DE2043366C2 - Mercapto- oder alkylthio-substituierte Terpenoide, deren Herstellung und Geschmack- bzw. Riechstoffkompositionen auf deren Basis - Google Patents
Mercapto- oder alkylthio-substituierte Terpenoide, deren Herstellung und Geschmack- bzw. Riechstoffkompositionen auf deren BasisInfo
- Publication number
- DE2043366C2 DE2043366C2 DE2043366A DE2043366A DE2043366C2 DE 2043366 C2 DE2043366 C2 DE 2043366C2 DE 2043366 A DE2043366 A DE 2043366A DE 2043366 A DE2043366 A DE 2043366A DE 2043366 C2 DE2043366 C2 DE 2043366C2
- Authority
- DE
- Germany
- Prior art keywords
- mercapto
- compounds
- flavor
- alkylthio
- compound
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title description 23
- 239000000796 flavoring agent Substances 0.000 title description 8
- 235000019634 flavors Nutrition 0.000 title description 8
- 239000003205 fragrance Substances 0.000 title description 7
- 150000003505 terpenes Chemical class 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 33
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- -1 dimethylmethylene group Chemical group 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000007858 starting material Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 235000014347 soups Nutrition 0.000 description 6
- 150000003464 sulfur compounds Chemical class 0.000 description 6
- 244000291564 Allium cepa Species 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- NZGWDASTMWDZIW-MRVPVSSYSA-N (+)-pulegone Chemical compound C[C@@H]1CCC(=C(C)C)C(=O)C1 NZGWDASTMWDZIW-MRVPVSSYSA-N 0.000 description 4
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 4
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZITBETUVISHUJS-UHFFFAOYSA-N 2-methyl-5-prop-1-en-2-yl-3-sulfanylcyclohexan-1-one Chemical compound CC1C(S)CC(C(C)=C)CC1=O ZITBETUVISHUJS-UHFFFAOYSA-N 0.000 description 3
- YSTPAHQEHQSRJD-UHFFFAOYSA-N 3-Carvomenthenone Chemical compound CC(C)C1CCC(C)=CC1=O YSTPAHQEHQSRJD-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 3
- 240000000467 Carum carvi Species 0.000 description 3
- 235000005747 Carum carvi Nutrition 0.000 description 3
- 239000005973 Carvone Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 3
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 3
- 235000013575 mashed potatoes Nutrition 0.000 description 3
- 229930006968 piperitone Natural products 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- DCSCXTJOXBUFGB-JGVFFNPUSA-N (R)-(+)-Verbenone Natural products CC1=CC(=O)[C@@H]2C(C)(C)[C@H]1C2 DCSCXTJOXBUFGB-JGVFFNPUSA-N 0.000 description 2
- DCSCXTJOXBUFGB-SFYZADRCSA-N (R)-(+)-verbenone Chemical compound CC1=CC(=O)[C@H]2C(C)(C)[C@@H]1C2 DCSCXTJOXBUFGB-SFYZADRCSA-N 0.000 description 2
- 240000006108 Allium ampeloprasum Species 0.000 description 2
- 235000005254 Allium ampeloprasum Nutrition 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 244000178937 Brassica oleracea var. capitata Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 235000021028 berry Nutrition 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 229940043350 citral Drugs 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 2
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 description 2
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 description 1
- RMIANEGNSBUGDJ-DTWKUNHWSA-N (2r,5s)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-one Chemical compound C[C@H]1CC[C@H](C(C)=C)C(=O)C1 RMIANEGNSBUGDJ-DTWKUNHWSA-N 0.000 description 1
- HJFSNLWDUINFTB-IUCAKERBSA-N (2s,5s)-5-methyl-2-(2-methylsulfanylpropan-2-yl)cyclohexan-1-one Chemical compound CSC(C)(C)[C@H]1CC[C@H](C)CC1=O HJFSNLWDUINFTB-IUCAKERBSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- BVACDZLXQCWKAF-UHFFFAOYSA-N 2-methyl-3-methylsulfanyl-5-prop-1-en-2-ylcyclohexan-1-one Chemical compound CSC1CC(C(C)=C)CC(=O)C1C BVACDZLXQCWKAF-UHFFFAOYSA-N 0.000 description 1
- SZWMVTCMSLWXLN-UHFFFAOYSA-N 3,7,7-trimethyl-3-methylsulfanylbicyclo[4.1.0]heptan-5-one Chemical compound O=C1CC(SC)(C)CC2C(C)(C)C12 SZWMVTCMSLWXLN-UHFFFAOYSA-N 0.000 description 1
- BQQWJKHFPSNFLB-UHFFFAOYSA-N 3,7-dimethyl-3-methylsulfanyloct-6-enal Chemical compound O=CCC(C)(SC)CCC=C(C)C BQQWJKHFPSNFLB-UHFFFAOYSA-N 0.000 description 1
- WDILKLCBAXJFIA-UHFFFAOYSA-N 3-Caren-5-one Chemical compound C1C(C)=CC(=O)C2C(C)(C)C12 WDILKLCBAXJFIA-UHFFFAOYSA-N 0.000 description 1
- YDBPGXCMNSBEHK-UHFFFAOYSA-N 4,7,7-trimethyl-3-methylsulfanylbicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(C)C(SC)CC2C(C)(C)C12 YDBPGXCMNSBEHK-UHFFFAOYSA-N 0.000 description 1
- SAFIHMIEMQFPDA-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[4.1.0]hept-3-en-5-one Chemical compound O=C1C(C)=CCC2C(C)(C)C12 SAFIHMIEMQFPDA-UHFFFAOYSA-N 0.000 description 1
- MBZRJSQZCBXRGK-UHFFFAOYSA-N 4-tert-Butylcyclohexyl acetate Chemical compound CC(=O)OC1CCC(C(C)(C)C)CC1 MBZRJSQZCBXRGK-UHFFFAOYSA-N 0.000 description 1
- HJFSNLWDUINFTB-UHFFFAOYSA-N 5-methyl-2-(2-methylsulfanylpropan-2-yl)cyclohexan-1-one Chemical compound CSC(C)(C)C1CCC(C)CC1=O HJFSNLWDUINFTB-UHFFFAOYSA-N 0.000 description 1
- KMRMUZKLFIEVAO-UHFFFAOYSA-N 7,7-dimethylbicyclo[3.1.1]hept-3-ene-4-carbaldehyde Chemical compound C1C2C(C)(C)C1CC=C2C=O KMRMUZKLFIEVAO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000010167 Allium cepa var aggregatum Nutrition 0.000 description 1
- 240000002234 Allium sativum Species 0.000 description 1
- 240000000662 Anethum graveolens Species 0.000 description 1
- 240000003291 Armoracia rusticana Species 0.000 description 1
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- MGYMHQJELJYRQS-UHFFFAOYSA-N Ascaridole Chemical compound C1CC2(C)OOC1(C(C)C)C=C2 MGYMHQJELJYRQS-UHFFFAOYSA-N 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- WDILKLCBAXJFIA-VXNVDRBHSA-N Car-3-en-5-one Natural products O=C1[C@@H]2C(C)(C)[C@@H]2CC(C)=C1 WDILKLCBAXJFIA-VXNVDRBHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- 244000178870 Lavandula angustifolia Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- KMRMUZKLFIEVAO-RKDXNWHRSA-N Myrtenal Natural products C1[C@H]2C(C)(C)[C@@H]1CC=C2C=O KMRMUZKLFIEVAO-RKDXNWHRSA-N 0.000 description 1
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 description 1
- 101100020663 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ppm-1 gene Proteins 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 244000299790 Rheum rhabarbarum Species 0.000 description 1
- 235000009411 Rheum rhabarbarum Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 240000002657 Thymus vulgaris Species 0.000 description 1
- 235000007303 Thymus vulgaris Nutrition 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 229930003651 acyclic monoterpene Natural products 0.000 description 1
- 150000002841 acyclic monoterpene derivatives Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- MGYMHQJELJYRQS-ZJUUUORDSA-N ascaridole Natural products C1C[C@]2(C)OO[C@@]1(C(C)C)C=C2 MGYMHQJELJYRQS-ZJUUUORDSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229930003642 bicyclic monoterpene Chemical class 0.000 description 1
- 150000001604 bicyclic monoterpene derivatives Chemical class 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000001172 carvone group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000001524 citrus aurantium oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229930003647 monocyclic monoterpene Chemical class 0.000 description 1
- 150000002767 monocyclic monoterpene derivatives Chemical class 0.000 description 1
- 235000013923 monosodium glutamate Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000012437 perfumed product Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000021397 ready fried onions Nutrition 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Classifications
-
- 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six 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
-
- 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
- A23L27/203—Alicyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/20—All rings being cycloaliphatic the ring system containing seven carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Seasonings (AREA)
- Seeds, Soups, And Other Foods (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1374869A CH525198A (de) | 1969-09-10 | 1969-09-10 | Verfahren zur Herstellung von neuen mercapto- oder alkylthio-substituierten Terpenoiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2043366A1 DE2043366A1 (de) | 1971-03-11 |
| DE2043366C2 true DE2043366C2 (de) | 1983-12-29 |
Family
ID=4394953
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2043366A Expired DE2043366C2 (de) | 1969-09-10 | 1970-09-01 | Mercapto- oder alkylthio-substituierte Terpenoide, deren Herstellung und Geschmack- bzw. Riechstoffkompositionen auf deren Basis |
| DE2043341A Expired DE2043341C3 (de) | 1969-09-10 | 1970-09-01 | Verwendung von p-Menthan-8-thiol-3-on als Riechstoff |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2043341A Expired DE2043341C3 (de) | 1969-09-10 | 1970-09-01 | Verwendung von p-Menthan-8-thiol-3-on als Riechstoff |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US3819712A (OSRAM) |
| JP (3) | JPS5031144B1 (OSRAM) |
| AT (2) | AT308283B (OSRAM) |
| AU (1) | AU1944870A (OSRAM) |
| BE (2) | BE755504A (OSRAM) |
| CA (2) | CA991084A (OSRAM) |
| CH (3) | CH525198A (OSRAM) |
| DE (2) | DE2043366C2 (OSRAM) |
| ES (2) | ES383474A1 (OSRAM) |
| FR (2) | FR2061637B1 (OSRAM) |
| GB (2) | GB1323467A (OSRAM) |
| GT (1) | GT197122379A (OSRAM) |
| IL (1) | IL35166A (OSRAM) |
| IT (2) | IT1050116B (OSRAM) |
| NL (2) | NL7012644A (OSRAM) |
| SE (1) | SE391728B (OSRAM) |
| SU (1) | SU379087A3 (OSRAM) |
| ZA (2) | ZA705808B (OSRAM) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3914316A (en) * | 1972-12-29 | 1975-10-21 | Dow Chemical Co | Preparation of 2-(sulfur-substituted)-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-ones |
| US4044164A (en) * | 1976-10-07 | 1977-08-23 | International Flavors & Fragrances Inc. | Uses of α-oxy(oxo) sulfides and ethers in foodstuffs and flavors for foodstuffs |
| US4024289A (en) * | 1976-09-15 | 1977-05-17 | International Flavors & Fragrances Inc. | Flavoring with α-oxy(oxo)mercaptans |
| US4045491A (en) * | 1976-10-07 | 1977-08-30 | International Flavors & Fragrances Inc. | α-Oxy(oxo) sulfides and ethers |
| US4053655A (en) * | 1976-10-07 | 1977-10-11 | International Flavors & Fragrances Inc. | Uses of α-oxy(oxo) sulfides and ethers in foodstuffs and flavors for foodstuffs |
| US4055691A (en) * | 1976-10-07 | 1977-10-25 | International Flavors & Fragrances Inc. | Uses of α-oxy(oxo) sulfides and ethers in foodstuffs and flavors for foodstuffs |
| US4053654A (en) * | 1976-10-07 | 1977-10-11 | International Flavors & Fragrances Inc. | Uses of α-oxy(oxo) sulfides and ethers in foodstuffs and flavors for foodstuffs |
| US4502985A (en) * | 1982-07-21 | 1985-03-05 | Dragoco Gerberding & Co. Gmbh | Use of 1,5-dimethyl-8-hydroximino-bicyclo[3.2.1]octane as perfuming ingredient |
| JPS5949339U (ja) * | 1982-09-27 | 1984-04-02 | 三菱電機株式会社 | フロ−スイツチ |
| US5578470A (en) * | 1987-01-30 | 1996-11-26 | Nederlandse Organisatie Voor Toegepast | Method for preparing thiol compounds with bacterial β-lyase |
| NL8700240A (nl) * | 1987-01-30 | 1988-08-16 | Tno | Werkwijze voor het bereiden van thiolverbindingen. |
| PL209377B1 (pl) * | 2001-12-13 | 2011-08-31 | Firmenich & Cie | Kompozycja zapachowa lub wyrób perfumowany, sposób poprawiania, zwiększania lub modyfikowania zapachu kompozycji zapachowej lub wyrobu perfumowanego, sposób perfumowania powierzchni, sposób intensyfikowania lub przedłużania efektu dyfundowania składnika zapachowego na powierzchni, oraz związek stanowiący składnik czynny |
| DE102009026698A1 (de) * | 2009-06-03 | 2010-12-09 | Symrise Gmbh & Co. Kg | Verwendung bestimmter Isopropylmethylcyclohexenthiole als Riech- und/oder Aromastoffe |
| JP6000438B2 (ja) * | 2012-03-20 | 2016-09-28 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | 活性な香料分子の制御放出のための化合物 |
| DE102013226216A1 (de) * | 2013-12-17 | 2015-06-18 | Henkel Ag & Co. Kgaa | Michael-Systeme für die Duftstoff-Stabilisierung |
| CN104109109B (zh) * | 2014-05-21 | 2016-09-14 | 陕西科技大学 | 一种利用长叶薄荷酮和硫化钠制备食用香精8-巯基马来酮的方法 |
| CN104109110B (zh) * | 2014-05-21 | 2016-08-24 | 陕西科技大学 | 一种食用香精8-巯基马来酮的制备方法 |
| KR20230097008A (ko) | 2020-10-26 | 2023-06-30 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 생체흡수성 섬유상 의료재료 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2212150A (en) * | 1938-12-06 | 1940-08-20 | Du Pont | Organic sulphur compounds |
| US2465882A (en) * | 1945-07-03 | 1949-03-29 | Ilford Ltd | Hydrocarbon-thio-cyclohexenones |
| US2586306A (en) * | 1949-10-26 | 1952-02-19 | Gen Aniline & Film Corp | Synthesis of vitamin a and intermediates therefor |
| US3248315A (en) * | 1964-07-06 | 1966-04-26 | Phillips Petroleum Co | Thiol production |
| US3723531A (en) * | 1968-07-11 | 1973-03-27 | Mobil Oil Corp | 2-substituted-thio-2-cyclohexene-1-one and method for preparing them |
| US3820975A (en) * | 1970-11-12 | 1974-06-28 | Chemagro Corp | Method for controlling plant growth with substituted cyclohexenones |
| CH551957A (de) * | 1970-12-08 | 1974-07-31 | Givaudan & Cie Sa | Verfahren zur herstellung von neuen jononderivaten. |
| JPS541422B2 (OSRAM) * | 1972-06-30 | 1979-01-24 |
-
1969
- 1969-09-10 CH CH1374869A patent/CH525198A/de not_active IP Right Cessation
- 1969-09-10 CH CH1687871A patent/CH530459A/de not_active IP Right Cessation
- 1969-09-10 CH CH1331170A patent/CH524581A/de not_active IP Right Cessation
-
1970
- 1970-08-24 ZA ZA705808A patent/ZA705808B/xx unknown
- 1970-08-24 ZA ZA705807A patent/ZA705807B/xx unknown
- 1970-08-25 IL IL35166A patent/IL35166A/xx unknown
- 1970-08-26 NL NL7012644A patent/NL7012644A/xx unknown
- 1970-08-26 NL NL7012643A patent/NL7012643A/xx unknown
- 1970-08-31 BE BE755504D patent/BE755504A/xx unknown
- 1970-08-31 BE BE755503A patent/BE755503A/xx not_active IP Right Cessation
- 1970-09-01 DE DE2043366A patent/DE2043366C2/de not_active Expired
- 1970-09-01 DE DE2043341A patent/DE2043341C3/de not_active Expired
- 1970-09-02 AU AU19448/70A patent/AU1944870A/en not_active Expired
- 1970-09-03 US US00069457A patent/US3819712A/en not_active Expired - Lifetime
- 1970-09-08 GB GB4288770A patent/GB1323467A/en not_active Expired
- 1970-09-08 GB GB4288670A patent/GB1323167A/en not_active Expired
- 1970-09-09 AT AT816470A patent/AT308283B/de active
- 1970-09-09 AT AT155172A patent/AT311324B/de not_active IP Right Cessation
- 1970-09-09 FR FR707032707A patent/FR2061637B1/fr not_active Expired
- 1970-09-09 ES ES383474A patent/ES383474A1/es not_active Expired
- 1970-09-09 ES ES383475A patent/ES383475A1/es not_active Expired
- 1970-09-09 FR FR7032708A patent/FR2061158A5/fr not_active Expired
- 1970-09-09 SU SU1482987A patent/SU379087A3/ru active
- 1970-09-09 CA CA092,642A patent/CA991084A/en not_active Expired
- 1970-09-09 SE SE7317031A patent/SE391728B/xx unknown
- 1970-09-10 IT IT29592/70A patent/IT1050116B/it active
- 1970-09-10 IT IT29591/70A patent/IT1034017B/it active
- 1970-09-10 JP JP45079631A patent/JPS5031144B1/ja active Pending
- 1970-09-10 JP JP45079630A patent/JPS5231862B1/ja active Pending
- 1970-09-10 CA CA092,755A patent/CA1040654A/en not_active Expired
-
1971
- 1971-11-05 GT GT197122379A patent/GT197122379A/es unknown
-
1973
- 1973-08-21 JP JP48093789A patent/JPS519015B1/ja active Pending
-
1975
- 1975-04-17 US US05/569,120 patent/US3974222A/en not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: LEDERER, F., DIPL.-CHEM. DR. MEYER-ROXLAU, R., DIP |
|
| 8125 | Change of the main classification |
Ipc: C07C149/26 |
|
| 8126 | Change of the secondary classification |
Free format text: A23L 1/226 A61K 7/46 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |