US20080199584A1 - Flavour Compositions - Google Patents
Flavour Compositions Download PDFInfo
- Publication number
- US20080199584A1 US20080199584A1 US12/065,189 US6518906A US2008199584A1 US 20080199584 A1 US20080199584 A1 US 20080199584A1 US 6518906 A US6518906 A US 6518906A US 2008199584 A1 US2008199584 A1 US 2008199584A1
- Authority
- US
- United States
- Prior art keywords
- flavour
- amino
- substances
- edible
- propanol
- 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.)
- Abandoned
Links
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 151
- 235000019634 flavors Nutrition 0.000 title claims abstract description 143
- 239000000203 mixture Substances 0.000 title claims abstract description 54
- 239000000126 substance Substances 0.000 claims abstract description 140
- 150000002148 esters Chemical class 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- LXQMHOKEXZETKB-UHFFFAOYSA-N 1-amino-2-methylpropan-2-ol Chemical compound CC(C)(O)CN LXQMHOKEXZETKB-UHFFFAOYSA-N 0.000 claims abstract description 26
- 235000013361 beverage Nutrition 0.000 claims abstract description 24
- 235000019505 tobacco product Nutrition 0.000 claims abstract description 20
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims abstract description 15
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims abstract description 9
- OZUKZEWKALBBMO-UHFFFAOYSA-N 2-hydroxy-n-(1-hydroxy-2-methylpropan-2-yl)propanamide Chemical compound CC(O)C(=O)NC(C)(C)CO OZUKZEWKALBBMO-UHFFFAOYSA-N 0.000 claims abstract description 9
- LHTPQZKJIPQADB-UHFFFAOYSA-N 2-hydroxy-n-(2-hydroxy-2-methylpropyl)propanamide Chemical compound CC(O)C(=O)NCC(C)(C)O LHTPQZKJIPQADB-UHFFFAOYSA-N 0.000 claims abstract description 9
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- KXBFLLVCUAQTJV-UHFFFAOYSA-N 2-hydroxy-n-(1-hydroxypropan-2-yl)propanamide Chemical compound CC(O)C(=O)NC(C)CO KXBFLLVCUAQTJV-UHFFFAOYSA-N 0.000 claims abstract description 7
- RBIYCFYMQYWICN-UHFFFAOYSA-N 2-hydroxy-n-(2-hydroxypropyl)propanamide Chemical compound CC(O)CNC(=O)C(C)O RBIYCFYMQYWICN-UHFFFAOYSA-N 0.000 claims abstract description 7
- RRMRMQQQWBIHPA-UHFFFAOYSA-N 2-hydroxy-n-(2-sulfanylpropyl)propanamide Chemical compound CC(S)CNC(=O)C(C)O RRMRMQQQWBIHPA-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003765 sweetening agent Substances 0.000 claims description 22
- 235000003599 food sweetener Nutrition 0.000 claims description 17
- PUQWHNDKVFSLDV-PXUUIUOKSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxy-n-(2-hydroxypropyl)hexanamide Chemical compound CC(O)CNC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO PUQWHNDKVFSLDV-PXUUIUOKSA-N 0.000 claims description 14
- 239000008122 artificial sweetener Substances 0.000 claims description 14
- 235000021311 artificial sweeteners Nutrition 0.000 claims description 14
- 150000001720 carbohydrates Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000006726 (C1-C5) alkenyl group Chemical group 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 235000019640 taste Nutrition 0.000 abstract description 39
- 230000001953 sensory effect Effects 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 16
- 235000013305 food Nutrition 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 235000009508 confectionery Nutrition 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- 229930006000 Sucrose Natural products 0.000 description 10
- 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 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000005720 sucrose Substances 0.000 description 10
- 229940116333 ethyl lactate Drugs 0.000 description 8
- 235000016623 Fragaria vesca Nutrition 0.000 description 7
- 240000009088 Fragaria x ananassa Species 0.000 description 7
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 235000015243 ice cream Nutrition 0.000 description 7
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 7
- 235000013618 yogurt Nutrition 0.000 description 7
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 6
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 6
- 0 [1*]C([2*])(C)C(=O)NCO.[1*]C([2*])(C)C(=O)NCS Chemical compound [1*]C([2*])(C)C(=O)NCO.[1*]C([2*])(C)C(=O)NCS 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 229960003681 gluconolactone Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000021092 sugar substitutes Nutrition 0.000 description 5
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 235000019658 bitter taste Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 230000000391 smoking effect Effects 0.000 description 4
- 235000014347 soups Nutrition 0.000 description 4
- 235000019583 umami taste Nutrition 0.000 description 4
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 3
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 3
- 206010013911 Dysgeusia Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000010630 cinnamon oil Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000174 gluconic acid Substances 0.000 description 3
- 235000012208 gluconic acid Nutrition 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229940041616 menthol Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 210000001706 olfactory mucosa Anatomy 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000019613 sensory perceptions of taste Nutrition 0.000 description 3
- 235000014214 soft drink Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000035923 taste sensation Effects 0.000 description 3
- AGFPRLRGCNTACW-UHFFFAOYSA-N (2-amino-2-methylpropyl) dihydrogen phosphate Chemical compound CC(C)(N)COP(O)(O)=O AGFPRLRGCNTACW-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-TXICZTDVSA-N (2r,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-TXICZTDVSA-N 0.000 description 2
- RGHNJXZEOKUKBD-STGXQOJASA-N (2s,3s,4s,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-STGXQOJASA-N 0.000 description 2
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-AIHAYLRMSA-N D-altronic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-AIHAYLRMSA-N 0.000 description 2
- RGHNJXZEOKUKBD-MGCNEYSASA-N D-galactonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-MGCNEYSASA-N 0.000 description 2
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 2
- RGHNJXZEOKUKBD-MBMOQRBOSA-N D-mannonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-MBMOQRBOSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 239000005770 Eugenol Substances 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-QTBDOELSSA-N L-gulonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-QTBDOELSSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SKNVOMKLSA-N L-idonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SKNVOMKLSA-N 0.000 description 2
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
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- 125000000217 alkyl group Chemical group 0.000 description 2
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- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 2
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- 230000008025 crystallization Effects 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000011850 desserts Nutrition 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 235000015071 dressings Nutrition 0.000 description 1
- 230000000504 effect on taste Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229940035034 maltodextrin Drugs 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 235000013923 monosodium glutamate Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical class [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000015504 ready meals Nutrition 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 210000002265 sensory receptor cell Anatomy 0.000 description 1
- 102000027509 sensory receptors Human genes 0.000 description 1
- 108091008691 sensory receptors Proteins 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- -1 terpene hydrocarbons Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 235000021119 whey protein Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
-
- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2022—Aliphatic compounds containing sulfur
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to the field of improving the flavour of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products. More particularly, the present invention provides flavour compositions that can be used to confer a fuller and richer taste to foodstuffs, beverages, pharmaceutics, tobacco products and oral care products.
- the flavour compositions according to the invention are characterised by the presence of one or more flavour modulating substances that are capable of improving and complementing the impact of other flavour imparting substances.
- the present invention also encompasses the use of the aforementioned flavour modulating substances for improving the taste of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products, as well as to foodstuffs, beverages, pharmaceutics, tobacco products and oral care products containing these substances.
- the flavour of foodstuffs and beverages consists of two parts: the aroma and the taste.
- aroma In general what is perceived through the olfactory epithelium in the nasal cavity is referred to as ‘aroma’, whereas the term ‘taste’ is generally used to describe the sensory impact that is perceived via the mouth, especially the tongue.
- the flavour sensation experienced upon consumption, especially the taste provides the final analysis of food prior to ingestion thereof.
- Visual and olfactory (smell) signals already give a first indication but only after intake of the food into the mouth the final decision is made either to ingest or to reject the food.
- Sweet taste is usually a signal that the food is safe (appetising) leading to ingestion of the food.
- Chlorogenic acids are claimed to enhance sweetness and to reduce bitterness (WO02100192).
- flavourings In sweet and beverage products, further examples of the importance of the gustative dimension of flavourings have been reported. These examples include taste attributes such as bitterness, tingling and cooling-freshness.
- bitterness is an essential aspect of some food flavours, among which chocolate taste.
- Purine alkaloids like theobromine and caffeine, as well as amino acids and peptides have been known for a long time as bitter substances.
- British patent no. GB 1420909 it is disclosed that the bitter flavour of cocoa can be reproduced using a combination of a purine alkaloid and an amino acid or an oligopeptide which ‘produces a surprisingly more natural simultaneously bitter and astringent flavour note than either of these types of substances alone’.
- Menthol an important constituent of peppermint oil, has a strong impact on flavoured products not only because of its mint smell but also because it imparts a cooling and fresh taste.
- menthol in other types of flavour to impart a cool taste.
- US patent application no. US2005013846 discloses how menthol and derivatives thereof can be used as flavouring in water continuous spreadable acidified food products to obtain table spreads exhibiting a fresh, cool taste impression.
- cinnamic aldehyde and eugenol constituents of cinnamon oil
- flavouring composition for confectionery products, not only for their smell but also because they impart a warm and tingling taste.
- the oral pungency of cinnamic aldehyde was described as burning and tingling by Cliff M and Heymann H [Journal of Sensory Studies 7 (1992)279-290]. According to the same authors eugenol exhibits a long-lasting numbing effect.
- Cinnamon oil has been proposed as a taste improving flavouring.
- International patent application no. WO9006689 discloses that cinnamon oil, among other spice extracts, added to a minty flavour formulation, can be used to improve the long-lasting flavour of chewing-gum.
- flavour modulating substances that provide a positive contribution to the flavour, especially taste, of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products they are incorporated in.
- One objective of the present invention therefore is to provide such substances and compositions comprising them.
- the present inventors have surprisingly found that the substances according to formulas (I) and (II) and edible salts and esters thereof can be used advantageously to improve the flavour of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products:
- the present flavour modulating substances can advantageously be employed to impart desirable taste attributes in a wide variety of applications and products, especially food, beverages and confectionery.
- the present flavour modulating substances are capable of modifying the taste and/or aroma impact of other flavour ingredients contained within these same products, thereby improving the overall flavour quality of these products.
- WO 92/06601 discloses certain amide based, non-caloric sugar substitutes derived from sugar carboxylic acids and amino alcohols, which possess similar physical rheological and colligative properties to sucrose. These substances may be used as sugar substitutes for formulated foods such as confectioneries, beverages, bakery products and the like, in order to simulate the structure, texture, freezing point depression, moisture retention, density, water solubility, solution viscosity properties, stability, non-reactivity and appearance characteristics of sucrose. Optionally these sugar substitutes may be used in combination with a high potency (artificial) sweetener, typical proportions thereof ranging from about 0.2 to 2.0 parts of artificial sweetener per 100 parts of the sugar substitute.
- WO 92/06601 discloses a foodstuff (yellow cake) comprising 28.3 wt % of the sugar substitute.
- the present invention thus relates to the aforementioned flavour modulating substances and to flavour compositions, foodstuffs, beverages, pharmaceutics, tobacco products and oral care products comprising one or more of these flavour modulating substances.
- Other aspects of the present invention relate to the use of said flavour modulating substances for improving the flavour of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products.
- Flavour modulating substances that can be used in accordance with the present invention are selected from the group of substances represented by the following formula (I) or (II), edible salts thereof and edible esters thereof:
- a first aspect of the invention therefore provides a flavour modulating substance selected from the group of substances represented by said formulas (I) or (II), edible salts thereof and edible esters thereof, as defined here above, with the proviso that said substance is not N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, an edible salt thereof or an edible ester thereof.
- Another aspect of the invention provides a composition comprising at least 0.001 ppm, preferably at least 0.01 ppm, more preferably at least 0.1 ppm, still more preferably at least 1 ppm of one or more flavour modulating substances selected from the group of substances represented by said formula (I) or formula (II), edible salts thereof and edible esters thereof, as defined here above, with the proviso that said one or more flavour modulating substances do not comprise N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, edible salts thereof and/or edible esters thereof.
- Still another aspect of the invention provides a flavour composition comprising i) at least 0.1 wt.
- flavour modulating substances selected from the group of substances represented by formula (I) or (II), edible salts thereof and edible esters thereof, with the proviso that if the composition comprises N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, an edible salt thereof and/or an edible ester thereof, the ratio between these flavour modulating substances and the flavouring substances is less than 50:1.
- the present (flavour) compositions do not comprise N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, edible salts thereof and/or edible esters thereof.
- flavouring substance encompasses any substance that is not represented by formula (I) and that is capable of imparting a detectable flavour impact, especially at a concentration below 0.1 wt. %, more preferably below 0.01 wt. %, as well as sweeteners, including saccharide sweeteners and artificial sweeteners.
- the present flavouring substance belongs to one of the chemical classes of alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said flavouring substances can be of natural or synthetic origin. Many of these are listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, N.J., USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of flavours.
- saccharide sweetener refers to sweeteners that contain one or more saccharide units and that exhibit a sweetness potency that is of the same order of magnitude as the sweetness potency of sucrose. Typically, the sweetness potency of such saccharide sweeteners is between 20% and 500% the sweetness potency of sucrose.
- artificial sweetener is used in here to refer to synthetic sweeteners that have a much higher sweetener potency than sucrose, especially a sweetness potency that exceeds the sweetness potency of sucrose by at least a factor 10, preferably by at least a factor 20.
- flavour modulating refers to the capability of a composition or substance to alter the taste and/or aroma impact of other, flavour imparting, substances present within the same product, with the proviso that this change in taste and/or aroma impact is not caused by the flavour contribution of said flavour modulating composition or substance per se, but instead that it mainly results from the combined effect of on the one hand the flavour modulating composition or substance and on the other hand the other flavour imparting substances.
- the present substances combine the capability of modulating the taste and/or aroma impact of other, flavour imparting, substances and a taste contribution of their own. The favourable impact of the present flavour modulating substances is believed to be the result of the combination of these two effects.
- the flavour composition according to the invention contains at least 0.1 wt. % of the flavour modulating substances as defined above.
- the amount of the flavour modulating substances does not exceed 90 wt. %, preferably it does not exceed 40 wt. %, even more preferably the flavour composition comprises less than 25 wt % of the flavour modulating substance, most preferably less than 5 wt %.
- flavour composition according to the invention comprises flavouring substances in an amount of at least 0.5 wt. %, preferably at least 1 wt. %, based on the total weight of the composition.
- amount of flavouring substances does not exceed 95 wt %, more preferably it does not exceed 50 wt %.
- flavour modulating substances and flavouring substances as defined herein before are employed in a weight ratio of less than 50:1, preferably less than 20:1.
- said weight ratio is within the range of 1:100 to 10:1, more preferably within the range of 1:50 to 5:1.
- the flavour modulating substances and flavouring substances are employed in a weight ratio that does not exceed 1:1.
- flavouring composition comprises a flavour modulating substance selected from N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, salts thereof and esters thereof, said flavouring composition comprising artificial sweetener, said ratio of the total amount of these flavour modulating substance(s) and the amount of artificial sweetener is less than 50:1, more preferably less than 20:1. Most preferably, the present flavouring composition contains essentially no artificial sweetener.
- the flavour composition according to the present invention may suitably be prepared in the form of a liquid, a paste or a powder.
- the flavour composition is a free flowing powder.
- the present flavour composition comprises at least one flavour carrier, i.e. a material which does not significantly alter the organoleptic properties of the composition.
- Said carrier may be liquid or solid. Suitable examples include maltodextrin, modified starch, gum Arabic, ethanol and propylene glycol.
- the present flavouring composition is selected from the group consisting of dairy flavourings, e.g. butter and milk flavourings, fruit flavourings, e.g. citrus and red fruit flavourings, savoury flavourings, e.g. meat and cheese flavourings, and bread flavourings.
- flavour modulating substances according to formulas (I) and (II) wherein one of R 1 and R 2 represent C 3 -C 4 alkyl or C 3 -C 4 alkenyl substituted with 3 or 4 substituents selected from hydroxyl and oxo, more preferably butyl wherein each carbon atom is substituted with a substituent selected from hydroxyl and oxo and one of R 1 and R 2 represents hydrogen.
- RK and/or R 1 represent C 1 -C 2 alkyl or C 1 -C 2 carboxyl each optionally substituted with a hydroxyl group. Still more preferably one of R 1 and R 2 represent a methyl group. In a most preferred embodiment one of RK and R 2 represents hydrogen.
- R 3 represents hydrogen
- X in formula (I) or (II) represents ethylene, substituted with 1-4 methyl groups. More preferably X represents ethylene substituted with 2-4 methyl groups, more preferably X represents ethylene substituted with 2 methyl groups, most preferably X represents 1,1-dimethylethylene, or 2,2-dimethylethylene.
- the one or more flavour modulating substances are selected from the group of substances represented by formula (I), edible alts thereof and edible esters thereof.
- the present invention relates to flavour modulating substances and to compositions comprising them, as defined herein before, wherein said flavour modulating substances are selected from the group of derivatives of ⁇ -hydroxycarboxylic acids, preferably lactic acid, malic acid, tartaric acid, citric acid, glucuronic acid, galactumic acid or an aldonic acid such as allonic acid, altronic acid, gluconic acid, mannonic acid, gulonic acid, idonic acid, galactonic acid and talonic acid; and an amine selected from 2-methyl-2-aminopropanol, 2-methyl-1-amino-2-propanol and 2-methyl-2-aminopropyl dihydrogen phosphate; most preferably derivatives of lactic acid or gluconic acid and 2-methyl-2-amino-1-propanol; as well as edible salts and esters thereof.
- said flavour modulating substances are selected from the group of derivatives of ⁇ -hydroxycarboxylic acids, preferably lactic acid, malic acid,
- said flavour modulating substances are selected from the group of 2-hydroxy-N-(2-hydroxy-2-methylpropyl)-propanamide, N-lactoyl 1-amino-2-propanol, N-lactoyl 2-amino-i-propanol, N-lactoyl 2-amino-2-methylpropanol, N-gluconyl 1-amino-2-methyl-2-propanol, N-gluconyl 1-amino-2-propanol, N-gluconyl 2-amino-1-propanol, N-gluconyl 2-amino-2-methylpropanol, N-(2-mercaptopropyl)lactamide, edible salts thereof and edible esters thereof.
- the flavour modulating substances are selected from the group of substances represented by formula (I), edible salts thereof, and edible esters thereof, even more preferably from the group of 2-hydroxy-N-(2-hydroxy-2-methylpropyl)-propanamide, N-lactoyl 1-amino-2-propanol, N-lactoyl 2-amino-1-propanol, N-lactoyl 2-amino-2-methylpropanol, N-gluconyl 1-amino-2-methyl-2-propanol, N-gluconyl 1-amino-2-propanol, N-gluconyl 2-amino-1-propanol, N-gluconyl 2-amino-2-methylpropanol edible salts thereof and edible esters thereof
- the term ‘edible esters thereof’ encompasses any edible derivative of the present flavour modulating substances and an acid.
- said acid is an organic acid such as a substituted or non-substituted, linear or branched C 1 -C 6 carboxylic acid, more preferably a C 1 -C 4 carboxylic acid, most preferably a C 1 -C 3 carboxylic acid, or alternatively an inorganic acid such as phosphoric acid.
- Such esters may be hydrolysed to produce flavour modulating substances according to the present invention during storage, processing and the like (acting as so called precursors).
- the present flavour modulating substance is selected from the group of substances represented by formulas (I) or (II) as defined herein before and edible salts thereof.
- flavour modulating substances are very useful ingredients which, in the presence of other flavouring substances, are capable of imparting highly appreciated taste sensations to the products in which they are incorporated, specifically “roundness”, “fullness”, “substance”, “continuity”, “ginger-like”, “tingling”, “fatty”, “metallic”, “umami” and/or “bitter”. Because of this, the present flavour modulating substances can be employed to improve the taste of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products.
- flavour modulating substances of the present invention are capable of imparting highly desirable taste attributes.
- flavour modulating substances according to the invention are capable of modifying and complementing the sensory impact of other, flavour imparting, substances contained in the aforementioned products.
- flavour modulating substances according to the invention are not particularly volatile, they do not produce a strong aroma impact, even though they can affect the aroma impact of other, flavour imparting, substances.
- aroma refers to the aspect of taste that is perceived through the olfactory epithelium. Because of the low volatility of the present flavour modulating substances it is believed that the advantageous properties of these substances are somehow associated with the impact that these substances have on the sensory receptors located within the mouth.
- WO 92/06601 describes ingredients that, because of the physical properties thereof, could be used to replace sucrose as a structuring and/or texturizing agent in sweetened foodstuffs such as confectionery products, bakery products and beverages.
- Two of the substances described in this document are N-[2-hydroxypropyl]-gluconamide and/or N-[2-hydroxypropyl]-glucoheptonamide.
- these ‘structuring agents’ have to be applied in major amounts in food applications.
- WO 92/06601 describes a yellow cake comprising 28.3 wt % of said structuring agent.
- WO 92/06601 only mentions that the structuring agents disclosed therein, have a sweetness potency corresponding to 0-100% of that of sucrose, and that, in order to accomplish the same final effect as sucrose in formulated foods, an amount of artificial high potency sweetener might be included in proportions ranging between 0.2-2.0 parts of sweetener per 100 parts of the structuring agent.
- present flavour modulating substances differs from this disclosure in that they are used only in minor amounts in order to impart a taste improving effect in combination with other (volatile) flavour substances.
- the contribution thereof on structure and texture, i.e. on the physical properties, is essentially insignificant.
- Yet another aspect of the present invention relates to a product selected from the group consisting of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products, said product comprising between 0.1 and 10,000 ppm (mg/kg) of one or more flavour modulating substances as defined herein before. More preferably, the product contains at least 1 ppm, most preferably at least 5 ppm of the one or more flavour modulating substances. Typically, the aforementioned products contain the flavour modulating substance(s) in a concentration of not more than 5,000 ppm, preferably of not more than 2,000 ppm. The present products may further comprise one or more other flavouring substances, typically in amounts of 5-20,000 ppm, more preferably 10-10,000 ppm. The precise level in which the present substances are incorporated depends on the nature of the flavour modulating substance(s) and the nature of the product, as will be clear to the skilled person.
- flavour modulating substances and flavouring substances as defined herein before are employed in a weight ratio of less than 50: 1, preferably less than 20:1.
- said weight ratio is within the range of 1:100 to 10:1, more preferably within the range of 1:50 to 5:1.
- the flavour modulating substances and flavouring substances are employed in a weight ratio that does not exceed 1:1.
- the present products comprising N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, edible salts thereof and/or edible esters thereof preferably exhibit a weight ratio of said flavour modulating substances and other flavouring substances of less than 50:1, preferably less than 10:1.
- the present product contains no N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, edible salts thereof and edible esters thereof.
- said product does not contain added saccharide sweetener or artificial sweetener.
- the product contains N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, edible salts thereof and/or edible esters thereof in combination with added sweetener, said product being characterised by the fact that the weight ratio of the flavour modulating substances and saccharide sweetener does not exceed 1:1, preferably does not exceed 1:2; and by the fact that the weight ratio of the taste improving substances and artificial sweetener is less than 50:1, preferably less than 10:1, even more preferably less than 1:1.
- Typical examples of foodstuffs according to the present invention include yoghurt, ice cream, desserts, confectioneries, bakery products, sweet snacks, seasonings, sauces, stock, soups, dressings and ready meals.
- the benefits of the present invention may also be realised in beverages, in oral care products such as toothpaste and mouthwash, in pharmaceutics such as pills and elixirs and in tobacco products, which includes any type of tobacco product for smoking as well as for non-smoking applications. It is noted that tobacco-like products are available for both smoking and non-smoking applications.
- the use of the present flavour modulating substances in these tobacco substitutes is also encompassed by the present invention.
- the present invention relates to a process of improving the flavour of a foodstuff, a beverage, a pharmaceutical product, a tobacco product or an oral care product, comprising adding to said product one or more flavour modulating substances as defined herein before. More preferably the present process comprises adding to said product an amount of at least 0.1 ppm (mg/kg), still more preferably at least 5 ppm, most preferably at least 10 ppm of the present one or more flavour modulating substances. It is furthermore preferred that said amount does not exceed 10,000 ppm (mg/kg), more preferably it does not exceed 5,000 ppm, most preferably it does not exceed 2,000 ppm.
- Substances according to formulas (I) and (II) are suitably produced by reacting an ⁇ -hydroxycarboxylic acid represented by the following formula (III) and/or edible salts and/or esters thereof and an amine represented by the following formula (IV) or formula (V) respectively, and/or edible salts and/or esters thereof:
- R1, R2, R3 and X have the same meaning as defined herein before with regard to formulas (I) and (II).
- flavour modulating substance preferably a flavour modulating substance as defined herein before, comprising reacting an a-hydroxycarboxylic acid represented by formula (III) and/or edible salts and/or esters thereof and an amine represented by formula (IV) or formula (V) and/or edible salts and/or esters thereof.
- the ⁇ -hydroxycarboxylic acid is selected from the group of lactic acid, malic acid, tartaric acid, citric acid, glucuronic acid, galactumic acid or an aldonic acid such as allonic acid, altronic acid, gluconic acid, mannonic acid, gulonic acid, idonic acid, galactonic acid and talonic acid; and the amine is selected from 2-methyl-2-aminopropanol, 2-methyl-1-amino-2-propanol, 2-methyl-2-aminopropyl dihydrogen phosphate and 1-aminopropane-2-thiol.
- said reaction is performed by heating to reflux said reactants in an organic solvent, such as toluene, hexane or benzylalcohol, for a period of between 0.1-10 hours.
- an organic solvent such as toluene, hexane or benzylalcohol
- the reaction product is typically obtained as a precipitate and can be isolated by evaporating the solvent and optionally further purified using any of the techniques known by the skilled person, such as chromatography and crystallization.
- Another aspect of the present invention relates to substances obtainable by this process.
- the reaction was carried out in a closed tube placed in a steam reaction block.
- the tube was charged with 20 g of a 32% aqueous ammonia solution and 5 g 2,2-dimethyl oxirane and kept at a temperature of 95° C. for 2 hours. Then the tube was cooled to room temperature. The excess ammonia was evaporated by heating the reaction mixture to 70° C. Water was removed on a rotary evaporator. 4.5 g of 1-amino-2-methyl-2-propanol was obtained and analyzed by GC.
- the crude product was then purified on a column filled with 50 g of silica gel 60 F254 (0.06-0.02mm) in 200 ml THF.
- 2.4 g crude N-lactoyl 1-amino-2-methyl-2-propanol was dissolved in THF and then the solution was transferred to the top of the silica gel column.
- the column was eluted with THF and fractions of 20 ml were collected. A total of 22 fractions were collected. Finally the column was rinsed with 100 ml methanol. All fractions were checked by TLC. Fractions were selected and combined, based on the results of TLC analysis (shown below in table 1). Then the solvent was removed on the rotary evaporator to furnish the purified product. Only the obtained product from fractions 3 till 5 was sampled for NMR analysis.
- Ice cream composition % Hydrogenated coconut fat (CN32) 8.00 Skimmed milkpowder 7.00 Whey protein concentrate 3.00 Sucrose 12.00 Corn syrup solids (DE39) 5.00 Sherex IC 9328 0.50 Flavour + Colour + Water Up to 100
- a standard chicken soup was prepared. The quantity was split in two. One part was kept as reference and the other part was dosed to contain 5 ppm of N-gluconyl 2-amino-2-methyl-propanol (as prepared in Example 8). The soups were tasted by a professional panel.
- the soup containing the N-gluconyl 2-amino-2-methyl-propanol was unanimously described as more tasteful, more complete, more body, more fatty.
- Two different soft drinks A and B were prepared by adding respectively 40 ppb and 4 ppm of N-lactoyl 2-amino-2-methyl-propanol (as prepared in Example 4) to a commercially available carbonated orange flavoured soft drink.
- Sample A was judged as more natural, with a more juicy character than the original.
- Sample B exhibited the tingling character typical of the flavour modulating substances of the present invention, which was judged as very pleasant and particularly well suited for the orange flavour.
Abstract
Description
- The present invention relates to the field of improving the flavour of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products. More particularly, the present invention provides flavour compositions that can be used to confer a fuller and richer taste to foodstuffs, beverages, pharmaceutics, tobacco products and oral care products. The flavour compositions according to the invention are characterised by the presence of one or more flavour modulating substances that are capable of improving and complementing the impact of other flavour imparting substances.
- The present invention also encompasses the use of the aforementioned flavour modulating substances for improving the taste of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products, as well as to foodstuffs, beverages, pharmaceutics, tobacco products and oral care products containing these substances.
- The flavour of foodstuffs and beverages consists of two parts: the aroma and the taste. In general what is perceived through the olfactory epithelium in the nasal cavity is referred to as ‘aroma’, whereas the term ‘taste’ is generally used to describe the sensory impact that is perceived via the mouth, especially the tongue. The flavour sensation experienced upon consumption, especially the taste, provides the final analysis of food prior to ingestion thereof. Visual and olfactory (smell) signals already give a first indication but only after intake of the food into the mouth the final decision is made either to ingest or to reject the food. Sweet taste is usually a signal that the food is safe (appetising) leading to ingestion of the food. The ‘reactions’ to salt and umami are really dependent on the strength of the signal. Bitter and sour are usually experienced as repulsive taste sensations that can lead to rejection. Temperature is another measure by which the food is judged just as well as aching sensations like capsaicin (hot pepper) and certain chemicals (like carbon dioxide).
- In short, this means that taste is a very important and very complex system. Until recently most flavour research was focused towards aroma. Especially the last years a series of publications relating to molecules with a (positive) contribution to the taste of foodstuffs has emerged.
- Such research has been stimulated significantly by the fact that quite some receptors which are involved in the different taste sensations have been characterized by now (B. Lindemann; Nature 413, 219 (2001)).
- Another interesting aspect of taste is that it can have an impact on aroma. It was reported that people having artificially sweetened water in their mouth were significantly more sensitive to the smell of benzaldehyde than people having plain water in their mouth (P. Dalton et al, Nature Neurosci. 3, 431-432 (2000)).
- Several screening systems have been described that make it possible to screen, in a short time, large series of molecules for their (modulating) effect on taste response (cf. WO04055048, GB2396414, WO0177292 and US2004/0072254).
- Most research on taste modulation so far has been devoted to taste enhancement in savoury products. Several, mainly Japanese, publications describe umami molecules, i.e. alternatives to mono sodium glutamate (MSG) (H Suzuki et al, J Agric Food Chem 50, 313-318 (2002); K Shima et al, J Agric Food Chem 46, 1465-1468 (1998); Y Ueda et al, Biosc Biotech Biochem 61 1977 (1997)).
- In EP 1291342, a ‘general taste enhancer’ is disclosed that was reported to be suitable for enhancing sweetness as well.
- In patent applications WO9704667 and WO04075663 tripeptides and amino acid condensates with lactic acid and succinic acid are described that have both their own taste as well as some enhancing properties. Alpha keto acids are reported to give body and mouthfeel to foodstuffs they are added to (U.S. Pat. No. 6,287,620).
- Chlorogenic acids are claimed to enhance sweetness and to reduce bitterness (WO02100192).
- Quite a bit of work has been devoted to find bitter taste suppressors (A. N. Pronin et al, Chemical Senses 29, 583-593 (2004); EP1401500; P. A. Breslin, Trends in Food Science & Technology 7, 390-399 (1996)).
- In sweet and beverage products, further examples of the importance of the gustative dimension of flavourings have been reported. These examples include taste attributes such as bitterness, tingling and cooling-freshness.
- Bitterness is an essential aspect of some food flavours, among which chocolate taste. Purine alkaloids, like theobromine and caffeine, as well as amino acids and peptides have been known for a long time as bitter substances. In British patent no. GB 1420909 it is disclosed that the bitter flavour of cocoa can be reproduced using a combination of a purine alkaloid and an amino acid or an oligopeptide which ‘produces a surprisingly more natural simultaneously bitter and astringent flavour note than either of these types of substances alone’.
- Menthol, an important constituent of peppermint oil, has a strong impact on flavoured products not only because of its mint smell but also because it imparts a cooling and fresh taste. Next to mint flavoured products, it has been suggested to employ menthol in other types of flavour to impart a cool taste. US patent application no. US2005013846 for example discloses how menthol and derivatives thereof can be used as flavouring in water continuous spreadable acidified food products to obtain table spreads exhibiting a fresh, cool taste impression.
- Similarly, cinnamic aldehyde and eugenol, constituents of cinnamon oil, are used in flavouring composition for confectionery products, not only for their smell but also because they impart a warm and tingling taste. The oral pungency of cinnamic aldehyde was described as burning and tingling by Cliff M and Heymann H [Journal of Sensory Studies 7 (1992)279-290]. According to the same authors eugenol exhibits a long-lasting numbing effect. Cinnamon oil has been proposed as a taste improving flavouring. International patent application no. WO9006689 discloses that cinnamon oil, among other spice extracts, added to a minty flavour formulation, can be used to improve the long-lasting flavour of chewing-gum.
- There is still a need for new so-called flavour modulating substances that provide a positive contribution to the flavour, especially taste, of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products they are incorporated in. One objective of the present invention therefore is to provide such substances and compositions comprising them.
- The present inventors have surprisingly found that the substances according to formulas (I) and (II) and edible salts and esters thereof can be used advantageously to improve the flavour of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products:
- The present flavour modulating substances can advantageously be employed to impart desirable taste attributes in a wide variety of applications and products, especially food, beverages and confectionery. In addition, the present flavour modulating substances are capable of modifying the taste and/or aroma impact of other flavour ingredients contained within these same products, thereby improving the overall flavour quality of these products.
- WO 92/06601 discloses certain amide based, non-caloric sugar substitutes derived from sugar carboxylic acids and amino alcohols, which possess similar physical rheological and colligative properties to sucrose. These substances may be used as sugar substitutes for formulated foods such as confectioneries, beverages, bakery products and the like, in order to simulate the structure, texture, freezing point depression, moisture retention, density, water solubility, solution viscosity properties, stability, non-reactivity and appearance characteristics of sucrose. Optionally these sugar substitutes may be used in combination with a high potency (artificial) sweetener, typical proportions thereof ranging from about 0.2 to 2.0 parts of artificial sweetener per 100 parts of the sugar substitute. WO 92/06601 discloses a foodstuff (yellow cake) comprising 28.3 wt % of the sugar substitute.
- The present invention thus relates to the aforementioned flavour modulating substances and to flavour compositions, foodstuffs, beverages, pharmaceutics, tobacco products and oral care products comprising one or more of these flavour modulating substances. Other aspects of the present invention relate to the use of said flavour modulating substances for improving the flavour of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products.
- Flavour modulating substances that can be used in accordance with the present invention are selected from the group of substances represented by the following formula (I) or (II), edible salts thereof and edible esters thereof:
- wherein
-
- R1 and R2 independently represent hydrogen, C1-C5 alkyl or C1-C5 alkenyl each optionally substituted with one or more substituents selected from hydroxyl, oxo and C1-C3 carboxyl;
- R3 represents hydrogen or C1-C3 alkyl; and
- X represents ethylene substituted with 1-4 substituents selected from methyl, ethyl and propyl.
- A first aspect of the invention therefore provides a flavour modulating substance selected from the group of substances represented by said formulas (I) or (II), edible salts thereof and edible esters thereof, as defined here above, with the proviso that said substance is not N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, an edible salt thereof or an edible ester thereof.
- Another aspect of the invention provides a composition comprising at least 0.001 ppm, preferably at least 0.01 ppm, more preferably at least 0.1 ppm, still more preferably at least 1 ppm of one or more flavour modulating substances selected from the group of substances represented by said formula (I) or formula (II), edible salts thereof and edible esters thereof, as defined here above, with the proviso that said one or more flavour modulating substances do not comprise N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, edible salts thereof and/or edible esters thereof. Still another aspect of the invention provides a flavour composition comprising i) at least 0.1 wt. % of one or more flavouring substances, optionally including saccharide sweetener in an amount of 0-20% by weight of the composition and/or artificial sweetener in an amount of 0-3% by weight of the composition; and ii) between 0.001 and 95 wt. % of one or more flavour modulating substances selected from the group of substances represented by formula (I) or (II), edible salts thereof and edible esters thereof, with the proviso that if the composition comprises N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, an edible salt thereof and/or an edible ester thereof, the ratio between these flavour modulating substances and the flavouring substances is less than 50:1.
- According to a preferred embodiment the present (flavour) compositions do not comprise N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, edible salts thereof and/or edible esters thereof.
- Throughout this document the term “flavouring substance” encompasses any substance that is not represented by formula (I) and that is capable of imparting a detectable flavour impact, especially at a concentration below 0.1 wt. %, more preferably below 0.01 wt. %, as well as sweeteners, including saccharide sweeteners and artificial sweeteners. Typically, the present flavouring substance belongs to one of the chemical classes of alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said flavouring substances can be of natural or synthetic origin. Many of these are listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, N.J., USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of flavours.
- The term “saccharide sweetener” as used in here refers to sweeteners that contain one or more saccharide units and that exhibit a sweetness potency that is of the same order of magnitude as the sweetness potency of sucrose. Typically, the sweetness potency of such saccharide sweeteners is between 20% and 500% the sweetness potency of sucrose.
- The term “artificial sweetener” is used in here to refer to synthetic sweeteners that have a much higher sweetener potency than sucrose, especially a sweetness potency that exceeds the sweetness potency of sucrose by at least a factor 10, preferably by at least a factor 20.
- Throughout this document the term “flavour” is to describe the sensory impact that is perceived via the mouth, especially the tongue, and the olfactory epithelium in the nasal cavity. The term “flavour modulating” as used herein refers to the capability of a composition or substance to alter the taste and/or aroma impact of other, flavour imparting, substances present within the same product, with the proviso that this change in taste and/or aroma impact is not caused by the flavour contribution of said flavour modulating composition or substance per se, but instead that it mainly results from the combined effect of on the one hand the flavour modulating composition or substance and on the other hand the other flavour imparting substances. The present substances combine the capability of modulating the taste and/or aroma impact of other, flavour imparting, substances and a taste contribution of their own. The favourable impact of the present flavour modulating substances is believed to be the result of the combination of these two effects.
- Preferably, the flavour composition according to the invention contains at least 0.1 wt. % of the flavour modulating substances as defined above. Typically, the amount of the flavour modulating substances does not exceed 90 wt. %, preferably it does not exceed 40 wt. %, even more preferably the flavour composition comprises less than 25 wt % of the flavour modulating substance, most preferably less than 5 wt %.
- In a preferred embodiment the flavour composition according to the invention comprises flavouring substances in an amount of at least 0.5 wt. %, preferably at least 1 wt. %, based on the total weight of the composition. Preferably, the amount of flavouring substances does not exceed 95 wt %, more preferably it does not exceed 50 wt %.
- Preferably, in the present flavour composition the flavour modulating substances and flavouring substances as defined herein before are employed in a weight ratio of less than 50:1, preferably less than 20:1. In a preferred embodiment said weight ratio is within the range of 1:100 to 10:1, more preferably within the range of 1:50 to 5:1. Most preferably, the flavour modulating substances and flavouring substances are employed in a weight ratio that does not exceed 1:1.
- Preferably, in case the flavouring composition comprises a flavour modulating substance selected from N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, salts thereof and esters thereof, said flavouring composition comprising artificial sweetener, said ratio of the total amount of these flavour modulating substance(s) and the amount of artificial sweetener is less than 50:1, more preferably less than 20:1. Most preferably, the present flavouring composition contains essentially no artificial sweetener.
- The flavour composition according to the present invention may suitably be prepared in the form of a liquid, a paste or a powder. In a particularly preferred embodiment the flavour composition is a free flowing powder. Typically, the present flavour composition comprises at least one flavour carrier, i.e. a material which does not significantly alter the organoleptic properties of the composition. Said carrier may be liquid or solid. Suitable examples include maltodextrin, modified starch, gum Arabic, ethanol and propylene glycol.
- In a preferred embodiment, the present flavouring composition is selected from the group consisting of dairy flavourings, e.g. butter and milk flavourings, fruit flavourings, e.g. citrus and red fruit flavourings, savoury flavourings, e.g. meat and cheese flavourings, and bread flavourings.
- It was found that particularly satisfying results can be obtained with flavour modulating substances according to formulas (I) and (II) wherein one of R1 and R2 represent C3-C4 alkyl or C3-C4 alkenyl substituted with 3 or 4 substituents selected from hydroxyl and oxo, more preferably butyl wherein each carbon atom is substituted with a substituent selected from hydroxyl and oxo and one of R1 and R2 represents hydrogen.
- In another equally preferred embodiment RK and/or R1 represent C1-C2 alkyl or C1-C2 carboxyl each optionally substituted with a hydroxyl group. Still more preferably one of R1 and R2 represent a methyl group. In a most preferred embodiment one of RK and R2 represents hydrogen.
- Preferably, in the aforementioned formulas (I) and (II), R3 represents hydrogen.
- According to yet another preferred embodiment, X in formula (I) or (II), represents ethylene, substituted with 1-4 methyl groups. More preferably X represents ethylene substituted with 2-4 methyl groups, more preferably X represents ethylene substituted with 2 methyl groups, most preferably X represents 1,1-dimethylethylene, or 2,2-dimethylethylene.
- According to still another preferred embodiment of the invention, the one or more flavour modulating substances are selected from the group of substances represented by formula (I), edible alts thereof and edible esters thereof.
- According to another preferred embodiment, the present invention relates to flavour modulating substances and to compositions comprising them, as defined herein before, wherein said flavour modulating substances are selected from the group of derivatives of α-hydroxycarboxylic acids, preferably lactic acid, malic acid, tartaric acid, citric acid, glucuronic acid, galactumic acid or an aldonic acid such as allonic acid, altronic acid, gluconic acid, mannonic acid, gulonic acid, idonic acid, galactonic acid and talonic acid; and an amine selected from 2-methyl-2-aminopropanol, 2-methyl-1-amino-2-propanol and 2-methyl-2-aminopropyl dihydrogen phosphate; most preferably derivatives of lactic acid or gluconic acid and 2-methyl-2-amino-1-propanol; as well as edible salts and esters thereof.
- According to a still more preferred embodiment said flavour modulating substances are selected from the group of 2-hydroxy-N-(2-hydroxy-2-methylpropyl)-propanamide, N-lactoyl 1-amino-2-propanol, N-lactoyl 2-amino-i-propanol, N-lactoyl 2-amino-2-methylpropanol, N-gluconyl 1-amino-2-methyl-2-propanol, N-gluconyl 1-amino-2-propanol, N-gluconyl 2-amino-1-propanol, N-gluconyl 2-amino-2-methylpropanol, N-(2-mercaptopropyl)lactamide, edible salts thereof and edible esters thereof. According to a particularly preferred embodiment of the invention, the flavour modulating substances are selected from the group of substances represented by formula (I), edible salts thereof, and edible esters thereof, even more preferably from the group of 2-hydroxy-N-(2-hydroxy-2-methylpropyl)-propanamide, N-lactoyl 1-amino-2-propanol, N-lactoyl 2-amino-1-propanol, N-lactoyl 2-amino-2-methylpropanol, N-gluconyl 1-amino-2-methyl-2-propanol, N-gluconyl 1-amino-2-propanol, N-gluconyl 2-amino-1-propanol, N-gluconyl 2-amino-2-methylpropanol edible salts thereof and edible esters thereof
- As used herein the term ‘edible esters thereof’ encompasses any edible derivative of the present flavour modulating substances and an acid. Typically said acid is an organic acid such as a substituted or non-substituted, linear or branched C1-C6 carboxylic acid, more preferably a C1-C4 carboxylic acid, most preferably a C1-C3 carboxylic acid, or alternatively an inorganic acid such as phosphoric acid. Such esters may be hydrolysed to produce flavour modulating substances according to the present invention during storage, processing and the like (acting as so called precursors).
- According to a particularly preferred embodiment the present flavour modulating substance is selected from the group of substances represented by formulas (I) or (II) as defined herein before and edible salts thereof.
- Yet another aspect of the present invention relates to the use of one or more of the aforementioned flavour modulating substances for improving the flavour of foodstuffs, beverages, pharmaceutics, tobacco products or oral care products. The inventors have found that the present flavour modulating substances are very useful ingredients which, in the presence of other flavouring substances, are capable of imparting highly appreciated taste sensations to the products in which they are incorporated, specifically “roundness”, “fullness”, “substance”, “continuity”, “ginger-like”, “tingling”, “fatty”, “metallic”, “umami” and/or “bitter”. Because of this, the present flavour modulating substances can be employed to improve the taste of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products. The flavour modulating substances of the present invention as such are capable of imparting highly desirable taste attributes. In addition, it has been found that the flavour modulating substances according to the invention are capable of modifying and complementing the sensory impact of other, flavour imparting, substances contained in the aforementioned products.
- Because the flavour modulating substances according to the invention are not particularly volatile, they do not produce a strong aroma impact, even though they can affect the aroma impact of other, flavour imparting, substances. Here the term “aroma” refers to the aspect of taste that is perceived through the olfactory epithelium. Because of the low volatility of the present flavour modulating substances it is believed that the advantageous properties of these substances are somehow associated with the impact that these substances have on the sensory receptors located within the mouth.
- As mentioned herein before, WO 92/06601 describes ingredients that, because of the physical properties thereof, could be used to replace sucrose as a structuring and/or texturizing agent in sweetened foodstuffs such as confectionery products, bakery products and beverages. Two of the substances described in this document are N-[2-hydroxypropyl]-gluconamide and/or N-[2-hydroxypropyl]-glucoheptonamide. In order to deliver the intended functionality these ‘structuring agents’ have to be applied in major amounts in food applications. For example, WO 92/06601 describes a yellow cake comprising 28.3 wt % of said structuring agent. With regard to taste characteristics, WO 92/06601 only mentions that the structuring agents disclosed therein, have a sweetness potency corresponding to 0-100% of that of sucrose, and that, in order to accomplish the same final effect as sucrose in formulated foods, an amount of artificial high potency sweetener might be included in proportions ranging between 0.2-2.0 parts of sweetener per 100 parts of the structuring agent.
- The use of the present flavour modulating substances differs from this disclosure in that they are used only in minor amounts in order to impart a taste improving effect in combination with other (volatile) flavour substances. As mentioned before, at the levels at which the present flavour modulating substances are typically applied in foodstuffs, beverages, pharmaceutics and oral care products, the contribution thereof on structure and texture, i.e. on the physical properties, is essentially insignificant.
- Yet another aspect of the present invention relates to a product selected from the group consisting of foodstuffs, beverages, pharmaceutics, tobacco products and oral care products, said product comprising between 0.1 and 10,000 ppm (mg/kg) of one or more flavour modulating substances as defined herein before. More preferably, the product contains at least 1 ppm, most preferably at least 5 ppm of the one or more flavour modulating substances. Typically, the aforementioned products contain the flavour modulating substance(s) in a concentration of not more than 5,000 ppm, preferably of not more than 2,000 ppm. The present products may further comprise one or more other flavouring substances, typically in amounts of 5-20,000 ppm, more preferably 10-10,000 ppm. The precise level in which the present substances are incorporated depends on the nature of the flavour modulating substance(s) and the nature of the product, as will be clear to the skilled person.
- Preferably, in the present products the flavour modulating substances and flavouring substances as defined herein before are employed in a weight ratio of less than 50: 1, preferably less than 20:1. In a preferred embodiment said weight ratio is within the range of 1:100 to 10:1, more preferably within the range of 1:50 to 5:1. Most preferably, the flavour modulating substances and flavouring substances are employed in a weight ratio that does not exceed 1:1.
- The present products comprising N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, edible salts thereof and/or edible esters thereof preferably exhibit a weight ratio of said flavour modulating substances and other flavouring substances of less than 50:1, preferably less than 10:1.
- In still another preferred embodiment, the present product contains no N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, edible salts thereof and edible esters thereof.
- In another embodiment, said product does not contain added saccharide sweetener or artificial sweetener.
- In yet another embodiment, the product contains N-[2-hydroxypropyl]-gluconamide, N-[2-hydroxypropyl]-glucoheptonamide, edible salts thereof and/or edible esters thereof in combination with added sweetener, said product being characterised by the fact that the weight ratio of the flavour modulating substances and saccharide sweetener does not exceed 1:1, preferably does not exceed 1:2; and by the fact that the weight ratio of the taste improving substances and artificial sweetener is less than 50:1, preferably less than 10:1, even more preferably less than 1:1.
- Typical examples of foodstuffs according to the present invention include yoghurt, ice cream, desserts, confectioneries, bakery products, sweet snacks, seasonings, sauces, stock, soups, dressings and ready meals. The benefits of the present invention may also be realised in beverages, in oral care products such as toothpaste and mouthwash, in pharmaceutics such as pills and elixirs and in tobacco products, which includes any type of tobacco product for smoking as well as for non-smoking applications. It is noted that tobacco-like products are available for both smoking and non-smoking applications. The use of the present flavour modulating substances in these tobacco substitutes is also encompassed by the present invention.
- Yet another aspect the present invention relates to a process of improving the flavour of a foodstuff, a beverage, a pharmaceutical product, a tobacco product or an oral care product, comprising adding to said product one or more flavour modulating substances as defined herein before. More preferably the present process comprises adding to said product an amount of at least 0.1 ppm (mg/kg), still more preferably at least 5 ppm, most preferably at least 10 ppm of the present one or more flavour modulating substances. It is furthermore preferred that said amount does not exceed 10,000 ppm (mg/kg), more preferably it does not exceed 5,000 ppm, most preferably it does not exceed 2,000 ppm.
- Substances according to formulas (I) and (II) are suitably produced by reacting an α-hydroxycarboxylic acid represented by the following formula (III) and/or edible salts and/or esters thereof and an amine represented by the following formula (IV) or formula (V) respectively, and/or edible salts and/or esters thereof:
- wherein R1, R2, R3 and X have the same meaning as defined herein before with regard to formulas (I) and (II).
- Thus another aspect of the invention relates to the process of producing a flavour modulating substance, preferably a flavour modulating substance as defined herein before, comprising reacting an a-hydroxycarboxylic acid represented by formula (III) and/or edible salts and/or esters thereof and an amine represented by formula (IV) or formula (V) and/or edible salts and/or esters thereof. Preferably, in said process the α-hydroxycarboxylic acid is selected from the group of lactic acid, malic acid, tartaric acid, citric acid, glucuronic acid, galactumic acid or an aldonic acid such as allonic acid, altronic acid, gluconic acid, mannonic acid, gulonic acid, idonic acid, galactonic acid and talonic acid; and the amine is selected from 2-methyl-2-aminopropanol, 2-methyl-1-amino-2-propanol, 2-methyl-2-aminopropyl dihydrogen phosphate and 1-aminopropane-2-thiol.
- According to another preferred embodiment said reaction is performed by heating to reflux said reactants in an organic solvent, such as toluene, hexane or benzylalcohol, for a period of between 0.1-10 hours. The reaction product is typically obtained as a precipitate and can be isolated by evaporating the solvent and optionally further purified using any of the techniques known by the skilled person, such as chromatography and crystallization.
- Another aspect of the present invention relates to substances obtainable by this process.
- The invention is further illustrated by means of the following examples
- a) Preparation of 1-amino-2-methyl-2-propanol from 2,2-dimethyl oxirane and ammonia:
- The reaction was carried out in a closed tube placed in a steam reaction block. The tube was charged with 20 g of a 32% aqueous ammonia solution and 5 g 2,2-dimethyl oxirane and kept at a temperature of 95° C. for 2 hours. Then the tube was cooled to room temperature. The excess ammonia was evaporated by heating the reaction mixture to 70° C. Water was removed on a rotary evaporator. 4.5 g of 1-amino-2-methyl-2-propanol was obtained and analyzed by GC.
- b) Preparation of N-lactoyl 1-amino-2-methyl-2-propanol:
- 4.2 g crude 1-amino-2-methyl-2-propanol was added to 10.5 g ethyl lactate at room temperature. The mixture was heated to 130° C. and stirred for 3 hours at 125-130° C. The ethanol formed was distilled off during the reaction. The reaction mixture was cooled to room temperature and subsequently transferred to a 50 ml distillation flask. The excess of ethyl lactate was removed from the reaction mixture by distillation.
- The remaining residue was cooled to room temperature and a sample was taken for analysis by NMR, which confirmed the formation of N-lactoyl 1-amino-2-methyl-2-propanol.
- The crude product was then purified on a column filled with 50 g of silica gel 60 F254 (0.06-0.02mm) in 200 ml THF. 2.4 g crude N-lactoyl 1-amino-2-methyl-2-propanol was dissolved in THF and then the solution was transferred to the top of the silica gel column. The column was eluted with THF and fractions of 20 ml were collected. A total of 22 fractions were collected. Finally the column was rinsed with 100 ml methanol. All fractions were checked by TLC. Fractions were selected and combined, based on the results of TLC analysis (shown below in table 1). Then the solvent was removed on the rotary evaporator to furnish the purified product. Only the obtained product from fractions 3 till 5 was sampled for NMR analysis.
-
TABLE 1 results of TLC analysis of fractionated extraction column eluent Fraction Results on TLC yield Fractions 1 and 2 no spot on TLC Fractions 3 till 5 one spot on TLC 1.8 g product Fractions 6 till 9 two spots on TLC 0.3 g product Fraction 10 till 22 one spot on the baseline of TLC 0.2 g product - 22.6 g 1-amino-2-propanol was added to 56.5 g ethyl lactate at room temperature. The mixture was heated to reflux and stirred for 4 hours. The reaction mixture was cooled and left to stand overnight at room temperature. The following day the ethanol formed and the excess of ethyl lactate were removed from the reaction mixture by distillation, using a 20 cm vigreux column. 43 g of N-lactoyl 1-amino-2-propanol (pale brown viscous liquid) was collected as residue and cooled to room temperature. The purity of the obtained product was confirmed by NMR analysis.
- 3.7 g ethyl lactate and 2.1 g 2-amino-1-propanol were mixed and subsequently heated to 110-115° C. for 2.5 hours. During the reaction, the ethanol formed was distilled off. After the reaction the excess of ethyl lactate was removed by vacuum distillation (bottom temperature: 150° C., 1 mbar), using a 20 cm vigreux column. 3.9 g of residual N-lactoyl 2-amino-1-propanol (brown viscous liquid) was collected, the purity of which was confirmed by NMR analysis. The yield of the reaction was 95%
- 15 g of ethyl lactate and 10 g of 2-amino-2-methyl-1-propanol were mixed and subsequently heated to 110-115° C. for 3.5 hours. During the reaction, the ethanol formed was distilled off. After the reaction, the excess of ethyl lactate was removed by vacuum distillation (bottom temperature: 160° C., 7 mbar), using a vigreux column. 15.5 g of residual brown viscous liquid was collected, which was confirmed to be pure N-lactoyl 2-amino-2-methylpropanol by NMR analysis.
- 4 g delta-gluconolactone and 2 g 1-amino-2-methyl-2-propanol were mixed and subsequently heated to 72° C. for 3 hours. The mixture was allowed to cool to room temperature and placed in the freezer overnight. The formed white crystals were filtered off, washed with ethanol and dried in the vacuum oven at 65° C. for 4 hours. The dried product (3.5 g of white crystals) was sampled for NMR and confirmed to be N-gluconyl 1-amino-2-methyl-2-propanol. The yield of the reaction was 67%.
- 18 g of delta-gluconolactone and 7.6 g of 1-amino-2-propanol were mixed in 110 g of ethanol and subsequently heated to 70° C. for 5 hours. The mixture was allowed to stand at room temperature for 48 hours. A white precipitate had formed which was filtered off, washed with ethanol and dried in the vacuum oven at 70° C. for 4 hours. 16 g of product (white crystals) was obtained. The product was sampled for NMR and confirmed to be pure.
- The mother liquor was partially evaporated and placed in a freezer overnight. 2 g of extra product (white crystals) was isolated. 17.9 g (0.071 mole) of N-gluconyl 1-amino-2-propanol was prepared. The material was pure, according the NMR analysis. The chemical yield of the reaction was 70%
- 2.4 g of delta-gluconolactone and 1 g of 2-amino-1-propanol were mixed in 30 g ethanol and subsequently heated to 70° C. for 5 hours. The unreacted gluconolactone (a white precipitate) was filtered off. The filtrate was placed in a freezer overnight. The formed white crystals were filtered off and dried in the vacuum oven at 70° C. The dried material (1 g) was sampled for NMR analysis. The chemical yield was 30%.
- 4 g of delta-gluconolactone and 2 g of 2-amino-2-methyl-1-propanol were mixed in 30 g ethanol and subsequently heated to 70° C. for 5 hours. The mixture was allowed to cool to room temperature and placed in a freezer for a weekend. No crystals were formed. Then the solvent was evaporated and the residue was sampled for NMR . To isolate the unreacted gluconolactone (30% in the obtained residue, according the NMR analysis), the residue was dissolved in IPA and placed in the freezer overnight. A paste-like product was obtained which was filtrated, washed and dried under vacuum. The dried product (3.5 g of a brown paste) was sampled for NMR and confirmed to contain mainly N-gluconyl 2-amin-2-methylpropanol.
- Four yoghurt samples were prepared:
-
- A: Yoghurt 0% fat+strawberry flavour+sucralose (25%) 300 ppm
- B: Yoghurt 0% fat+strawberry flavour+sucralose (25%) 300 ppm+10 ppm N-gluconyl 2-amino-2-methyl-propanol (as prepared in Example 8)
- C: Yoghurt 0% fat+strawberry flavour+4% sugar
- D: Yoghurt 0% fat+strawberry flavour+4% sugar+10 ppm N-gluconyl 2-amino-2-methyl-propanol (as prepared in Example 8)
The yoghurts were tasted by a professional panel. There was general agreement among the group on the taste descriptions: - A: sweet , bitter, metallic, aftertaste.
- B: fuller more round and natural taste, more sugar sweetness, significantly less bitter metallic aftertaste compared to A.
- C: tart, acidic.
-
- D: fuller more round and natural taste, more intense sweet compared to C.
- Three ice cream (8% vegetable fat) samples were prepared:
-
- A: Ice cream (see table 2)+strawberry flavour
- B: Ice cream (see table 2)+strawberry flavour+7 ppm N-gluconyl 1-amino-2-methyl-2-propanol (as prepared in Example 5)
The ice creams were tasted by a professional panel. There was general agreement among the group on the taste descriptions: - A: sweet, strawberry, creamy aftertaste.
- B: more round and natural taste, very clear sweet enhancement and increased creaminess.
-
TABLE 2 ice cream composition Ice cream composition: % Hydrogenated coconut fat (CN32) 8.00 Skimmed milkpowder 7.00 Whey protein concentrate 3.00 Sucrose 12.00 Corn syrup solids (DE39) 5.00 Sherex IC 9328 0.50 Flavour + Colour + Water Up to 100 - A standard chicken soup was prepared. The quantity was split in two. One part was kept as reference and the other part was dosed to contain 5 ppm of N-gluconyl 2-amino-2-methyl-propanol (as prepared in Example 8). The soups were tasted by a professional panel.
- The soup containing the N-gluconyl 2-amino-2-methyl-propanol was unanimously described as more tasteful, more complete, more body, more fatty.
- Two aqueous solutions were prepared:
-
- A. 0.5% NaCl
- B. 0.5% Na Cl and 12 ppm of N-lactoyl 2-amino-2-methyl-propanol (as prepared in Example 4)
- The solutions were tasted by a sensory panel:
-
- Solution A was described as: “salty”.
- Solution B was described as: “high impact”, “bouillon”, “meaty”, “salty”, “umami” and “salivating”.
- Two different soft drinks A and B were prepared by adding respectively 40 ppb and 4 ppm of N-lactoyl 2-amino-2-methyl-propanol (as prepared in Example 4) to a commercially available carbonated orange flavoured soft drink.
- The three soft drinks were evaluated and compared to the original drink. Sample A was judged as more natural, with a more juicy character than the original. Sample B exhibited the tingling character typical of the flavour modulating substances of the present invention, which was judged as very pleasant and particularly well suited for the orange flavour.
Claims (20)
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EP05108087 | 2005-09-02 | ||
EP05108087.7 | 2005-09-02 | ||
PCT/NL2006/050216 WO2007027095A1 (en) | 2005-09-02 | 2006-09-04 | Improved flavour compositions |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US20120015089A1 (en) * | 2009-02-19 | 2012-01-19 | Givaudan S.A. | Geranylamine Derivatives As Flavouring Agents |
US8816102B2 (en) | 2009-06-25 | 2014-08-26 | Givaudan S.A. | Compounds |
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US9101160B2 (en) | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
US8017168B2 (en) | 2006-11-02 | 2011-09-13 | The Coca-Cola Company | High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
US9028804B2 (en) * | 2012-04-17 | 2015-05-12 | L'oreal | Water resistant compositions containing a lactone compound and an amine compound chosen from amino alcohol compounds and alkoxylated amine compounds |
CN110999980A (en) * | 2019-12-19 | 2020-04-14 | 新疆石河子职业技术学院(石河子市技工学校) | Wine wash-dipped cheese processing method |
WO2022218942A1 (en) * | 2021-04-15 | 2022-10-20 | Givaudan Sa | Taste modifier |
GB202114766D0 (en) | 2021-10-15 | 2021-12-01 | Givaudan Sa | Organic compounds |
WO2023172372A1 (en) * | 2022-03-11 | 2023-09-14 | Firmenich Incorporated | Amide compounds and their use as flavor modifiers |
WO2023209006A1 (en) | 2022-04-27 | 2023-11-02 | Givaudan Sa | Organic compounds |
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EP0506952A4 (en) * | 1990-10-11 | 1993-02-10 | The Nutrasweet Company | Amides derived from sugar alcohols suitable as sugar substitutes |
EP0620000A3 (en) * | 1992-12-18 | 1994-11-02 | Rhone-Poulenc Rorer Gmbh | Cosmetic or pharmaceutical use of N-acylalcanolamines |
ES2185782T3 (en) * | 1995-07-26 | 2003-05-01 | Firmenich & Cie | AROMATIZED PRODUCTS AND PROCEDURE FOR PREPARATION. |
BR9610312A (en) * | 1995-08-29 | 1999-07-06 | Mane V Fils Sa | Refreshing compositions |
JP4213159B2 (en) * | 2003-11-20 | 2009-01-21 | 株式会社カネカ | Bitter seasoning |
WO2005096843A1 (en) * | 2004-04-06 | 2005-10-20 | Quest International B.V. | Taste improving substances |
PL1758468T3 (en) * | 2004-04-20 | 2011-08-31 | Givaudan Nederland Services Bv | Taste improving substances |
BRPI0513498B1 (en) * | 2004-07-20 | 2016-03-08 | Givaudan Nederland Services Bv | flavoring composition, substance, use of one or more flavor enhancing substances, process for improving the taste of a food product, a beverage, a pharmaceutical product, a tobacco product or an oral care product, and, |
ATE535508T1 (en) * | 2004-10-29 | 2011-12-15 | Givaudan Nederland Services Bv | FLAVOR-MODULATING SUBSTANCES |
-
2006
- 2006-09-04 CN CN2006800315240A patent/CN101252847B/en not_active Expired - Fee Related
- 2006-09-04 WO PCT/NL2006/050216 patent/WO2007027095A1/en active Application Filing
- 2006-09-04 BR BRPI0615416-6A patent/BRPI0615416B1/en not_active IP Right Cessation
- 2006-09-04 AU AU2006285498A patent/AU2006285498B2/en not_active Ceased
- 2006-09-04 DE DE602006021436T patent/DE602006021436D1/en active Active
- 2006-09-04 AT AT06783962T patent/ATE505958T1/en not_active IP Right Cessation
- 2006-09-04 MX MX2008002781A patent/MX2008002781A/en active IP Right Grant
- 2006-09-04 JP JP2008528974A patent/JP4695692B2/en not_active Expired - Fee Related
- 2006-09-04 KR KR1020087005287A patent/KR101350724B1/en active IP Right Grant
- 2006-09-04 EP EP06783962A patent/EP1919303B1/en not_active Not-in-force
- 2006-09-04 US US12/065,189 patent/US20080199584A1/en not_active Abandoned
- 2006-09-04 RU RU2008112673/13A patent/RU2008112673A/en not_active Application Discontinuation
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US4296255A (en) * | 1972-04-18 | 1981-10-20 | Wilkinson Sword Limited | Acyclic carboxamides having a physiological cooling effect |
US4143159A (en) * | 1976-07-12 | 1979-03-06 | Henkel Kommanditgesellschaft Auf Aktien | Skin-care agents containing hydroxyalkyl carboxamides and process |
Cited By (3)
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US20120015089A1 (en) * | 2009-02-19 | 2012-01-19 | Givaudan S.A. | Geranylamine Derivatives As Flavouring Agents |
US8815321B2 (en) * | 2009-02-19 | 2014-08-26 | Givaudan S.A. | Geranylamine derivatives as flavouring agents |
US8816102B2 (en) | 2009-06-25 | 2014-08-26 | Givaudan S.A. | Compounds |
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DE602006021436D1 (en) | 2011-06-01 |
EP1919303A1 (en) | 2008-05-14 |
US9155329B2 (en) | 2015-10-13 |
KR20080038201A (en) | 2008-05-02 |
CN101252847B (en) | 2012-05-23 |
BRPI0615416A8 (en) | 2016-07-05 |
JP2009506768A (en) | 2009-02-19 |
CN101252847A (en) | 2008-08-27 |
ATE505958T1 (en) | 2011-05-15 |
BRPI0615416A2 (en) | 2011-05-17 |
AU2006285498B2 (en) | 2012-12-06 |
EP1919303B1 (en) | 2011-04-20 |
BRPI0615416B1 (en) | 2019-06-04 |
RU2008112673A (en) | 2009-10-10 |
JP4695692B2 (en) | 2011-06-08 |
US20140349001A1 (en) | 2014-11-27 |
WO2007027095A1 (en) | 2007-03-08 |
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AU2006285498A1 (en) | 2007-03-08 |
MX2008002781A (en) | 2008-04-07 |
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