear or branched alkyl group having 1 to 3 carbon atoms, such as methyl, ethyl, propyl, and isopropyl. .
  • lower alkanol group examples include alkanol groups having 2 to 4 carbon atoms, such as acetyl, propionyl, and butyryl.
  • lower alkoxy group examples include a straight or branched alkoxy group having 1 to 3 carbon atoms, such as methoxy, ethoxy, propoxy, and isopropoxy.
  • the “lower alkylene group” includes a straight or branched alkylene group having 1 to 5 carbon atoms, for example, methylene, ethylene, trimethylene, tetramethylene, pentamethylene. , Butylene, amirene and the like.
  • n is an integer of 1 to 4, preferably n is 1, more preferably n is 1 and the substituent is bonded to the p-position. It is. —
  • the non-toxic salts of the phenoxyalkanoic acids represented by the general formula (I) are non-toxic, acceptable salts of foods, pharmaceuticals, etc., for example, alkali metal salts such as sodium and potassium. And alkaline earth metal salts such as calcium, magnesium and the like, and ammonium salts. Of these, preferred salts are alkali metal salts such as sodium and calcium.
  • the present invention includes both of these optical isomers and racemic mixtures (one of these isomers has a strong activity and the other has a weak activity. Usually, it shows an intermediate activity between the two optical isomers, so that the compound with the stronger activity can be separated by optical resolution and the compound can be used to improve the inhibitory effect on sweetness. Can be.
  • the compounds belonging to the general formula (I) include the following: c (sat) 12 — phenoxypropionic acid, S— (1) 12 — phenoxypropionic acid, (sat) 12 — Enoxybutyric acid, S— (1-) 1-2—phenoxybutyric acid, ( ⁇ ) —2—p—Methoxyphenoxybutyric acid, (Earth) 1-2— ⁇ -Methylphenoxypropionic acid, S— (1-) 1-2— p-Methylphenoxypropionic acid, (Sat) 1 2 — p-Ethylphenoxypropionic acid, (Sat) 1 2 — p—Methoxyphenoxypropionic acid, S — (—) 1 2 — p—Met Xyphenoxypropionic acid, 2 — ⁇ -Methoxyphenoxy- 1 2 —Methylpropionic acid, ( ⁇ ) — 2 p—Ethoxyphenoki Cipropionic acid, p—
  • the present invention includes these salts, for example, alkali metal salts such as sodium and potassium, and these phenoxyalkanoic acids can be used alone or in combination.
  • preferred compounds are phenoxyalkanoic acid and compounds having a methyl, ethyl, methoxy or ethoxy substituent at the para-position of phenoxyalkanoic acid, for example, phenoxyacetic acid, 2-phenoxypropionic acid, 2-phenoxybutyric acid, 2-p-methoxyphenoxypropionic acid, 2-p-ethoxyquinoxypropionic acid, 2-p-ethylphenoxypropionic acid, p-methoxyphenoxyacetic acid, 2- p-Methoxyphenoxybutyric acid, p-ethylphenoxyacetic acid, 2-p-methylphenoxypropionic acid, 2-p-ethoxyphenoxybutyric acid, 2—; Can be
  • the compound of the general formula (I) can be synthesized by a known method such as condensation.
  • a known method such as condensation.
  • Journal of the American 'Chemical' Society J. Amer. Chem. Soc.
  • 53, 304 (1931) Journal of the 'Ob' Chemical ' It can be synthesized according to the method described in Society (J. Chem. Soc.) 1891 (1956), but there are also compounds available from Aldrich.
  • Examples of the sweet-tasting functional substance used in the present invention include amino acids, proteins and glycosides.
  • amino acids include sweet amino acids such as glycine, alanine, triptophan, kynurenine, and betain, and derivatives thereof. Body.
  • proteins include formatin, monelin, miraculin, and lysozyme.
  • glycosides are as follows: Amacilla powder and Amatilla extract, Potassium powder and Canzo extract, Enzyme-treated Canzo, Enzyme-degrading potato, Stevia powder and Stevia extract, Enzyme-treated Stevia, Tianling tea Powdered and sweetened tea extract, powdered racan and powdered racan, powdered white ginseng and powdered white ginseng, mixed leaf grape and powdered double grape extract, or dihydrochalcone such as prunin, naringin and neohesperidin And the like.
  • the amount of phenoxyalkanoic acid and its salt used may be such that the sweetness of the sweet-tasting functional substance is suppressed.
  • the degree of suppression of sweetness can be adjusted by the amount of phenoxyalkanoic acid and a salt thereof so that the functionality of each sweet taste functional substance is emphasized.
  • 0.0001 to 100 000 parts by weight of phenoxysulfonic acid and a salt thereof are added to 100 parts by weight of the sweet-tasting functional substance.
  • the phenolalkanoic acids and salts thereof of the present invention can be used as they are, but generally, it is desirable to dissolve or suspend them in a solvent capable of dissolving them.
  • the solvent that can be used is not particularly limited, and examples thereof include water, alcohols such as ethanol and isopropanol, and propylene glycol.
  • the sweet-tasting functional substance can be dissolved. This dissolution order may be reversed.
  • a phenolic alkanoic acid and a salt thereof may be added and dissolved in an extract or a mother liquor of the sweet-tasting functional substance, or the solution may be dried or co-crystallized by any method.
  • phenoxyalkanoic acid and a salt thereof may be added and dissolved during the production process.
  • the sweet-tasting functional substance and the phenolic alkanoic acid and a salt thereof may be mixed together in a solid state and dissolved in a solvent at the time of use.
  • the sweetness suppressing method of the present invention can be applied to foods, feeds, pet foods, pharmaceuticals, quasi-drugs, cosmetics, and the like.
  • applicable foods include side dishes, juices, seafood paste products, and the like.
  • These foods contain about 0.1 to 5% of a sweet-tasting functional substance, and 0.05 to 1 parts by weight of phenolic alkanoic acid per 100 parts by weight of the sweet-tasting functional substance.
  • the addition of the derivative reduces unpleasant sweetness and makes it edible.
  • Applicable feed and pet food include feed for cattle, pigs, poultry, and the like. These feeds and pet foods contain about 0.01 to 1 of the sweet-tasting functional substance, and 1 to 400 parts by weight of phenol per 100 parts by weight of the sweet-tasting functional substance.
  • By adding the xylanic acid derivative it is possible to provide a feed and a feed that can be eaten well by animals.
  • Next applicable pharmaceuticals include anti-ulcer, anti-inflammatory, antitussive and the like, which are generally produced from extracts of fruits, herbs, rhizomes and the like. These medicines contain about 0.1 to 10% of sweet-tasting functional substances. By adding 0.7 to 70 parts by weight of a phenokine alkanoic acid derivative per 100 parts by weight of the sweet-tasting functional substance, the inherent sweetness contained in the sweet-tasting functional substance is added. It is suppressed and can be taken easily.
  • the next applicable quasi-drug is dentifrice.
  • These quasi-drugs contain about 0.01 to 1% of the sweet-tasting functional substance, and 100 to 100 parts by weight of the sweet-tasting functional substance per 100 parts by weight.
  • applicable cosmetics include lipstick. These cosmetics contain about 0.01 to 0.1% of a sweet-tasting functional substance, and 100 to 100 parts by weight of 100 parts by weight of the sweet-tasting functional substance.
  • a sweet-tasting functional substance has two effects, such as intrinsic sweetness and antibacterial properties, antioxidant properties, flavor enhancement properties, physical property improvement properties, or physiological activities. Functionality cannot be emphasized enough. However, by applying the sweetness suppressing method of the present invention, utilization of the above functionality becomes easy.
  • Glycine 2% (0.0 0.001%, 0.0 0.000% 0 1%, 0.01%, 0.02%, 0.04%, 0.08% and 0.01% (/ v) Prepare a mixed solution containing sodium methoxyphenoxypropionate and a single solution of glycine 2% (/ V) without sodium (Sat) 12-p-methoxyphenoxypropionate did.
  • the degree of sweetness inhibition of glycine by addition of sodium (Sat) 2-p-methoxyphenoxypropionate was determined by the following method.
  • the sensory test for glycine sweetness is as follows.
  • a sweet standard solution of glycine of 0 to 2% (w / V) was prepared at a concentration interval of 0.2% (w / V).
  • the glycine 2% (w / v) and 5% (w / v) solutions exhibited a characteristic sweetness and discomfort. No discomfort The lysine concentration is less than 0.2% (w / V), and no antibacterial effect can be expected at this concentration.
  • Foods high in protein and starch require the addition of glycine in a minimum of 1% or more. At this concentration, sodium (Sat), which gives an unpleasant sweetness, is used to produce sodium 2-P-methoxypropionic acid sodium. By adding 0.02%, unpleasant sweetness was suppressed, and the antibacterial activity was exerted without impairing the flavor of the composition to be added.
  • 0.0 1%, 0.09%, 0.08%, '0.01%, and 0% of the sweetness of the riematine solution are 10 °, 90, 80, — Defined as a sweetness of 10 and 0.
  • a sweet standard solution of glycyrrhizin of 0 to 0.15% (w / v) was prepared at a concentration interval of 0.015% (w / v).
  • Lysozyme 0.1% (w / V) 0.00 0 0 1%, 0.00 0 1%, 0.01%, 0.02%, 0.04% in solution , 0.008%, and 0.01% (w / V) of sodium phenoxyacetate and lysozyme without sodium phenoxyacetate 1% (wv ) A single solution was prepared. The degree of sweetness suppression of lysozyme by the addition of sodium phenoxyacetate was determined by the following method.
  • the sensory test for lysozyme sweetness is as follows.
  • a sweet standard solution of lysozyme having a concentration of 0 to 0.01 (wZv) was prepared at a concentration interval of 0.01 ⁇ wZv).
  • the standard agar medium was used for the single-use section of ribozyme and the combined use section of ribozyme and sodium phenyloxyacetate at each concentration, and the antibacterial mosquito against the microorganism Bacillus sp.
  • Lysozyme 0.1% (wZv) solution has a unique sweetness. Gave discomfort. However, no unpleasant sweetness was observed in the sodium phenoxyacetate-administered group. At a lysozyme concentration of 0.05% (wZv), unpleasant sweetness is not felt, but the ability to completely suppress the growth of microorganisms.
  • a sweet standard solution of neohesperidin dihydrochalcone of 0-0.03% (w / V) was prepared at a concentration interval of 0.003% (w / V).
  • xanthan gum 0.1 part by weight of xanthan gum is dissolved in 16 parts by weight of commercially available vinegar, and 2 parts by weight of salt, 3 parts by weight of d1-alanin or 3 parts by weight of d1-aranine and 0.02 parts of p-ethoxyphenoxyacetic acid Parts by weight, ( ⁇ ) — 2 — p — Ethoxyphenoxypropionic acid 0.0 2 parts by weight and ( ⁇ ) — 2 — p — Methylfuninoxybutyric acid 0.02 parts by weight, then yolk 1 Mix 0 parts by weight and 0.5 parts by weight of spices. While stirring the mixture, 70 parts by weight of salad oil is added and emulsified.
  • the mixed solution was dispensed into glass bottles with a capacity of 150 m 1 up to 10'0 m 1, stored in a thermostat at 38 for 1 month, and the peroxide value of the salad oil was measured.
  • d 1 -alanine single use plot showed unpleasant sweetness and was not suitable for edible use, but P-ethoxyphenoxyacetic acid, (Sat) 1 2-p-Ethoxyphenoxypropionic acid and (Sat) The group to which the mixture of _ 2-p-methylfunoxybutyric acid was added had no unpleasant sweetness and was delicious.
  • the storage test showed that the addition of 0.05 part by weight, which did not exhibit the unpleasant sweetness of d 1 -alanine, oxidized the salad oil and made it unsuitable for eating.
  • the sweetness suppressing method of this invention the sweetness intrinsic

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  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Seasonings (AREA)

Abstract

Procédé de suppression du goût sucré d'une substance édulcorante choisie dans le groupe des acides aminés, des protéines et des glycosides, consistant à ajouter à ladite substance au moins soit un acide phénoxyalcanoïque de formule générale (I) soit un sel dudit acide. Dans ladite formule (I), les R représentent chacun indépendamment hydrogène, halogène, hydroxy, alkyle inférieur, alcanoyle inférieur ou alkoxy inférieur; n représente un nombre entier de 0 à 4 et A représente alkylène inférieur C1-C5 linéaire ou ramifié. Le présent procédé sert à faire ressortir très efficacement la fonction de la substance édulcorante.
PCT/JP1994/001269 1993-08-05 1994-08-01 Procede de suppression du gout sucre WO1995004476A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP50632695A JP3514459B2 (ja) 1993-08-05 1994-08-01 甘味抑制方法
AU72391/94A AU7239194A (en) 1993-08-05 1994-08-01 Method of suppressing sweetness

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP19498593 1993-08-05
JP5/194985 1993-08-05

Publications (1)

Publication Number Publication Date
WO1995004476A1 true WO1995004476A1 (fr) 1995-02-16

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Application Number Title Priority Date Filing Date
PCT/JP1994/001269 WO1995004476A1 (fr) 1993-08-05 1994-08-01 Procede de suppression du gout sucre

Country Status (3)

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JP (1) JP3514459B2 (fr)
AU (1) AU7239194A (fr)
WO (1) WO1995004476A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100386880B1 (ko) * 2000-04-28 2003-06-11 주식회사 비엠아이 코리아 세포배양용 배지
CN112876353A (zh) * 2021-02-05 2021-06-01 华南理工大学 2-(3-丙基苯氧基)丙酸及其制备方法和应用
JP6926350B1 (ja) * 2021-01-29 2021-08-25 キユーピー株式会社 酸性水中油型乳化食品及びその焼成時の焼き色改善方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993010677A1 (fr) * 1991-11-27 1993-06-10 Bioresearch, Inc. Modificateur du gout specifique comestible

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993010677A1 (fr) * 1991-11-27 1993-06-10 Bioresearch, Inc. Modificateur du gout specifique comestible

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100386880B1 (ko) * 2000-04-28 2003-06-11 주식회사 비엠아이 코리아 세포배양용 배지
JP6926350B1 (ja) * 2021-01-29 2021-08-25 キユーピー株式会社 酸性水中油型乳化食品及びその焼成時の焼き色改善方法
JP2022117038A (ja) * 2021-01-29 2022-08-10 キユーピー株式会社 酸性水中油型乳化食品及びその焼成時の焼き色改善方法
CN112876353A (zh) * 2021-02-05 2021-06-01 华南理工大学 2-(3-丙基苯氧基)丙酸及其制备方法和应用
CN112876353B (zh) * 2021-02-05 2022-03-29 华南理工大学 2-(3-丙基苯氧基)丙酸及其制备方法和应用

Also Published As

Publication number Publication date
JP3514459B2 (ja) 2004-03-31
AU7239194A (en) 1995-02-28

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