DE2333581A1 - Thiazolidine als riech- und/oder geschmackstoffe - Google Patents
Thiazolidine als riech- und/oder geschmackstoffeInfo
- Publication number
- DE2333581A1 DE2333581A1 DE19732333581 DE2333581A DE2333581A1 DE 2333581 A1 DE2333581 A1 DE 2333581A1 DE 19732333581 DE19732333581 DE 19732333581 DE 2333581 A DE2333581 A DE 2333581A DE 2333581 A1 DE2333581 A1 DE 2333581A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- radical
- aliphatic
- alkyl
- thiazolidine
- 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.)
- Withdrawn
Links
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 title claims description 12
- 239000000796 flavoring agent Substances 0.000 title claims description 12
- 235000019634 flavors Nutrition 0.000 title claims description 11
- 239000003205 fragrance Substances 0.000 title claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 150000004862 dioxolanes Chemical class 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- -1 aromatic radical Chemical class 0.000 description 37
- 235000019640 taste Nutrition 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 235000009508 confectionery Nutrition 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 6
- 244000046052 Phaseolus vulgaris Species 0.000 description 6
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 6
- 229960003151 mercaptamine Drugs 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000003548 thiazolidines Chemical class 0.000 description 5
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 4
- DQMLFUMEBNHPPB-UHFFFAOYSA-N 2-Methylthiazolidine Chemical compound CC1NCCS1 DQMLFUMEBNHPPB-UHFFFAOYSA-N 0.000 description 3
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 244000003416 Asparagus officinalis Species 0.000 description 3
- 235000005340 Asparagus officinalis Nutrition 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229930194542 Keto Natural products 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 235000013736 caramel Nutrition 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 2
- SNPQRYOQWLOTFA-UHFFFAOYSA-N 2,2-dimethyl-1,3-thiazolidine Chemical compound CC1(C)NCCS1 SNPQRYOQWLOTFA-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- CFAKWWQIUFSQFU-UHFFFAOYSA-N 2-hydroxy-3-methylcyclopent-2-en-1-one Chemical compound CC1=C(O)C(=O)CC1 CFAKWWQIUFSQFU-UHFFFAOYSA-N 0.000 description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000001543 Corylus americana Nutrition 0.000 description 2
- 235000007466 Corylus avellana Nutrition 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 229940011037 anethole Drugs 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229960001867 guaiacol Drugs 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229940043353 maltol Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- UDJJSTNTIKWCCW-UHFFFAOYSA-N (±)-2-propylthiazolidine Chemical compound CCCC1NCCS1 UDJJSTNTIKWCCW-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 1
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 1
- SKZVARYTMFXSBC-UHFFFAOYSA-N 1-(2-ethyl-1,3-thiazolidin-2-yl)ethanone Chemical compound CCC1(C(C)=O)NCCS1 SKZVARYTMFXSBC-UHFFFAOYSA-N 0.000 description 1
- WLXIBDDBHZVOIL-UHFFFAOYSA-N 1-(2-methyl-1,3-thiazolidin-2-yl)ethanone Chemical compound CC(=O)C1(C)NCCS1 WLXIBDDBHZVOIL-UHFFFAOYSA-N 0.000 description 1
- OFSMWMYSVZFQBG-UHFFFAOYSA-N 1-(2-methyl-1,3-thiazolidin-2-yl)ethyl acetate Chemical compound C(C)(=O)OC(C)C1(SCCN1)C OFSMWMYSVZFQBG-UHFFFAOYSA-N 0.000 description 1
- RWTJAJIRSFVUSE-UHFFFAOYSA-N 1-(2-methyl-1,3-thiazolidin-2-yl)propan-1-one Chemical compound CCC(=O)C1(C)NCCS1 RWTJAJIRSFVUSE-UHFFFAOYSA-N 0.000 description 1
- JQIBJYGPKFIOHE-UHFFFAOYSA-N 2,2-diethyl-1,3-thiazolidine Chemical compound CCC1(CC)NCCS1 JQIBJYGPKFIOHE-UHFFFAOYSA-N 0.000 description 1
- VBGXKCKAHZVOKE-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)-1,3-thiazolidine Chemical compound N1CCSC1C1=CC=CN1 VBGXKCKAHZVOKE-UHFFFAOYSA-N 0.000 description 1
- BIKPZSXYGBGIBF-UHFFFAOYSA-N 2-(2,2-dimethoxyethyl)-2-methyl-1,3-thiazolidine Chemical compound COC(OC)CC1(C)NCCS1 BIKPZSXYGBGIBF-UHFFFAOYSA-N 0.000 description 1
- RSQOHBZETPYFDN-UHFFFAOYSA-N 2-(2-ethylsulfanylethyl)-1,3-thiazolidine Chemical compound C(C)SCCC1SCCN1 RSQOHBZETPYFDN-UHFFFAOYSA-N 0.000 description 1
- WEQRMLKGBRBINL-UHFFFAOYSA-N 2-(4-methylpent-3-enyl)-1,3-thiazolidine Chemical compound CC(C)=CCCC1NCCS1 WEQRMLKGBRBINL-UHFFFAOYSA-N 0.000 description 1
- HXQNTXBXKKMEFR-UHFFFAOYSA-N 2-(furan-2-yl)-1,3-thiazolidine Chemical compound N1CCSC1C1=CC=CO1 HXQNTXBXKKMEFR-UHFFFAOYSA-N 0.000 description 1
- MOVBGBMWKHJQKI-UHFFFAOYSA-N 2-Pentylthiazolidine Chemical compound CCCCCC1NCCS1 MOVBGBMWKHJQKI-UHFFFAOYSA-N 0.000 description 1
- OJMCHODKAHUBRT-UHFFFAOYSA-N 2-benzyl-1,3-thiazolidine Chemical compound C=1C=CC=CC=1CC1NCCS1 OJMCHODKAHUBRT-UHFFFAOYSA-N 0.000 description 1
- FIEBNWSCVQZSGR-UHFFFAOYSA-N 2-butan-2-yl-1,3-thiazolidine Chemical compound CCC(C)C1NCCS1 FIEBNWSCVQZSGR-UHFFFAOYSA-N 0.000 description 1
- SZLVYXIKAAFTFY-UHFFFAOYSA-N 2-ethyl-1,3-thiazolidine Chemical compound CCC1NCCS1 SZLVYXIKAAFTFY-UHFFFAOYSA-N 0.000 description 1
- AGSHBVNPPGEAMB-UHFFFAOYSA-N 2-ethyl-2-methyl-1,3-thiazolidine Chemical compound CCC1(C)NCCS1 AGSHBVNPPGEAMB-UHFFFAOYSA-N 0.000 description 1
- FNEKTYBDXBVEBO-UHFFFAOYSA-N 2-methyl-2-nonyl-1,3-thiazolidine Chemical compound CCCCCCCCCC1(C)NCCS1 FNEKTYBDXBVEBO-UHFFFAOYSA-N 0.000 description 1
- JCIUYTAMMGYKAQ-UHFFFAOYSA-N 2-methyl-2-pentyl-1,3-thiazolidine Chemical compound CCCCCC1(C)NCCS1 JCIUYTAMMGYKAQ-UHFFFAOYSA-N 0.000 description 1
- SFVFUOJSSAQDKQ-UHFFFAOYSA-N 2-methyl-2-propan-2-yl-1,3-thiazolidine Chemical compound CC(C)C1(C)NCCS1 SFVFUOJSSAQDKQ-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- ULMSGFRYPNGQEL-UHFFFAOYSA-N 2-thiophen-2-yl-1,3-thiazolidine Chemical compound N1CCSC1C1=CC=CS1 ULMSGFRYPNGQEL-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 240000002234 Allium sativum Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 244000304217 Brassica oleracea var. gongylodes Species 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 240000009226 Corylus americana Species 0.000 description 1
- 240000007582 Corylus avellana Species 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 244000303040 Glycyrrhiza glabra Species 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 241000146226 Physalis ixocarpa Species 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 241000219492 Quercus Species 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 241001237745 Salamis Species 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 244000042295 Vigna mungo Species 0.000 description 1
- 235000010716 Vigna mungo Nutrition 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000007961 artificial flavoring substance Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- RJWLXGOSIRVRAR-UHFFFAOYSA-N dimethylresorcinol Natural products CC1=CC=C(O)C(C)=C1O RJWLXGOSIRVRAR-UHFFFAOYSA-N 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- RAWRTSJLYLJMPZ-UHFFFAOYSA-N ethyl 2-(2-methyl-1,3-thiazolidin-2-yl)acetate Chemical compound CCOC(=O)CC1(C)NCCS1 RAWRTSJLYLJMPZ-UHFFFAOYSA-N 0.000 description 1
- GUTUCYRFQRRGML-UHFFFAOYSA-N ethyl 2-methyl-1,3-thiazolidine-2-carboxylate Chemical compound CCOC(=O)C1(C)NCCS1 GUTUCYRFQRRGML-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000011477 liquorice Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000019639 meaty taste Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 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
- 235000011929 mousse Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000015175 salami Nutrition 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 230000001755 vocal effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- 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
- A23L27/2056—Heterocyclic compounds having at least two different hetero atoms, at least one being a nitrogen 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
- A23L27/27—Smoke flavours
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Seasonings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Fats And Perfumes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH998972A CH577272A5 (xx) | 1972-07-04 | 1972-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2333581A1 true DE2333581A1 (de) | 1974-01-24 |
Family
ID=4357905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732333581 Withdrawn DE2333581A1 (de) | 1972-07-04 | 1973-07-02 | Thiazolidine als riech- und/oder geschmackstoffe |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5730462B2 (xx) |
| CH (1) | CH577272A5 (xx) |
| DE (1) | DE2333581A1 (xx) |
| FR (1) | FR2190378B1 (xx) |
| GB (2) | GB1393478A (xx) |
| NL (1) | NL7308284A (xx) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3025461A1 (de) * | 1979-07-04 | 1981-01-29 | Sogo Pharm | Verfahren zur herstellung von mineralsaeuresalzen von cysteaminen |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI283168B (en) * | 2000-09-14 | 2007-07-01 | Ajinomoto Kk | Composition for enhancing or improving the flavor of foods or drinks and method thereof |
| JP5174231B1 (ja) * | 2011-12-15 | 2013-04-03 | 小川香料株式会社 | ピーナッツ風味を有する飲食品の香味改善剤 |
-
1972
- 1972-07-04 CH CH998972A patent/CH577272A5/xx not_active IP Right Cessation
-
1973
- 1973-06-14 NL NL7308284A patent/NL7308284A/xx not_active Application Discontinuation
- 1973-07-02 DE DE19732333581 patent/DE2333581A1/de not_active Withdrawn
- 1973-07-03 JP JP7517673A patent/JPS5730462B2/ja not_active Expired
- 1973-07-04 GB GB4368874A patent/GB1393478A/en not_active Expired
- 1973-07-04 FR FR7324547A patent/FR2190378B1/fr not_active Expired
- 1973-07-04 GB GB3181073A patent/GB1393477A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3025461A1 (de) * | 1979-07-04 | 1981-01-29 | Sogo Pharm | Verfahren zur herstellung von mineralsaeuresalzen von cysteaminen |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1393478A (en) | 1975-05-07 |
| FR2190378A1 (xx) | 1974-02-01 |
| JPS5730462B2 (xx) | 1982-06-29 |
| GB1393477A (en) | 1975-05-07 |
| CH577272A5 (xx) | 1976-07-15 |
| FR2190378B1 (xx) | 1977-02-18 |
| JPS4942859A (xx) | 1974-04-22 |
| NL7308284A (xx) | 1974-01-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2417385C3 (de) | Verfahren zur Veränderung des Aromas von Fleisch- und Geflügelgeschmackszusammensetzungen | |
| DE1932799A1 (de) | Verfahren zur Herstellung von Aromasubstanzen | |
| US4011233A (en) | 2-methyl-2-(4-methyl-3-pentene-1-yl) thiazolidine | |
| DE2336356A1 (de) | Geschmacks- und aromabeeinflussung mit einer 5- oder 6-gliedrigen heterozyklischen dithioverbindung | |
| DE2152557A1 (de) | Wuerz- und Aromamittel sowie neue substituierte Thiazole mit Wuerz- und Duftstoffcharakter | |
| DE2333581A1 (de) | Thiazolidine als riech- und/oder geschmackstoffe | |
| DE2226780A1 (de) | Neue geschmackstoffe | |
| DE2120413A1 (de) | Cycloaliphatische Crotonoylverbindungen | |
| DE2353795A1 (de) | Verfahren und mittel zur aenderung der organoleptischen eigenschaften von verbrauchbaren materialien | |
| DE2359891A1 (de) | Verfahren zur herstellung von furanonderivaten | |
| DE2003525B2 (de) | Furanderivate und deren verwendung als zusatz zu nahrungsmitteln zur erzielung eines geschmacks von gebratenem fleisch | |
| DE2605286C2 (de) | 3-Furylalkylsulfide und deren Verwendung | |
| CH623568A5 (en) | Process for the preparation of novel perfumes and/or flavourings | |
| CH590857A5 (en) | Substd. thiazolidine odourants flavourants - having a wide aroma spectrum and usable in small concns. | |
| AT340748B (de) | Verfahren zur aromatisierung von lebensmitteln | |
| DE2166810C3 (de) | 5,7-Dihydrothieno [3,4-b] pyrazine, Verfahren zu deren Herstellung und ihre Verwendung | |
| US3944561A (en) | 2-Methyl-2-acetyl-thiazolidine | |
| DE2345065A1 (de) | Aromakompositionen | |
| DE1964276C3 (de) | 2-Acyl-2-thiazoline, ihre Herstellung und Verwendung | |
| DE2528459A1 (de) | 3 eckige klammer auf (2-mercapto- 1-methylpropyl) thio eckige klammer zu -2-butanol sowie verfahren zu dessen herstellung | |
| DE1921560A1 (de) | Ungesaettigte Aldehyde | |
| DE2604340C3 (de) | 3-Furylalkyldisulfide, Verfahren zu deren Herstellung und ihre Verwendung als Würzmittel | |
| DE2043585A1 (en) | Substituted heterocyclic nitrogen compounds, processes for producing the same, flavour and fragrance compositions comprising the same and process for preparing such compositions | |
| DE2233245C3 (de) | 1,3-Dioxolane und Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Geschmackstoff zusammensetzungen | |
| DE2214540A1 (de) | Heterocyclische Schwefelverbindungen und Verfahren zu ihrer Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8139 | Disposal/non-payment of the annual fee |