SG174391A1 - Carbonothioates as flavours and fragrances - Google Patents
Carbonothioates as flavours and fragrances Download PDFInfo
- Publication number
- SG174391A1 SG174391A1 SG2011066370A SG2011066370A SG174391A1 SG 174391 A1 SG174391 A1 SG 174391A1 SG 2011066370 A SG2011066370 A SG 2011066370A SG 2011066370 A SG2011066370 A SG 2011066370A SG 174391 A1 SG174391 A1 SG 174391A1
- Authority
- SG
- Singapore
- Prior art keywords
- ethyl
- formula
- flavour
- carbonothioate
- coffee
- Prior art date
Links
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 29
- 235000019634 flavors Nutrition 0.000 title claims abstract description 29
- 239000003205 fragrance Substances 0.000 title claims abstract description 17
- WRWHFVRDUAQRIQ-UHFFFAOYSA-N carbonothioic O,O-acid Chemical class OC(O)=S WRWHFVRDUAQRIQ-UHFFFAOYSA-N 0.000 title claims description 3
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000004615 ingredient Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 34
- -1 O-ethyl S-4-hydroxy-3-methylbutan-2-yl carbonothioate O-ethyl S-4-hydroxy-3-methylpentan-2-yl carbonothioate O-ethyl S-4-hydroxy-2-methylbutan-2-yl carbonothioate Chemical compound 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000001782 FEMA 4730 Substances 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- GWLIQCMCWOYRMA-UHFFFAOYSA-N ethyl 1-methoxyhexan-3-ylsulfanylformate Chemical compound COCCC(CCC)SC(=O)OCC GWLIQCMCWOYRMA-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 235000013353 coffee beverage Nutrition 0.000 description 22
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000284 extract Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 235000013361 beverage Nutrition 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- 241000533293 Sesbania emerus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000008373 coffee flavor Substances 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 3
- MFEIKQPHQINPRI-UHFFFAOYSA-N 3-Ethylpyridine Chemical compound CCC1=CC=CN=C1 MFEIKQPHQINPRI-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 240000001890 Ribes hudsonianum Species 0.000 description 2
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 2
- 235000001466 Ribes nigrum Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FINHMKGKINIASC-UHFFFAOYSA-N Tetramethylpyrazine Chemical compound CC1=NC(C)=C(C)N=C1C FINHMKGKINIASC-UHFFFAOYSA-N 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- POIARNZEYGURDG-FNORWQNLSA-N beta-damascenone Chemical compound C\C=C\C(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-FNORWQNLSA-N 0.000 description 2
- 235000015123 black coffee Nutrition 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 229940113120 dipropylene glycol Drugs 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 235000021539 instant coffee Nutrition 0.000 description 2
- 229940074928 isopropyl myristate Drugs 0.000 description 2
- ZVTZHSNSHRDTEM-UHFFFAOYSA-N methyl 1-methoxyhexan-3-ylsulfanylformate Chemical compound COCCC(CCC)SC(=O)OC ZVTZHSNSHRDTEM-UHFFFAOYSA-N 0.000 description 2
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 229960002622 triacetin Drugs 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- IAEGWXHKWJGQAZ-UHFFFAOYSA-N trimethylpyrazine Chemical compound CC1=CN=C(C)C(C)=N1 IAEGWXHKWJGQAZ-UHFFFAOYSA-N 0.000 description 2
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 1
- KUPODEXLSGEWFR-PLNGDYQASA-N (z)-1-methoxyhex-3-ene Chemical compound CC\C=C/CCOC KUPODEXLSGEWFR-PLNGDYQASA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
- LNIMMWYNSBZESE-UHFFFAOYSA-N 2-Ethyl-3-methylpyrazine, 9CI Chemical compound CCC1=NC=CN=C1C LNIMMWYNSBZESE-UHFFFAOYSA-N 0.000 description 1
- ZFFTZDQKIXPDAF-UHFFFAOYSA-N 2-Furanmethanethiol Chemical compound SCC1=CC=CO1 ZFFTZDQKIXPDAF-UHFFFAOYSA-N 0.000 description 1
- XBTDLLKONSPIBM-UHFFFAOYSA-N 2-ethyl-3-(2-methoxyethyl)thiirane Chemical compound CCC1SC1CCOC XBTDLLKONSPIBM-UHFFFAOYSA-N 0.000 description 1
- 239000001837 2-hydroxy-3-methylcyclopent-2-en-1-one Substances 0.000 description 1
- YOMSJEATGXXYPX-UHFFFAOYSA-N 2-methoxy-4-vinylphenol Chemical compound COC1=CC(C=C)=CC=C1O YOMSJEATGXXYPX-UHFFFAOYSA-N 0.000 description 1
- OMNGOGILVBLKAS-UHFFFAOYSA-N 2-methoxyphenol Chemical compound COC1=CC=CC=C1O.COC1=CC=CC=C1O OMNGOGILVBLKAS-UHFFFAOYSA-N 0.000 description 1
- JHWFWLUAUPZUCP-UHFFFAOYSA-N 3-Ethyl-2-hydroxycyclopent-2-en-1-one Chemical compound CCC1=C(O)C(=O)CC1 JHWFWLUAUPZUCP-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 244000288157 Passiflora edulis Species 0.000 description 1
- 235000000370 Passiflora edulis Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000014448 bouillon/stock cubes Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 235000014613 canned/preserved soup Nutrition 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XQZBFNBDEAPJMX-UHFFFAOYSA-N ethyl (4-hydroxy-2-methylbutan-2-yl)sulfanylformate Chemical compound CCOC(=O)SC(C)(C)CCO XQZBFNBDEAPJMX-UHFFFAOYSA-N 0.000 description 1
- XRUZRUJCRJMESO-UHFFFAOYSA-N ethyl (4-hydroxy-2-methylpentan-2-yl)sulfanylformate Chemical compound CCOC(=O)SC(C)(C)CC(C)O XRUZRUJCRJMESO-UHFFFAOYSA-N 0.000 description 1
- RIMNXNCUAGYIMU-UHFFFAOYSA-N ethyl (4-hydroxy-3-methylpentan-2-yl)sulfanylformate;(4-hydroxy-3-methylbutan-2-yl)sulfanylformic acid Chemical compound OCC(C)C(C)SC(O)=O.CCOC(=O)SC(C)C(C)C(C)O RIMNXNCUAGYIMU-UHFFFAOYSA-N 0.000 description 1
- BKMMJZITPOYKJN-UHFFFAOYSA-N ethyl 1-hydroxyhexan-3-ylsulfanylformate Chemical compound CCCC(CCO)SC(=O)OCC BKMMJZITPOYKJN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000020335 flavoured tea Nutrition 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 235000008378 frozen soup Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- 235000020603 homogenised milk Nutrition 0.000 description 1
- 235000014109 instant soup Nutrition 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- CFAKWWQIUFSQFU-UHFFFAOYSA-N maple lactone Natural products CC1=C(O)C(=O)CC1 CFAKWWQIUFSQFU-UHFFFAOYSA-N 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000003928 nasal cavity Anatomy 0.000 description 1
- 210000001706 olfactory mucosa Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000015504 ready meals Nutrition 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229930007850 β-damascenone Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/02—Monothiocarbonic acids; Derivatives thereof
- C07C329/04—Esters of monothiocarbonic acids
- C07C329/06—Esters of monothiocarbonic acids having sulfur atoms of thiocarbonic groups bound to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2022—Aliphatic compounds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0011—Aliphatic compounds containing S
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Nutrition Science (AREA)
- Fats And Perfumes (AREA)
- Tea And Coffee (AREA)
- Seasonings (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0906009.6A GB0906009D0 (en) | 2009-04-07 | 2009-04-07 | Organic compounds |
| PCT/EP2010/054582 WO2010115920A1 (en) | 2009-04-07 | 2010-04-07 | Carbonothioates as flavours and fragrances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG174391A1 true SG174391A1 (en) | 2011-11-28 |
Family
ID=40750238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2011066370A SG174391A1 (en) | 2009-04-07 | 2010-04-07 | Carbonothioates as flavours and fragrances |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8765204B2 (https=) |
| EP (1) | EP2417105B1 (https=) |
| JP (1) | JP5805070B2 (https=) |
| CN (1) | CN102365267B (https=) |
| BR (1) | BRPI1014384B1 (https=) |
| GB (1) | GB0906009D0 (https=) |
| SG (1) | SG174391A1 (https=) |
| WO (1) | WO2010115920A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6805477B2 (ja) * | 2015-07-30 | 2020-12-23 | 味の素株式会社 | 油脂含有乳風味飲食品のコク味増強方法 |
| DE102015217864A1 (de) * | 2015-09-17 | 2017-03-23 | Henkel Ag & Co. Kgaa | Parfümzusammensetzung mit Geruchsmodulatorverbindungen zur Steigerung der Duftintensität |
| WO2018113925A1 (de) * | 2016-12-20 | 2018-06-28 | Symrise Ag | Aromamischung zur reduktion des geruchs oder geschmacks biogener amine |
| GB201707639D0 (en) * | 2017-05-12 | 2017-06-28 | Givaudan Sa | Improvements in or relating to organic compounds |
| JP6697429B2 (ja) * | 2017-11-06 | 2020-05-20 | 長谷川香料株式会社 | 新規アルカンチオ酸誘導体および該化合物を含有する香料組成物 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1379019A (en) | 1970-12-07 | 1975-01-02 | Unilever Ltd | Flavouring food products |
| US3885051A (en) * | 1972-10-30 | 1975-05-20 | Int Flavors & Fragrances Inc | Flavoring and aromatising with 3-acetyl-2,5-dialkyl furans or thiophenes |
| US3978240A (en) * | 1973-12-30 | 1976-08-31 | Lever Brothers Company | Foodstuff containing a diester of monothiocarbonic acid |
| NZ328102A (en) * | 1996-06-24 | 1998-04-27 | Givaudan Roure Int | Fragrance precursors and deodorant compositions |
| ES2187105T3 (es) * | 1998-08-21 | 2003-05-16 | Firmenich & Cie | Eteres; su utilizacion como agentes perfumantes y aromatizantes; su preparacion. |
| EP1170295B1 (en) | 2000-07-07 | 2007-12-19 | Quest International B.V. | Thiocarbonates as flavour precursors |
| EP1264547A1 (en) | 2001-06-06 | 2002-12-11 | Givaudan SA | Flavour and fragrance compositions |
| DE10323703A1 (de) * | 2003-05-22 | 2004-12-23 | Beiersdorf Ag | Mikrobizide Zubereitungen und ihre Verwendung |
| GB0519171D0 (en) * | 2005-09-21 | 2005-10-26 | Givaudan Sa | Organic compounds |
-
2009
- 2009-04-07 GB GBGB0906009.6A patent/GB0906009D0/en not_active Ceased
-
2010
- 2010-04-07 BR BRPI1014384A patent/BRPI1014384B1/pt active IP Right Grant
- 2010-04-07 CN CN201080015291.1A patent/CN102365267B/zh active Active
- 2010-04-07 US US13/262,267 patent/US8765204B2/en active Active
- 2010-04-07 SG SG2011066370A patent/SG174391A1/en unknown
- 2010-04-07 EP EP10714876A patent/EP2417105B1/en active Active
- 2010-04-07 JP JP2012504006A patent/JP5805070B2/ja active Active
- 2010-04-07 WO PCT/EP2010/054582 patent/WO2010115920A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI1014384A2 (pt) | 2016-05-24 |
| CN102365267A (zh) | 2012-02-29 |
| EP2417105A1 (en) | 2012-02-15 |
| US8765204B2 (en) | 2014-07-01 |
| GB0906009D0 (en) | 2009-05-20 |
| US20120052178A1 (en) | 2012-03-01 |
| EP2417105B1 (en) | 2013-04-03 |
| BRPI1014384B1 (pt) | 2019-01-29 |
| WO2010115920A1 (en) | 2010-10-14 |
| JP5805070B2 (ja) | 2015-11-04 |
| JP2012522826A (ja) | 2012-09-27 |
| CN102365267B (zh) | 2014-07-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100569738C (zh) | 共轭二烯酰胺及其制备方法，含共轭二烯酰胺的组合物及其用途 | |
| JP2007510634A (ja) | 芳香物質としてのアルケンカルボン酸ｎ−アルキルアミドの使用 | |
| ES2373589T3 (es) | Nuevos tioalcanales de furilo útiles en la industria de los aromas. | |
| EP2417105B1 (en) | Carbonothioates as flavours and fragrances | |
| US6610346B1 (en) | Mercapto-alkanol flavor compounds | |
| KR100957887B1 (ko) | 방향제 조성물 | |
| US10178875B2 (en) | Methods of modifying or imparting taste using organic compounds | |
| JP5868811B2 (ja) | 香味付与乃至増強剤 | |
| JP5645389B2 (ja) | 持続性香気賦与剤 | |
| JP6113256B2 (ja) | 天然感あふれるオイリー感付与乃至増強剤 | |
| EP3621953B1 (en) | Alkenyl carbonothioates as flavour ingredients | |
| JP7554716B2 (ja) | ジスルフィド化合物を含む香味付与組成物 | |
| JP2019187345A (ja) | 飲食品の風味改善剤 | |
| JP5911202B2 (ja) | 香料組成物 | |
| JP2008011788A (ja) | アズキ食品添加用香料組成物、アズキ食品及びアズキ食品の香味改善方法 | |
| JP3619857B2 (ja) | 香料組成物 | |
| JP6113257B2 (ja) | 柑橘果皮をイメージさせるピーリーなフレッシュ感付与乃至増強剤 | |
| JP2021143150A (ja) | 含硫化合物および香味付与剤 | |
| JP7326243B2 (ja) | シクロプロパン骨格を有するラクトン化合物 | |
| JP7362591B2 (ja) | 含硫ラクトン化合物 | |
| WO2008009926A2 (en) | Safrole replacements | |
| US20100291275A1 (en) | Flavorant and Fragrance Furan-2(5H)-One Compounds | |
| WO2012144604A1 (ja) | 香味料組成物 | |
| MXPA00005205A (en) | Mercapto alcohols as flavouring compounds |