CA2117284A1 - Modificateurs du gout specifiques comestibles - Google Patents
Modificateurs du gout specifiques comestiblesInfo
- Publication number
- CA2117284A1 CA2117284A1 CA002117284A CA2117284A CA2117284A1 CA 2117284 A1 CA2117284 A1 CA 2117284A1 CA 002117284 A CA002117284 A CA 002117284A CA 2117284 A CA2117284 A CA 2117284A CA 2117284 A1 CA2117284 A1 CA 2117284A1
- Authority
- CA
- Canada
- Prior art keywords
- tastand
- physiologically acceptable
- acceptable salts
- acid
- group
- 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
- 235000019640 taste Nutrition 0.000 title claims abstract description 167
- 239000003607 modifier Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 129
- 230000009967 tasteless effect Effects 0.000 claims abstract description 33
- 235000002639 sodium chloride Nutrition 0.000 claims description 477
- 150000003839 salts Chemical class 0.000 claims description 409
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical group [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 393
- 239000001103 potassium chloride Substances 0.000 claims description 197
- 235000011164 potassium chloride Nutrition 0.000 claims description 196
- 239000000203 mixture Substances 0.000 claims description 183
- 125000001424 substituent group Chemical group 0.000 claims description 170
- 238000000034 method Methods 0.000 claims description 151
- 235000019658 bitter taste Nutrition 0.000 claims description 146
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 129
- 229910052739 hydrogen Inorganic materials 0.000 claims description 107
- 229910052717 sulfur Inorganic materials 0.000 claims description 81
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 77
- 229910052760 oxygen Inorganic materials 0.000 claims description 69
- 239000011780 sodium chloride Substances 0.000 claims description 64
- 230000002829 reductive effect Effects 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- -1 2,4-dihydroxyphenyl Chemical group 0.000 claims description 54
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 50
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 49
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 48
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 229960003080 taurine Drugs 0.000 claims description 44
- 235000009508 confectionery Nutrition 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- 235000003599 food sweetener Nutrition 0.000 claims description 35
- 239000003765 sweetening agent Substances 0.000 claims description 35
- 150000001413 amino acids Chemical group 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 34
- YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 229910052796 boron Inorganic materials 0.000 claims description 30
- 235000019643 salty taste Nutrition 0.000 claims description 29
- 229940024606 amino acid Drugs 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 27
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 27
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 claims description 26
- 229910052698 phosphorus Inorganic materials 0.000 claims description 26
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 235000019260 propionic acid Nutrition 0.000 claims description 25
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 25
- 239000011593 sulfur Substances 0.000 claims description 25
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 108010011485 Aspartame Proteins 0.000 claims description 20
- 239000000605 aspartame Substances 0.000 claims description 20
- 235000010357 aspartame Nutrition 0.000 claims description 20
- 229960003438 aspartame Drugs 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- 230000003993 interaction Effects 0.000 claims description 19
- 235000019204 saccharin Nutrition 0.000 claims description 19
- 229940081974 saccharin Drugs 0.000 claims description 19
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 19
- 239000004094 surface-active agent Substances 0.000 claims description 18
- 150000001768 cations Chemical class 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 238000006467 substitution reaction Methods 0.000 claims description 16
- MIEKOFWWHVOKQX-UHFFFAOYSA-N (S)-2-(4-Methoxyphenoxy)propanoic acid Chemical compound COC1=CC=C(OC(C)C(O)=O)C=C1 MIEKOFWWHVOKQX-UHFFFAOYSA-N 0.000 claims description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 15
- 230000002209 hydrophobic effect Effects 0.000 claims description 15
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 15
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 claims description 13
- 229940114055 beta-resorcylic acid Drugs 0.000 claims description 13
- 235000013615 non-nutritive sweetener Nutrition 0.000 claims description 13
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims description 13
- IBHWREHFNDMRPR-UHFFFAOYSA-N 2,4,6-Trihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=C(O)C=C1O IBHWREHFNDMRPR-UHFFFAOYSA-N 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 12
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 12
- 239000008123 high-intensity sweetener Substances 0.000 claims description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- CDAISMWEOUEBRE-UHFFFAOYSA-N inositol Chemical compound OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 11
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 11
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 10
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 claims description 10
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 10
- 239000000619 acesulfame-K Substances 0.000 claims description 10
- 235000013305 food Nutrition 0.000 claims description 10
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 9
- 150000004000 hexols Chemical class 0.000 claims description 9
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 9
- 229950000244 sulfanilic acid Drugs 0.000 claims description 9
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims description 8
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 8
- 108091005708 gustatory receptors Proteins 0.000 claims description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- GPNNOCMCNFXRAO-UHFFFAOYSA-N 2-aminoterephthalic acid Chemical compound NC1=CC(C(O)=O)=CC=C1C(O)=O GPNNOCMCNFXRAO-UHFFFAOYSA-N 0.000 claims description 7
- FRYULLIZUDQONW-IMJSIDKUSA-N Asp-Asp Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CC(O)=O)C(O)=O FRYULLIZUDQONW-IMJSIDKUSA-N 0.000 claims description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 claims description 7
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 claims description 7
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 claims description 7
- 235000013361 beverage Nutrition 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229940029575 guanosine Drugs 0.000 claims description 7
- 235000014347 soups Nutrition 0.000 claims description 7
- 229940082044 2,3-dihydroxybenzoic acid Drugs 0.000 claims description 6
- ZCYXGVJUZBKJAI-UHFFFAOYSA-N 3,4,5-trimethoxydihydrocinnamic acid Chemical compound COC1=CC(CCC(O)=O)=CC(OC)=C1OC ZCYXGVJUZBKJAI-UHFFFAOYSA-N 0.000 claims description 6
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 claims description 6
- LEGPZHPSIPPYIO-UHFFFAOYSA-N 3-Methoxyphenylacetic acid Chemical compound COC1=CC=CC(CC(O)=O)=C1 LEGPZHPSIPPYIO-UHFFFAOYSA-N 0.000 claims description 6
- LBKFGYZQBSGRHY-UHFFFAOYSA-N 3-hydroxy-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1O LBKFGYZQBSGRHY-UHFFFAOYSA-N 0.000 claims description 6
- OMTDIBZSUZNVJK-UHFFFAOYSA-N 4-(4-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(C(=O)CCC(O)=O)C=C1 OMTDIBZSUZNVJK-UHFFFAOYSA-N 0.000 claims description 6
- NFPYJDZQOKCYIE-UHFFFAOYSA-N 4-amino-3-hydroxybenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1O NFPYJDZQOKCYIE-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229930010555 Inosine Natural products 0.000 claims description 6
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 6
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 235000019270 ammonium chloride Nutrition 0.000 claims description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 150000001720 carbohydrates Chemical class 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 6
- 229960003786 inosine Drugs 0.000 claims description 6
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 claims description 6
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 claims description 6
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- DSHDHKLHCMKZCS-ZETCQYMHSA-N 2-[[(2s)-2-amino-3-carboxypropanoyl]amino]benzoic acid Chemical compound OC(=O)C[C@H](N)C(=O)NC1=CC=CC=C1C(O)=O DSHDHKLHCMKZCS-ZETCQYMHSA-N 0.000 claims description 5
- CSPCBKHSMMVMKX-QMMMGPOBSA-N 4-[[(2s)-2-amino-3-carboxypropanoyl]amino]benzoic acid Chemical compound OC(=O)C[C@H](N)C(=O)NC1=CC=C(C(O)=O)C=C1 CSPCBKHSMMVMKX-QMMMGPOBSA-N 0.000 claims description 5
- NALWOULWGHTVDA-UWVGGRQHSA-N Asp-Tyr Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 NALWOULWGHTVDA-UWVGGRQHSA-N 0.000 claims description 5
- CKLJMWTZIZZHCS-UWTATZPHSA-N D-aspartic acid Chemical compound OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims description 5
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 5
- BJXXCOMGRRCAGN-CLFAGFIQSA-N [2,2-bis(hydroxymethyl)-3-[(z)-octadec-9-enoyl]oxypropyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(CO)(CO)COC(=O)CCCCCCC\C=C/CCCCCCCC BJXXCOMGRRCAGN-CLFAGFIQSA-N 0.000 claims description 5
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 claims description 5
- 150000001721 carbon Chemical class 0.000 claims description 5
- 239000002738 chelating agent Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 235000013599 spices Nutrition 0.000 claims description 5
- DVUFTQLHHHJEMK-DMTCNVIQSA-N (3s)-3-amino-4-[[(1r)-1-carboxyethyl]amino]-4-oxobutanoic acid Chemical compound OC(=O)[C@@H](C)NC(=O)[C@@H](N)CC(O)=O DVUFTQLHHHJEMK-DMTCNVIQSA-N 0.000 claims description 4
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 4
- DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 claims description 4
- 230000000295 complement effect Effects 0.000 claims description 4
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims description 4
- UFIVEPVSAGBUSI-UHFFFAOYSA-N dihydroorotic acid Chemical compound OC(=O)C1CC(=O)NC(=O)N1 UFIVEPVSAGBUSI-UHFFFAOYSA-N 0.000 claims description 4
- 235000014655 lactic acid Nutrition 0.000 claims description 4
- 239000004310 lactic acid Substances 0.000 claims description 4
- 229930014626 natural product Natural products 0.000 claims description 4
- 239000000892 thaumatin Substances 0.000 claims description 4
- 235000010436 thaumatin Nutrition 0.000 claims description 4
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 3
- LYZONRZEOLEFOU-NTXUUIFSSA-N (2S)-2-amino-4-methyl-N-[(2R)-1-oxo-1-[(1,2,2,3-tetramethylcyclopentyl)amino]propan-2-yl]pentanamide Chemical compound CC1CCC(C1(C)C)(C)NC(=O)[C@@H](C)NC(=O)[C@H](CC(C)C)N LYZONRZEOLEFOU-NTXUUIFSSA-N 0.000 claims description 3
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 claims description 3
- MYGVPKMVGSXPCQ-UHFFFAOYSA-N (3-amino-4-hydroxy-4-oxobutyl)-dimethylsulfanium chloride Chemical compound [Cl-].C[S+](C)CCC(N)C(O)=O MYGVPKMVGSXPCQ-UHFFFAOYSA-N 0.000 claims description 3
- QPUZSCXGJMEHBV-QMMMGPOBSA-N (3s)-3-amino-4-oxo-4-(4-sulfoanilino)butanoic acid Chemical compound OC(=O)C[C@H](N)C(=O)NC1=CC=C(S(O)(=O)=O)C=C1 QPUZSCXGJMEHBV-QMMMGPOBSA-N 0.000 claims description 3
- NVKQKAZYUPPRJX-UHFFFAOYSA-N 1,3,5-tribromo-2-(2,5-dibromophenyl)benzene Chemical compound BrC1=CC=C(Br)C(C=2C(=CC(Br)=CC=2Br)Br)=C1 NVKQKAZYUPPRJX-UHFFFAOYSA-N 0.000 claims description 3
- BVRNERFWPQRVJB-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yl)acetic acid Chemical compound O1CCOC2=CC(CC(=O)O)=CC=C21 BVRNERFWPQRVJB-UHFFFAOYSA-N 0.000 claims description 3
- IVEWTCACRDEAOB-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetic acid Chemical compound COC1=CC=CC=C1CC(O)=O IVEWTCACRDEAOB-UHFFFAOYSA-N 0.000 claims description 3
- VNQCEHOLSJDEMQ-UHFFFAOYSA-N 2-(4-ethoxyphenoxy)propanoic acid Chemical compound CCOC1=CC=C(OC(C)C(O)=O)C=C1 VNQCEHOLSJDEMQ-UHFFFAOYSA-N 0.000 claims description 3
- KBDLTYNZHQRMQC-UHFFFAOYSA-N 2-(4-methoxyphenyl)propanoic acid Chemical compound COC1=CC=C(C(C)C(O)=O)C=C1 KBDLTYNZHQRMQC-UHFFFAOYSA-N 0.000 claims description 3
- JALOHEZOHSEEMS-LURJTMIESA-N 2-[[(2s)-2,5-diaminopentanoyl]amino]ethanesulfonic acid Chemical compound NCCC[C@H](N)C(=O)NCCS(O)(=O)=O JALOHEZOHSEEMS-LURJTMIESA-N 0.000 claims description 3
- GOYZLPIPTDNVIG-ZETCQYMHSA-N 2-[[(2s)-2,6-diaminohexanoyl]amino]ethanesulfonic acid Chemical compound NCCCC[C@H](N)C(=O)NCCS(O)(=O)=O GOYZLPIPTDNVIG-ZETCQYMHSA-N 0.000 claims description 3
- ABOWENPAEUTPIO-LURJTMIESA-N 2-[[(2s)-2-amino-4-methylsulfanylbutanoyl]amino]ethanesulfonic acid Chemical compound CSCC[C@H](N)C(=O)NCCS(O)(=O)=O ABOWENPAEUTPIO-LURJTMIESA-N 0.000 claims description 3
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- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
- A23L27/37—Halogenated sugars
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- 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
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- 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
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
- A23L27/2028—Carboxy compounds
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- 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
- A23L27/203—Alicyclic 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
- A23L27/204—Aromatic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
-
- 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
- A23L27/205—Heterocyclic compounds
- A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
-
- 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
- A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
- A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Seasonings (AREA)
- Confectionery (AREA)
- General Preparation And Processing Of Foods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US79920791A | 1991-11-27 | 1991-11-27 | |
US799,207 | 1991-11-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2117284A1 true CA2117284A1 (fr) | 1993-06-10 |
Family
ID=25175300
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002117284A Abandoned CA2117284A1 (fr) | 1991-11-27 | 1992-11-24 | Modificateurs du gout specifiques comestibles |
Country Status (11)
Country | Link |
---|---|
EP (1) | EP0661932A4 (fr) |
JP (1) | JPH07504810A (fr) |
AU (1) | AU675778B2 (fr) |
BG (1) | BG98818A (fr) |
CA (1) | CA2117284A1 (fr) |
CZ (1) | CZ129094A3 (fr) |
FI (1) | FI942463A (fr) |
HU (1) | HUT68764A (fr) |
NO (1) | NO941972L (fr) |
SK (1) | SK62094A3 (fr) |
WO (1) | WO1993010677A1 (fr) |
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JP3514459B2 (ja) * | 1993-08-05 | 2004-03-31 | 三栄源エフ・エフ・アイ株式会社 | 甘味抑制方法 |
AU7239394A (en) * | 1993-08-05 | 1995-02-28 | San-Ei Gen F.F.I., Inc. | Method of increasing sourness |
WO1995004479A1 (fr) * | 1993-08-05 | 1995-02-16 | San-Ei Gen F.F.I., Inc. | Procede d'augmentation du gout epice |
AU7239494A (en) * | 1993-08-05 | 1995-02-28 | San-Ei Gen F.F.I., Inc. | Method of increasing bitterness and/or astringency |
US5766622A (en) * | 1996-08-14 | 1998-06-16 | The Procter & Gamble Company | Inhibiting undesirable taste in oral compositions |
ATE278330T1 (de) * | 1998-07-07 | 2004-10-15 | Mcneil Ppc Inc | Vefahren zur verbesserung der süssefreigabe von sucralose |
EP1210880B8 (fr) * | 1998-10-28 | 2009-06-03 | San-Ei Gen F.F.I., Inc. | Compositions contenant la sucralose et leur utilisation |
GB9903216D0 (en) * | 1999-02-13 | 1999-04-07 | Zylepsis Ltd | Preservative compounds,compositions and methods of making and using the same |
JP4545868B2 (ja) * | 2000-02-21 | 2010-09-15 | 東洋水産株式会社 | 新規なテルペノイドおよびそれらの生物学的活性を利用する医薬 |
US7803982B2 (en) | 2001-04-20 | 2010-09-28 | The Mount Sinai School Of Medicine Of New York University | T1R3 transgenic animals, cells and related methods |
EP1402892A4 (fr) * | 2001-06-11 | 2006-11-08 | Kyowa Hakko Kogyo Kk | Compositions anti-inflammatoires et antitussives |
KR100703068B1 (ko) * | 2003-12-30 | 2007-04-05 | 에스케이케미칼주식회사 | 피리딘 유도체와 이의 제조방법, 및 이를 포함하는약제조성물 |
BRPI0510221A (pt) | 2004-05-14 | 2007-10-23 | Emisphere Tech Inc | composto de aril cetona, composição, forma de dosagem unitária, uso da composição e método para preparar uma composição |
JP4531494B2 (ja) * | 2004-09-01 | 2010-08-25 | 三栄源エフ・エフ・アイ株式会社 | ペプチド含有飲料 |
FR2883873B1 (fr) * | 2005-03-31 | 2009-07-10 | Pharmamens Sarl | Inhibiteurs d'age |
EP1949798A4 (fr) | 2005-11-14 | 2012-12-26 | Kao Corp | Assaisonnement liquide |
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 |
JP5066742B2 (ja) * | 2007-09-28 | 2012-11-07 | 株式会社林原 | 飲食物の塩から味及び/又は旨味増強方法 |
CN101932253B (zh) | 2008-01-31 | 2013-09-25 | 花王株式会社 | 豆酱(味噌) |
EA018270B1 (ru) * | 2008-09-05 | 2013-06-28 | Унилевер Н.В. | Соединения и композиции для снижения или устранения горечи, вызываемой флаван-3-олами |
TWI527584B (zh) * | 2009-03-30 | 2016-04-01 | Shiseido Co Ltd | UV damage mitigation composition |
US8962684B2 (en) | 2009-09-29 | 2015-02-24 | Shiseido Company, Ltd. | Antioxidant composition |
ES2389709T3 (es) | 2010-02-01 | 2012-10-30 | Symrise Ag | Uso de 1-(2,4-dihidroxifenil)-3-(3-hidroxi-4-metoxifenil)-propan-1-ona |
MX2012011996A (es) * | 2010-04-15 | 2013-11-27 | Chromocell Corp | Compuestos , composiciones y metodos para reducir o eliminar el sabor amargo. |
PE20130638A1 (es) | 2010-04-15 | 2013-07-01 | Chromocell Corp | Compuestos, composiciones y metodos para reducir o eliminar el sabor amargo |
JP6021166B2 (ja) * | 2010-12-24 | 2016-11-09 | 三井農林株式会社 | 血圧降下剤 |
KR20140076629A (ko) | 2011-10-20 | 2014-06-20 | 크로모셀 코포레이션 | 쓴맛을 감소시키거나 또는 제거하기 위한 화합물, 조성물 및 방법 |
WO2013111716A1 (fr) * | 2012-01-27 | 2013-08-01 | キリンホールディングス株式会社 | Composition d'édulcorant, et procédé d'amélioration de sucrosité de substance sucrée |
CN104254253B (zh) | 2012-03-30 | 2017-12-29 | 奇华顿股份有限公司 | 作为食品加香化合物的n‑酰化甲硫氨酸衍生物 |
KR102045590B1 (ko) | 2012-03-30 | 2019-11-15 | 지보당 에스아 | 식품 향미 화합물로서의 n-아실화된 1-아미노사이클로알킬 카복실산 |
EP2830438B1 (fr) * | 2012-03-30 | 2019-09-04 | Givaudan SA | Dérivés n-acylés d'acide gamma amino-butyrique en tant que composés d'arôme alimentaire, composition en poudre les comprenant. |
CN106220546B (zh) | 2012-03-30 | 2018-11-30 | 奇华顿股份有限公司 | 作为食品加香化合物的n-酰基脯氨酸衍生物 |
US10836712B2 (en) | 2012-03-30 | 2020-11-17 | Givaudan S.A. | Organic compounds |
BR112014023448B1 (pt) | 2012-03-30 | 2021-06-22 | Givaudan Sa | Composição comestível ou bebida compreendendo derivados de n-acila de ácido gama amino-butírico e solução padrão |
EP2830439B1 (fr) | 2012-03-30 | 2020-11-04 | Givaudan SA | Dérivés n-acyl gaba pour l'amélioration du profil aromatique de compositions alimentaires |
JP6058280B2 (ja) * | 2012-05-01 | 2017-01-11 | Mcフードスペシャリティーズ株式会社 | 食塩およびアルコールを含有する調味料 |
JP6038483B2 (ja) * | 2012-05-01 | 2016-12-07 | Mcフードスペシャリティーズ株式会社 | みりん |
CN103288673B (zh) * | 2013-05-28 | 2015-05-06 | 广东药学院 | 一种铂配体及其配合物 |
EP3057448B1 (fr) | 2013-10-02 | 2017-12-06 | Givaudan S.A. | Composés organiques présentant des propriétés de modification du goût |
WO2015048991A1 (fr) | 2013-10-02 | 2015-04-09 | Givaudan Sa | Composés organiques présentant des propriétés de modification du goût |
EP3057446B1 (fr) | 2013-10-02 | 2017-12-06 | Givaudan S.A. | Composés organiques présentant des propriétés de modification du goût |
US11122826B2 (en) | 2013-10-02 | 2021-09-21 | Givaudan Sa | Organic compounds |
GB201317424D0 (en) | 2013-10-02 | 2013-11-13 | Givaudan Sa | Improvements in or relating to organic compounds |
US10834950B2 (en) | 2013-10-02 | 2020-11-17 | Givaudan S.A. | Organic compounds |
WO2015050535A1 (fr) | 2013-10-02 | 2015-04-09 | Givaudan S.A. | Composés organiques |
EP3057445B1 (fr) | 2013-10-02 | 2018-07-04 | Givaudan SA | Composés organiques présentant des propriétés de modification du goût |
WO2018093828A1 (fr) * | 2016-11-16 | 2018-05-24 | International Flavors & Fragrances Inc. | Nouvelles compositions de renforcement du goût |
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US4001455A (en) * | 1970-03-25 | 1977-01-04 | E. R. Squibb & Sons, Inc. | Sweetening compositions |
US3860732A (en) * | 1970-03-30 | 1975-01-14 | Cumberland Packing Corp | Salt substitute |
US3649298A (en) * | 1970-04-16 | 1972-03-14 | Gen Mills Inc | Carbonation concentrates for beverages and process of producing carbonated beverages |
US3903255A (en) * | 1971-05-17 | 1975-09-02 | Rohm & Haas | Effervescent potassium chloride tablet |
DE2211019C3 (de) * | 1972-03-08 | 1980-08-28 | Bayer Ag, 5090 Leverkusen | Geschmacksverbessernde Formulierungen oraler Penicilline |
US3934047A (en) * | 1974-04-02 | 1976-01-20 | General Foods Corporation | Taste modifier for artificial sweeteners |
US4031265A (en) * | 1975-06-18 | 1977-06-21 | The United States Of America As Represented By The Secretary Of Agriculture | Method of reducing bitterness in citrus juices |
US4216244A (en) * | 1978-09-19 | 1980-08-05 | Allen Alfred E Jr | Low sodium salt seasoning |
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US4219579A (en) * | 1979-01-25 | 1980-08-26 | Carl Piampiano | Means and method improving taste of saccharine sweetened food products |
US4642240A (en) * | 1982-09-30 | 1987-02-10 | General Foods Corporation | Foodstuffs containing 3-aminobenzesulfonic acid as a sweetener inhibitor |
US4871570A (en) * | 1983-03-22 | 1989-10-03 | General Foods Corp. | Foodstuffs containing hydrobenzene organic acids as sweetness modifying agents |
GB8309855D0 (en) * | 1983-04-12 | 1983-05-18 | Tate & Lyle Plc | Flavour modifiers |
CA1208966A (fr) * | 1983-07-13 | 1986-08-05 | Ronald E. Barnett | Produits alimentaires contenant des agents modifiant le gout sucre |
US4544565A (en) * | 1984-03-29 | 1985-10-01 | General Foods Corporation | Foodstuffs containing sweetness inhibiting agents |
IL74842A (en) * | 1984-04-12 | 1988-04-29 | Tate & Lyle Plc | Method of modifying taste |
US4913921A (en) * | 1987-09-11 | 1990-04-03 | General Mills, Inc. | Food products containing fish oils stabilized with fructose |
US4910031A (en) * | 1988-12-19 | 1990-03-20 | Frito-Lay, Inc. | Topped savory snack foods |
US4994490A (en) * | 1989-04-03 | 1991-02-19 | The Nutrasweet Company | Novel N-(sulfomethyl)-N'-arylureas |
US5094862A (en) * | 1989-08-25 | 1992-03-10 | Warner-Lambert Company | Salt substitute granule and method of making same |
US4917913A (en) * | 1989-09-29 | 1990-04-17 | International Flavors & Fragrances Inc. | Use of sclareolide in augmenting or enhancing the organoleptic properties of foodstuffs |
US4988532A (en) * | 1989-09-29 | 1991-01-29 | International Flavors & Fragrances Inc. | Use of sclareolide to debitter a coffee beverage |
US5021249A (en) * | 1989-11-09 | 1991-06-04 | Warner-Lambert Company | Method of making a savory flavor granule and a free flowing savory flavor granule |
US5232735A (en) * | 1990-06-01 | 1993-08-03 | Bioresearch, Inc. | Ingestibles containing substantially tasteless sweetness inhibitors as bitter taste reducers or substantially tasteless bitter inhibitors as sweet taste reducers |
-
1992
- 1992-11-24 EP EP93900657A patent/EP0661932A4/fr not_active Withdrawn
- 1992-11-24 CA CA002117284A patent/CA2117284A1/fr not_active Abandoned
- 1992-11-24 SK SK620-94A patent/SK62094A3/sk unknown
- 1992-11-24 HU HU9401598A patent/HUT68764A/hu unknown
- 1992-11-24 JP JP5510237A patent/JPH07504810A/ja active Pending
- 1992-11-24 CZ CZ941290A patent/CZ129094A3/cs unknown
- 1992-11-24 AU AU32250/93A patent/AU675778B2/en not_active Ceased
- 1992-11-24 WO PCT/US1992/010179 patent/WO1993010677A1/fr not_active Application Discontinuation
-
1994
- 1994-05-26 NO NO941972A patent/NO941972L/no not_active Application Discontinuation
- 1994-05-26 FI FI942463A patent/FI942463A/fi unknown
- 1994-05-31 BG BG98818A patent/BG98818A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
AU675778B2 (en) | 1997-02-20 |
EP0661932A4 (fr) | 1996-06-05 |
SK62094A3 (en) | 1995-04-12 |
BG98818A (en) | 1995-02-28 |
HU9401598D0 (en) | 1994-09-28 |
FI942463A (fi) | 1994-07-26 |
EP0661932A1 (fr) | 1995-07-12 |
HUT68764A (en) | 1995-07-28 |
NO941972L (no) | 1994-07-14 |
NO941972D0 (no) | 1994-05-26 |
AU3225093A (en) | 1993-06-28 |
CZ129094A3 (en) | 1995-12-13 |
WO1993010677A1 (fr) | 1993-06-10 |
FI942463A0 (fi) | 1994-05-26 |
JPH07504810A (ja) | 1995-06-01 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDE | Discontinued |