CN113015716A - 用作增香剂的乙酸酯化合物 - Google Patents
用作增香剂的乙酸酯化合物 Download PDFInfo
- Publication number
- CN113015716A CN113015716A CN201880099475.7A CN201880099475A CN113015716A CN 113015716 A CN113015716 A CN 113015716A CN 201880099475 A CN201880099475 A CN 201880099475A CN 113015716 A CN113015716 A CN 113015716A
- Authority
- CN
- China
- Prior art keywords
- methyl
- cyclopropyl
- compound
- trimethylbicyclo
- carbon
- 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.)
- Granted
Links
- 239000003205 fragrance Substances 0.000 title claims description 13
- 150000001242 acetic acid derivatives Chemical class 0.000 title abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- -1 1-methyl-2-((1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)methyl)cyclopropane acetic acid Chemical compound 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
- 239000004615 ingredient Substances 0.000 claims description 14
- 150000001721 carbon Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- OAKFACUIGQLOCA-SEOXFTARSA-N [1-methyl-2-[[(1s,3r,5r)-1,2,2-trimethyl-3-bicyclo[3.1.0]hexanyl]methyl]cyclopropyl]methanol Chemical compound OCC1(C)CC1C[C@@H]1C(C)(C)[C@@]2(C)C[C@H]2C1 OAKFACUIGQLOCA-SEOXFTARSA-N 0.000 claims description 4
- OAKFACUIGQLOCA-UHFFFAOYSA-N [1-methyl-2-[(1,2,2-trimethyl-3-bicyclo[3.1.0]hexanyl)methyl]cyclopropyl]methanol Chemical compound OCC1(C)CC1CC1C(C)(C)C2(C)CC2C1 OAKFACUIGQLOCA-UHFFFAOYSA-N 0.000 claims description 3
- AGBCTQFJGIGNDM-PJRJKOOISA-N [1-methyl-2-[[(1S,3R,5R)-1,2,2-trimethyl-3-bicyclo[3.1.0]hexanyl]methyl]cyclopropyl]methyl acetate Chemical compound CC1(C(C1)C[C@@H]1C([C@]2(C[C@H]2C1)C)(C)C)COC(C)=O AGBCTQFJGIGNDM-PJRJKOOISA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 239000002304 perfume Substances 0.000 abstract description 10
- 235000008632 Santalum album Nutrition 0.000 abstract description 4
- 241000221035 Santalaceae Species 0.000 abstract 1
- 229940022663 acetate Drugs 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
- 239000002671 adjuvant Substances 0.000 description 6
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 239000002936 woody odorant Substances 0.000 description 5
- 150000001298 alcohols Chemical class 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
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 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
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 240000000513 Santalum album Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- AGBCTQFJGIGNDM-UHFFFAOYSA-N [1-methyl-2-[(1,2,2-trimethyl-3-bicyclo[3.1.0]hexanyl)methyl]cyclopropyl]methyl acetate Chemical compound C(C)(=O)OCC1(C(C1)CC1C(C2(CC2C1)C)(C)C)C AGBCTQFJGIGNDM-UHFFFAOYSA-N 0.000 description 3
- 235000000484 citronellol Nutrition 0.000 description 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 3
- 239000000341 volatile oil Substances 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
- 239000001306 (7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol Substances 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
- QZFSNJAQFWEXEA-MDZDMXLPSA-N (e)-3,3-dimethyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol Chemical compound CC(O)C(C)(C)\C=C\C1CC=C(C)C1(C)C QZFSNJAQFWEXEA-MDZDMXLPSA-N 0.000 description 2
- 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 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- HMKKIXGYKWDQSV-KAMYIIQDSA-N alpha-Amylcinnamaldehyde Chemical compound CCCCC\C(C=O)=C\C1=CC=CC=C1 HMKKIXGYKWDQSV-KAMYIIQDSA-N 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
- 235000006708 antioxidants Nutrition 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 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
- 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
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229930007790 rose oxide Natural products 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- KHQDWCKZXLWDNM-KPKJPENVSA-N (e)-2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol Chemical compound CC\C(CO)=C/CC1CC=C(C)C1(C)C KHQDWCKZXLWDNM-KPKJPENVSA-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- YQYKESUTYHZAGG-UHFFFAOYSA-N 1-(1,2,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethanone Chemical compound C1CC(C(C)=O)(C)C(C)C2=C1CCCC2(C)C YQYKESUTYHZAGG-UHFFFAOYSA-N 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
- 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
- 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
- ZJVRYPHKSDHLTC-UHFFFAOYSA-N 7-methoxy-3,7-dimethyloctan-2-ol Chemical compound COC(C)(C)CCCC(C)C(C)O ZJVRYPHKSDHLTC-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
- 240000007436 Cananga odorata Species 0.000 description 1
- 241000499489 Castor canadensis 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
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 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
- QILMAYXCYBTEDM-IWQZZHSRSA-N Isoambrettolide Chemical compound O=C1CCCCCCC\C=C/CCCCCCO1 QILMAYXCYBTEDM-IWQZZHSRSA-N 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
- 235000011779 Menyanthes trifoliata Nutrition 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
- 241001496113 Santalum Species 0.000 description 1
- 235000008631 Santalum Nutrition 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FZJGUXHGESJNGN-UHFFFAOYSA-N [1-methyl-2-[(2,2,3-trimethylcyclopent-3-en-1-yl)methyl]cyclopropyl]methyl acetate Chemical compound C(C)(=O)OCC1(C(C1)CC1C(C(=CC1)C)(C)C)C FZJGUXHGESJNGN-UHFFFAOYSA-N 0.000 description 1
- OYQCYBDSHGUVLJ-UHFFFAOYSA-N [1-methyl-2-[(2,2,3-trimethylcyclopentyl)methyl]cyclopropyl]methyl acetate Chemical compound C(C)(=O)OCC1(C(C1)CC1C(C(CC1)C)(C)C)C OYQCYBDSHGUVLJ-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
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 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
- 239000003153 chemical reaction reagent Substances 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
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000005888 cyclopropanation reaction Methods 0.000 description 1
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
- 239000001939 cymbopogon martini roxb. stapf. oil Substances 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 229930002886 farnesol Natural products 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-undecanolactone Chemical compound CCCCCCC[C@H]1CCC(=O)O1 PHXATPHONSXBIL-JTQLQIEISA-N 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010656 jasmine oil Substances 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-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
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000005580 one pot reaction Methods 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 235000013599 spices Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 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
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 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
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-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
- 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
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 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
- C11B9/0042—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- 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
- C07C2602/18—All rings being cycloaliphatic the ring system containing six carbon atoms
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)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及具有木香乳脂样檀香气味特性的乙酸酯。本发明还涉及包含它们的香料组合物和消费品。
Description
本发明涉及具有木香乳脂样檀香嗅觉特性的新型增香剂。本发明还涉及它们的生产方法,以及包含它们的香料组合物。
在香料和香精工业中,香料制造商和调香师持续寻求新的化合物。
令人惊奇地,我们目前已经发现一类新的乙酸酯,其具有木香乳脂样檀香气味特征。
在第一个实施方案中,提供了式(I)的化合物
其中
R1和R2与它们所连接的碳原子一起形成环丙基或双键,或R1和R2为氢;且
R3和R4与它们所连接的碳原子一起形成环丙基或双键,且虚线与碳-碳键一起形成单键;或
R3和R4为氢,且虚线与碳-碳键一起形成双键。
式(I)的化合物包含一个或多个手性中心,且照此可以以立体异构体的混合物形式存在,或者可以将它们拆分为异构体纯形式。
拆分立体异构体增加了这些化合物的制备和纯化的复杂性,因此单纯出于经济原因,优选将化合物作为其立体异构体的混合物使用。然而,如果期望制备单独的立体异构体,则可以根据本领域已知的方法,例如通过制备型HPLC和GC、结晶或立体选择性合成来实现这一目的。
作为式(I)的化合物的具体实例,可以举出乙酸(1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)-甲酯作为非限制性实例,其具有温和的木香乳脂样檀香香质与温和的果香花香香调(紫罗兰/鸢尾方向(direction))。该化合物的所有四种非对映异构体均有助于其总体气味特征,但仅发现一种非对映异构体构成主要的气味载体(rel-(1S,2S)-(1-甲基-2-(((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基)-环丙基)甲醇)。
此外,非限制性实例为式(I)的化合物,其选自:
乙酸(E)-2-甲基-4-(1,2,2-三甲基二环[3.1.0]己-3-基)丁-2-烯-1-基酯;
乙酸(E)-2-甲基-4-(1,2,2-三甲基二环[3.1.0]己-3-基)丁-3-烯-1-基酯,
乙酸(E)-2-甲基-4-(2,2,3-三甲基环戊基)丁-3-烯-1-基酯;
乙酸(E)-2-甲基-4-(2,2,3-三甲基环戊基)丁-2-烯-1-基酯;
乙酸(E)-2-甲基-4-(2,2,3-三甲基环戊-3-烯-1-基)丁-3-烯-1-基酯;
乙酸(E)-2-甲基-4-(2,2,3-三甲基环戊-3-烯-1-基)丁-2-烯-1-基酯;
乙酸(1-甲基-2-((2,2,3-三甲基环戊-3-烯-1-基)甲基)环丙基)甲酯;和
乙酸(1-甲基-2-((2,2,3-三甲基环戊基)甲基)环丙基)甲酯。
式(I)的化合物可以单独使用,或可以作为立体异构体混合物使用,或可以与已知的增香剂分子联用,所述增香剂分子选自广泛范围的天然产物和目前可利用的合成分子,例如精油,醇类,醛类和酮类,醚类和缩醛类,酯类和内酯类,大环类和杂环类,和/或与通常与香料组合物中的增香剂一起使用的一种或多种成分或赋形剂的混合物,例如,载体材料和本领域常用的其他助剂。
如本文所用,“载体材料”是指从增香剂的观点来看实际上是中性的材料,即不会显著改变增香剂感官特性的材料。
术语“助剂”是指出于与所述组合物的嗅觉性能没有特别关系的原因而可用于香料组合物中的成分,例如,助剂可以为用作加工香料成分或多种成分的助剂的成分,或含有所述成分的组合物,或它可以改善香料成分或含有该成分的组合物的处理或储存,它也可以是提供额外益处(例如赋予颜色或质地)的成分。也可以为对包含在香料组合物中的一种或多种成分赋予耐光性或化学稳定性的成分。在包含香料的香料组合物中常用的助剂的性质和类型的详细描述不能穷尽,但必须提及的是,所述成分对于本领域技术人员而言是众所周知的。
如本文所用,“香料组合物”是指包含式(I)的化合物和基质材料的任何组合物,所述基质材料例如为通常与增香剂结合使用的稀释剂,例如邻苯二甲酸二乙酯(DEP),一缩二丙二醇(DPG),肉豆蔻酸异丙酯(IPM),戊-1,2-二醇,柠檬酸三乙酯(TEC)和醇(例如乙醇)。任选地,该组合物可以包含抗氧化剂助剂。所述抗氧化剂可以选自TT(BASF)、Q(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,CAS 128-37-0)和相关的酚类,氢醌类(CAS 121-31-9)。
下列清单包含已知增香剂分子的实例,其可以与式(I)的化合物合并:
-精油和提取物,例如,海狸,木香根油,橡苔净油,香叶油,树苔净油,罗勒油,果油如香柠檬油和橘子油,香桃木油,玫瑰草油,广藿香油,橙叶油,茉莉油,玫瑰油,檀香油,苦艾油,熏衣草油和/或依兰-依兰油;
-醇类,例如肉桂醇((E)-3-苯基丙-2-烯-1-醇);顺式-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);金合欢醇((2E,6Z)-3,7,11-三甲基十二碳-2,6,10-三烯-1-醇);香叶醇((E)-3,7-二甲基辛-2,6-二烯-1-醇);Super MuguetTM((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;甲基柏木基酮;甲基紫罗兰酮;马鞭草烯酮;和/或香草醛;
-醚类和缩醛类,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[二环[4.1.0]庚烷-2,5'-[1,3]二噁烷]);
-酯类和内酯类,例如乙酸苄酯;乙酸柏木酯(乙酸(1S,6R,8aR)-1,4,4,6-四甲基八氢-1H-5,8a-亚甲基甘菊环-6-基酯);γ-癸内酯(6-戊基四氢-2H-吡喃-2-酮);(丙酸2-(1-(3,3-二甲基环己基)乙氧基)-2-甲基丙酯);γ-十一烷酸内酯(5-庚基氧杂戊环-2-酮);和/或乙酸岩兰草酯(乙酸(4,8-二甲基-2-丙-2-亚基-3,3a,4,5,6,8a-六氢-1H-甘菊环-6-基)酯);
-杂环类,例如异丁基喹啉(2-异丁基喹啉)。
在一个具体的实施方案中,式(I)的化合物可以与其他已知的木香增香剂例如JavanolTM(1-甲基-2-[[(1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基]甲基]环丙烷甲醇)、EbanolTM((E)-3-甲基-5-(2,2,3-三甲基-3-环戊烯-1-基)-4-戊烯-2-醇、RadjanolTM(2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇)、PolysantolTM(3,3-二甲基-5-(2,2,3-三甲基-3-环戊烯-1-基)-4-戊烯-2-醇、OsyrolTM(3,7-二甲基-7-甲氧基-2-辛醇)、SandaloreTM(3-甲基-5-(2,2,3-三甲基环戊-3-烯-1-基)戊-2-醇)、SandelaTM(3-(5,5,6-三甲基二环[2.2.1]庚-2-基)环己-1-醇)、PolysantTM(3,3-二甲基-5-(2,2,3-三甲基-3-环戊烯-1-基)-4-戊烯-2-醇)等合并以增强天然木香特性。
在某些实施方案中,式(I)的化合物可以与其他木香增香剂合并,其范围为0.05:99.95至99.95:0.05(例如其范围为0.5:99.5至5:95(式(I)的化合物或其混合物:木香增香剂))。
在一个具体的实施方案中,式(I)的化合物为乙酸(1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)甲酯,而其他的木香增香剂为(1-甲基-2-(((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基)-环丙基)甲醇,其组合范围为0.05:99.95至99.95:0.05(例如其范围为0.1:99.5至5:95(包括0.2:99.8;0.3:99.7;0.4:99.6)。
在另一个具体的实施方案中,式(I)的化合物为乙酸(1-甲基-2-(1S,3R,5R)-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)甲酯,而其他的木香增香剂为(1-甲基-2-(((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基)-环丙基)甲醇,其组合范围为0.05:99.95至99.95:0.05(例如其范围为0.1:99.5至5:95(包括0.2:99.8;0.3:99.7;0.4:99.6;0.5:99.5;0.6:99.4;0.7:99.3;0.8:99.2;0.9:99.1;1:99;1.5:98.5)。
式(I)的化合物可以通过在本领域技术人员众所周知的条件下使相应的醇乙酰化来制备。相应醇的制备描述在例如EP0801049中。
任选地,式(I)的化合物,其中R1和R2与它们所连接的碳原子一起形成环丙基和/或R3和R4与它们所连接的碳原子一起形成环丙基,环丙烷化和乙酰化二者可以在单罐法中在锌和例如乙酰氯存在下进行。醇与乙酸酯之比由所用的试剂的量和适当选择的粗产物的蒸馏级分控制。
现在参考下文的非限制性实施例进一步描述本发明。这些实施例仅出于示例目的,并且应当理解,本领域的技术人员可以做出变化和变型。
实施例1:乙酸(1-甲基-2-(((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)甲酯
在氮气气氛中向带有回流冷凝器的反应器中加入1-甲基-2-[[(1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基]甲基]环丙烷甲醇)(非对映异构体的混合物;异构体1:40.9%;异构体2:53.4%;50g;纯度:94.3%;212mmol)、吡啶(20g;253mmol)和甲苯(200g)。在0℃向搅拌的该混合物中滴加乙酰氯(18g;229mmol),历时15分钟。使得到的反应混合物升至20℃,再搅拌2小时。加入水。分离有机层,洗涤(水),通过旋转蒸馏浓缩(60℃;10mbar),得到58g淡黄色油状物,其包含90%的乙酸(1-甲基-2-(((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)-甲酯。再通过使用15cm Vigreux柱在0.08托下蒸馏进一步纯化,得到48g(纯度:93.9%;异构体1:41.4%;异构体2:52.5%;170mmol)的乙酸(1-甲基-2-(((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)-甲酯。再从8.7g弃去的级分(82%纯)中回收产物。基于(1-甲基-2-(1,2,2-三甲基双环(3.1.0)己-3-基甲基)环丙基)甲醇的乙酸(1-甲基-2-(((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基)-基于环丙基)甲酯摩尔收率为约80%,未考虑弃去的级分。将第二次蒸馏后得到的48g进一步使用Sulzer柱(20cm)蒸馏,得到40g的98%(异构体1:43.2%;异构体2:54.8%)的嗅觉纯的产物(乙酸(1-甲基-2-(((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)甲酯)。
气味描述:温和的,木香乳脂样檀香香质,带有温和的果香花香香调(紫罗兰/鸢尾方向)。
异构体1(rel-乙酸(1R,2R)-(1-甲基-2-(((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)甲酯):1H NMR(C6D6,600MHz):
3.83(d,J=11.3,1H),3.77(d,J=10.9,1H),1.95(dd,J=12.4,6.4,1H),1.73(s,3H),1.37(td,J=11.7,4.1,1H),1.22-1.16(m,2H),1.04(s,3H),1.03(s,3H),1.01-0.93(m,2H),0.92(s,3H),0.74(s,3H),0.55-0.47(m,3H),0.08(dd,J=7.5,4.5,1H),-0.13(brt,J=4.5,1H)。
13C NMR(C6D6,150MHz):170.0,73.2,45.1,41.1,32.4,31.2,29.5,22.8,22.75,21.4,20.3,19.5,18.7,17.4,17.3,15.3,14.0。
异构体2(rel-乙酸(1S,2S)-(1-甲基-2-(((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)甲酯):1H NMR(C6D6,600MHz):3.84(d,J=11.3,1H),3.79(d,J=10.9,1H),1.88(dd,J=12.1,6.8,1H),1.72(s,3H),1.37(td,J=11.7,4.1,1H),1.22-1.13(m,2H),1.09-1.06(m,1H),1.04(s,3H),1.04(s,3H),1.00-0.97(m,1H),0.93(s,3H),0.74(s,3H),0.54-0.47(m,3H),0.06(dd,J=7.9,4.9,1H),-0.18(br t,J=4.5,1H)。
13C NMR(C6D6,150MHz):170.0,73.2,44.8,41.1,32.2,31.3,28.8,22.8,22.6,21.9,20.2,19.6,19.6,17.2,16.8,15.9,13.9。
实施例2:木香,东方香料谐香
用乙酸(1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)-甲酯(即式(I)的化合物)替代4份上述谐香的DPG可以使所述谐香在新鲜和干燥后均温和,且特别是可以给干燥后的香型带来温和的乳脂样鸢尾紫罗兰香味。
用乙酸(1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)-甲酯和(1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)-甲醇的混合物(2:98之比)替代20份上述谐香的DPG,醇递送了性能和整体檀香香质,与乙酸酯组合可使其温和,具有一般的檀香香质,其显得更自然,更接近檀香精油的效果和香质,具有温和的果香花香的鸢尾方面(facet)。
Claims (10)
2.权利要求1的化合物,其中R1和R2和/或R3和R4与它们所连接的碳原子一起形成环丙基。
3.权利要求2的化合物,其中该化合物为乙酸(1-甲基-2-((1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)-甲酯,为其立体异构体的任意一种或其混合物的形式。
4.权利要求3的化合物,其中该化合物为乙酸(1-甲基-2-(((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)-甲酯。
5.香料组合物,包含下列成分或由下列成分组成:
a)至少一种如权利要求1或2中所定义的式(I)的化合物,和
b)[1-甲基2-[(1,2,2-三甲基二环[3.1.0]己-3-基)甲基]环丙基]甲醇,为其立体异构体的任意一种或其混合物的形式。
6.权利要求5的香料组合物,其中式(I)的化合物为乙酸(1-甲基-2-(((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基)环丙基)-甲酯(成分a)),且成分b)为[1-甲基2-[((1S,3R,5R)-1,2,2-三甲基二环[3.1.0]己-3-基)甲基]环丙基]甲醇。
7.权利要求5或权利要求6的香料组合物,其特征在于成分a)与b)的重量比在0.05:99.95至5:95(a:b)的范围。
8.消费品,包含如权利要求1中所定义的式(I)的化合物或如权利要求5、权利要求6或权利要求7中所定义的香料组合物和消费品基质。
10.改善、增强或改变消费品基质的方法,通过向其中添加嗅觉可接受量的如权利要求1所定义的式(I)的化合物或如权利要求3-5之一中所定义的香料组合物来进行。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/EP2018/081156 WO2020098927A1 (en) | 2018-11-14 | 2018-11-14 | Acetate compounds useful as odorants |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113015716A true CN113015716A (zh) | 2021-06-22 |
CN113015716B CN113015716B (zh) | 2024-09-13 |
Family
ID=64332050
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201880099475.7A Active CN113015716B (zh) | 2018-11-14 | 2018-11-14 | 用作增香剂的乙酸酯化合物 |
Country Status (8)
Country | Link |
---|---|
US (1) | US12012570B2 (zh) |
EP (1) | EP3880648B1 (zh) |
JP (1) | JP7196299B2 (zh) |
CN (1) | CN113015716B (zh) |
ES (1) | ES2992045T3 (zh) |
MX (1) | MX2021004555A (zh) |
SG (1) | SG11202104156PA (zh) |
WO (1) | WO2020098927A1 (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022058018A1 (en) | 2020-09-18 | 2022-03-24 | Symrise Ag | Cyclopropanated sandalwood type compounds |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3937723A (en) * | 1973-02-09 | 1976-02-10 | Firmenich S.A. | Cycloaliphatic compounds as odour- and taste-modifying agents |
CN101528655A (zh) * | 2006-10-18 | 2009-09-09 | 吉万奥丹股份有限公司 | 用作增香剂的2,3,3-三甲基环戊-3-烯甲醛衍生物 |
WO2011101181A1 (de) * | 2010-02-18 | 2011-08-25 | Henkel Ag & Co. Kgaa | Parfümzusammensetzung |
CN102361844A (zh) * | 2009-03-24 | 2012-02-22 | 弗门尼舍有限公司 | 作为檀香添味剂的醇 |
CN106232569A (zh) * | 2014-04-21 | 2016-12-14 | 高砂香料工业株式会社 | 新化合物及含有该化合物的香料组合物 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2827957C2 (de) * | 1978-06-26 | 1982-03-18 | Dragoco Gerberding & Co Gmbh, 3450 Holzminden | Cyclopenten-Derivate, Verfahren zu deren Herstellung und ihre Verwendung als Riechstoffe |
EP1003469A2 (en) | 1996-02-21 | 2000-05-31 | Givaudan-Roure (International) S.A. | Fragrance precursors |
EP0801049B1 (en) | 1996-04-09 | 2001-11-21 | Givaudan SA | Cyclopentanebutanol derivatives as odorants |
-
2018
- 2018-11-14 ES ES18803938T patent/ES2992045T3/es active Active
- 2018-11-14 MX MX2021004555A patent/MX2021004555A/es unknown
- 2018-11-14 WO PCT/EP2018/081156 patent/WO2020098927A1/en unknown
- 2018-11-14 EP EP18803938.2A patent/EP3880648B1/en active Active
- 2018-11-14 SG SG11202104156PA patent/SG11202104156PA/en unknown
- 2018-11-14 US US17/290,632 patent/US12012570B2/en active Active
- 2018-11-14 CN CN201880099475.7A patent/CN113015716B/zh active Active
- 2018-11-14 JP JP2021526223A patent/JP7196299B2/ja active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3937723A (en) * | 1973-02-09 | 1976-02-10 | Firmenich S.A. | Cycloaliphatic compounds as odour- and taste-modifying agents |
CN101528655A (zh) * | 2006-10-18 | 2009-09-09 | 吉万奥丹股份有限公司 | 用作增香剂的2,3,3-三甲基环戊-3-烯甲醛衍生物 |
CN102361844A (zh) * | 2009-03-24 | 2012-02-22 | 弗门尼舍有限公司 | 作为檀香添味剂的醇 |
WO2011101181A1 (de) * | 2010-02-18 | 2011-08-25 | Henkel Ag & Co. Kgaa | Parfümzusammensetzung |
CN106232569A (zh) * | 2014-04-21 | 2016-12-14 | 高砂香料工业株式会社 | 新化合物及含有该化合物的香料组合物 |
Non-Patent Citations (3)
Title |
---|
CE´LINE DELASALLE, ET AL.: "Structure Odor Relationships of Semisynthetic b-Santalol Analogs", 《CHEMISTRY & BIODIVERSITY》, vol. 11, pages 1843 - 1860, XP055808697, DOI: 10.1002/cbdv.201400082 * |
JERZY A. BAJGROWICZ, ET AL.: "Synthesis and Structure Elucidation of a New Potent Sandalwood-Oil Substitute", 《HELVETICA CHIMICA ACTA》, vol. 81, pages 1349 - 1358, XP002362562, DOI: 10.1002/hlca.19980810545 * |
LI PING CHENG, ET AL.: "QSAR of a-campholenic derivatives with sandalwood odor, and molecular design", 《MONATSH CHEM》, vol. 141, pages 953 - 959, XP019853517 * |
Also Published As
Publication number | Publication date |
---|---|
SG11202104156PA (en) | 2021-05-28 |
WO2020098927A1 (en) | 2020-05-22 |
JP2022517714A (ja) | 2022-03-10 |
BR112021007671A2 (pt) | 2021-07-27 |
EP3880648A1 (en) | 2021-09-22 |
US20220119733A1 (en) | 2022-04-21 |
MX2021004555A (es) | 2021-06-15 |
JP7196299B2 (ja) | 2022-12-26 |
CN113015716B (zh) | 2024-09-13 |
EP3880648B1 (en) | 2024-08-28 |
ES2992045T3 (es) | 2024-12-05 |
US12012570B2 (en) | 2024-06-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5399908B2 (ja) | 有機化合物 | |
SG194518A1 (en) | Terpene alcohols for use in fragrance compositions and perfumed products | |
JPH1036298A (ja) | 新規着香剤 | |
WO2018210828A1 (en) | Organic compounds | |
CN112930335A (zh) | 烷氧基苯甲醛衍生物及其前体 | |
JP2010506861A (ja) | 匂い物質として有用な2,2,3−トリメチルシクロペンタ−3−エンカルバルデヒド誘導体 | |
CN113015716A (zh) | 用作增香剂的乙酸酯化合物 | |
US8445732B2 (en) | Organic compounds | |
JP5248114B2 (ja) | 有機化合物 | |
CN115397798A (zh) | 有机化合物中或与之相关的改进 | |
JP2011511813A (ja) | 有機化合物 | |
CN109476570B (zh) | 作为香料成分的6-异丙基-2,4-二甲基环己烯-1-醇化合物 | |
US11426339B2 (en) | Organic compounds | |
JP4751884B2 (ja) | サリチル酸4−ヘプテン−2−イルおよびフレグランス成分としてのその使用 | |
JP3955628B2 (ja) | カルボニル化合物 | |
WO2024003176A1 (en) | Organic compounds | |
WO2023072718A1 (en) | Alicyclic aliphatic 1,3-dicarbonyl derivatives useful as fragrances | |
JP2025508565A (ja) | 有機化合物 | |
EP3867338A1 (en) | Organic compounds | |
WO2008148235A1 (en) | Organic compounds | |
JP2002529435A (ja) | カルボニル化合物および香料としてのその使用 | |
WO2008071025A1 (en) | Cycloalkenyl butenones and fragrance compositions comprising them |
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 | ||
GR01 | Patent grant | ||
GR01 | Patent grant |