JP2017517509A5 - - Google Patents
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- JP2017517509A5 JP2017517509A5 JP2016568821A JP2016568821A JP2017517509A5 JP 2017517509 A5 JP2017517509 A5 JP 2017517509A5 JP 2016568821 A JP2016568821 A JP 2016568821A JP 2016568821 A JP2016568821 A JP 2016568821A JP 2017517509 A5 JP2017517509 A5 JP 2017517509A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- mixture
- compound
- odor
- enyl
- 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
- 239000000203 mixture Substances 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 51
- 239000003205 fragrance Substances 0.000 claims description 35
- 239000000126 substance Substances 0.000 claims description 26
- 239000000047 product Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000006071 cream Substances 0.000 claims description 10
- 239000006210 lotion Substances 0.000 claims description 10
- 239000002304 perfume Substances 0.000 claims description 10
- 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 claims description 9
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 8
- 230000002708 enhancing effect Effects 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000645 desinfectant Substances 0.000 claims description 4
- 239000003599 detergent Substances 0.000 claims description 4
- 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 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- -1 6,6-dimethoxy-2,5,5-trimethylhex-2-ene 2,6-dimethylocta-7-en-2-ol Chemical compound 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000001953 sensory effect Effects 0.000 claims description 3
- 241000207199 Citrus Species 0.000 claims description 2
- 241000402754 Erythranthe moschata Species 0.000 claims description 2
- 244000172533 Viola sororia Species 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 239000002386 air freshener Substances 0.000 claims description 2
- 230000001166 anti-perspirative effect Effects 0.000 claims description 2
- 239000003213 antiperspirant Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 235000020971 citrus fruits Nutrition 0.000 claims description 2
- 210000001072 colon Anatomy 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 239000002979 fabric softener Substances 0.000 claims description 2
- 239000000077 insect repellent Substances 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 238000010409 ironing Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 239000001993 wax Substances 0.000 claims description 2
- 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 claims 4
- 239000000463 material Substances 0.000 claims 4
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims 2
- 239000001716 (4-methyl-1-propan-2-yl-1-cyclohex-2-enyl) acetate Substances 0.000 claims 2
- VADBNYMWNNFOSH-UHFFFAOYSA-N (4-methyl-1-propan-2-ylcyclohex-2-en-1-yl) acetate Chemical compound CC(=O)OC1(C(C)C)CCC(C)C=C1 VADBNYMWNNFOSH-UHFFFAOYSA-N 0.000 claims 2
- ZGEHHVDYDNXYMW-OWOJBTEDSA-N (8e)-cyclohexadec-8-en-1-one Chemical compound O=C1CCCCCCC\C=C\CCCCCC1 ZGEHHVDYDNXYMW-OWOJBTEDSA-N 0.000 claims 2
- 239000001244 (E)-1-(2,6,6-trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one Substances 0.000 claims 2
- MOLZHSROFREFLG-QSYFUGGGSA-N (E)-4-[(1S)-1,2,6,6-tetramethylcyclohex-2-en-1-yl]but-3-en-2-one Chemical compound C[C@]1(C(=CCCC1(C)C)C)/C=C/C(C)=O MOLZHSROFREFLG-QSYFUGGGSA-N 0.000 claims 2
- BLOXMGXSDAAJGX-PLNGDYQASA-N (Z)-hex-3-en-1-yl methyl carbonate Chemical compound CC\C=C/CCOC(=O)OC BLOXMGXSDAAJGX-PLNGDYQASA-N 0.000 claims 2
- LMWNGLDCJDIIBR-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1=C(C)CCCC1(C)C LMWNGLDCJDIIBR-CMDGGOBGSA-N 0.000 claims 2
- VPKMGDRERYMTJX-UHFFFAOYSA-N 1-(2,6,6-trimethylcyclohex-2-en-1-yl)pent-1-en-3-one Chemical compound CCC(=O)C=CC1C(C)=CCCC1(C)C VPKMGDRERYMTJX-UHFFFAOYSA-N 0.000 claims 2
- UWKAYLJWKGQEPM-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl acetate Chemical compound CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 claims 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 claims 2
- VJYFMQREUJXCQV-UHFFFAOYSA-N Limonene aldehyde Chemical compound O=CCC(C)C1CCC(C)=CC1 VJYFMQREUJXCQV-UHFFFAOYSA-N 0.000 claims 2
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- ONKNPOPIGWHAQC-UHFFFAOYSA-N galaxolide Chemical compound C1OCC(C)C2=C1C=C1C(C)(C)C(C)C(C)(C)C1=C2 ONKNPOPIGWHAQC-UHFFFAOYSA-N 0.000 claims 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims 2
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 claims 2
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 claims 2
- BVDMQAQCEBGIJR-UHFFFAOYSA-N 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol Chemical compound CCCC(O)CCC1C(C)CCCC1(C)C BVDMQAQCEBGIJR-UHFFFAOYSA-N 0.000 claims 1
- RTPMDRYHLHGFGT-UHFFFAOYSA-N 2',2',8',8'-tetramethylspiro[1,3-dioxolane-2,10'-octahydro-1h-2,4a-methanonapthalene] Chemical compound CC1(C)C(C2)CCC2(C(CC2)(C)C)C1C12OCCO1 RTPMDRYHLHGFGT-UHFFFAOYSA-N 0.000 claims 1
- TVSGBEJPUDTIBF-ARJAWSKDSA-N 3-[(z)-hex-3-enoxy]propanenitrile Chemical compound CC\C=C/CCOCCC#N TVSGBEJPUDTIBF-ARJAWSKDSA-N 0.000 claims 1
- RDHNTAXPFZIMDN-UHFFFAOYSA-N 6,6-Dimethoxy-2,5,5-trimethyl-2-hexene Chemical compound COC(OC)C(C)(C)CC=C(C)C RDHNTAXPFZIMDN-UHFFFAOYSA-N 0.000 claims 1
- VLVTUDUYHCPENC-ONYUMSKCSA-N CC(=O)\C=C\C1C(C)=CCCC1(C)C.CC(=O)\C=C\C1C(C)=CCCC1(C)C Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C.CC(=O)\C=C\C1C(C)=CCCC1(C)C VLVTUDUYHCPENC-ONYUMSKCSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- MIZGSAALSYARKU-UHFFFAOYSA-N cashmeran Chemical compound CC1(C)C(C)C(C)(C)C2=C1C(=O)CCC2 MIZGSAALSYARKU-UHFFFAOYSA-N 0.000 claims 1
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 claims 1
- 229930008394 dihydromyrcenol Natural products 0.000 claims 1
- VQNUNMBDOKEZHS-UHFFFAOYSA-N ethoxymethoxycyclododecane Chemical compound CCOCOC1CCCCCCCCCCC1 VQNUNMBDOKEZHS-UHFFFAOYSA-N 0.000 claims 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 description 7
- 238000004821 distillation Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 239000011541 reaction mixture Substances 0.000 description 4
- JKXYOXWILXQDTG-UHFFFAOYSA-N 4,6-dioxatetracyclo[6.5.1.01,10.03,7]tetradeca-3(7),8,10,12-tetraene Chemical compound C1C2(C3)C=CC=C2C=C1C1=C3OCO1 JKXYOXWILXQDTG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IRAQOCYXUMOFCW-UHFFFAOYSA-N di-epi-alpha-cedrene Natural products C1C23C(C)CCC3C(C)(C)C1C(C)=CC2 IRAQOCYXUMOFCW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14169354.9A EP2947078B1 (de) | 2014-05-21 | 2014-05-21 | Neue Mischungen mit (4aR,5R,7aS,9R)-Octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-Methanoazuleno(5,6-d)-1,3-dioxol) (Ambrocenide®) |
| EP14169354.9 | 2014-05-21 | ||
| PCT/EP2015/054027 WO2015176833A1 (de) | 2014-05-21 | 2015-02-26 | Neue mischungen mit (4ar,5r,7as,9r)-octahydro-2,2,5,8,8,9a-hexamethyl-4h-4a,9-methanoazuleno(5,6-d)-1,3-dioxol) (ambrocenide®) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017517509A JP2017517509A (ja) | 2017-06-29 |
| JP2017517509A5 true JP2017517509A5 (https=) | 2018-04-05 |
| JP6564399B2 JP6564399B2 (ja) | 2019-08-21 |
Family
ID=50732983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016568821A Active JP6564399B2 (ja) | 2014-05-21 | 2015-02-26 | （４ａＲ，５Ｒ，７ａＳ，９Ｒ）−オクタヒドロ−２，２，５，８，８，９ａ−ヘキサメチル−４Ｈ−４ａ，９−メタノアズレノ（５，６−ｄ）−１，３−ジオキソール）（Ａｍｂｒｏｃｅｎｉｄｅ（登録商標））を有する新規混合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10526563B2 (https=) |
| EP (1) | EP2947078B1 (https=) |
| JP (1) | JP6564399B2 (https=) |
| CN (1) | CN106458959B (https=) |
| BR (1) | BR112016027144B1 (https=) |
| ES (1) | ES2671641T3 (https=) |
| MX (1) | MX362230B (https=) |
| TR (1) | TR201808510T4 (https=) |
| WO (1) | WO2015176833A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201521861D0 (en) | 2015-12-11 | 2016-01-27 | Givaudan Sa | Improvements in or relating to organic compounds |
| CN111108100B (zh) * | 2017-08-09 | 2023-08-01 | 西姆莱斯有限公司 | 帝王龙涎用于增强铃兰调的用途 |
| DE202017007101U1 (de) | 2017-08-25 | 2019-07-10 | Symrise Ag | Mischungen enthaltend enantiomerenreines Ambrocenide® |
| WO2017186973A2 (de) | 2017-08-25 | 2017-11-02 | Symrise Ag | Mischungen enthaltend enantiomerenreines ambrocenide® |
| ES2887600T3 (es) * | 2017-11-28 | 2021-12-23 | Firmenich & Cie | Ambar odorante |
| SG11202108961WA (en) * | 2019-03-13 | 2021-09-29 | Givaudan Sa | (3aS,4aR,5S,7aS,9R,9aR)-2,2,5,8,8,9a-hexamethyloctahydro-4H-4a,9-methanoazuleno[5,6-d][1,3]dioxole |
| EP3997234A1 (en) * | 2019-07-08 | 2022-05-18 | Symrise AG | Biotechnological production of diols |
| WO2025233712A1 (en) | 2024-05-09 | 2025-11-13 | Politecnico Di Milano | Synthesis method of cedrene cis-diol |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19704484A1 (de) * | 1997-02-06 | 1998-09-03 | Dragoco Gerberding Co Ag | Cyclische Cedren-Acetale, ihre Herstellung und ihre Verwendung |
| CN1142156C (zh) * | 1998-08-07 | 2004-03-17 | 希姆莱塞两合公司 | 环雪松烯缩醛、其制备和其应用 |
| US7419943B2 (en) * | 2004-08-20 | 2008-09-02 | International Flavors & Fragrances Inc. | Methanoazuenofurans and methanoazulenone compounds and uses of these compounds as fragrance materials |
| ATE496111T1 (de) * | 2007-01-02 | 2011-02-15 | Symrise Ag | Mischungen von 3-(4-methyl-cyclohex-3-enyl)- butyraldehyd und ambro-cenide sowie deren verwendungen und verfahren |
| EP2287158B1 (de) * | 2010-09-29 | 2012-11-14 | Symrise AG | Ambra-Riechstoff auf Basis von 9-Methanoazuleno(5,6-d)-1,3-dioxolen |
| CN102134228B (zh) * | 2011-01-30 | 2012-11-28 | 北京安胜瑞力科技有限公司 | 一种木香-龙涎香型的香料的制备方法 |
| EP2474301B1 (de) * | 2011-12-14 | 2014-04-16 | Symrise AG | Riechstoffmischungen enthaltend Cyclopent-2-Enyl-Essigsäureethylester |
-
2014
- 2014-05-21 TR TR2018/08510T patent/TR201808510T4/tr unknown
- 2014-05-21 ES ES14169354.9T patent/ES2671641T3/es active Active
- 2014-05-21 EP EP14169354.9A patent/EP2947078B1/de active Active
-
2015
- 2015-02-26 WO PCT/EP2015/054027 patent/WO2015176833A1/de not_active Ceased
- 2015-02-26 US US15/312,545 patent/US10526563B2/en active Active
- 2015-02-26 JP JP2016568821A patent/JP6564399B2/ja active Active
- 2015-02-26 BR BR112016027144-0A patent/BR112016027144B1/pt active IP Right Grant
- 2015-02-26 CN CN201580026098.0A patent/CN106458959B/zh active Active
- 2015-02-26 MX MX2016014973A patent/MX362230B/es active IP Right Grant
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