GB2180534A - Benzoyloxyacetic acid derivatives useful as sweetness inhibitors - Google Patents
Benzoyloxyacetic acid derivatives useful as sweetness inhibitors Download PDFInfo
- Publication number
- GB2180534A GB2180534A GB08619592A GB8619592A GB2180534A GB 2180534 A GB2180534 A GB 2180534A GB 08619592 A GB08619592 A GB 08619592A GB 8619592 A GB8619592 A GB 8619592A GB 2180534 A GB2180534 A GB 2180534A
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- GB
- United Kingdom
- Prior art keywords
- compound
- acid
- sweetness
- hydroxy
- foodstuff
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 239000003112 inhibitor Substances 0.000 title abstract description 29
- GLRLYEVLJAZIFU-UHFFFAOYSA-N 2-benzoyloxyacetic acid Chemical class OC(=O)COC(=O)C1=CC=CC=C1 GLRLYEVLJAZIFU-UHFFFAOYSA-N 0.000 title abstract description 3
- -1 methylenedioxy ring Chemical group 0.000 claims abstract description 39
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 24
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000000524 functional group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 6
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 39
- 235000003599 food sweetener Nutrition 0.000 claims description 18
- 239000003765 sweetening agent Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 14
- 229930006000 Sucrose Natural products 0.000 claims description 10
- 239000005720 sucrose Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 230000008447 perception Effects 0.000 claims description 9
- MZSAEUPZUUESSL-UHFFFAOYSA-N 2-(4-methoxybenzoyl)oxyacetic acid Chemical compound COC1=CC=C(C(=O)OCC(O)=O)C=C1 MZSAEUPZUUESSL-UHFFFAOYSA-N 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 239000006188 syrup Substances 0.000 claims description 7
- 235000020357 syrup Nutrition 0.000 claims description 7
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 108010011485 Aspartame Proteins 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- 108010016626 Dipeptides Proteins 0.000 claims description 3
- 229930091371 Fructose Natural products 0.000 claims description 3
- 239000005715 Fructose Substances 0.000 claims description 3
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- 239000004378 Glycyrrhizin Substances 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- UEDUENGHJMELGK-HYDKPPNVSA-N Stevioside Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UEDUENGHJMELGK-HYDKPPNVSA-N 0.000 claims description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 3
- 240000008042 Zea mays Species 0.000 claims description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 claims description 3
- 239000000605 aspartame Substances 0.000 claims description 3
- 235000010357 aspartame Nutrition 0.000 claims description 3
- 229960003438 aspartame Drugs 0.000 claims description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 3
- 235000005822 corn Nutrition 0.000 claims description 3
- 229940109275 cyclamate Drugs 0.000 claims description 3
- 239000008121 dextrose Substances 0.000 claims description 3
- 150000002303 glucose derivatives Chemical class 0.000 claims description 3
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 claims description 3
- 229960004949 glycyrrhizic acid Drugs 0.000 claims description 3
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 claims description 3
- 235000019410 glycyrrhizin Nutrition 0.000 claims description 3
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 claims description 3
- 235000019534 high fructose corn syrup Nutrition 0.000 claims description 3
- 229960004903 invert sugar Drugs 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 3
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019204 saccharin Nutrition 0.000 claims description 3
- 229940081974 saccharin Drugs 0.000 claims description 3
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- 235000010356 sorbitol Nutrition 0.000 claims description 3
- 229940013618 stevioside Drugs 0.000 claims description 3
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019202 steviosides Nutrition 0.000 claims description 3
- 239000000892 thaumatin Substances 0.000 claims description 3
- 235000010436 thaumatin Nutrition 0.000 claims description 3
- 239000000811 xylitol Substances 0.000 claims description 3
- 235000010447 xylitol Nutrition 0.000 claims description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 3
- 229960002675 xylitol Drugs 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 claims description 2
- PXLWOFBAEVGBOA-UHFFFAOYSA-N dihydrochalcone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC(C(=O)CC(O)C=2C=CC(O)=CC=2)=C1O PXLWOFBAEVGBOA-UHFFFAOYSA-N 0.000 claims description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims 2
- 125000000185 sucrose group Chemical group 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 235000013305 food Nutrition 0.000 description 21
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 235000019605 sweet taste sensations Nutrition 0.000 description 6
- 235000009508 confectionery Nutrition 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 235000019658 bitter taste Nutrition 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 235000019640 taste Nutrition 0.000 description 3
- YNUBJERORXITEM-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)oxyacetic acid Chemical compound OC(=O)COC(=O)C1=CC=C(O)C=C1 YNUBJERORXITEM-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 235000019647 acidic taste Nutrition 0.000 description 2
- 230000000578 anorexic effect Effects 0.000 description 2
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 description 2
- 239000008122 artificial sweetener Substances 0.000 description 2
- 235000021311 artificial sweeteners Nutrition 0.000 description 2
- JHVLLYQQQYIWKX-UHFFFAOYSA-N benzyl 2-bromoacetate Chemical compound BrCC(=O)OCC1=CC=CC=C1 JHVLLYQQQYIWKX-UHFFFAOYSA-N 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000013365 dairy product Nutrition 0.000 description 2
- 206010061428 decreased appetite Diseases 0.000 description 2
- 235000011850 desserts Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000015243 ice cream Nutrition 0.000 description 2
- 235000021096 natural sweeteners Nutrition 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000019643 salty taste Nutrition 0.000 description 2
- 235000019614 sour taste Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- OMTDIBZSUZNVJK-UHFFFAOYSA-N 4-(4-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(C(=O)CCC(O)=O)C=C1 OMTDIBZSUZNVJK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 235000013409 condiments Nutrition 0.000 description 1
- 235000019788 craving Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Seasonings (AREA)
Abstract
Novel benzoyloxyacetic acid derivatives of the formula <IMAGE> wherein R1 is hydroxy or C1-C4 alkoxy or R1 and an adjacent R2 together form a methylenedioxy ring, each R2 is H, C1-C3 alkyl, alkoxy of up to 2 carbon atoms, hydroxy or carboxymethoxy with the proviso that when R2 individually is a functional group of alkyl, alkoxy, hydroxy or carboxymethoxy, the number of each of these functional groups present will not exceed 2, and R3 is H or methyl, or non-toxic salts thereof act as sweetness inhibitors, foodstuffs containing the novel inhibitors and a process for inhibiting the sweetness of a foodstuff.
Description
SPECIFICATION
Sweetness inhibitors
Background of the Invention
This invention relates generally to sweetness modification and more particularly to benzoyloxyacetic or 2-propionic acid derivatives, particularly well suited as sweetness inhibitors in edible foodstuffs.
Sweetness is one of the primary taste cravings of both animals and humans. Thus, the utilization of sweetening agents in foods in order to satisfy this sensory desire is well established.
Sweetening agents can be used in foods to provide functions other than sweetening, such as to act as fillers, bulking agents, antimicrobial agents, freezing point depressants, however, the amount of sweetening agent employed for these alternate functions provides an excessively sweet taste, thereby requiring a modification of the formulation to reduce the sweetener level with a concurrent reduction in providing the alternate function to the food product. One solution of the art, with very limited success, was to add bitter or acidic ingredients to the food to reduce the sweetness perception; however, the resultant food then had an undesirable bitter or acidic taste.
Accordingly, in view of the aforementioned disadvantages associated with the use of sweeteners, e.g., naturally occurring, artificial or combinations thereof, it becomes readily apparent that it would be highly desirable to provide a sweetness inhibitor which when added to foodstuffs can greatly reduce the organoleptic of deleterious sweetener normally required and concomitantly eliminate or greatly diminish the disadvantages associated with sweeteners. Moreover, it would be highly desirable to provide sweetness inhibitor agents which do not result in off-taste and which when added to foodstuffs reduce the level of sweetness perceived without concurrent reduction in the desirable properties of the foodstuff.
Arylalkylketones, arylcycloalkylketones, and 3-(4'-rnethoxybenzoyl) propionic acid, are known in the prior art to possess anorexic and/or cholinergic activity in experimental animals such as rats, when introduced to the animals orally in feeds or injected via solutions thereof. See, for example, C. R. Acad. Sc. Paris, T.283 (October 27, 1976), "Therapeutic Chemistry-Anorexic Activity of Acids of Arylcycloalkylketones on Rats," by Oralesi, H. et al. and Eur. J. Med. Chem
Chimica Therapeutica, May June 1978, "Anorexic Activity of Acids of Arylalkylketones and
Arylcycloalkylketones," by Oralesi, H. et al. These papers, however, neither disclose nor remotely suggest the sweetness inhibiting properties of the compounds as described and utilized according to the present invention.
In a patent application, U.S. Serial No. 594,600 filed March 29, 1984 commonly assigned in regard to the present application to General Foods Corporation, there is disclosed and claimed the use of arylalkylketo acids such as 3-(4'-methoxybenzoyl) propionic acid as sweetness inhibitors in foodstuffs. In the present invention, another class of sweetness inhibitors has been discovered.
Summary of the Invention
A new class of sweetness inhibitors has been discovered which when added to edible materials particularly foodstuffs, greatly reduce or eliminate unwanted or unpleasant sweet tastes, thus increasing the palatability of overly sweet products. The novel sweetness inhibitors of this invention in foodstuff compositions inhibit the sweetness perception of the foodstuff without adding any off-tastes such as bitterness, acidity, etc. to the foodstuff. Additionally, there is provided a process for inhibiting the sweetness perception of a foodstuff.
In this invention, new and novel food acceptable sweetness inhibitors are provided which when added to a foodstuff inhibit the sweet taste perceived from the foodstuff. The food acceptable sweetness inhibiting compounds have the general formula:
wherein R, is hydroxy or alkoxy containing 1 to 4 carbon atoms and R1 and adjacent R2 forms a methylenedioxy ring; each R2 individually is selected from the group consisting of hydrogen, alkyl containing from 1 to 3 carbon atoms, alkoxy containing up to 2 carbon atoms, hydroxy and carbomethoxy group with the proviso that when R2, individually, is a functional group of alkyl, alkoxy, hydroxy or carbomethoxy, the number of each of these functional groups present will not exceed 2; R3 is hydrogen or methyl; and non-toxic salts of said compound.
Detailed Description of the Invention
In accordance with the present invention, it has been suprisingly discovered that the sweet taste perceived in a food product can be inhibited by the addition to the food product of a compound within the formula above.
Thus, according to the present invention, it has been found that the compounds within the scope of the formula above are effective sweetness inhibitors when used in conjunction with any of a number of known natural and/or artificial sweeteners including, for example, sucrose, fructose, corn syrup solids, high fructose corn syrup, dextrose, xylitol, sorbitol, mannitol, acetosulfam, thaumatin, invert sugar, saccharin, cyclamate, dihydrochalcone, hydrogenated glucose syrups, aspartame (L-aspartyl-L-phenylalanine methyl ester) and dipeptides, glycyrrhizin, stevioside, chlorinated carbohydrates, chlorosucrose and the like.
Typical edible material intended for consumption, including pharmaceutical preparations, in which the sweetness inhibitors of the present invention may be used are, for example, beverages, including soft drinks, carbonated beverages, ready to mix beverages and the like, infused foods (e.g. fruits or vegetables), sauces, condiments, salad dressings, juices, syrups, desserts, including puddings, gelatin, baked goods and frozen desserts, like ice creams and sherbets, icings and fillings, soft frozen products, such as soft frozen creams, soft frozen ice creams and yogurts, soft frozen toppings, such as dairy or non-dairy whipped topping, confections, toothpaste, mouthwashes, chewing gum, intermediate moisture foods (e.g. rice and dog foods).
The benzoyloxyacetic or 2-propionic acid derivatives of this invention can be readily prepared in the manner similar to the synthesis of 4-methoxybenzoyloxyacetic acid. The initial step requires the dissolving of a substituted benzoic acid in a solvent such as acetone in the presence of an alkali metal carbonate. To this mixture is added a benzyl 2-bromoacetate and the mixture is refluxed. Upon completion, the reaction mixture is filtered and the solvent is evaporated. The resulting product is deprotected by hydrogenation using a suitable hydrogenetion catalyst such as 10% palladium or platinum on carbon in the presence of a solvent such as ethanol. The product is then filtered and the solvent removed to obtain the substituted benzoyloxyacetic acid.
Illustrative compounds within the scope of this invention include, among others: 4-hydroxybenzoyloxyacetic acid; 4-methoxybenzoyloxyacetic acid; 4-ethoxybenzoyloxyacetic acid; 3,4-methylendioxybenzoyloxyacetic acid; 4'-hydroxybenzoyloxy-2-propionic acid; 4-methoxylbenzoyloxy-2propionic acid; 4'-ethoxybenzoyloxy-2-propionic acid; 3',4'-methylenedioxybenzoyloxy-2-propionic acid; 3,4-dimethoxybenzoyloxyacetic acid; 2,4-dimethoxybenzoyloxyacetic acid; 2-methyl-4-methoxybenzoyloxyacetic acid; 2,6-dimethyl-4-methoxybenzoyloxyacetic acid; 2-ethoxy-4-methoxybenzoyloxyacetic acid; 2,6-dimethyl-4-hydroxybenzoyloxyacetic acid; 2-carbomethoxy-4-methoxybenzoyloxyacetic acid; and the like.
The non-toxic carboxylic acid and/or phenolic salts of the sweetness inhibiting compounds of the formula above are also contemplated for use herein. Suitable salts include the sodium, potassium, ammonium, calcium or magnesium salts. Sodium salts are preferred.
In accordance with the present invention, a sweetness inhibitor is defined to be a compound which, when mixed with a sweetener, reduces or eliminates the perceived sweetness without substantially contributing a bitter, salty or sour taste of its own. Furthermore, it must be shown that any bitter, salty or sour taste is not sufficient to account for the substantial loss in sweetness perception.
Thus, one significant aspect of the present invention is that the inhibiting of the sweet taste of a food product by the sweetness inhibitors of the present invention is not due to the taste of the compound itself, but rather is due to an unexpected and highly surprising effect which results when the sweetness inhibitor is combined with a sweetener in the food product and tasted by the consumer.
Accordingly, what is readily apparent from the discovery herein is that the utilization of even very small quantities of the inhibiting compounds described herein can reduce or even eliminate the undesirable sweet and/or lingering after tastes of certain sweeteners in food products containing natural and/or artificial sweeteners, without affecting the other desirable tastes and properties of the food.
The versatility of the inhibitor compounds of the present invention in the formulation of food product is manifested in several manners. For example, the inhibitors can be added to an undesirably sweet product, for example, an overly sweet soft frozen product or infused vegetable product, to reduce or eliminate the undesirable sweet taste, but maintain the necessary soft frozen or infusion properties of the product. On the other hand, the inhibitors can be incorporated into products in conjunction with added amounts of sweetener in order to formulate novel soft frozen products.
In order to achieve the inhibiting results of the present invention, the sweetness inhibiting compounds described herein are generally added to the food product at a level which is effective to inhibit the sweetness perception of the food product. More particularly, it has been found that the results provided by the present invention occur when the inhibitor is added to the food product (containing a sweetener) in an amount in the range of from about 0.005 to about 2.0% by weight based on the weight of the consumed product. Greater amounts are operable but not practical. Preferred amounts are in the range of from about 0.01% to about 0.5% and most preferably from about 0.03% to about 0.5% by weight of the foodstuff.
The sweetener content of the foodstuffs in which the inhibitors of the present invention are utilized to inhibit sweetness, in general, may be in the range of from about threshold to about 50% sucrose equivalency.
It is understood that the afore-recited amounts are based on the consumed weight of the foodstuff. Thus, the amounts of inhibitor employed in a product, for example, a pre-mix, prior to taking its consumed form by the addition of diluents or solvent such as water, will necessarily vary accordingly in the pre-consumed form of the foodstuff. Moreover, it is further understood that the afore-recited amounts are based on the free acid form of the sweetness inhibiting compound. Thus, when salts are employed, the amount of the salt should be at least sufficient to provide to the afore-described amounts of the free acid.
Generally, the inhibiting effect provided by the present compounds is experienced over a wide pH range, e.g. about 2 to about 10, and in buffered or unbuffered formulations.
Depending upon the particular foodstuffs, the amounts and kind of sweetener contained therein and concomitant amount of inhibitor employed, reductions in perceived sweetness of from about 1% to about 100% in the foodstuff product are achieved. Generally, when the inhibitors of the present invention are employed in the afore-noted preferred amounts, reductions in perceived sweetness of from about 5% to about 50% or greater in the foodstuff product are observed.
In order that those skilled in the art may better understand how the present invention may be practiced, the following examples are given by way of illustration and not by way of limitation.
EXAMPLE 1
Synthesis of 4-Methoxybenzoyloxyacetic Acid
In acetone, 15.2 grams of 4-methoxybenzoic acid is dissolved with 13.8 grams of potassium carbonate. To this combination is added 22.9 grams of benzyl 2-bromoacetate and refluxed for
16 hours. Upon completion, the product is filtered and the solvent evaporated to obtain 26 grams (89.69ó yield) of benzyl (p-methoxybenzoyloxy) acetate. Deprotection of benzyl (p-methoxybenzoyloxy) acetate was accomplished via catalytic hydrogenation using palladium (10%) on carbon in 100% ethanol. The product was filtered and the solvent removed to obtain 16.8 grams of 4-methoxybenzoyloxyacetic acid, a white crystalline solid (89.8%, overall yield 80%).
EXAMPLE 2
4-methoxybenzoyloxyacetic acid was tested at two levels of 0.05 and 0.025% by weight in two 5% aqueous sucrose solutions adjusted to a pH of 3 and 7.
Inhibitor Concentration Sucrose Match added to 5% sucrose solution pH 3.0 pH 7.0 0.05% 0% 0% 0.025% 0% 1.7%
The above results indicate that 4-methoxybenzoyioxyacetic acid at a pH of 3 and at 0.05% and 0.025% reduces the sweetness perception of 5% sucrose solution to 0%. At a pH of 7, the use of 0.05% inhibitor reduces the sweetness perception of 5% sucrose solution to 0% while at 0.025% inhibitor the sweetness perception of 5% sucrose is reduced to 1.7%.
Similar results above are obtained using the following sweetness inhibitors: 4-hydroxybenzoyloxyacetic acid; 3,4-dimethoxybenzoyloxyacetic acid; 4-ethoxybenzoyloxyacetic acid; 4-methoxybenzoyloxy-2-propionic acid; and 3,4-methylenedioxybenzoyloxyacetic acid.
Obviously, other modifications and variations of the present invention are possible in light of the above teachings. It is therefore to be understood that changes may be made in the particular embodiments of this invention which are within the full intended scope of the invention as defined by the appended claims.
Claims (21)
1. A compound having the formula:
wherein R, is hydroxy or alkoxy containing 1 to 4 carbon atoms and R, and an adjacent R2 together form a methylenedioxy ring; each R2 individually, is selected from the group consisting of hydrogen, alkyl containing from 1 to 3 carbon atoms, alkoxy containing up to 2 carbon atoms, hydroxy and carboxymethoxy group with the proviso that when R2, individually, is a functional group of alkyl, alkoxy, hydroxy or carboxymethoxy, the number of each of these functional groups present will not exceed 2; R3 is hydrogen or methyl; and non-toxic salts of said compound.
2. The compound of claim 1 wherein the compound is 4-methoxybenzoyloxyacetic acid.
3. The compound of claim 1 wherein the compound is 4-ethoxybenzoyloxyacetic acid.
4. The compound of claim 1 wherein the compound is 3,4-methylenedioxybenzoyloxyacetic acid.
5. The compound of claim 1 wherein the compound is 3,4-dimethoxybenxoyloxyacetic acid.
6. The compound of claim 1 wherein the compound is 4'-methoxybenzoyloxy-2-propionic acid.
7. An edible material intended for consumption comprising an edible base, a sweetener, and a sweetness inhibiting amount of a sweetness inhibiting compound having the general formula:
wherein R1 is hydroxy or alkoxy containing 1 to 4 carbon atoms and R1 and an adjacent R2 together form a methylenedioxy ring; each R2 individually, is selected from the group consisting of hydrogen, alkyl containing from 1 to 3 carbon atoms, alkoxy containing up to 2 carbon atoms, hydroxy and carbomethoxy group with the proviso that when R2 individually, is a functional group of alkyl, alkoxy, hydroxy or carbomethoxy, the number of each of these functional groups present will not exceed 2; R3 is hydrogen and methyl; and non-toxic salts of said compound.
8. The foodstuff composition of claim 7 wherein said sweetness inhibiting compound is present in a food-acceptable amount in the range of from about 0.005 to about 2.0% by weight of the foodstuff composition.
9. The foodstuff composition of claim 7 wherein said sweetness inhibiting compound is present in a food-acceptable amount in the range of from about 0.03 to about 0.5% by weight of the foodstuff composition.
10. The foodstuff composition of any one of claims 7 to 9 wherein said sweetener is selected from the group consisting of sucrose, fructose, corn syrup solids, high fructose corn syrups, dextrose, xylitol, sorbitol, mannitol, acetosulfam, thaumatin, invert sugar, saccharin, cyclamate, dihydrochalcone, hydrogenated glucose syrups, aspartame and other dipeptides, chlorosucrose, stevioside, glycyrrhizin and mixtures thereof.
11. The foodstuff composition of any one of claims 7 to 10 wherein the sweetness inhibiting compound is 4-methoxybenzoyloxyacetic acid.
12. The foodstuff of any one of claims 7 to 10 wherein the sweetness inhibiting compound is 4-ethoxybenzoyioxyacetic acid.
13. The foodstuff of any one of claims 7 to 10 wherein the sweetness inhibiting compound is 3,4-methylenedioxybenzoyloxyacetic acid.
14. The foodstuff of any one of claims 7 to 10 wherein the sweetness inhibiting compound is 4'-methoxybenzoyloxy-2-propionic acid.
15. The compound of any one of claims 7 to 10 wherein the sweetness inhibiting compound is 2,4-dimethoxybenzoyloxyacetic acid.
16. A process for inhibiting the sweetness perception of a foodstuff, said process comprising adding to a foodstuff containing a sweetener, a food-acceptable sweetness inhibiting amount of a sweetness inhibiting compound having the general formula:
wherein R1 is hydroxy or alkoxy containing 1 to 4 carbon atoms and Rl and an adjacent R2 together form a methylenedioxy ring; each R2, individually, is selected from the group consisting of hydrogen, alkyl containing from 1 to 3 carbon atoms, alkoxy containing up to 2 carbon atoms, hydroxy and carboxymethoxy group with the proviso that when R2, individually, is a functional group of alkyl, alkoxy, hydroxy or carboxymethoxy, the number of each of these functional groups present will not exceed 2; R3 is hydrogen or methyl; and non-toxic salts of said compound.
17. The process of claim 9 wherein s.aid sweetener is selected from the group consisting of sucrose, fructose, corn syrup solids, high fructose corn syrups, dextrose, xylitol, sorbitol, mannitol, acetosulfam, thaumatin, invert sugar, saccharin, cyclamate, dihydroxhalcone, hydrogenated glucose syrups, aspartame and other dipeptides, stevioside, chlorosucrose, glycyrrhizin and mixtures thereof.
18. The process of claim 16 wherein the inhibiting agent is 4-methoxybenzoyloxyacetic acid.
19. A compound according to claim 1 substantially as hereinbefore specifically described with particular reference to the Examples.
20. An edible material according to claim 7 substantially as hereinbefore specifically described with particular reference to the Examples.
21. A process according to claim 16 substantially as hereinbefore specifically described with particular reference to the Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77781985A | 1985-09-19 | 1985-09-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8619592D0 GB8619592D0 (en) | 1986-09-24 |
| GB2180534A true GB2180534A (en) | 1987-04-01 |
Family
ID=25111382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08619592A Withdrawn GB2180534A (en) | 1985-09-19 | 1986-08-12 | Benzoyloxyacetic acid derivatives useful as sweetness inhibitors |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2180534A (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4994490A (en) * | 1989-04-03 | 1991-02-19 | The Nutrasweet Company | Novel N-(sulfomethyl)-N'-arylureas |
| US5021249A (en) * | 1989-11-09 | 1991-06-04 | Warner-Lambert Company | Method of making a savory flavor granule and a free flowing savory flavor granule |
| EP0351973A3 (en) * | 1988-07-21 | 1991-12-04 | Warner-Lambert Company | Savoury flavoured nonsweet compositions using sweet carbohydrate bulking agents and processes for their preparation |
| US5094862A (en) * | 1989-08-25 | 1992-03-10 | Warner-Lambert Company | Salt substitute granule and method of making same |
| US5266717A (en) * | 1989-04-03 | 1993-11-30 | Glenn Roy | N-(sulfomethyl)-N'arylureas |
| EP0727151A3 (en) * | 1990-06-01 | 2000-05-03 | Bioresearch, Inc. | Ingestibles containing substantially tasteless sweetness inhibitors as bitter taste reducers or substantially tasteless bitter inhibitors as sweet taste reducers |
| US6090428A (en) * | 1997-06-25 | 2000-07-18 | Joseph Ventura Rancho | Spreadable protein compositions |
| WO2001023341A1 (en) * | 1999-09-28 | 2001-04-05 | British Sugar Plc | Processes for the preparation of chemical compounds |
| WO2007022069A1 (en) | 2005-08-12 | 2007-02-22 | Cadbury Adams Usa Llc | Mouth-moistening compositions, delivery systems containing same and methods of making same |
| WO2008099730A1 (en) * | 2007-02-14 | 2008-08-21 | Kaneka Corporation | Method for production of amine compound using optically active 2-(aroyloxy)propionic acid |
| WO2012024469A1 (en) | 2010-08-18 | 2012-02-23 | Kraft Foods Global Brands Llc | Mouth-moistening gum compositions and products containing the same |
| WO2012024410A1 (en) | 2010-08-18 | 2012-02-23 | Kraft Foods Global Brands Llc | Mouth-moistening gum compositions and products containing the same |
| EP2478775A1 (en) * | 2007-03-14 | 2012-07-25 | The Concentrate Manufacturing Company of Ireland | Beverage products with non-nutritive sweetener and bitterant |
| US9314048B2 (en) | 2007-03-14 | 2016-04-19 | The Concentrate Manufacturing Company Of Ireland | Beverage products with non-nutritive sweetener and bitterant |
-
1986
- 1986-08-12 GB GB08619592A patent/GB2180534A/en not_active Withdrawn
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| Title |
|---|
| CA 61:548A * |
| CA 65:3082C * |
| CA 67(13):63467M * |
| CA 80(5):26880 P * |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0351973A3 (en) * | 1988-07-21 | 1991-12-04 | Warner-Lambert Company | Savoury flavoured nonsweet compositions using sweet carbohydrate bulking agents and processes for their preparation |
| US4994490A (en) * | 1989-04-03 | 1991-02-19 | The Nutrasweet Company | Novel N-(sulfomethyl)-N'-arylureas |
| US5266717A (en) * | 1989-04-03 | 1993-11-30 | Glenn Roy | N-(sulfomethyl)-N'arylureas |
| US5094862A (en) * | 1989-08-25 | 1992-03-10 | Warner-Lambert Company | Salt substitute granule and method of making same |
| US5021249A (en) * | 1989-11-09 | 1991-06-04 | Warner-Lambert Company | Method of making a savory flavor granule and a free flowing savory flavor granule |
| EP0727151A3 (en) * | 1990-06-01 | 2000-05-03 | Bioresearch, Inc. | Ingestibles containing substantially tasteless sweetness inhibitors as bitter taste reducers or substantially tasteless bitter inhibitors as sweet taste reducers |
| US6090428A (en) * | 1997-06-25 | 2000-07-18 | Joseph Ventura Rancho | Spreadable protein compositions |
| WO2001023341A1 (en) * | 1999-09-28 | 2001-04-05 | British Sugar Plc | Processes for the preparation of chemical compounds |
| WO2007022069A1 (en) | 2005-08-12 | 2007-02-22 | Cadbury Adams Usa Llc | Mouth-moistening compositions, delivery systems containing same and methods of making same |
| WO2008099730A1 (en) * | 2007-02-14 | 2008-08-21 | Kaneka Corporation | Method for production of amine compound using optically active 2-(aroyloxy)propionic acid |
| EP2478775A1 (en) * | 2007-03-14 | 2012-07-25 | The Concentrate Manufacturing Company of Ireland | Beverage products with non-nutritive sweetener and bitterant |
| US9314048B2 (en) | 2007-03-14 | 2016-04-19 | The Concentrate Manufacturing Company Of Ireland | Beverage products with non-nutritive sweetener and bitterant |
| WO2012024469A1 (en) | 2010-08-18 | 2012-02-23 | Kraft Foods Global Brands Llc | Mouth-moistening gum compositions and products containing the same |
| WO2012024410A1 (en) | 2010-08-18 | 2012-02-23 | Kraft Foods Global Brands Llc | Mouth-moistening gum compositions and products containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8619592D0 (en) | 1986-09-24 |
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