CN111689940A - 六甲基八氢桥亚甲基甘菊环并间二氧杂环戊烯 - Google Patents
六甲基八氢桥亚甲基甘菊环并间二氧杂环戊烯 Download PDFInfo
- Publication number
- CN111689940A CN111689940A CN202010157372.0A CN202010157372A CN111689940A CN 111689940 A CN111689940 A CN 111689940A CN 202010157372 A CN202010157372 A CN 202010157372A CN 111689940 A CN111689940 A CN 111689940A
- Authority
- CN
- China
- Prior art keywords
- formula
- compound
- mixture
- iii
- composition
- 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.)
- Pending
Links
- -1 methyleneazulene dioxoles Chemical class 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 178
- 239000000203 mixture Substances 0.000 claims abstract description 111
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002304 perfume Substances 0.000 claims description 21
- 239000004615 ingredient Substances 0.000 claims description 9
- 230000000873 masking effect Effects 0.000 claims description 4
- 230000002708 enhancing effect Effects 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 17
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 24
- IRAQOCYXUMOFCW-UHFFFAOYSA-N di-epi-alpha-cedrene Natural products C1C23C(C)CCC3C(C)(C)C1C(C)=CC2 IRAQOCYXUMOFCW-UHFFFAOYSA-N 0.000 description 17
- UEBJJCFHNQKAIK-NWRUSUDLSA-N (3r,5r,6r)-3,6,9,9-tetramethyl-2,3,4,5,7,8,9a,10-octahydro-1h-tricyclo[6.3.1.0^{1,5}]dodecane-5,6-diol Chemical compound C1[C@@H](O)[C@](C)(O)C2CC(C)(C)C3CC[C@@H](C)C31C2 UEBJJCFHNQKAIK-NWRUSUDLSA-N 0.000 description 9
- IRAQOCYXUMOFCW-OSFYFWSMSA-N cedr-8-ene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(C)=CC2 IRAQOCYXUMOFCW-OSFYFWSMSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000006210 lotion Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 6
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000000484 citronellol Nutrition 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 150000002118 epoxides Chemical group 0.000 description 3
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 3
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 3
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- CRDAMVZIKSXKFV-GNESMGCMSA-N (2-trans,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C\CO CRDAMVZIKSXKFV-GNESMGCMSA-N 0.000 description 2
- AVJMJMPVWWWELJ-DHZHZOJOSA-N (2e)-1-methoxy-3,7-dimethylocta-2,6-diene Chemical compound COC\C=C(/C)CCC=C(C)C AVJMJMPVWWWELJ-DHZHZOJOSA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- KRLBLPBPZSSIGH-CSKARUKUSA-N (6e)-3,7-dimethylnona-1,6-dien-3-ol Chemical compound CC\C(C)=C\CCC(C)(O)C=C KRLBLPBPZSSIGH-CSKARUKUSA-N 0.000 description 2
- GLZPCOQZEFWAFX-JXMROGBWSA-N (E)-Geraniol Chemical compound CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-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
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 241000218645 Cedrus Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- HZRFVTRTTXBHSE-VJOISMJWSA-N cedrene epoxide Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)C1C1(C)OC1C2 HZRFVTRTTXBHSE-VJOISMJWSA-N 0.000 description 2
- HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 2
- 229930008394 dihydromyrcenol Natural products 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002979 fabric softener Substances 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 229930007790 rose oxide Natural products 0.000 description 2
- 239000000126 substance Substances 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
- 239000000341 volatile oil Substances 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- 239000001724 (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulen-6-yl) acetate Substances 0.000 description 1
- DCSCXTJOXBUFGB-JGVFFNPUSA-N (R)-(+)-Verbenone Natural products CC1=CC(=O)[C@@H]2C(C)(C)[C@H]1C2 DCSCXTJOXBUFGB-JGVFFNPUSA-N 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- DCSCXTJOXBUFGB-SFYZADRCSA-N (R)-(+)-verbenone Chemical compound CC1=CC(=O)[C@H]2C(C)(C)[C@@H]1C2 DCSCXTJOXBUFGB-SFYZADRCSA-N 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
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 1
- 239000000267 (Z)-hex-3-en-1-ol Substances 0.000 description 1
- RNLHVODSMDJCBR-SOFGYWHQSA-N (e)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol Chemical compound CC(O)C(C)\C=C\C1CC=C(C)C1(C)C RNLHVODSMDJCBR-SOFGYWHQSA-N 0.000 description 1
- GTLKSTALFRGBQG-NYYWCZLTSA-N (e)-6-ethyl-3-methyloct-6-en-1-ol Chemical compound CC\C(=C/C)CCC(C)CCO GTLKSTALFRGBQG-NYYWCZLTSA-N 0.000 description 1
- KVDORLFQOZGRPI-CHNJZELVSA-N (z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO.CC\C=C/CCO KVDORLFQOZGRPI-CHNJZELVSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- FVUGZKDGWGKCFE-UHFFFAOYSA-N 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethanone Chemical compound CC1(C)CCCC2=C1CC(C(C)=O)(C)C(C)C2 FVUGZKDGWGKCFE-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
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PSIOIPWJOZPZPA-UHFFFAOYSA-N 2,4,7-trimethylocta-2,6-dien-1-ol Chemical compound CC(CC=C(C)C)C=C(C)CO PSIOIPWJOZPZPA-UHFFFAOYSA-N 0.000 description 1
- FAVZTHXOOBZCOB-UHFFFAOYSA-N 2,6-Bis(1,1-dimethylethyl)-4-methyl phenol Natural products CC(C)CC1=CC(C)=CC(CC(C)C)=C1O FAVZTHXOOBZCOB-UHFFFAOYSA-N 0.000 description 1
- DGJXPLQJXLEEQL-UHFFFAOYSA-N 2-(2-methylpropyl)quinoline Chemical compound C1=CC=CC2=NC(CC(C)C)=CC=C21.C1=CC=CC2=NC(CC(C)C)=CC=C21 DGJXPLQJXLEEQL-UHFFFAOYSA-N 0.000 description 1
- HZADPBZMDMUMRD-UHFFFAOYSA-N 2-hydroxyethyl 13-oxotridecanoate Chemical compound OCCOC(=O)CCCCCCCCCCCC=O HZADPBZMDMUMRD-UHFFFAOYSA-N 0.000 description 1
- 229930008411 3,7-dimethylocta-2,6-dien-1-ol Natural products 0.000 description 1
- JRJBVWJSTHECJK-PKNBQFBNSA-N 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one Chemical compound CC(=O)C(\C)=C\C1C(C)=CCCC1(C)C JRJBVWJSTHECJK-PKNBQFBNSA-N 0.000 description 1
- UKZXPOJABTXLMK-UHFFFAOYSA-N 3-[2-methyl-4-(2-methylpropyl)phenyl]propanal Chemical compound CC(C)CC1=CC=C(CCC=O)C(C)=C1 UKZXPOJABTXLMK-UHFFFAOYSA-N 0.000 description 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 1
- 235000003097 Artemisia absinthium Nutrition 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
- 235000017731 Artemisia dracunculus ssp. dracunculus Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- CUFNKYGDVFVPHO-UHFFFAOYSA-N Azulene Natural products C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- YDXBMXMUCYTHQX-UHFFFAOYSA-N CCCCCC(C=O)=CC1=CC=CC=C1.CCCCCC(C=O)=CC1=CC=CC=C1 Chemical compound CCCCCC(C=O)=CC1=CC=CC=C1.CCCCCC(C=O)=CC1=CC=CC=C1 YDXBMXMUCYTHQX-UHFFFAOYSA-N 0.000 description 1
- 240000007436 Cananga odorata 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
- 244000068485 Convallaria majalis Species 0.000 description 1
- 235000009046 Convallaria majalis Nutrition 0.000 description 1
- 241000218691 Cupressaceae Species 0.000 description 1
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000402754 Erythranthe moschata Species 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
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- 241000721662 Juniperus Species 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
- 241000700110 Myocastor coypus Species 0.000 description 1
- 240000005125 Myrtus communis Species 0.000 description 1
- 235000013418 Myrtus communis Nutrition 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 240000000513 Santalum album Species 0.000 description 1
- 235000008632 Santalum album Nutrition 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 241000218636 Thuja Species 0.000 description 1
- UAVFEMBKDRODDE-UHFFFAOYSA-N Vetiveryl acetate Chemical compound CC1CC(OC(C)=O)C=C(C)C2CC(=C(C)C)CC12 UAVFEMBKDRODDE-UHFFFAOYSA-N 0.000 description 1
- LSTSBZKIQFOPHA-UHFFFAOYSA-N [2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methylpropyl] propanoate Chemical compound CCC(=O)OCC(C)(C)OC(C)C1CCCC(C)(C)C1 LSTSBZKIQFOPHA-UHFFFAOYSA-N 0.000 description 1
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000002386 air freshener Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 239000001138 artemisia absinthium Substances 0.000 description 1
- 239000010619 basil oil Substances 0.000 description 1
- 229940018006 basil oil Drugs 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229930002312 cedrane Natural products 0.000 description 1
- 241000902900 cellular organisms Species 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000001071 citrus reticulata blanco var. mandarin Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000001939 cymbopogon martini roxb. stapf. oil Substances 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 230000002951 depilatory effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 229930002886 farnesol Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 description 1
- PHXATPHONSXBIL-JTQLQIEISA-N gamma-Undecalactone Natural products CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 description 1
- 229940020436 gamma-undecalactone Drugs 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010656 jasmine oil Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 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
- QAPTWHXHEYAIKG-RCOXNQKVSA-N n-[(1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 QAPTWHXHEYAIKG-RCOXNQKVSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 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
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- HZRFVTRTTXBHSE-AYJHFOLZSA-N α-cedrene epoxide Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C1(C)OC1C2 HZRFVTRTTXBHSE-AYJHFOLZSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- 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
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
- 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
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
-
- 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
-
- 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
- C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
-
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
-
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
- C11B9/0053—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms both rings being six-membered
-
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
-
- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
-
- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0088—Spiro compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D9/00—Compositions of detergents based essentially on soap
- C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
- C11D9/22—Organic compounds, e.g. vitamins
- C11D9/26—Organic compounds, e.g. vitamins containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D9/00—Compositions of detergents based essentially on soap
- C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
- C11D9/44—Perfumes; Colouring materials; Brightening agents ; Bleaching agents
- C11D9/442—Perfumes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Fats And Perfumes (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明提供了化合物(3aS,4aR,5S,7aS,9R,9aR)‑2,2,5,8,8,9a‑六甲基八氢‑4H‑4a,9‑桥亚甲基甘菊环并[5,6‑d][1,3]间二氧杂环戊烯、包含该化合物的组合物和消费产品、该化合物的制备方法以及该化合物的各种用途。
Description
技术领域
本发明总体上涉及式(I)的化合物(3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-六甲基八氢-4H-4a,9-桥亚甲基甘菊环并[5,6-d][1,3]间二氧杂环戊烯。本发明进一步涉及包含式(I)的化合物的组合物和消费产品、制备式(I)的化合物的方法以及式(I)的化合物的各种用途。
背景技术
(4aR,5R,7aS,9R)-2,2,5,8,8,9a-六甲基八氢-4H-4a,9-桥亚甲基甘菊环并[5,6-d][1,3]间二氧杂环戊烯(也称为)被用作香料成分以提供木质和龙涎(ambery)的气味。已被描述为包含式(II)、(III)、(IV)和(V)的四个非对映异构体的一个或多个(参见US2017/0114299A1和WO2017/186973,其内容是通过引用并入本文)
发明内容
根据本发明的第一方面,提供了式(I)的化合物(3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-六甲基八氢-4H-4a,9-桥亚甲基甘菊环并[5,6-d][1,3]间二氧杂环戊烯
根据本发明的第二方面,提供了一种异构体混合物,其包含式(I)的化合物和选自式(II)、(III)、(IV)和(V)的化合物中的至少一种(一、二、三或四种)化合物
在某些实施方式中,所述异构体混合物包含式(II)的化合物。组合物中式(I)的化合物与式(II)的化合物的重量比可以在约0.01:99.99至约5:95的范围内,例如在约0.1:99.9至约1:99的范围内。
在某些实施方式中,所述混合物不包含式(III)的化合物、式(IV)的化合物和式(V)的化合物中的一种或多种。在某些实施方式中,所述混合物不包含式(III)的化合物。
在某些实施方式中,所述异构体混合物还包含选自式(XI)、(XII)和(XIII)的化合物的一种或多种化合物
根据本发明的第三方面,提供了一种香料组合物,其包含本发明的第一方面的化合物或本发明的第二方面的异构体混合物。
在某些实施方式中,所述组合物还包含一种或多种其他已知的香料成分。
在某些实施方式中,组合物包含式(VI)的柏木烷酮(cedralone),例如式(VIa)和/或式(VIb)的柏木烷酮,
根据本发明的第四方面,提供了一种消费产品,其包含本发明的第一方面的化合物,本发明的第二方面的异构体混合物或本发明的第三方面的组合物。
在某些实施方式中,所述消费产品是个人护理组合物。在某些实施方式中,所述消费产品是清洁产品。在某些实施方式中,所述消费产品是家庭用品组合物。
根据本发明的第五方面,提供了本发明的第一方面的化合物或本发明的第二方面的混合物作为香料的用途。
根据本发明的第六方面,提供了式(I)的化合物
用于掩盖或减少一种或多种令人不愉悦的嗅觉印象和/或增强一种或多种令人愉悦的嗅觉印象的强度的用途。
所述一种或多种令人不愉悦的嗅觉印象可以是,例如,刺激的绿色龙涎香调。所述一种或多种令人愉悦的嗅觉印象可以是,例如,木质和/或龙涎气味。
所述一种或多种令人不愉悦的和/或一种或多种令人愉悦的嗅觉印象可以由,例如,式(II)的化合物、式(III)的化合物、式(IV)的化合物和/或式(V)的化合物提供
根据本发明的第七方面,提供了一种制备式(I)的化合物的方法,其中,所述方法包括使式(Xa)的柏木烷二醇或其异构体混合物(即式(X)的柏木烷二醇)
与反应性丙烷衍生物在合适的条件下反应来形成式(I)的化合物:
在某些实施方式中,该方法包括使式(Xa)的柏木烷二醇或其异构体混合物(即式(X)的柏木烷二醇)与二甲氧基丙烷反应来形成式(I)的化合物。例如,这可以在酸催化的条件下发生。
本发明的任意方面的某些实施方式可以提供以下的一个或多个优点:
木质和/或龙涎气味;
减少了刺激的绿色龙涎香调;
对于本发明的任何特定一个或多个所述方面所提供的细节、实例和优选将在本文中被进一步描述,并且同样适用于本发明的所有方面。除非本文另外指出或与上下文明显矛盾,否则本发明涵盖本文所述的实施方式、实施例和优选在其所有可能的变化中的任何组合。
附图说明
可以参考以下非限制性附图来描述本发明,其中:
图1是实施例1中描述的制备式(I)的化合物的方法的反应式。
具体实施方式
本发明基于以下令人惊讶的发现,即式(I)的化合物(3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-六甲基八氢-4H-4a,9-桥亚甲基甘菊环并
因此,本文提供了式(I)的化合物(3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-六甲基八氢-4H-4a,9-桥亚甲基甘菊环并[5,6-d][1,3]间二氧杂环戊烯
本文还提供了包含式(I)的化合物(3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-六甲基八氢-4H-4a,9-桥亚甲基甘菊环并[5,6-d][1,3]间二氧杂环戊烯和选自式(II)、(III)、(IV)和(V)的化合物中的至少一种(一、二、三或四种)化合物的异构体混合物
例如,该混合物可以包含选自式(II)、(III)、(IV)和(V)的化合物中的两种、三种或四种化合物。
例如,该混合物可以包含式(I)的化合物和式(II)的化合物、基本上由其组成或者由其组成。
可选地,例如,该混合物可以包含式(I)的化合物、式(II)的化合物和式(IV)的化合物、基本上由其组成或者由其组成。例如,该混合物可以包含式(I)的化合物、式(II)的化合物和式(V)的化合物、基本上由其组成或者由其组成。
可选地,例如,该混合物可以包含式(I)的化合物、式(II)的化合物、式(IV)的化合物和式(V)的化合物、基本上由其组成或者由其组成。例如,该混合物可以不包含式(III)的化合物。
例如,式(I)的化合物与式(II)的化合物(当存在时)的重量比可以在约0.01:99.99至约5:95的范围内。例如,式(I)的化合物与式(II)的化合物(当存在时)的重量比可以在约0.01:99.99至约4:96、或约0.01:99.99至约3:97、或约0.01:99.99至约2:98、或约0.01:99.99至约1:99、或约0.01:99.99至约0.5:99.95的范围内(例如,约0.2:99.8)。例如,式(I)的化合物与式(II)的化合物(当存在时)的重量比可以在约0.05:99.95至约5:95、或约0.1:99.9至约2:98、或约0.5:99.5至约1:99的范围内。
基于混合物中的式(I)、(II)、(III)、(IV)和(V)的化合物的总重量,式(I)的化合物可以以等于或大于约0.01重量%的量存在于所述混合物中。例如,基于混合物中的式(I)、(II)、(III)、(IV)和(V)的化合物的总重量,式(I)的化合物可以以等于或大于约0.05重量%、或等于或大于约0.1重量%、或等于或大于约0.5重量%的量存在。基于混合物中的式(I)、(II)、(III)、(IV)和(V)的化合物的总重量,式(I)的化合物可以以等于或小于约5重量%的量存在。例如,基于混合物中的式(I)、(II)、(III)、(IV)和(V)的化合物的总重量,式(I)的化合物可以以等于或小于约4重量%、或等于或小于约3重量%、或等于或小于约2重量%、或等于或小于约1重量%的量存在。例如,式(I)的化合物可以以约0.01重量%至约5重量%、或约0.05重量%至约4重量%、或约0.1重量%至约3重量%、或约0.2重量%至约2重量%、或约0.3重量%至约1重量%的范围内的量存在于所述混合物中。
例如,所述混合物可以基本上由式(I)的化合物和选自式(II)、(III)、(IV)和(V)的化合物的至少一种(一、二、三或四种)化合物组成,或者由其组成。例如,该混合物可以基本上由式(I)的化合物和式(II)的化合物组成,或者由其组成。
例如,所述混合物还可以包含式(XI)的化合物、式(XII)的化合物和式(XIII)的化合物中的一种或多种
例如,所述混合物可以包含选自式(XI)、(XII)和(XIII)的化合物的至少两种化合物。
例如,该混合物还可以包含式(XI)的化合物和式(XII)的化合物。例如,该混合物还可以包含式(XI)的化合物和式(XIII)的化合物。例如,该混合物可还包含式(XII)的化合物和式(XIII)的化合物。
本文所用的术语“基本上由...组成”是指混合物包含至少约90重量%或至少约95重量%或至少约98重量%或至少约99重量%的所述组分。本文使用的术语“由...组成”是指混合物包含100重量%的所述组分。
本文进一步提供了一种组合物,其包含式(I)的化合物和选自式(II)、(III)、(IV)和(V)的至少一种(一、二、三或四种)化合物的异构体混合物,还包含式(VI)的柏木烷酮,例如式(的VIa)的柏木烷酮:
当存在时,基于组合物的总重量,柏木烷酮在组合物中可以以约0.01重量%至约1重量%的范围内的量存在。
例如,所述柏木烷酮可以是用于制备式(I)的化合物和/或式(II)的化合物的方法的副产物。
该组合物还可以包含另外的香料成分。下面的清单包含已知的香料成分的实例,其可以与式(I)的化合物组合使用:
–精油和提取物,例如海狸香、木香根油、橡苔净油、天竺葵精油、树苔净油、罗勒油、果油(如佛手柑油和橘子油)、桃金娘油、玫瑰草油、广藿香油、橙叶油、茉莉油、玫瑰油、檀香油、艾草油、薰衣草油和/或依兰油;
–醇类,例如肉桂醇((E)-3-苯基丙-2-烯-1-醇);顺-3-己烯醇((Z)-己-3-烯-1-醇);香茅醇(3,7-二甲基辛-6-烯-1-醇);二氢月桂烯醇(2,6-二甲基辛-7-烯-2-醇);EbanolTM((E)-3-甲基-5-(2,2,3-三甲基环戊-3-烯-1-基)戊-4-烯-2-醇);丁香酚(4-烯丙基-2-甲氧基苯酚);乙基芳樟醇((E)-3,7-二甲基壬-1,6-二烯-3-醇);法尼醇((2E,6Z)-3,7,11-三甲基十二-2,6,10-三烯-1-醇);香叶醇((E)-3,7-二甲基辛-2,6-二烯-1-醇);SuperMuguetTM((E)-6-乙基-3-甲基辛-6-烯-1-醇);芳樟醇(3,7-二甲基辛-1,6-二烯-3-醇);薄荷醇(2-异丙基-5-甲基环己醇);橙花醇(3,7-二甲基-2,6-辛二烯-1-醇);苯乙醇(2-苯基乙醇);RhodinolTM(3,7-二甲基辛-6-烯-1-醇);SandaloreTM(3-甲基-5-(2,2,3-三甲基环戊-3-烯-1-基)戊-2-醇);松油醇(2-(4-甲基环己-3-烯-1-基)丙-2-醇);或者TimberolTM(1-(2,2,6-三甲基环己基)己-3-醇);2,4,7-三甲基辛-2,6-二烯-1-醇和/或[1-甲基-2(5-甲基己-4-烯-2-基)环丙基]-甲醇;
–醛类和酮类,例如茴香醛(4-甲氧基苯甲醛);α-戊基肉桂醛(2-亚苄基庚醛);GeorgywoodTM(1-(1,2,8,8-四甲基-1,2,3,4,5,6,7,8-八氢萘-2-基)乙酮);羟基香茅醛(7-羟基-3,7-二甲基辛醛);Iso E(1-(2,3,8,8-四甲基-1,2,3,4,5,6,7,8-八氢萘-2-基)乙酮);((E)-3-甲基-4-(2,6,6-三甲基环己-2-烯-1-基)丁-3-烯-2-酮);(3-氧代-2-戊基环戊烷乙酸甲酯);3-(4-异丁基-2-甲基苯基)丙醛;麦芽酚;甲基柏木酮;甲基紫罗兰酮;马鞭草烯酮;和/或香兰素;
–醚和缩醛类,例如(3a,6,6,9a-四甲基2,4,5,5a,7,8,9,9b-八氢-1H-苯并[e][1]苯并呋喃);香叶基甲基醚((2E)-1-甲氧基-3,7-二甲基辛-2,6-二烯);玫瑰醚(4-甲基-2-(2-甲基丙-1-烯-1-基)四氢-2H-吡喃);和/或(2',2',3,7,7-五甲基螺[双环[4.1.0]庚烷-2,5'-[1,3]二氧六环]);
–酯类和内酯类,例如,乙酸苄酯;乙酸柏木酯((1S,6R,8aR)-1,4,4,6-四甲基八氢-1H-5,8a-桥亚甲基甘菊环-6-基乙酸酯);γ-癸内酯(6-戊基四氢-2H-吡喃-2-酮);(2-(1-(3,3-二甲基环己基)乙氧基)-2-甲基丙基丙酸酯);γ-十一内酯(5-庚基草脲胺-2-酮);和/或乙酸香根草酯((4,8-二甲基-2-丙-2-亚烷基-3,3a,4,5,6,8a-六氢-1H-甘菊环-6-基)乙酸酯);
–杂环类,例如异丁基喹啉(2-异丁基喹啉)。
例如,本文所述的化合物和混合物可以是基本结晶的形式。“基本结晶”是指至少约90重量%的化合物或混合物为结晶形式。例如,本文所述的化合物或混合物的至少约95重量%或至少约96重量%或至少约97重量%或至少约98重量%或至少约99重量%可以是结晶形式。
或者,本文所述的化合物和混合物可以在溶液中。
通常与香料成分结合使用的稀释剂包括如邻苯二甲酸二乙酯(DEP)、二丙二醇(DPG)、肉豆蔻酸异丙酯(IPM)、戊烷-1,2-二醇、柠檬酸三乙酯(TEC)和醇(例如乙醇)的成分。任选地,由此获得的溶液可以包含抗氧化剂佐剂。所述抗氧化剂可以选自TT(BASF)、Q(BASF)、TS(BASF)、生育酚(包括其异构体,CAS 59-02-9;364-49-8;18920-62-2;121854-78-2)、2,6-双(1,1-二甲基乙基)-4-甲基苯酚(BHT,CAS128-37-0)和相关的苯酚、氢醌(CAS121-31-9)。
本文进一步提供了包含式(I)的化合物或本文所述的混合物的香料组合物。基于香料组合物的总重量,式(I)的化合物或包含式(I)的化合物和选自式(II)、(III)、(IV)和(V)的化合物的至少一种(一、二、三或四种)化合物的本文所述的混合物可以,例如,以约0.001重量%至约10重量%的范围内的量存在于消费产品中。例如,式(I)的化合物或本文所述的混合物可以以约0.05重量%至约8重量%、或约0.1重量%至约5重量%、或约0.5重量%至约3重量%的范围内的量存在于所述香料组合物中。
本文进一步提供了包含本文所述的化合物、混合物或组合物的消费产品。消费产品是指个人或家庭出于非商业目的购买使用的任何产品。
所述消费产品可以,例如是个人护理产品,例如香精、香水、淡香水、须后水、古龙水、须前产品、喷溅古龙水、加香清洁纸巾、身体护理产品、香皂、液体沐浴露、护发产品(例如洗发水、护发素)、除臭剂、止汗剂、护手霜和乳液、护足霜和乳液、脱毛霜和乳液、须后霜和乳液、晒黑霜和乳液以及装饰性化妆产品(例如化妆品)。
所述消费产品可以,例如是清洁产品,例如,酸性、碱性和中性清洁剂,织物清新剂、熨烫助剂、液体洗涤剂、织物柔顺剂、洗涤皂、洗涤片、消毒剂(例如表面消毒剂)、空气清新剂、喷雾剂、蜡和抛光剂。
所述消费产品可以,例如是家用产品,例如,蜡烛、灯油、香棒、杀虫剂、驱虫剂和推进剂。
基于消费产品的总重量,式(I)的化合物或包含式(I)的化合物和选自式(II)、(III)、(IV)和(V)的化合物的至少一种(一、二、三或四种)化合物的混合物可以,例如,以约0.0001重量%(或者甚至更低,例如0.05ppm以下)至约30重量%的范围内的量存在于消费产品中。在一个实施方式中,式(I)的化合物或本文所述的混合物可以以0.001至0.3重量%的量应用于织物柔顺剂中。在另一个实施方式中,式(I)的化合物或本文所述的混合物可以以0.01至30重量%(例如高至约10或高至20重量%)、更优选在0.01和5重量%之间的量应用于高级香水中。但是,这些值仅作为示例给出,因为有经验的调香师也可以以更低或更高的浓度来达到效果或产生新的匹配。
本文进一步提供了式(I)的化合物或包含式(I)的化合物和选自式(II)、(III)、(IV)和(V)的化合物的至少一种化合物的混合物作为香料成分的用途。例如,式(I)的化合物可以与式(II)的化合物、式(III)的化合物、式(IV)的化合物和/或式(V)的化合物组合使用。作为香料成分的用途是指其用量足以提供可识别的气味。由式(I)的化合物或包含式(I)的化合物和选自式(II)、(III)、(IV)和(V)的化合物的至少一种化合物的混合物提供的气味可以,例如是木质和/或龙涎气味,与例如在WO2015/176833中所公开的相比,其可以,例如具有降低的刺激的绿色龙涎香调。
本文进一步提供了式(I)的化合物用于掩盖或减少具有以下化学结构的(WO2015/176833)的一种或多种令人不愉悦的香调的用途,其包括式(II)、(III)、(IV)和(V)的四种非对映异构体。所述一种或多种令人不愉快的嗅觉印象可以,例如是刺激的绿色龙涎香调,其可以是极化的,并限制了在香料组合物中可以使用的可接受的量。
例如,所述用途可以包括将式(I)的化合物与选自式(II)、(III)、(IV)和(V)的化合物的至少一种(一、二、三或四种)化合物混合。或者,式(I)的化合物可以与式(II)的化合物、式(III)的化合物、式(IV)的化合物和式(V)的化合物中的一种或多种直接一起制备。相对于包含式(I)的化合物和式(II)的化合物、式(III)的化合物、式(IV)的化合物和式(V)的化合物的一种或多种的混合物,式(I)的化合物可以,例如以本文所述的量和/或比例存在。
本文进一步提供了制备式(I)的化合物的方法。该方法可以使用仅包含单一立体异构体的原料和/或中间材料来进行,或者可以使用包括立体异构体的混合物的原料和/或中间材料来进行。该方法的最终产物可以,例如仅是单一立体异构体或者可以是立体异构体的混合物。可以选择不同的反应条件以产生不同比例的立体异构体。
原料和/或中间材料和/或最终产物的特定立体异构体可以通过本领域普通技术人员已知的任何方法来纯化,例如通过制备型HPLC和GC、结晶或立体选择性合成。
所述方法可以,例如包括使式(Xa)的柏木烷二醇或异构体混合物(即式(X)的柏木烷二醇)反应性丙烷衍生物在合适的条件下反应来形成式(I)的化合物。本领域技术人员已知的任何合适的反应性丙烷衍生物可以用于形成式(I)的化合物。
该方法可以,例如包括使用各种溶剂(如甲苯、环己烷、石脑油馏分或二乙醚)使式(Xa)的柏木烷二醇与脂肪族醛类和酮类反应。
该方法可以,例如包括使式(Xa)的柏木烷二醇与二烷氧基丙烷,如二甲氧基丙烷(例如2,2-二甲氧基丙烷)反应,以形成式(I)的化合物。该反应可以,例如在酸催化下发生。式(Xa)的化合物(或异构体混合物)与二烷氧基丙烷(例如二甲氧基丙烷)的摩尔比可以,例如为至少约1:5、例如约1:1至约1:4。
然后,可以例如从醇水溶液中结晶出式(I)的化合物。
可以使用本领域技术人员已知的任何合适的环氧化物开环剂来形成式(X)的化合物。例如,通过酸催化开环(Houben-Weyl)可以使式(IX)的化合物反应来形成式(X)的化合物。
可以使用本领域技术人员已知的任何合适的环氧化剂来形成式(IX)的化合物。
式(VIII)的化合物可以,例如与过乙酸反应来形成式(IX)的柏木烯环氧化物(参见,例如Organikum,Organisch-Chemisches Grundpraktikum[Basic Practical OrganicChemistry],VEB Deutscher Verlag der Wissenschaften,柏林,1986年,第5714576号,568页)。
该表-(-)-α-柏木烯可以,例如使用由Niels H.Andersen等人(TetrahedronLettere No.10,899-902,1972)描述的过程来获得。或者,它可以从天然来源获得,例如,通过蒸馏诸如杜松、柏树、檀香和香柏的木材,或从植物(例如侧柏属、Yupressus、台湾杉属和翠柏属)的木材、根和叶蒸馏、压榨或化学提取。
可通过仔细选择作为原料的α-柏木烯的品质来影响本文所述的混合物的组成。例如,相对于选自式(II)、(III)、(IV)和(V)的化合物的至少一种化合物,表-(-)-α-柏木烯的量越高,式(I)的化合物的量就越高。不受理论的束缚,据信立体化学条件在随后的α-柏木烯的反应中基本保持不变。
现将参考以下的非限制性实施例进一步描述本发明。对于本领域技术人员而言显而易见的变化和修改意图落入由所附权利要求书限定的本发明的范围内。
实施例
实施例1:包含式(I)的(3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-六甲基八氢-
4H-4a,9-桥亚甲基甘菊环并[5,6-d][1,3]间二氧杂环戊烯的组合物的制备
通过图1中所示的反应式制备包含式(I)的(3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-六甲基八氢-4H-4a,9-桥亚甲基甘菊环并[5,6-d][1,3]间二氧杂环戊烯的组合物。
1.1–α-制备柏木烯环氧化物的混合物
由α-柏木烯(包含约1重量%的表-(-)-α-柏木烯)通过在本领域已知的条件下进行环氧化(参见Organikum,Organisch-Chemisches Grundpraktikum[Basic PracticalOrganic Chemistry],VEB Deutscher Verlag der Wissenschaften,柏林,1986,第5714576号,568页)以获得α-柏木烯环氧化物((-)-α-柏木烯环氧化物和表-(-)-α-柏木烯环氧化物)的混合物。
1.2–制备柏木烷二醇的混合物
向装有机械搅拌器、冷却器和氮气鼓泡器的2L夹套式实验室反应器中加入1682.5g水、317.5g 63%的硫酸和3.0g 336(已知为Stark’s催化剂的季铵盐)。将该混合物稳定在20℃,并且在十分钟内进料如上所述制备的包含(-)-α-柏木烯环氧化物(81.6%GC,[α]20/D:-72.3,n 20/D:1.4967)的α-柏木烯环氧化物的混合物。将得到的混合物在20℃进一步高速搅拌48小时。过滤白色沉淀物,并用200g 2%的NaOH和用200g水(pH:8)洗涤两次。将所得的粗二醇混合物(88.5g)中的80g在1333mL的环己烷中重结晶出47.9g的白色晶体。
柏木烷二醇混合物的异构体组合物(晶体)为59重量%的化合物2a(如图1中的反应式所示)、31重量%的化合物2d(如图1中的反应式所示)以及约0.5重量%的化合物(Xa)。
1.3–制备2,2,5,8,8,9a-六甲基八氢-4H-4a,9-桥亚甲基甘菊环并[5,6-d][1,3]间二氧杂环戊烯异构体的混合物
将10.0g的2,2-二甲氧基丙烷(DMP)、12.4g丙酮和10.0g如上所述制备的结晶二醇混合物添加到装有冷却器和氮气鼓泡器的100ml三颈圆底烧瓶中。在2小时内在温度保持在30℃以下的同时,进料10.0g的工业硫酸在丙酮中的溶液(40g中为1.08g)。将得到的混合物在20℃进一步搅拌3小时,此时,缓慢加入另外的2.0g硫酸的丙酮溶液。在22℃另外搅拌2小时后,将混合物用碳酸钠水溶液淬灭,并在真空下蒸发大部分轻物质(lights)。
将残余物重新吸收在甲基叔丁基醚(MTBE)和水中,并浓缩有机层。然后将残余物用冷的正庚烷稀释并过滤。蒸发滤液,并在乙醇-水混合物中重结晶。
获得的异构体混合物为如本文所述的96.4重量%的式(II)的化合物与0.2重量%的式(I)的化合物。
实施例2-分离(3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-六甲基八氢-4H-4a,9-
桥亚甲基甘菊环并[5,6-d][1,3]间二氧杂环戊烯(式(I))
通过制备型气相色谱由实施例1.3中获得的重结晶混合物中分离出式(I)的(3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-六甲基八氢-4H-4a,9-桥亚甲基甘菊环并[5,6-d][1,3]间二氧杂环戊烯。
然后通过NMR鉴定分离的级分。
基于以下NMR结果指定式(I)的(3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-六甲基八氢-4H-4a,9-桥亚甲基甘菊环并[5,6-d][1,3]间二氧杂环戊烯的结构。
1H NMR(C6D6,600MHz):4.02(t,J=7.7,1H),2.03(dd,J=13.2,7.3,1H),1.97-1.94(m,2H),1.62-1.56(m,1H),1.60(s,3H),1.58(s,3H),1.54-1.50(m,1H),1.52(s,3H),1.45-1.35(m,3H),1.25-1.18(m,2H),1.14-1.11(m,1H),0.97(s,3H),0.87(d,J=6.7,3H),0.85(s,3H)。
13C NMR(C6D6,150MHz):108.7,84.9,78.7,57.3,55.8,53.9,44.0,43.1,42.3,33.5,31.7,30.9,30.3,29.8,27.7,27.6,24.4,13.7。
实施例3–感官分析
由调香师评价实施例2中获得的式(I)的化合物和实施例1中获得的混合物的气味分布。令人惊讶地发现,式(I)的化合物的软木龙涎品质与很好地结合。它强化了的原有的木质龙涎特性并软化了其刺激的绿色龙涎香调。结果,在实施例1中获得的混合物更通用并且更易于加入香料组合物中,同时仍然提供期望的木质龙涎特性和性能。
实施例4:香料组合物
此香料具有化妆品的乳脂感、带有经典的花醛式结构(floral aldehydicstructure)、麝香粉状柔和的尾调和现代的绿色铃兰紫罗兰前调。所述香料,例如适合以约1.5重量%的剂量使香皂增香。
通过用实施例1的结晶混合物代替上述香料组合物中的2份DPG,增强了总体的嗅觉冲击,并且总体的嗅觉特性更加平衡,更加女性化且多元化。当与例如皂基混合时,气味性能也明显改善。
Claims (13)
3.根据权利要求2所述的异构体混合物,其为基本结晶的形式。
4.根据权利要求2或3所述的异构体混合物,其中,所述混合物不包含式(III)的化合物。
6.根据权利要求5所述的组合物,其中,所述异构体混合物包含式(II)的化合物。
7.根据权利要求6所述的组合物,其中,所述式(I)的化合物与所述式(II)的化合物的重量比在0.01:99.99至5:95的范围内。
8.根据权利要求5、6或7所述的组合物,其中,所述组合物不包含式(III)的化合物。
10.一种消费产品,其包含式(I)的化合物,权利要求2至4中任一项所述的异构体混合物,或权利要求5至9中任一项所述的组合物。
12.权利要求1的化合物用于掩盖或减少一种或多种令人不愉悦的嗅觉印象的用途,例如,掩盖或减少刺激的绿色龙涎香调和/或增强一种或多种令人愉悦的嗅觉印象的强度的用途,例如,用于增强木质和/或龙涎气味的强度的用途。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202310745639.1A CN116751183A (zh) | 2019-03-13 | 2020-03-09 | 六甲基八氢桥亚甲基甘菊环并间二氧杂环戊烯 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IBPCT/EP2019/056332 | 2019-03-13 | ||
PCT/EP2019/056332 WO2019141881A1 (en) | 2019-03-13 | 2019-03-13 | (3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-hexamethyloctahydro-4H-4a,9-methanoazuleno[5,6-d][1,3]dioxole |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202310745639.1A Division CN116751183A (zh) | 2019-03-13 | 2020-03-09 | 六甲基八氢桥亚甲基甘菊环并间二氧杂环戊烯 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN111689940A true CN111689940A (zh) | 2020-09-22 |
Family
ID=65861262
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202310745639.1A Pending CN116751183A (zh) | 2019-03-13 | 2020-03-09 | 六甲基八氢桥亚甲基甘菊环并间二氧杂环戊烯 |
CN202010157372.0A Pending CN111689940A (zh) | 2019-03-13 | 2020-03-09 | 六甲基八氢桥亚甲基甘菊环并间二氧杂环戊烯 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202310745639.1A Pending CN116751183A (zh) | 2019-03-13 | 2020-03-09 | 六甲基八氢桥亚甲基甘菊环并间二氧杂环戊烯 |
Country Status (11)
Country | Link |
---|---|
US (2) | US11634402B2 (zh) |
EP (1) | EP3911636B1 (zh) |
JP (1) | JP7331122B2 (zh) |
CN (2) | CN116751183A (zh) |
BR (1) | BR112021016274A2 (zh) |
ES (1) | ES2941042T3 (zh) |
IL (1) | IL286241A (zh) |
MX (1) | MX2021010012A (zh) |
PL (1) | PL3911636T3 (zh) |
SG (1) | SG11202108961WA (zh) |
WO (1) | WO2019141881A1 (zh) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101068802A (zh) * | 2004-12-02 | 2007-11-07 | 吉万奥丹股份有限公司 | 间二氧杂环戊烯三环化合物及其作为芳香剂的用途 |
CN102076676A (zh) * | 2008-07-01 | 2011-05-25 | 奇华顿股份有限公司 | 适合作为增香剂的异长叶烷基-衍生物 |
CN106458959A (zh) * | 2014-05-21 | 2017-02-22 | 西姆莱斯有限公司 | 新型混合物 |
WO2017174827A1 (de) * | 2017-08-09 | 2017-10-12 | Symrise Ag | Verwendung von ambrocenide® zur verstärkung einer maiglöckchen-note |
WO2017186973A2 (de) * | 2017-08-25 | 2017-11-02 | Symrise Ag | Mischungen enthaltend enantiomerenreines ambrocenide® |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4226930B2 (ja) | 2002-04-02 | 2009-02-18 | 昭和電工株式会社 | 電解コンデンサ電極用アルミニウム材、エッチングされた電解コンデンサ電極用アルミニウム材、ならびに電解コンデンサ |
-
2019
- 2019-03-13 BR BR112021016274-7A patent/BR112021016274A2/pt unknown
- 2019-03-13 MX MX2021010012A patent/MX2021010012A/es unknown
- 2019-03-13 PL PL19712539.6T patent/PL3911636T3/pl unknown
- 2019-03-13 US US17/434,147 patent/US11634402B2/en active Active
- 2019-03-13 WO PCT/EP2019/056332 patent/WO2019141881A1/en unknown
- 2019-03-13 EP EP19712539.6A patent/EP3911636B1/en active Active
- 2019-03-13 JP JP2021554620A patent/JP7331122B2/ja active Active
- 2019-03-13 ES ES19712539T patent/ES2941042T3/es active Active
- 2019-03-13 SG SG11202108961WA patent/SG11202108961WA/en unknown
-
2020
- 2020-03-09 CN CN202310745639.1A patent/CN116751183A/zh active Pending
- 2020-03-09 CN CN202010157372.0A patent/CN111689940A/zh active Pending
-
2021
- 2021-09-09 IL IL286241A patent/IL286241A/en unknown
-
2023
- 2023-03-22 US US18/124,762 patent/US20230219918A1/en active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101068802A (zh) * | 2004-12-02 | 2007-11-07 | 吉万奥丹股份有限公司 | 间二氧杂环戊烯三环化合物及其作为芳香剂的用途 |
CN102076676A (zh) * | 2008-07-01 | 2011-05-25 | 奇华顿股份有限公司 | 适合作为增香剂的异长叶烷基-衍生物 |
CN106458959A (zh) * | 2014-05-21 | 2017-02-22 | 西姆莱斯有限公司 | 新型混合物 |
WO2017174827A1 (de) * | 2017-08-09 | 2017-10-12 | Symrise Ag | Verwendung von ambrocenide® zur verstärkung einer maiglöckchen-note |
WO2017186973A2 (de) * | 2017-08-25 | 2017-11-02 | Symrise Ag | Mischungen enthaltend enantiomerenreines ambrocenide® |
Also Published As
Publication number | Publication date |
---|---|
JP2022532827A (ja) | 2022-07-20 |
WO2019141881A1 (en) | 2019-07-25 |
JP7331122B2 (ja) | 2023-08-22 |
US20230219918A1 (en) | 2023-07-13 |
IL286241A (en) | 2021-10-31 |
EP3911636A1 (en) | 2021-11-24 |
ES2941042T3 (es) | 2023-05-16 |
CN116751183A (zh) | 2023-09-15 |
US11634402B2 (en) | 2023-04-25 |
PL3911636T3 (pl) | 2023-05-08 |
US20220041569A1 (en) | 2022-02-10 |
EP3911636B1 (en) | 2023-01-04 |
BR112021016274A2 (pt) | 2021-10-13 |
MX2021010012A (es) | 2021-09-21 |
SG11202108961WA (en) | 2021-09-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US10040776B2 (en) | Pyran derivatives and their preparation | |
JP4038282B2 (ja) | 付臭性組成物 | |
CN106458959B (zh) | 具有(4aR,5R,7aS,9R)-八氢-2,2,5,8,8,9a-六甲基-4H-4a,9-亚甲基薁并 (5,6-d)-1,3-二氧杂环戊烯的混合物 | |
JP5479466B2 (ja) | 匂い物質として適するイソロンギホラニル誘導体 | |
JP2017517509A5 (zh) | ||
JP7177086B2 (ja) | 2,3,7-トリメチルオクタ-6-エニルアセテート及び3,7-ジメチル-2-メチレン-オクタ-6-エニルアセテート、並びにそれらの誘導体、並びに芳香化学物質としてのそれらの使用 | |
WO2012160189A1 (en) | Terpene alcohols for use in fragrance compositions and perfumed products | |
GB2529901A (en) | Organic compounds | |
US20090263336A1 (en) | Novel pyran derivatives and their preparation | |
CN111050855B (zh) | 包含对映纯Ambrocenide®的混合物 | |
JP7331122B2 (ja) | (3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-ヘキサメチルオクタヒドロ-4H-4a,9-メタノアズレノ[5,6-d][1,3]ジオキソール | |
EP3707120B1 (en) | Aldehydes for use as odorants | |
WO2021198525A1 (en) | (s,z)-3,7-dimethylnon-6-en-1-ol and its use as fragrance | |
EP2424852B1 (en) | 2-oxaspiro[5,5]undec-8-ene derivatives useful in fragrance compositions | |
ES2388648T3 (es) | Fragancia | |
EP0976708B1 (en) | Cycloalkyl ethers and perfume compositions containing them | |
WO2023089158A1 (en) | Organic compounds as fragrance | |
US20220186140A1 (en) | Improvements in or relating to organic compounds | |
WO2024045134A1 (en) | Organic compounds | |
WO2024000260A1 (en) | Organic compounds | |
JP2004527502A (ja) | 2,3,5,5−テトラメチルヘキサナール誘導体 | |
WO2023067044A1 (en) | Organic compounds | |
WO2016037987A1 (en) | Organic compounds with a woody-peppery odour | |
JP2002529435A (ja) | カルボニル化合物および香料としてのその使用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200922 |