WO2022196825A1 - Hot taste enhancer - Google Patents
Hot taste enhancer Download PDFInfo
- Publication number
- WO2022196825A1 WO2022196825A1 PCT/JP2022/012875 JP2022012875W WO2022196825A1 WO 2022196825 A1 WO2022196825 A1 WO 2022196825A1 JP 2022012875 W JP2022012875 W JP 2022012875W WO 2022196825 A1 WO2022196825 A1 WO 2022196825A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pungent
- citral
- present
- component
- containing product
- Prior art date
Links
- 239000003623 enhancer Substances 0.000 title claims abstract description 34
- 235000019604 hot taste sensations Nutrition 0.000 title abstract 6
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims abstract description 100
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims abstract description 46
- 229940043350 citral Drugs 0.000 claims abstract description 44
- 230000002708 enhancing effect Effects 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 7
- 235000019633 pungent taste Nutrition 0.000 claims description 86
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 abstract description 14
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 24
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 24
- 235000013305 food Nutrition 0.000 description 16
- 244000203593 Piper nigrum Species 0.000 description 14
- 235000008184 Piper nigrum Nutrition 0.000 description 14
- 235000002566 Capsicum Nutrition 0.000 description 13
- 239000006002 Pepper Substances 0.000 description 13
- 235000016761 Piper aduncum Nutrition 0.000 description 13
- 235000017804 Piper guineense Nutrition 0.000 description 13
- 235000000760 Wasabia japonica Nutrition 0.000 description 13
- 244000195452 Wasabia japonica Species 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 12
- 229960002504 capsaicin Drugs 0.000 description 12
- 235000017663 capsaicin Nutrition 0.000 description 12
- MXXWOMGUGJBKIW-YPCIICBESA-N piperine Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCCC1 MXXWOMGUGJBKIW-YPCIICBESA-N 0.000 description 12
- 235000019100 piperine Nutrition 0.000 description 12
- 229940075559 piperine Drugs 0.000 description 12
- WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- 241000219198 Brassica Species 0.000 description 9
- 235000003351 Brassica cretica Nutrition 0.000 description 9
- 235000003343 Brassica rupestris Nutrition 0.000 description 9
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 235000010460 mustard Nutrition 0.000 description 9
- 239000003814 drug Substances 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 240000003291 Armoracia rusticana Species 0.000 description 6
- 235000011330 Armoracia rusticana Nutrition 0.000 description 6
- 244000131415 Zanthoxylum piperitum Species 0.000 description 6
- 235000008853 Zanthoxylum piperitum Nutrition 0.000 description 6
- 241000234314 Zingiber Species 0.000 description 6
- 235000006886 Zingiber officinale Nutrition 0.000 description 6
- PFRGXCVKLLPLIP-UHFFFAOYSA-N diallyl disulfide Chemical compound C=CCSSCC=C PFRGXCVKLLPLIP-UHFFFAOYSA-N 0.000 description 6
- 235000008397 ginger Nutrition 0.000 description 6
- 235000002780 gingerol Nutrition 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000006072 paste Substances 0.000 description 6
- 240000002234 Allium sativum Species 0.000 description 5
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 5
- 241000951471 Citrus junos Species 0.000 description 5
- -1 citral compound Chemical class 0.000 description 5
- 235000004611 garlic Nutrition 0.000 description 5
- NLDDIKRKFXEWBK-AWEZNQCLSA-N gingerol Chemical compound CCCCC[C@H](O)CC(=O)CCC1=CC=C(O)C(OC)=C1 NLDDIKRKFXEWBK-AWEZNQCLSA-N 0.000 description 5
- JZLXEKNVCWMYHI-UHFFFAOYSA-N gingerol Natural products CCCCC(O)CC(=O)CCC1=CC=C(O)C(OC)=C1 JZLXEKNVCWMYHI-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 244000178993 Brassica juncea Species 0.000 description 4
- 240000004160 Capsicum annuum Species 0.000 description 4
- 235000007862 Capsicum baccatum Nutrition 0.000 description 4
- 235000013361 beverage Nutrition 0.000 description 4
- 239000001728 capsicum frutescens Substances 0.000 description 4
- 235000011850 desserts Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000019640 taste Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QAFYGHBGWCPRCI-CSKARUKUSA-N (3e)-4,8-dimethylnona-3,7-dien-2-one Chemical compound CC(C)=CCC\C(C)=C\C(C)=O QAFYGHBGWCPRCI-CSKARUKUSA-N 0.000 description 3
- 235000002568 Capsicum frutescens Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920001144 Hydroxy alpha sanshool Polymers 0.000 description 3
- PSKIOIDCXFHNJA-UHFFFAOYSA-N Sanshool Natural products CC=CC=CC=CCCC=CC=CC(=O)NC(C)C PSKIOIDCXFHNJA-UHFFFAOYSA-N 0.000 description 3
- AZPPBYINNXLPQZ-PKNBQFBNSA-N [(3e)-4,8-dimethylnona-3,7-dien-2-yl] acetate Chemical compound CC(=O)OC(C)\C=C(/C)CCC=C(C)C AZPPBYINNXLPQZ-PKNBQFBNSA-N 0.000 description 3
- SBXYHCVXUCYYJT-UEOYEZOQSA-N alpha-Sanshool Chemical compound C\C=C\C=C\C=C/CC\C=C\C(=O)NCC(C)C SBXYHCVXUCYYJT-UEOYEZOQSA-N 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 235000015067 sauces Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 239000000606 toothpaste Substances 0.000 description 3
- NYPOJSCNHYUZRG-CSKARUKUSA-N (3e)-4,8-dimethylnona-3,7-dien-2-ol Chemical compound CC(O)\C=C(/C)CCC=C(C)C NYPOJSCNHYUZRG-CSKARUKUSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 229940029982 garlic powder Drugs 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- 235000012149 noodles Nutrition 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 235000021110 pickles Nutrition 0.000 description 2
- 235000014347 soups Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical class OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000134874 Geraniales Species 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 244000294411 Mirabilis expansa Species 0.000 description 1
- 235000015429 Mirabilis expansa Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 241001247145 Sebastes goodei Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000013614 black pepper Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000008376 breath freshener Substances 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- WTEVQBCEXWBHNA-YFHOEESVSA-N citral B Natural products CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000021185 dessert Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000021456 frozen pasta Nutrition 0.000 description 1
- 235000021255 galacto-oligosaccharides Nutrition 0.000 description 1
- 150000003271 galactooligosaccharides Chemical class 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000014080 ginger ale Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 235000015220 hamburgers Nutrition 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 235000014109 instant soup Nutrition 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000013536 miso Nutrition 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 235000013606 potato chips Nutrition 0.000 description 1
- 235000012434 pretzels Nutrition 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000019685 rice crackers Nutrition 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 235000012046 side dish Nutrition 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 235000021259 spicy food Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
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
-
- 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
Definitions
- the present invention relates to a pungent taste enhancer, a method for enhancing pungent taste, a pungent component-containing product, and a method for producing the same.
- Pachet taste imparted to food and drink by pepper, wasabi, mustard, pepper, Japanese pepper, ginger, etc. can bring about improvement of flavor, appetite enhancement, etc., such as adding an accent to the flavor of food and drink, and enjoying the pungent taste itself. . Therefore, spicy food and drink are enjoyed in a wide variety of ways in various cultural spheres.
- spiciness is a taste that many people like, so not only have spices exhibiting spiciness been explored since ancient times, but in recent years, attempts have been made to enhance the spiciness of food materials. There is a strong demand for the development of new ingredients that enhance the pungent taste of foods.
- An object of the present invention is to provide a novel pungent taste enhancing method using a component that has not been known to have a pungent taste enhancing effect.
- the present invention provides the following terms: Section 1.
- R 2 represents an alkyl group having 1 to 4 carbon atoms.
- Section 2. Item 1. The pungent taste enhancer for the pungent ingredient-containing product according to Item 1, wherein when the pungent taste enhancer contains a citral analogue represented by the general formula (1), R represents an alkyl group having 1 carbon atoms. Pungent enhancer. Item 3.
- Ac represents an acetyl group.
- R 2 represents an alkyl group having 1 to 4 carbon atoms.
- R 2 represents an alkyl group having 1 carbon atom.
- Item 5. A method for producing a pungent component-containing product, comprising adding the pungent taste enhancer according to item 1 or 2 to the pungent component-containing product.
- Item 6. Item 3. A pungent component-containing product containing the pungent taste enhancer according to Item 1 or 2.
- the present invention provides a pungent component-containing product containing at least one selected from the group consisting of citral and citral analogues represented by the following general formula (1).
- Ac represents an acetyl group.
- R 2 represents an alkyl group having 1 to 4 carbon atoms.
- Citral in the present invention denotes a mixture of neral and geranial.
- the citral analogue represented by the general formula (1) may be simply referred to as citral analogue (1).
- Ac represents an acetyl group.
- an alkyl group represents a linear or branched saturated hydrocarbon group.
- the number of carbon atoms in the alkyl group is 1 to 4, preferably 1 to 3, more preferably 1 to 2, and even more preferably 1.
- the alkyl group having 1 to 4 carbon atoms includes methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, iso-butyl group and tert-butyl group. is mentioned.
- citral analogue (1) has isomers such as geometric isomers, stereoisomers, and optical isomers, unless otherwise specified, these isomers are included in citral analogue (1).
- general formula (1) can include each cis isomer, trans isomer, and mixtures thereof. More specifically, for example, when R 1 is —CH(OH)— (alcohol form), general formula (1) has
- citral and citral analogues (1) may simply be referred to as a citral compound.
- the citral analogue (1) is known or can be synthesized according to a known method.
- Commercially available products of citral or citral analogues include, for example, citral that is sold under trade names such as Citral F (manufactured by Shandong NHU Pharmaceutical Co., Ltd.). In the present invention, these citral and citral analogues (1) may be used singly or in combination.
- Citral or a citral analogue (1) may be used in a purified state in the pungent taste enhancer of the present invention, but is not limited to this, and citral or a citral analogue within a range that does not impair the effects of the present invention.
- Natural materials containing (1) can be used as the pungent enhancer of the present invention. Such natural materials include, but are not limited to: natural materials containing citral include lemons, citrus fruits, and the like.
- the pungent taste enhancer of the present invention is used, for example, to enhance the pungent taste of target pungent component-containing products described later.
- the form is not limited, it can have a solid form such as powder, granules, tablets, capsules, etc., and a semi-solid or liquid form such as syrup, emulsion, liquid, gel, etc.
- the pungent taste enhancer of the present invention may consist of only citral or a citral analogue (1), or in addition to citral or a citral analogue (1), depending on its form, it is pharmaceutically acceptable
- a carrier or a carrier that can be blended into food and drink can also be blended as appropriate.
- the total amount of citral or citral analogue (1) in the pungent enhancer of the present invention is 0.00000001 depending on the mode of use of the pungent enhancer of the present invention and the presence or absence of other ingredients. It can be appropriately set from the range of to 99% by mass (0.0001 to 990000 ppm).
- the present invention provides a pungent component-containing product containing the pungent taste enhancer of the present invention.
- the pungency enhancer of the present invention comprises citral or a citral analogue (1).
- the present invention provides a pungent ingredient-containing product comprising citral or a citral analogue (1).
- the pungent component-containing product of the present invention can be easily prepared by adding and blending the pungent taste enhancer of the present invention described above to the target pungent component-containing product described below.
- the pungent component-containing product targeted by the present invention is a product containing a pungent component, typically an edible product containing a pungent component.
- target products include food and drink; oral pharmaceuticals; oral pharmaceuticals; oral care products (including pharmaceuticals and quasi-drugs) such as toothpaste and mouthwash; be.
- the pungent components targeted by the present invention include capsaicin, allyl isothiocyanate, piperine, sanshool, diallyl disulfide, gingerol, and the like. These may be used singly or in any combination of two or more.
- the pungent component may be used in the form of being contained in a food material or a processed product thereof containing one or more of the pungent components.
- the food materials include red pepper, wasabi, horseradish, Japanese mustard, pepper, Japanese pepper, garlic, ginger, and the like
- the processed products include red pepper paste, yuzu pepper, tom yum paste, doubanjiang, and mustard.
- the shape of these pungent components is not particularly limited. For example, it may be powdery, semi-solid, or liquid.
- the ratio of the pungent component contained in the pungent component-containing product of the present invention can be appropriately set according to the purpose and/or type of the pungent component-containing product of the present invention. Although not limited, for example, the ratio of the pungent component contained in the pungent component-containing product of the present invention can be 0.000001 to 20% by mass.
- the proportion of capsaicin contained in the pungent component-containing product of the present invention can be exemplified from 0.00001 to 10% by mass.
- the ratio of allyl isothiocyanate contained in the pungent component-containing product of the present invention is exemplified as 0.000001 to 10% by mass. can be done.
- the ratio of piperine contained in the pungent component-containing product of the present invention can be exemplified from 0.001 to 20% by mass.
- the ratio of gingerol contained in the pungent component-containing product of the present invention can be exemplified from 0.001 to 10% by mass.
- the pungent taste enhancing effect is useful because the content of pungent components (compounds such as capsaicin, allyl isothiocyanate, piperine, etc.) in products containing pungent components can be reduced.
- the present invention provides capsaicin contained in hot peppers and the like; allyl isothiocyanate contained in Japanese mustard, wasabi, horseradish and the like; piperine contained in black pepper and the like; sanshool contained in Japanese pepper and the like; diallyl disulfide contained in garlic and the like; It is very useful because it can enhance not only any of the gingerols contained in ginger and the like, but also all of these different types of pungent taste.
- citral and citral analogue (1) are not compounds that themselves exhibit pungent taste, the effect of the present invention that pungent taste can be enhanced by adding them to pungent component-containing products cannot be expected from the prior art. There is nothing.
- Confectionery such as rice crackers, biscuits, pretzels, cakes, chocolates, gums, candies, gummies, tablet confectionery containing the above-mentioned pungent ingredient; snacks such as potato chips; instant soups. Soups such as instant miso soup; Frozen cooked foods such as frozen hamburgers and frozen takoyaki; Chilled cooked foods such as chilled meatballs and chilled gyoza; Other cooked foods such as tamagoyaki and corn dogs; Chilled desserts such as chilled puddings and fruit sauces; Ice creams; Frozen desserts such as soft mixes and frozen desserts; Dry desserts such as dry jelly and dessert bases; Frozen cooked rice; Noodles such as noodles, chilled ramen, frozen pasta; other staples such as side dish bread, okonomiyaki mix; red pepper paste, yuzu pepper, tom yum paste, powdered wasabi, kneaded wasabi, mustard, powdered pepper, salt and pepper, Seasonings such as Japanese pepper powder, garlic powder,
- Oral pharmaceuticals include lozenges, drinks, granules, powders (powder formulations), tablets, capsules, etc. containing the aforementioned pungent ingredient, and oral pharmaceuticals include sprays containing the aforementioned pungent ingredient.
- oral care products include liquid toothpastes, toothpastes, mouthwashes, breath fresheners and the like containing the aforementioned pungent component.
- the citral or citral analogue (1) relative to the pungent component-containing product has a final concentration in the pungent component-containing product of the present invention of, for example, 0.005 to 200 ppm, more preferably 0 0.02 to 50 ppm, more preferably 0.1 to 10 ppm.
- a final concentration in the pungent component-containing product of the present invention of, for example, 0.005 to 200 ppm, more preferably 0 0.02 to 50 ppm, more preferably 0.1 to 10 ppm.
- each of them preferably falls within the above concentration range.
- the final concentration of citral or citral analogue (1) in the pungent component-containing product can be appropriately set according to the type of target pungent component-containing product. 005 ppm or more, preferably 0.02 ppm or more, more preferably 0.1 ppm or more.
- the upper limit of the final concentration of citral or citral analogue (1) in the pungent component-containing product is 200 ppm or less as described above, preferably 50 ppm or less, more preferably 10 ppm or less.
- the total amount of citral or citral analogues (1) is in the concentration range of 0.005 to 200 ppm with respect to the pungent component-containing product. is preferably from 0.02 to 50 ppm, and even more preferably from 0.1 to 10 ppm.
- the blending ratio (mass ratio) of the citral compound to capsaicin is preferably 0.00000001 to 1, more preferably 0.000001 to 0.5, and 0.5. 0001 to 0.2 is more preferred.
- the mixing ratio (mass ratio) of the citral compound to allyl isothiocyanate is preferably 0.0000001 to 1000, more preferably 0.00001 to 10, and 0.000001 to 1000. 001 to 0.1 is more preferred.
- the mixing ratio (mass ratio) of the citral compound to piperine is preferably from 0.00000002 to 1, more preferably from 0.000005 to 0.5, and from 0.001 to 0.001. 0.2 is more preferred.
- "Pitcht taste” in the present invention is a stimulating taste (or stimulus, pain sensation) possessed by the above-mentioned pungent component.
- the spiciness is derived from non-volatile ingredients such as red pepper, pepper, sansho pepper, and ginger, which are hot in the mouth, and volatile ingredients such as wasabi, mustard, and garlic. Derived from the ingredients, it is roughly divided into two types, one that stimulates the mucous membrane of the nose and feels hot.
- the present invention can enhance the pungency of both of these two strains. Therefore, in the present invention, "pungent taste” includes both of these two types of pungent taste.
- the pungent taste includes, for example, pungent taste brought about by at least one selected from the group consisting of capsaicin, allyl isothiocyanate, piperine, sanshool, diallyl disulfide and gingerol, and the like.
- pungent taste brought about by at least one selected from the group consisting of capsaicin, allyl isothiocyanate, piperine, sanshool, diallyl disulfide and gingerol, and the like. include capsaicin, allyl isothiocyanate, piperine and the like.
- the pungent component-containing product of the present invention can be produced by adding the pungent taste enhancer of the present invention to the pungent component-containing product. Accordingly, in one embodiment, the present invention provides a method of making a pungent-containing product comprising adding a pungent-enhancing agent of the present invention to the pungent-containing product. Moreover, as described above, the pungent taste enhancer of the present invention contains citral or a citral analogue (1). Accordingly, in one embodiment, the present invention provides a method for producing a pungent component-containing product, comprising adding at least one selected from the group consisting of citral and citral analogues (1) to the pungent component-containing product. . The meaning of each term in this production method, the mixing ratio of each component, etc. are the same as described above. Citral or citral analogue (1) can be added at any stage of the manufacturing process of the pungent ingredient-containing product of the present invention.
- the pungent taste of a pungent component-containing product can be enhanced without requiring an increase in the amount of the pungent component and/or an improvement in quality. That is, by the production method of the present invention, a pungent component-containing product with enhanced pungency can be produced simply and inexpensively. Moreover, by using the present invention, it can be expected that the pungent taste is enhanced, the taste is improved, and the palatability is improved. Conversely, according to the present invention, the amount of the pungent component used can be suppressed without greatly reducing or impairing the pungent taste.
- Whether or not the pungent taste of the pungent component-containing product of the present invention is enhanced is determined by comparing the pungent taste of the pungent component-containing product of the present invention in which citral or citral analogue (1) is blended. It can be evaluated by comparing the pungent taste of a composition (comparative composition) having the same composition as the pungent component-containing product of the present invention except that it is not blended, and the pungent component of the present invention is compared with the comparative composition. If the pungent taste of the product is increased, it can be determined that the pungent component-containing product of the present invention has enhanced pungent taste. Although it is not limited, it can be specifically evaluated according to the description of Examples described later.
- the pungent taste of the pungent component-containing product of the present invention is enhanced, so that the pungent component of the present invention has a pungent taste similar to that of a composition containing a larger amount of the pungent component than it actually is.
- Inclusion products can be prepared.
- the present invention provides a method for enhancing pungent taste of a pungent component-containing product, comprising adding the pungent taste enhancer of the present invention to the pungent component-containing product.
- the pungent taste enhancer of the present invention contains citral or a citral analogue (1).
- the present invention provides a method for enhancing pungency of a pungent component-containing product, comprising adding at least one selected from the group consisting of citral and citral analogues (1) to the pungent component-containing product. do.
- the meaning of each term, the mixing ratio of each component, etc. in the method for enhancing pungency are the same as described above.
- Citral or citral analogue (1) can be added at any stage of the manufacturing process of the pungent ingredient-containing product of the present invention.
- citral F manufactured by Shandong NHU Pharmaceutical Co., Ltd.
- citral analogues include 4,8-dimethyl-3,7-nonadien-2-ol, 4,8-dimethyl-3,7-nonadien-2-yl acetate and 4,8-dimethyl-3,7 - nonadien-2-one was used.
- citral and citral analogues enhanced the pungency of allyl isothiocyanate, piperine and capsaicin.
- 4,8-dimethyl-3,7-nonadien-2-ol and 4,8-dimethyl-3,7-nonadien-2-yl acetate further enhance the pungent taste of allyl isothiocyanate
- 4,8- Dimethyl-3,7-nonadien-2-yl acetate and 4,8-dimethyl-3,7-nonadien-2-one enhance the pungency of piperine more strongly
- 4,8-dimethyl-3,7-nonadien- 2-one enhanced the pungent taste of capsaicin more strongly.
- citral and citral analogues enhanced the pungent taste of horseradish, Japanese mustard, yuzu pepper and wasabi.
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Abstract
The problem to be solved by the present invention is to provide a novel hot taste enhancing method using an ingredient that is not known to have a hot taste enhancing effect until now. The present invention provides a hot taste enhancer for a product containing a hot taste ingredient, the hot taste enhancer comprising at least one component selected from the group consisting of citral and a citral analogue represented by general formula (1): H3C-C(CH3)=CH-CH2-CH2-C(CH3)=CH-R1-R2 [wherein R1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-; Ac represents an acetyl group; and R2 represents an alkyl group having 1 to 4 carbon atoms].
Description
本出願は、２０２１年３月１９日に出願された、日本国特許出願第２０２１－０４５４０５号明細書（その開示全体が参照により本明細書中に援用される）に基づく優先権を主張する。本発明は、辛味増強剤、辛味を増強する方法、辛味成分含有製品及びその製造方法に関する。
This application claims priority based on Japanese Patent Application No. 2021-045405 filed on March 19, 2021 (the entire disclosure of which is incorporated herein by reference). TECHNICAL FIELD The present invention relates to a pungent taste enhancer, a method for enhancing pungent taste, a pungent component-containing product, and a method for producing the same.
トウガラシ、ワサビ、辛子、コショウ、山椒、生姜等により飲食品に付与される辛味は、飲食品の風味にアクセントを加えたり、辛味自身を楽しんだりする等の風味の向上、食欲増進等をもたらし得る。そのため、辛味を有する飲食品は、様々な文化圏において多種多様なかたちで楽しまれている。
Pungent taste imparted to food and drink by pepper, wasabi, mustard, pepper, Japanese pepper, ginger, etc. can bring about improvement of flavor, appetite enhancement, etc., such as adding an accent to the flavor of food and drink, and enjoying the pungent taste itself. . Therefore, spicy food and drink are enjoyed in a wide variety of ways in various cultural spheres.
このように辛味は多くの人に好まれる味のため、辛味を呈するスパイス等が古来探求されているだけでなく、近年は、食品素材が有する辛味を増強しようとする試みがされており、飲食品等の辛味を増強する新たな成分の開発が熱望されている。
As described above, spiciness is a taste that many people like, so not only have spices exhibiting spiciness been explored since ancient times, but in recent years, attempts have been made to enhance the spiciness of food materials. There is a strong demand for the development of new ingredients that enhance the pungent taste of foods.
本発明は、これまで辛味増強効果を有することが知られていなかった成分を用いる、新規辛味増強方法を提供することを課題とする。
An object of the present invention is to provide a novel pungent taste enhancing method using a component that has not been known to have a pungent taste enhancing effect.
かかる状況の下、本発明者らは鋭意検討した結果、シトラール又はその特定の類縁体を用いることによりかかる課題を解決し得ることを見出した。本発明はかかる新規の知見に基づくものである。従って、本発明は以下の項を提供する：
項１．シトラール及び下記一般式（１）で表されるシトラール類縁体からなる群より選択される少なくとも一種を含有する、辛味成分含有製品の辛味増強剤：
Ｈ3Ｃ－Ｃ（ＣＨ3）＝ＣＨ－ＣＨ2－ＣＨ2－Ｃ（ＣＨ3）＝ＣＨ－Ｒ1－Ｒ2 （１）
［式中、Ｒ1は－ＣＨ（ＯＨ）－、－Ｃ（＝Ｏ）－又は－ＣＨ（ＯＡｃ）－を示し、Ａｃはアセチル基を示す。Ｒ2は炭素数１～４のアルキル基を示す。］
項２．項１に記載の辛味成分含有製品の辛味増強剤であって、該辛味増強剤が一般式（１）で表されるシトラール類縁体を含む場合、Ｒ2は炭素数１のアルキル基を示す、辛味増強剤。
項３．シトラール及び下記一般式（１）で表されるシトラール類縁体からなる群より選択される少なくとも一種を辛味成分含有製品に添加することを含む、辛味成分含有製品の辛味を増強する方法：
Ｈ3Ｃ－Ｃ（ＣＨ3）＝ＣＨ－ＣＨ2－ＣＨ2－Ｃ（ＣＨ3）＝ＣＨ－Ｒ1－Ｒ2 （１）
［式中、Ｒ1は－ＣＨ（ＯＨ）－、－Ｃ（＝Ｏ）－又は－ＣＨ（ＯＡｃ）－を示し、Ａｃはアセチル基を示す。Ｒ2は炭素数１～４のアルキル基を示す。］
項４．項３に記載の方法であって、前記辛味成分含有製品に一般式（１）で表されるシトラール類縁体を添加する場合、Ｒ2は炭素数１のアルキル基を示す、方法。
項５．項１又は２記載の辛味増強剤を辛味成分含有製品に添加することを含む、辛味成分含有製品の製造方法。
項６．項１又は２記載の辛味増強剤を含有する、辛味成分含有製品。 Under such circumstances, the present inventors have made intensive studies and found that the use of citral or specific analogues thereof can solve these problems. The present invention is based on such new findings. Accordingly, the present invention provides the following terms:
Section 1. A pungent enhancer for pungent component-containing products, containing at least one selected from the group consisting of citral and citral analogues represented by the following general formula (1):
H 3 C—C(CH 3 )=CH—CH 2 —CH 2 —C(CH 3 )=CH—R 1 —R 2 (1)
[In the formula, R 1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-, and Ac represents an acetyl group. R 2 represents an alkyl group having 1 to 4 carbon atoms. ]
Section 2. Item 1. The pungent taste enhancer for the pungent ingredient-containing product according to Item 1, wherein when the pungent taste enhancer contains a citral analogue represented by the general formula (1), R represents an alkyl group having 1 carbon atoms. Pungent enhancer.
Item 3. A method for enhancing the pungent taste of a pungent component-containing product, comprising adding at least one selected from the group consisting of citral and citral analogues represented by the following general formula (1) to the pungent component-containing product:
H 3 C—C(CH 3 )=CH—CH 2 —CH 2 —C(CH 3 )=CH—R 1 —R 2 (1)
[In the formula, R 1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-, and Ac represents an acetyl group. R 2 represents an alkyl group having 1 to 4 carbon atoms. ]
Section 4. Item 4. The method according to item 3, wherein when the citral analogue represented by the general formula (1) is added to the pungent component-containing product, R 2 represents an alkyl group having 1 carbon atom.
Item 5. Item 3. A method for producing a pungent component-containing product, comprising adding the pungent taste enhancer according to item 1 or 2 to the pungent component-containing product.
Item 6. Item 3. A pungent component-containing product containing the pungent taste enhancer according to Item 1 or 2.
項１．シトラール及び下記一般式（１）で表されるシトラール類縁体からなる群より選択される少なくとも一種を含有する、辛味成分含有製品の辛味増強剤：
Ｈ3Ｃ－Ｃ（ＣＨ3）＝ＣＨ－ＣＨ2－ＣＨ2－Ｃ（ＣＨ3）＝ＣＨ－Ｒ1－Ｒ2 （１）
［式中、Ｒ1は－ＣＨ（ＯＨ）－、－Ｃ（＝Ｏ）－又は－ＣＨ（ＯＡｃ）－を示し、Ａｃはアセチル基を示す。Ｒ2は炭素数１～４のアルキル基を示す。］
項２．項１に記載の辛味成分含有製品の辛味増強剤であって、該辛味増強剤が一般式（１）で表されるシトラール類縁体を含む場合、Ｒ2は炭素数１のアルキル基を示す、辛味増強剤。
項３．シトラール及び下記一般式（１）で表されるシトラール類縁体からなる群より選択される少なくとも一種を辛味成分含有製品に添加することを含む、辛味成分含有製品の辛味を増強する方法：
Ｈ3Ｃ－Ｃ（ＣＨ3）＝ＣＨ－ＣＨ2－ＣＨ2－Ｃ（ＣＨ3）＝ＣＨ－Ｒ1－Ｒ2 （１）
［式中、Ｒ1は－ＣＨ（ＯＨ）－、－Ｃ（＝Ｏ）－又は－ＣＨ（ＯＡｃ）－を示し、Ａｃはアセチル基を示す。Ｒ2は炭素数１～４のアルキル基を示す。］
項４．項３に記載の方法であって、前記辛味成分含有製品に一般式（１）で表されるシトラール類縁体を添加する場合、Ｒ2は炭素数１のアルキル基を示す、方法。
項５．項１又は２記載の辛味増強剤を辛味成分含有製品に添加することを含む、辛味成分含有製品の製造方法。
項６．項１又は２記載の辛味増強剤を含有する、辛味成分含有製品。 Under such circumstances, the present inventors have made intensive studies and found that the use of citral or specific analogues thereof can solve these problems. The present invention is based on such new findings. Accordingly, the present invention provides the following terms:
Section 1. A pungent enhancer for pungent component-containing products, containing at least one selected from the group consisting of citral and citral analogues represented by the following general formula (1):
H 3 C—C(CH 3 )=CH—CH 2 —CH 2 —C(CH 3 )=CH—R 1 —R 2 (1)
[In the formula, R 1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-, and Ac represents an acetyl group. R 2 represents an alkyl group having 1 to 4 carbon atoms. ]
Section 2. Item 1. The pungent taste enhancer for the pungent ingredient-containing product according to Item 1, wherein when the pungent taste enhancer contains a citral analogue represented by the general formula (1), R represents an alkyl group having 1 carbon atoms. Pungent enhancer.
Item 3. A method for enhancing the pungent taste of a pungent component-containing product, comprising adding at least one selected from the group consisting of citral and citral analogues represented by the following general formula (1) to the pungent component-containing product:
H 3 C—C(CH 3 )=CH—CH 2 —CH 2 —C(CH 3 )=CH—R 1 —R 2 (1)
[In the formula, R 1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-, and Ac represents an acetyl group. R 2 represents an alkyl group having 1 to 4 carbon atoms. ]
Section 4. Item 4. The method according to item 3, wherein when the citral analogue represented by the general formula (1) is added to the pungent component-containing product, R 2 represents an alkyl group having 1 carbon atom.
Item 5. Item 3. A method for producing a pungent component-containing product, comprising adding the pungent taste enhancer according to item 1 or 2 to the pungent component-containing product.
Item 6. Item 3. A pungent component-containing product containing the pungent taste enhancer according to Item 1 or 2.
本発明によれば、これまで辛味増強効果を有することが知られていなかった成分を用いる、新規辛味増強方法を提供することができる。
According to the present invention, it is possible to provide a novel pungent taste enhancing method using a component that has not been known to have a pungent taste enhancing effect.
（Ｉ）辛味増強剤
第１の実施形態において、本発明は、シトラール及び下記一般式（１）で表されるシトラール類縁体からなる群より選択される少なくとも一種を含有する、辛味成分含有製品の辛味増強剤を提供する：
Ｈ3Ｃ－Ｃ（ＣＨ3）＝ＣＨ－ＣＨ2－ＣＨ2－Ｃ（ＣＨ3）＝ＣＨ－Ｒ1－Ｒ2 （１）
［式中、Ｒ1は－ＣＨ（ＯＨ）－、－Ｃ（＝Ｏ）－又は－ＣＨ（ＯＡｃ）－を示し、Ａｃはアセチル基を示す。Ｒ2は炭素数１～４のアルキル基を示す。］
本発明においてシトラールとはネラールとゲラニアールとの混合物を示す。また、本明細書において、一般式（１）で表されるシトラール類縁体を、単にシトラール類縁体（１）と示すことがある。本発明において、上記一般式（１）において、Ａｃはアセチル基を示す。また、アルキル基とは、直鎖又は分枝鎖状の飽和炭化水素基を示す。本発明において、アルキル基の炭素数は１～４であり、１～３が好ましく、１～２がより好ましく、１がさらに好ましい。より具体的には、炭素数１～４のアルキル基としては、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、ｓｅｃ－ブチル基、ｉｓｏ－ブチル基、ｔｅｒｔ－ブチル基が挙げられる。また、シトラール類縁体（１）には、幾何異性体、立体異性体、光学異性体等の異性体が存在する場合、特に明記しない限り、これらの異性体はシトラール類縁体（１）に包含される。例えば、一般式（１）には、それぞれのシス体、トランス体及びこれらの混合物が包含され得る。より具体的には、例えば、Ｒ1が－ＣＨ（ＯＨ）－の場合（アルコール体）、一般式（１）には、 (I) Pungent enhancer In the first embodiment, the present invention provides a pungent component-containing product containing at least one selected from the group consisting of citral and citral analogues represented by the following general formula (1). Providing pungency enhancers:
H 3 C—C(CH 3 )=CH—CH 2 —CH 2 —C(CH 3 )=CH—R 1 —R 2 (1)
[In the formula, R 1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-, and Ac represents an acetyl group. R 2 represents an alkyl group having 1 to 4 carbon atoms. ]
Citral in the present invention denotes a mixture of neral and geranial. Further, in this specification, the citral analogue represented by the general formula (1) may be simply referred to as citral analogue (1). In the present invention, in the above general formula (1), Ac represents an acetyl group. Moreover, an alkyl group represents a linear or branched saturated hydrocarbon group. In the present invention, the number of carbon atoms in the alkyl group is 1 to 4, preferably 1 to 3, more preferably 1 to 2, and even more preferably 1. More specifically, the alkyl group having 1 to 4 carbon atoms includes methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, iso-butyl group and tert-butyl group. is mentioned. In addition, when citral analogue (1) has isomers such as geometric isomers, stereoisomers, and optical isomers, unless otherwise specified, these isomers are included in citral analogue (1). be. For example, general formula (1) can include each cis isomer, trans isomer, and mixtures thereof. More specifically, for example, when R 1 is —CH(OH)— (alcohol form), general formula (1) has
第１の実施形態において、本発明は、シトラール及び下記一般式（１）で表されるシトラール類縁体からなる群より選択される少なくとも一種を含有する、辛味成分含有製品の辛味増強剤を提供する：
Ｈ3Ｃ－Ｃ（ＣＨ3）＝ＣＨ－ＣＨ2－ＣＨ2－Ｃ（ＣＨ3）＝ＣＨ－Ｒ1－Ｒ2 （１）
［式中、Ｒ1は－ＣＨ（ＯＨ）－、－Ｃ（＝Ｏ）－又は－ＣＨ（ＯＡｃ）－を示し、Ａｃはアセチル基を示す。Ｒ2は炭素数１～４のアルキル基を示す。］
本発明においてシトラールとはネラールとゲラニアールとの混合物を示す。また、本明細書において、一般式（１）で表されるシトラール類縁体を、単にシトラール類縁体（１）と示すことがある。本発明において、上記一般式（１）において、Ａｃはアセチル基を示す。また、アルキル基とは、直鎖又は分枝鎖状の飽和炭化水素基を示す。本発明において、アルキル基の炭素数は１～４であり、１～３が好ましく、１～２がより好ましく、１がさらに好ましい。より具体的には、炭素数１～４のアルキル基としては、メチル基、エチル基、ｎ－プロピル基、イソプロピル基、ｎ－ブチル基、ｓｅｃ－ブチル基、ｉｓｏ－ブチル基、ｔｅｒｔ－ブチル基が挙げられる。また、シトラール類縁体（１）には、幾何異性体、立体異性体、光学異性体等の異性体が存在する場合、特に明記しない限り、これらの異性体はシトラール類縁体（１）に包含される。例えば、一般式（１）には、それぞれのシス体、トランス体及びこれらの混合物が包含され得る。より具体的には、例えば、Ｒ1が－ＣＨ（ＯＨ）－の場合（アルコール体）、一般式（１）には、 (I) Pungent enhancer In the first embodiment, the present invention provides a pungent component-containing product containing at least one selected from the group consisting of citral and citral analogues represented by the following general formula (1). Providing pungency enhancers:
H 3 C—C(CH 3 )=CH—CH 2 —CH 2 —C(CH 3 )=CH—R 1 —R 2 (1)
[In the formula, R 1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-, and Ac represents an acetyl group. R 2 represents an alkyl group having 1 to 4 carbon atoms. ]
Citral in the present invention denotes a mixture of neral and geranial. Further, in this specification, the citral analogue represented by the general formula (1) may be simply referred to as citral analogue (1). In the present invention, in the above general formula (1), Ac represents an acetyl group. Moreover, an alkyl group represents a linear or branched saturated hydrocarbon group. In the present invention, the number of carbon atoms in the alkyl group is 1 to 4, preferably 1 to 3, more preferably 1 to 2, and even more preferably 1. More specifically, the alkyl group having 1 to 4 carbon atoms includes methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, iso-butyl group and tert-butyl group. is mentioned. In addition, when citral analogue (1) has isomers such as geometric isomers, stereoisomers, and optical isomers, unless otherwise specified, these isomers are included in citral analogue (1). be. For example, general formula (1) can include each cis isomer, trans isomer, and mixtures thereof. More specifically, for example, when R 1 is —CH(OH)— (alcohol form), general formula (1) has
がいずれも包含され得る。同様に、Ｒ1が－Ｃ（＝Ｏ）－の場合（ケトン体）、一般式（１）には、
can be included. Similarly, when R 1 is -C(=O)- (ketone body), general formula (1) has
がいずれも包含され得る。また、Ｒ1が－ＣＨ（ＯＡｃ）－の場合（エステル体）、一般式（１）には、
can be included. Further, when R 1 is —CH(OAc)— (ester form), general formula (1) includes
がいずれも包含され得る。
can be included.
本発明において、「シトラール及びシトラール類縁体（１）からなる群より選択される少なくとも一種」を単にシトラール化合物と示すことがある。
In the present invention, "at least one selected from the group consisting of citral and citral analogues (1)" may simply be referred to as a citral compound.
シトラール類縁体（１）は公知又は公知の方法に準じて合成可能である。シトラール又はシトラール類縁体の市販品としては、例えば、シトラールとしては、シトラールＦ（Ｓｈａｎｄｏｎｇ ＮＨＵ Ｐｈａｍａｃｅｕｔｉｃａｌ Ｃｏ．，Ｌｔｄ社製）等の商品名で販売されているものが挙げられる。本発明においては、これらのシトラール及びシトラール類縁体（１）は、１種類を単独で用いても、複数種類を組み合わせて用いてもよい。
The citral analogue (1) is known or can be synthesized according to a known method. Commercially available products of citral or citral analogues include, for example, citral that is sold under trade names such as Citral F (manufactured by Shandong NHU Pharmaceutical Co., Ltd.). In the present invention, these citral and citral analogues (1) may be used singly or in combination.
本発明の辛味増強剤においてシトラール又はシトラール類縁体（１）は精製された状態で用いられてもよいが、これに制限されず、本発明の作用効果を損なわない範囲において、シトラール又はシトラール類縁体（１）を含有する天然の材料を本発明の辛味増強剤として使用することができる。このような天然の材料としては、これらに限定されるものではないが、例えば：シトラールを含有する天然の材料として、レモン、シトラスフルーツ等を挙げることができる。
Citral or a citral analogue (1) may be used in a purified state in the pungent taste enhancer of the present invention, but is not limited to this, and citral or a citral analogue within a range that does not impair the effects of the present invention. Natural materials containing (1) can be used as the pungent enhancer of the present invention. Such natural materials include, but are not limited to: natural materials containing citral include lemons, citrus fruits, and the like.
本発明の辛味増強剤は、例えば後述する対象の辛味成分含有製品の辛味を増強するために用いられる。その形態を問わないが、粉末状、顆粒状、タブレット状、カプセル剤状等の固体の形態、ならびにシロップ状、乳液状、液状、ジェル状等の半固体又は液体の形態を有することができる。
The pungent taste enhancer of the present invention is used, for example, to enhance the pungent taste of target pungent component-containing products described later. Although the form is not limited, it can have a solid form such as powder, granules, tablets, capsules, etc., and a semi-solid or liquid form such as syrup, emulsion, liquid, gel, etc.
本発明の辛味増強剤は、シトラール又はシトラール類縁体（１）のみからなるものであってもよいし、シトラール又はシトラール類縁体（１）に加え、その形態に応じて、薬学的に許容される担体、又は飲食品に配合可能な担体を適宜配合することもできる。かかる担体としては、本発明の辛味増強剤の作用効果に影響を与えない範囲で、イソマルトオリゴ糖、ガラクトオリゴ糖、フラクトオリゴ糖等のオリゴ糖類；デキストリン、セルロース、アラビアガム、でん粉（コーンスターチ等）等の多糖類；水、エタノール等の溶剤等を挙げることができる。さらに本発明の辛味増強剤の作用効果に影響を与えない範囲で、飲食品、医薬品等に通常使用されるような香料、色素、酸味料、又は日持向上剤等を配合することもできる。かかる実施形態において、本発明の辛味増強剤中のシトラール又はシトラール類縁体（１）の合計量は、本発明の辛味増強剤の使用態様、及び他の成分の有無等に応じて、０．０００００００１～９９質量％（０．０００１～９９００００ｐｐｍ）の範囲から適宜設定することができる。
The pungent taste enhancer of the present invention may consist of only citral or a citral analogue (1), or in addition to citral or a citral analogue (1), depending on its form, it is pharmaceutically acceptable A carrier or a carrier that can be blended into food and drink can also be blended as appropriate. Examples of such carriers include oligosaccharides such as isomalto-oligosaccharides, galacto-oligosaccharides and fructo-oligosaccharides; polysaccharides; solvents such as water and ethanol; Furthermore, flavor enhancers, pigments, acidulants, shelf life improvers, etc., which are commonly used in foods, beverages, pharmaceuticals, etc., can be blended as long as they do not affect the action and effect of the pungent taste enhancer of the present invention. In such an embodiment, the total amount of citral or citral analogue (1) in the pungent enhancer of the present invention is 0.00000001 depending on the mode of use of the pungent enhancer of the present invention and the presence or absence of other ingredients. It can be appropriately set from the range of to 99% by mass (0.0001 to 990000 ppm).
（ＩＩ）辛味成分含有製品
本発明は、前記本発明の辛味増強剤を含む辛味成分含有製品を提供する。前述のように、本発明の辛味増強剤はシトラール又はシトラール類縁体（１）を含む。従って、本発明は、シトラール又はシトラール類縁体（１）を含む辛味成分含有製品を提供する。当該本発明の辛味成分含有製品は、前述する本発明の辛味増強剤を、後述する対象の辛味成分含有製品に添加配合することで簡便に調製することができる。 (II) Pungent component-containing product The present invention provides a pungent component-containing product containing the pungent taste enhancer of the present invention. As noted above, the pungency enhancer of the present invention comprises citral or a citral analogue (1). Accordingly, the present invention provides a pungent ingredient-containing product comprising citral or a citral analogue (1). The pungent component-containing product of the present invention can be easily prepared by adding and blending the pungent taste enhancer of the present invention described above to the target pungent component-containing product described below.
本発明は、前記本発明の辛味増強剤を含む辛味成分含有製品を提供する。前述のように、本発明の辛味増強剤はシトラール又はシトラール類縁体（１）を含む。従って、本発明は、シトラール又はシトラール類縁体（１）を含む辛味成分含有製品を提供する。当該本発明の辛味成分含有製品は、前述する本発明の辛味増強剤を、後述する対象の辛味成分含有製品に添加配合することで簡便に調製することができる。 (II) Pungent component-containing product The present invention provides a pungent component-containing product containing the pungent taste enhancer of the present invention. As noted above, the pungency enhancer of the present invention comprises citral or a citral analogue (1). Accordingly, the present invention provides a pungent ingredient-containing product comprising citral or a citral analogue (1). The pungent component-containing product of the present invention can be easily prepared by adding and blending the pungent taste enhancer of the present invention described above to the target pungent component-containing product described below.
本発明が対象とする辛味成分含有製品は、辛味成分を含有する製品であり、典型的には、辛味成分を含有する可食製品である。対象となる製品としては、例えば飲食品；経口医薬品；口腔用医薬品；歯磨き、洗口液等のオーラルケア製品（医薬品又は医薬部外品を含む）等を挙げることができ、好ましくは飲食品である。
The pungent component-containing product targeted by the present invention is a product containing a pungent component, typically an edible product containing a pungent component. Examples of target products include food and drink; oral pharmaceuticals; oral pharmaceuticals; oral care products (including pharmaceuticals and quasi-drugs) such as toothpaste and mouthwash; be.
本発明が対象とする辛味成分としては、カプサイシン、イソチオシアン酸アリル、ピペリン、サンショオール、ジアリルジスルフィド、ジンゲロール等が挙げられる。これらは１種単独でも、また２種以上を任意に組み合わせて使用されていてもよい。また辛味成分は、当該辛味成分を１種又は２種以上含有する食品素材又はその加工物に含まれるかたちで用いてもよい。かかる実施形態において、例えば、前記食品素材としては唐辛子、ワサビ、ホースラディッシュ、和辛子、胡椒、山椒、ニンニク、生姜等が、また加工物としては唐辛子ペースト、柚子胡椒、トムヤムペースト、豆板醤、辛子明太子、粉ワサビ、練りワサビ、ワサビ漬け、粉辛子、練り辛子、マスタード、粉胡椒、塩胡椒、粉山椒、ガーリックパウダー、すりおろしニンニク、すりおろし生姜等を例示することができる。なお、これらの辛味成分の形状は特に制限されない。例えば、粉末状、半固形状、液体状のいずれの形状であってもよい。本発明の辛味成分含有製品に含まれる辛味成分の割合は、本発明の辛味成分含有製品の目的及び／又は種類に応じて適宜設定することができる。制限はされないものの、例えば、本発明の辛味成分含有製品に含まれる辛味成分の割合としては０．０００００１～２０質量％を挙げることができる。また、辛味成分としてカプサイシン、当該カプサイシンを含む素材、加工物等を用いる場合、本発明の辛味成分含有製品に含まれるカプサイシンの割合としては０．００００１～１０質量％を例示することができる。辛味成分としてイソチオシアン酸アリル、当該イソチオシアン酸アリルを含む素材、加工物等を用いる場合、本発明の辛味成分含有製品に含まれるイソチオシアン酸アリルの割合としては０．０００００１～１０質量％を例示することができる。辛味成分としてピペリン、当該ピペリンを含む素材、加工物等を用いる場合、本発明の辛味成分含有製品に含まれるピペリンの割合としては０．００１～２０質量％を例示することができる。辛味成分としてジンゲロール、当該ジンゲロールを含む素材、加工物等を用いる場合、本発明の辛味成分含有製品に含まれるジンゲロールの割合としては０．００１～１０質量％を例示することができる。また、本発明の好ましい実施形態において、辛味増強効果により、辛味成分含有製品における辛味成分（カプサイシン、イソチオシアン酸アリル、ピペリン等の化合物）の含有量を減量することができるため有用である。本発明は、トウガラシ等に含まれるカプサイシン；和辛子、ワサビ、ホースラディッシュ等に含まれるイソチオシアン酸アリル；黒コショウ等に含まれるピペリン；山椒等に含まれるサンショオール；ニンニク等に含まれるジアリルジスルフィド；生姜等に含まれるジンゲロール等のいずれかだけでなく、これらの種類の異なる辛味を全て増強することができるため非常に有用である。また、シトラール及びシトラール類縁体（１）は、自体が辛味を呈する化合物ではないため、これらを辛味成分含有製品に添加することにより辛味増強できるという本発明の効果は、従来技術からは予想し得ないものである。
The pungent components targeted by the present invention include capsaicin, allyl isothiocyanate, piperine, sanshool, diallyl disulfide, gingerol, and the like. These may be used singly or in any combination of two or more. Moreover, the pungent component may be used in the form of being contained in a food material or a processed product thereof containing one or more of the pungent components. In such an embodiment, for example, the food materials include red pepper, wasabi, horseradish, Japanese mustard, pepper, Japanese pepper, garlic, ginger, and the like, and the processed products include red pepper paste, yuzu pepper, tom yum paste, doubanjiang, and mustard. Mentaiko, powdered wasabi, wasabi paste, pickled wasabi, mustard powder, mustard paste, mustard, powdered pepper, salted pepper, powdered Japanese pepper, garlic powder, grated garlic, grated ginger and the like can be exemplified. The shape of these pungent components is not particularly limited. For example, it may be powdery, semi-solid, or liquid. The ratio of the pungent component contained in the pungent component-containing product of the present invention can be appropriately set according to the purpose and/or type of the pungent component-containing product of the present invention. Although not limited, for example, the ratio of the pungent component contained in the pungent component-containing product of the present invention can be 0.000001 to 20% by mass. When using capsaicin as a pungent component, or a material or processed product containing the capsaicin, the proportion of capsaicin contained in the pungent component-containing product of the present invention can be exemplified from 0.00001 to 10% by mass. When using allyl isothiocyanate as a pungent component, or a material or processed product containing the allyl isothiocyanate, the ratio of allyl isothiocyanate contained in the pungent component-containing product of the present invention is exemplified as 0.000001 to 10% by mass. can be done. When using piperine as a pungent component, or a material or processed product containing the piperine, the ratio of piperine contained in the pungent component-containing product of the present invention can be exemplified from 0.001 to 20% by mass. When using gingerol as a pungent component, or a material or processed product containing the gingerol, the ratio of gingerol contained in the pungent component-containing product of the present invention can be exemplified from 0.001 to 10% by mass. Moreover, in a preferred embodiment of the present invention, the pungent taste enhancing effect is useful because the content of pungent components (compounds such as capsaicin, allyl isothiocyanate, piperine, etc.) in products containing pungent components can be reduced. The present invention provides capsaicin contained in hot peppers and the like; allyl isothiocyanate contained in Japanese mustard, wasabi, horseradish and the like; piperine contained in black pepper and the like; sanshool contained in Japanese pepper and the like; diallyl disulfide contained in garlic and the like; It is very useful because it can enhance not only any of the gingerols contained in ginger and the like, but also all of these different types of pungent taste. In addition, since citral and citral analogue (1) are not compounds that themselves exhibit pungent taste, the effect of the present invention that pungent taste can be enhanced by adding them to pungent component-containing products cannot be expected from the prior art. There is nothing.
飲食品としては、具体的に、前述する辛味成分を含有する、米菓、ビスケット、プレッツェル、ケーキ、チョコレート、ガム、キャンディ、グミ、錠菓等の菓子類；ポテトチップス等のスナック菓子類；インスタントスープ、即席みそ汁等のスープ類；冷凍ハンバーグ、冷凍たこ焼き等の冷凍調理済食品；チルドミートボール、チルドギョーザ等のチルド調理済食品；卵焼き、アメリカンドッグ等のその他調理済食品；チューハイ、ノンアルコールチューハイ等のアルコール飲料；チルドプリン、フルーツソース等のチルドデザート；アイスクリーム類；ソフトミックス、氷菓等のフローズンデザート；ドライゼリー、デザートベース等のドライデザート；冷凍米飯類；リゾット等の米飯類；カップめん、袋めん、チルドラーメン、冷凍パスタ等のめん類；総菜パン、お好み焼きミックス等のその他ステープル；唐辛子ペースト、柚子胡椒、トムヤムペースト、粉ワサビ、練りワサビ、粉辛子、練り辛子、マスタード、粉胡椒、塩胡椒、粉山椒、ガーリックパウダー、すりおろしニンニク、すりおろし生姜、ドレッシング、焼肉のたれ、浅漬けの素、ラー油、豆板醤、マヨネーズ等の調味料；レトルトカレー、パスタソース、炒飯の素等の調味食品；漬物、ワサビ漬け、味付けメンマ等の農産加工品；ハム類；サラダチキン等の畜産加工品；水産練製品；昆布佃煮、辛子明太子等の水産加工品；マーガリン類、チーズ類等の乳油製品；果汁飲料、野菜飲料等の果実飲料；コーラ、ジンジャーエール等の炭酸飲料；乳酸菌飲料、ドリンクヨーグルト等の乳性飲料；コーヒー、紅茶、ゼリー飲料等の嗜好飲料；ドリンク類、機能性清涼飲料、スポーツドリンク等の健康飲料；清涼飲料、フレーバードウォーター等のその他飲料；ポーションコーヒー、プレミックス飲料等の嗜好品等を挙げることができる。
Confectionery such as rice crackers, biscuits, pretzels, cakes, chocolates, gums, candies, gummies, tablet confectionery containing the above-mentioned pungent ingredient; snacks such as potato chips; instant soups. Soups such as instant miso soup; Frozen cooked foods such as frozen hamburgers and frozen takoyaki; Chilled cooked foods such as chilled meatballs and chilled gyoza; Other cooked foods such as tamagoyaki and corn dogs; Chilled desserts such as chilled puddings and fruit sauces; Ice creams; Frozen desserts such as soft mixes and frozen desserts; Dry desserts such as dry jelly and dessert bases; Frozen cooked rice; Noodles such as noodles, chilled ramen, frozen pasta; other staples such as side dish bread, okonomiyaki mix; red pepper paste, yuzu pepper, tom yum paste, powdered wasabi, kneaded wasabi, mustard, powdered pepper, salt and pepper, Seasonings such as Japanese pepper powder, garlic powder, grated garlic, grated ginger, dressing, grilled meat sauce, lightly pickled base, chili oil, bean sauce, mayonnaise; Agricultural processed products such as pickles, wasabi pickles, and seasoned bamboo shoots; hams; livestock processed products such as salad chicken; Fruit drinks such as beverages and vegetable drinks; Carbonated drinks such as cola and ginger ale; Milky drinks such as lactic acid drinks and drink yogurt; Other beverages such as soft drinks and flavored water; and luxury goods such as portioned coffee and premixed beverages.
また経口医薬品としては、前述する辛味成分を含有する、トローチ、ドリンク剤、顆粒剤、散剤（粉末剤）、錠剤、カプセル剤等を、口腔用医薬品としては、前述する辛味成分を含有する、スプレー剤、軟膏剤、パスタ剤等を、またオーラルケア製品としては、前述する辛味成分を含有する、液体歯磨き、練り歯磨き、口中洗浄剤、口臭除去剤等を挙げることができる。
Oral pharmaceuticals include lozenges, drinks, granules, powders (powder formulations), tablets, capsules, etc. containing the aforementioned pungent ingredient, and oral pharmaceuticals include sprays containing the aforementioned pungent ingredient. and oral care products include liquid toothpastes, toothpastes, mouthwashes, breath fresheners and the like containing the aforementioned pungent component.
本発明の好ましい実施形態において、辛味成分含有製品に対してシトラール又はシトラール類縁体（１）は、本発明の辛味成分含有製品中の最終濃度が、例えば、０．００５～２００ｐｐｍ、より好ましくは０．０２～５０ｐｐｍ、さらに好ましくは０．１～１０ｐｐｍとなるように配合される。かかる実施形態において、シトラール又はシトラール類縁体（１）として２種類以上を配合する場合は、それらの各々が上記濃度範囲となることが好ましい。かかる辛味成分含有製品中のシトラール又はシトラール類縁体（１）の最終濃度は、対象とする辛味成分含有製品の種類等に応じて適宜設定することができ、例えば下限値としては、前記の通り０．００５ｐｐｍ以上を挙げることができるが、好ましくは０．０２ｐｐｍ以上、より好ましくは０．１ｐｐｍ以上である。また辛味成分含有製品中のシトラール又はシトラール類縁体（１）の最終濃度の上限値としては、前記の通り２００ｐｐｍ以下を挙げることができるが、好ましくは５０ｐｐｍ以下、より好ましくは１０ｐｐｍ以下である。また、シトラール又はシトラール類縁体（１）として２種類以上を配合する場合は、シトラール又はシトラール類縁体（１）の合計量として、辛味成分含有製品中に対し、０．００５～２００ｐｐｍの濃度範囲となることが好ましく、０．０２～５０ｐｐｍがより好ましく、０．１～１０ｐｐｍがさらに好ましい。
In a preferred embodiment of the present invention, the citral or citral analogue (1) relative to the pungent component-containing product has a final concentration in the pungent component-containing product of the present invention of, for example, 0.005 to 200 ppm, more preferably 0 0.02 to 50 ppm, more preferably 0.1 to 10 ppm. In such an embodiment, when two or more types of citral or citral analogue (1) are blended, each of them preferably falls within the above concentration range. The final concentration of citral or citral analogue (1) in the pungent component-containing product can be appropriately set according to the type of target pungent component-containing product. 005 ppm or more, preferably 0.02 ppm or more, more preferably 0.1 ppm or more. The upper limit of the final concentration of citral or citral analogue (1) in the pungent component-containing product is 200 ppm or less as described above, preferably 50 ppm or less, more preferably 10 ppm or less. In addition, when two or more types of citral or citral analogues (1) are blended, the total amount of citral or citral analogues (1) is in the concentration range of 0.005 to 200 ppm with respect to the pungent component-containing product. is preferably from 0.02 to 50 ppm, and even more preferably from 0.1 to 10 ppm.
また、本発明の辛味成分含有製品がカプサイシンを含む場合、カプサイシンに対する、シトラール化合物の配合割合（質量比）は、０．０００００００１～１が好ましく、０．０００００１～０．５がより好ましく、０．０００１～０．２がさらに好ましい。本発明の辛味成分含有製品がイソチオシアン酸アリルを含む場合、イソチオシアン酸アリルに対する、シトラール化合物の配合割合（質量比）は、０．００００００１～１０００が好ましく、０．００００１～１０がより好ましく、０．００１～０．１がさらに好ましい。本発明の辛味成分含有製品がピペリンを含む場合、ピペリンに対する、シトラール化合物の配合割合（質量比）は、０．０００００００２～１が好ましく、０．０００００５～０．５がより好ましく、０．００１～０．２がさらに好ましい。
When the pungent component-containing product of the present invention contains capsaicin, the blending ratio (mass ratio) of the citral compound to capsaicin is preferably 0.00000001 to 1, more preferably 0.000001 to 0.5, and 0.5. 0001 to 0.2 is more preferred. When the pungent component-containing product of the present invention contains allyl isothiocyanate, the mixing ratio (mass ratio) of the citral compound to allyl isothiocyanate is preferably 0.0000001 to 1000, more preferably 0.00001 to 10, and 0.000001 to 1000. 001 to 0.1 is more preferred. When the pungent component-containing product of the present invention contains piperine, the mixing ratio (mass ratio) of the citral compound to piperine is preferably from 0.00000002 to 1, more preferably from 0.000005 to 0.5, and from 0.001 to 0.001. 0.2 is more preferred.
本発明において「辛味」とは、前記辛味成分が有している刺激的な味（もしくは、刺激、痛覚）である。辛味には、トウガラシ、コショウ、山椒、生姜等のように不揮発性成分に由来し、口の中で熱いという刺激から辛さを感じる系統のものと、ワサビ、辛子、ニンニク等のように揮発性成分に由来し、鼻の粘膜を刺激され辛さを感じる系統のものとの大きく2つに分かれる。本発明は、これらの２つの系統の辛味をいずれも増強することができる。従って、本発明において「辛味」には、これら２つの系統の辛味がいずれも包含される。本発明の典型的な実施形態において、辛味としては、例えば、カプサイシン、イソチオシアン酸アリル、ピペリン、サンショオール、ジアリルジスルフィド及びジンゲロールからなる群より選択される少なくとも一種によりもたらされる辛味等が挙げられ、好ましくはカプサイシン、イソチオシアン酸アリル、ピペリン等が挙げられる。
"Pungent taste" in the present invention is a stimulating taste (or stimulus, pain sensation) possessed by the above-mentioned pungent component. The spiciness is derived from non-volatile ingredients such as red pepper, pepper, sansho pepper, and ginger, which are hot in the mouth, and volatile ingredients such as wasabi, mustard, and garlic. Derived from the ingredients, it is roughly divided into two types, one that stimulates the mucous membrane of the nose and feels hot. The present invention can enhance the pungency of both of these two strains. Therefore, in the present invention, "pungent taste" includes both of these two types of pungent taste. In a typical embodiment of the present invention, the pungent taste includes, for example, pungent taste brought about by at least one selected from the group consisting of capsaicin, allyl isothiocyanate, piperine, sanshool, diallyl disulfide and gingerol, and the like. include capsaicin, allyl isothiocyanate, piperine and the like.
本発明の辛味成分含有製品は、本発明の辛味増強剤を辛味成分含有製品に添加することにより製造することができる。従って、一実施形態において、本発明は、本発明の辛味増強剤を辛味成分含有製品に添加することを含む、辛味成分含有製品の製造方法を提供する。また前述のように、本発明の辛味増強剤は、シトラール又はシトラール類縁体（１）を含有する。従って、一実施形態において、本発明は、シトラール及びシトラール類縁体（１）からなる群より選択される少なくとも一種を辛味成分含有製品に添加することを含む、辛味成分含有製品の製造方法を提供する。かかる製造方法における各用語の意味、各成分の配合割合等は前記と同様である。シトラール又はシトラール類縁体（１）は、本発明の辛味成分含有製品の製造過程の任意の段階で添加することができる。
The pungent component-containing product of the present invention can be produced by adding the pungent taste enhancer of the present invention to the pungent component-containing product. Accordingly, in one embodiment, the present invention provides a method of making a pungent-containing product comprising adding a pungent-enhancing agent of the present invention to the pungent-containing product. Moreover, as described above, the pungent taste enhancer of the present invention contains citral or a citral analogue (1). Accordingly, in one embodiment, the present invention provides a method for producing a pungent component-containing product, comprising adding at least one selected from the group consisting of citral and citral analogues (1) to the pungent component-containing product. . The meaning of each term in this production method, the mixing ratio of each component, etc. are the same as described above. Citral or citral analogue (1) can be added at any stage of the manufacturing process of the pungent ingredient-containing product of the present invention.
本発明を用いることにより、辛味成分の配合量の増大及び／又は質の改善を要することなく、辛味成分含有製品の辛味を増強することができる。すなわち、本発明の製造方法により、簡便かつ安価に、辛味が増強された辛味成分含有製品を製造することができる。また、本発明を用いることにより、辛味が増強され、味を改善し、嗜好性の向上が期待できる。逆にいえば、本発明によれば、辛味を大きく低減ないし損なうことなく、辛味成分の使用量を抑えることができる。
By using the present invention, the pungent taste of a pungent component-containing product can be enhanced without requiring an increase in the amount of the pungent component and/or an improvement in quality. That is, by the production method of the present invention, a pungent component-containing product with enhanced pungency can be produced simply and inexpensively. Moreover, by using the present invention, it can be expected that the pungent taste is enhanced, the taste is improved, and the palatability is improved. Conversely, according to the present invention, the amount of the pungent component used can be suppressed without greatly reducing or impairing the pungent taste.
本発明の辛味成分含有製品について辛味が増強されているか否かは、シトラール又はシトラール類縁体（１）が配合された本発明の辛味成分含有製品の辛味を、シトラール又はシトラール類縁体（１）が配合されていない以外は本発明の辛味成分含有製品と同じ組成の組成物（比較組成物）の辛味と比較することで評価することができ、比較組成物と比較して本発明の辛味成分含有製品の辛味のほうが、上昇している場合に、本発明の辛味成分含有製品について辛味が増強されていると判断することができる。制限されないものの、具体的には、後述する実施例の記載に従って評価することができる。シトラール又はシトラール類縁体（１）の配合により本発明の辛味成分含有製品の辛味が増強されることで、実際よりも多くの辛味成分を配合した組成物と同様の辛味を有する本発明の辛味成分含有製品を調製することができる。
Whether or not the pungent taste of the pungent component-containing product of the present invention is enhanced is determined by comparing the pungent taste of the pungent component-containing product of the present invention in which citral or citral analogue (1) is blended. It can be evaluated by comparing the pungent taste of a composition (comparative composition) having the same composition as the pungent component-containing product of the present invention except that it is not blended, and the pungent component of the present invention is compared with the comparative composition. If the pungent taste of the product is increased, it can be determined that the pungent component-containing product of the present invention has enhanced pungent taste. Although it is not limited, it can be specifically evaluated according to the description of Examples described later. By adding citral or citral analogue (1), the pungent taste of the pungent component-containing product of the present invention is enhanced, so that the pungent component of the present invention has a pungent taste similar to that of a composition containing a larger amount of the pungent component than it actually is. Inclusion products can be prepared.
（ＩＩＩ）辛味成分含有製品の辛味増強方法
本発明は、本発明の辛味増強剤を辛味成分含有製品に添加することを含む、辛味成分含有製品の辛味増強方法を提供する。また前述のように、本発明の辛味増強剤は、シトラール又はシトラール類縁体（１）を含有する。従って、一実施形態において、本発明は、シトラール及びシトラール類縁体（１）からなる群より選択される少なくとも一種を辛味成分含有製品に添加することを含む、辛味成分含有製品の辛味増強方法を提供する。かかる辛味増強方法における各用語の意味、各成分の配合割合等は前記と同様である。
シトラール又はシトラール類縁体（１）は、本発明の辛味成分含有製品の製造過程の任意の段階で添加することができる。 (III) Method for enhancing pungency of pungent component-containing product The present invention provides a method for enhancing pungent taste of a pungent component-containing product, comprising adding the pungent taste enhancer of the present invention to the pungent component-containing product. Moreover, as described above, the pungent taste enhancer of the present invention contains citral or a citral analogue (1). Accordingly, in one embodiment, the present invention provides a method for enhancing pungency of a pungent component-containing product, comprising adding at least one selected from the group consisting of citral and citral analogues (1) to the pungent component-containing product. do. The meaning of each term, the mixing ratio of each component, etc. in the method for enhancing pungency are the same as described above.
Citral or citral analogue (1) can be added at any stage of the manufacturing process of the pungent ingredient-containing product of the present invention.
本発明は、本発明の辛味増強剤を辛味成分含有製品に添加することを含む、辛味成分含有製品の辛味増強方法を提供する。また前述のように、本発明の辛味増強剤は、シトラール又はシトラール類縁体（１）を含有する。従って、一実施形態において、本発明は、シトラール及びシトラール類縁体（１）からなる群より選択される少なくとも一種を辛味成分含有製品に添加することを含む、辛味成分含有製品の辛味増強方法を提供する。かかる辛味増強方法における各用語の意味、各成分の配合割合等は前記と同様である。
シトラール又はシトラール類縁体（１）は、本発明の辛味成分含有製品の製造過程の任意の段階で添加することができる。 (III) Method for enhancing pungency of pungent component-containing product The present invention provides a method for enhancing pungent taste of a pungent component-containing product, comprising adding the pungent taste enhancer of the present invention to the pungent component-containing product. Moreover, as described above, the pungent taste enhancer of the present invention contains citral or a citral analogue (1). Accordingly, in one embodiment, the present invention provides a method for enhancing pungency of a pungent component-containing product, comprising adding at least one selected from the group consisting of citral and citral analogues (1) to the pungent component-containing product. do. The meaning of each term, the mixing ratio of each component, etc. in the method for enhancing pungency are the same as described above.
Citral or citral analogue (1) can be added at any stage of the manufacturing process of the pungent ingredient-containing product of the present invention.
なお、本明細書において、「含む」及び「含有する」という用語には、「から実質的になる」及び「からなる」の意味が包含される。
In this specification, the terms "include" and "contain" include the meanings of "consisting essentially of" and "consisting of".
本発明の内容を以下の実験例及び実施例を用いて具体的に説明する。しかし、本発明はこれらに何ら限定されるものではない。下記において、特に言及する場合を除いて、実験は大気圧及び常温条件下で行っている。また特に言及する場合を除いて、「％」は「質量％」を、「部」は「質量部」を意味する。
The contents of the present invention will be specifically explained using the following experimental examples and examples. However, the present invention is by no means limited to these. In the following, experiments are conducted under atmospheric pressure and normal temperature conditions, unless otherwise specified. Unless otherwise specified, "%" means "% by mass" and "parts" means "parts by mass."
以下の実験例において、シトラールとしては、シトラールＦ（Ｓｈａｎｄｏｎｇ ＮＨＵ Ｐｈａｍａｃｅｕｔｉｃａｌ Ｃｏ．，Ｌｔｄ社製）を使用した。また、シトラール類縁体としては、４，８－ジメチル－３，７－ノナジエン－２－オール、４，８－ジメチル－３，７－ノナジエン－２－イルアセテート及び４，８－ジメチル－３，７－ノナジエン－２－オンを使用した。
In the following experimental examples, citral F (manufactured by Shandong NHU Pharmaceutical Co., Ltd.) was used as citral. Further, citral analogues include 4,8-dimethyl-3,7-nonadien-2-ol, 4,8-dimethyl-3,7-nonadien-2-yl acetate and 4,8-dimethyl-3,7 - nonadien-2-one was used.
実験例１ 辛味増強剤の辛味増強作用の評価
（１）評価方法
水に表１に記載の各辛味成分を当該表に記載の濃度で添加し、各検体を表１に記載の濃度で添加したものを準備した。また、コントロールとして、各辛味成分のみを当該表に記載の濃度で水に添加し、各検体を添加しないサンプルも調製した。飲食品の味質の官能評価に従事し訓練して社内試験に合格したパネル（以下の実験例においても同じ）８名によって、各サンプルの辛味を評価した。
１点：辛味のエンハンス効果を全く感じない（コントロールと同程度の辛味）
２点：僅かに辛味のエンハンス効果がある（１点と３点との間の辛味）
３点：辛味のエンハンス効果がある（コントロールの１．５倍の辛味）
４点：辛味のエンハンス効果が強い（３点と５点との間の辛味）
５点：辛味のエンハンス効果がかなり強い（コントロールの２倍以上の辛味）
（２）評価結果
結果を表１に示す。 Experimental Example 1 Evaluation of pungent taste enhancing action of pungent taste enhancer (1) Evaluation method Each pungent component shown in Table 1 was added to water at the concentration shown in the table, and each sample was added at the concentration shown in Table 1. prepared something. Also, as a control, a sample was prepared by adding only each pungent component to water at the concentration shown in the table and without adding each sample. The spiciness of each sample was evaluated by 8 panelists (the same applies to the following experimental examples) who had been engaged in sensory evaluation of the taste of food and drink, had been trained, and had passed an in-house test.
1 point: Absolutely no enhancement effect of pungent taste (pungent taste similar to control)
2 points: Slightly pungent enhancement effect (pungency between 1 and 3 points)
3 points: There is a pungent enhancement effect (1.5 times pungent than the control)
4 points: strong enhancement effect of pungent taste (pungent taste between 3 and 5 points)
5 points: The spiciness enhancement effect is quite strong (spiciness more than twice that of the control)
(2) Evaluation results Table 1 shows the results.
（１）評価方法
水に表１に記載の各辛味成分を当該表に記載の濃度で添加し、各検体を表１に記載の濃度で添加したものを準備した。また、コントロールとして、各辛味成分のみを当該表に記載の濃度で水に添加し、各検体を添加しないサンプルも調製した。飲食品の味質の官能評価に従事し訓練して社内試験に合格したパネル（以下の実験例においても同じ）８名によって、各サンプルの辛味を評価した。
１点：辛味のエンハンス効果を全く感じない（コントロールと同程度の辛味）
２点：僅かに辛味のエンハンス効果がある（１点と３点との間の辛味）
３点：辛味のエンハンス効果がある（コントロールの１．５倍の辛味）
４点：辛味のエンハンス効果が強い（３点と５点との間の辛味）
５点：辛味のエンハンス効果がかなり強い（コントロールの２倍以上の辛味）
（２）評価結果
結果を表１に示す。 Experimental Example 1 Evaluation of pungent taste enhancing action of pungent taste enhancer (1) Evaluation method Each pungent component shown in Table 1 was added to water at the concentration shown in the table, and each sample was added at the concentration shown in Table 1. prepared something. Also, as a control, a sample was prepared by adding only each pungent component to water at the concentration shown in the table and without adding each sample. The spiciness of each sample was evaluated by 8 panelists (the same applies to the following experimental examples) who had been engaged in sensory evaluation of the taste of food and drink, had been trained, and had passed an in-house test.
1 point: Absolutely no enhancement effect of pungent taste (pungent taste similar to control)
2 points: Slightly pungent enhancement effect (pungency between 1 and 3 points)
3 points: There is a pungent enhancement effect (1.5 times pungent than the control)
4 points: strong enhancement effect of pungent taste (pungent taste between 3 and 5 points)
5 points: The spiciness enhancement effect is quite strong (spiciness more than twice that of the control)
(2) Evaluation results Table 1 shows the results.
上記結果から、シトラール及びシトラール類縁体がいずれも、イソチオシアン酸アリル、ピペリン及びカプサイシンの辛味を増強した。また、４，８－ジメチル－３，７－ノナジエン－２－オール及び４，８－ジメチル－３，７－ノナジエン－２－イルアセテートはイソチオシアン酸アリルの辛味をより強く増強し、４，８－ジメチル－３，７－ノナジエン－２－イルアセテート及び４，８－ジメチル－３，７－ノナジエン－２－オンはピペリンの辛味をより強く増強し、４，８－ジメチル－３，７－ノナジエン－２－オンはカプサイシンの辛味をより強く増強した。
From the above results, both citral and citral analogues enhanced the pungency of allyl isothiocyanate, piperine and capsaicin. In addition, 4,8-dimethyl-3,7-nonadien-2-ol and 4,8-dimethyl-3,7-nonadien-2-yl acetate further enhance the pungent taste of allyl isothiocyanate, and 4,8- Dimethyl-3,7-nonadien-2-yl acetate and 4,8-dimethyl-3,7-nonadien-2-one enhance the pungency of piperine more strongly, and 4,8-dimethyl-3,7-nonadien- 2-one enhanced the pungent taste of capsaicin more strongly.
実験例２ 辛味増強剤の辛味増強作用の評価
（１）評価方法
表２に記載の対象食品に、各検体を当該表に記載の種類、濃度で添加したものを準備した。また、コントロールとして、各検体を添加しない対象食品も準備した。パネル１０名によって、各サンプルの辛味を評価した。
１点：辛味のエンハンス効果を全く感じない（コントロールと同程度の辛味）
２点：僅かに辛味のエンハンス効果がある（１点と３点との間の辛味）
３点：辛味のエンハンス効果がある（コントロールの１．５倍の辛味）
４点：辛味のエンハンス効果が強い（３点と５点との間の辛味）
５点：辛味のエンハンス効果がかなり強い（コントロールの２倍以上の辛味）
尚、本試験で使用した食品は以下のとおりである；
ホースラディッシュ：ホースラディッシュすりおろし（エスビースパイス工業（株）製「Ｓ＆Ｂ ホースラディッシュ」）
和辛子：練りからし（ハウス食品（株）製「ねりからし」）
柚子胡椒：青唐辛子と柚子果皮のすり潰し（フンドーキン醤油（株）製「セブンプレミアム ゆずこしょう」）
ワサビ：本わさびすりおろし（エスビー食品（株）製「本生本わさび」）
（２）評価結果
結果を表２に示す。 Experimental Example 2 Evaluation of pungent taste enhancing action of pungent taste enhancer (1) Evaluation method To the target food shown in Table 2, each sample was added at the type and concentration shown in the table. In addition, as a control, a target food was also prepared without adding each sample. A panel of 10 people evaluated the pungency of each sample.
1 point: Absolutely no enhancement effect of pungent taste (pungent taste similar to control)
2 points: Slightly pungent enhancement effect (pungency between 1 and 3 points)
3 points: There is a pungent enhancement effect (1.5 times pungent than the control)
4 points: strong enhancement effect of pungent taste (pungent taste between 3 and 5 points)
5 points: The spiciness enhancement effect is quite strong (spiciness more than twice that of the control)
The foods used in this test are as follows;
Horseradish: Grated horseradish (“S&B Horseradish” manufactured by SB Spice Industry Co., Ltd.)
Japanese mustard: kneaded mustard (House Foods Co., Ltd. “kneaded mustard”)
Yuzu pepper: ground green chili pepper and yuzu peel (“Seven Premium Yuzukosho” manufactured by Fundokin Soy Sauce Co., Ltd.)
Wasabi: grated real wasabi (“Honsei Honwasabi” manufactured by SB Foods Co., Ltd.)
(2) Evaluation results Table 2 shows the results.
（１）評価方法
表２に記載の対象食品に、各検体を当該表に記載の種類、濃度で添加したものを準備した。また、コントロールとして、各検体を添加しない対象食品も準備した。パネル１０名によって、各サンプルの辛味を評価した。
１点：辛味のエンハンス効果を全く感じない（コントロールと同程度の辛味）
２点：僅かに辛味のエンハンス効果がある（１点と３点との間の辛味）
３点：辛味のエンハンス効果がある（コントロールの１．５倍の辛味）
４点：辛味のエンハンス効果が強い（３点と５点との間の辛味）
５点：辛味のエンハンス効果がかなり強い（コントロールの２倍以上の辛味）
尚、本試験で使用した食品は以下のとおりである；
ホースラディッシュ：ホースラディッシュすりおろし（エスビースパイス工業（株）製「Ｓ＆Ｂ ホースラディッシュ」）
和辛子：練りからし（ハウス食品（株）製「ねりからし」）
柚子胡椒：青唐辛子と柚子果皮のすり潰し（フンドーキン醤油（株）製「セブンプレミアム ゆずこしょう」）
ワサビ：本わさびすりおろし（エスビー食品（株）製「本生本わさび」）
（２）評価結果
結果を表２に示す。 Experimental Example 2 Evaluation of pungent taste enhancing action of pungent taste enhancer (1) Evaluation method To the target food shown in Table 2, each sample was added at the type and concentration shown in the table. In addition, as a control, a target food was also prepared without adding each sample. A panel of 10 people evaluated the pungency of each sample.
1 point: Absolutely no enhancement effect of pungent taste (pungent taste similar to control)
2 points: Slightly pungent enhancement effect (pungency between 1 and 3 points)
3 points: There is a pungent enhancement effect (1.5 times pungent than the control)
4 points: strong enhancement effect of pungent taste (pungent taste between 3 and 5 points)
5 points: The spiciness enhancement effect is quite strong (spiciness more than twice that of the control)
The foods used in this test are as follows;
Horseradish: Grated horseradish (“S&B Horseradish” manufactured by SB Spice Industry Co., Ltd.)
Japanese mustard: kneaded mustard (House Foods Co., Ltd. “kneaded mustard”)
Yuzu pepper: ground green chili pepper and yuzu peel (“Seven Premium Yuzukosho” manufactured by Fundokin Soy Sauce Co., Ltd.)
Wasabi: grated real wasabi (“Honsei Honwasabi” manufactured by SB Foods Co., Ltd.)
(2) Evaluation results Table 2 shows the results.
上記結果から、シトラール及びシトラール類縁体は、ホースラディッシュ、和辛子、柚子胡椒及びワサビの辛味を増強した。
From the above results, citral and citral analogues enhanced the pungent taste of horseradish, Japanese mustard, yuzu pepper and wasabi.
Claims (6)
- シトラール及び下記一般式（１）で表されるシトラール類縁体からなる群より選択される少なくとも一種を含有する、辛味成分含有製品の辛味増強剤：
Ｈ3Ｃ－Ｃ（ＣＨ3）＝ＣＨ－ＣＨ2－ＣＨ2－Ｃ（ＣＨ3）＝ＣＨ－Ｒ1－Ｒ2 （１）
［式中、Ｒ1は－ＣＨ（ＯＨ）－、－Ｃ（＝Ｏ）－又は－ＣＨ（ＯＡｃ）－を示し、Ａｃはアセチル基を示す。Ｒ2は炭素数１～４のアルキル基を示す。］ A pungent enhancer for pungent component-containing products, containing at least one selected from the group consisting of citral and citral analogues represented by the following general formula (1):
H 3 C—C(CH 3 )=CH—CH 2 —CH 2 —C(CH 3 )=CH—R 1 —R 2 (1)
[In the formula, R 1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-, and Ac represents an acetyl group. R 2 represents an alkyl group having 1 to 4 carbon atoms. ] - 請求項１に記載の辛味成分含有製品の辛味増強剤であって、該辛味増強剤が一般式（１）で表されるシトラール類縁体を含む場合、Ｒ2は炭素数１のアルキル基を示す、辛味増強剤。 The pungent taste enhancer for a pungent component-containing product according to claim 1, wherein when the pungent taste enhancer contains a citral analogue represented by the general formula (1), R 2 represents an alkyl group having 1 carbon atom. , pungent enhancer.
- シトラール及び下記一般式（１）で表されるシトラール類縁体からなる群より選択される少なくとも一種を辛味成分含有製品に添加することを含む、辛味成分含有製品の辛味を増強する方法：
Ｈ3Ｃ－Ｃ（ＣＨ3）＝ＣＨ－ＣＨ2－ＣＨ2－Ｃ（ＣＨ3）＝ＣＨ－Ｒ1－Ｒ2 （１）
［式中、Ｒ1は－ＣＨ（ＯＨ）－、－Ｃ（＝Ｏ）－又は－ＣＨ（ＯＡｃ）－を示し、Ａｃはアセチル基を示す。Ｒ2は炭素数１～４のアルキル基を示す。］ A method for enhancing the pungent taste of a pungent component-containing product, comprising adding at least one selected from the group consisting of citral and citral analogues represented by the following general formula (1) to the pungent component-containing product:
H 3 C—C(CH 3 )=CH—CH 2 —CH 2 —C(CH 3 )=CH—R 1 —R 2 (1)
[In the formula, R 1 represents -CH(OH)-, -C(=O)- or -CH(OAc)-, and Ac represents an acetyl group. R 2 represents an alkyl group having 1 to 4 carbon atoms. ] - 請求項３に記載の方法であって、前記辛味成分含有製品に一般式（１）で表されるシトラール類縁体を添加する場合、Ｒ2は炭素数１のアルキル基を示す、方法。 4. The method according to claim 3, wherein when the citral analogue represented by general formula (1) is added to the pungent component-containing product, R2 represents an alkyl group having 1 carbon atoms.
- 請求項１又は２記載の辛味増強剤を辛味成分含有製品に添加することを含む、辛味成分含有製品の製造方法。 A method for producing a pungent component-containing product, comprising adding the pungent taste enhancer according to claim 1 or 2 to a pungent component-containing product.
- 請求項１又は２記載の辛味増強剤を含有する、辛味成分含有製品。 A pungent component-containing product containing the pungent taste enhancer according to claim 1 or 2.
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| JP2023507211A JPWO2022196825A1 (en) | 2021-03-19 | 2022-03-18 |
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| PCT/JP2022/012875 WO2022196825A1 (en) | 2021-03-19 | 2022-03-18 | Hot taste enhancer |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1070965A (en) * | 1996-08-30 | 1998-03-17 | House Foods Corp | Compound having horseradish flavor and food having horseradish taste |
| JPH10155451A (en) * | 1996-12-03 | 1998-06-16 | House Foods Corp | Hot taste preparation and hot taste product |
| JP2005143308A (en) * | 2003-11-11 | 2005-06-09 | Takasago Internatl Corp | Pungency-expression regulant |
-
2022
- 2022-03-18 WO PCT/JP2022/012875 patent/WO2022196825A1/en active Application Filing
- 2022-03-18 JP JP2023507211A patent/JPWO2022196825A1/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1070965A (en) * | 1996-08-30 | 1998-03-17 | House Foods Corp | Compound having horseradish flavor and food having horseradish taste |
| JPH10155451A (en) * | 1996-12-03 | 1998-06-16 | House Foods Corp | Hot taste preparation and hot taste product |
| JP2005143308A (en) * | 2003-11-11 | 2005-06-09 | Takasago Internatl Corp | Pungency-expression regulant |
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| JPWO2022196825A1 (en) | 2022-09-22 |
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