BRPI0717878B1 - derivados de 2,2,3-trimetilciclopentano, composição de fragrância, uso da mesma e métodos de fabricação da referida composição e para melhorar, intensificar ou modificar a fragrância de uma composição de fragrância ou aplicação de fragrância - Google Patents
derivados de 2,2,3-trimetilciclopentano, composição de fragrância, uso da mesma e métodos de fabricação da referida composição e para melhorar, intensificar ou modificar a fragrância de uma composição de fragrância ou aplicação de fragrância Download PDFInfo
- Publication number
- BRPI0717878B1 BRPI0717878B1 BRPI0717878A BRPI0717878A BRPI0717878B1 BR PI0717878 B1 BRPI0717878 B1 BR PI0717878B1 BR PI0717878 A BRPI0717878 A BR PI0717878A BR PI0717878 A BRPI0717878 A BR PI0717878A BR PI0717878 B1 BRPI0717878 B1 BR PI0717878B1
- Authority
- BR
- Brazil
- Prior art keywords
- fragrance
- methyl
- composition
- enhancing
- compound
- Prior art date
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- 239000003205 fragrance Substances 0.000 title claims abstract description 50
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 230000002708 enhancing effect Effects 0.000 title claims description 6
- 230000000051 modifying effect Effects 0.000 title claims description 4
- WINCSBAYCULVDU-UHFFFAOYSA-N 1,1,2-trimethylcyclopentane Chemical class CC1CCCC1(C)C WINCSBAYCULVDU-UHFFFAOYSA-N 0.000 title abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- -1 2,2,3-trimethyl-pentyl Chemical group 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000004615 ingredient Substances 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
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- 235000008632 Santalum album Nutrition 0.000 description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VTJWOQAFUFIQNP-GLGOKHISSA-N 2-ethyl-4-[(1r)-2,2,3-trimethylcyclopentyl]but-2-en-1-ol Chemical compound CCC(CO)=CC[C@H]1CCC(C)C1(C)C VTJWOQAFUFIQNP-GLGOKHISSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
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- 239000010671 sandalwood oil Substances 0.000 description 5
- DHFSQQGEXRKGSP-IDTBKSBVSA-N 1-[1-methyl-2-[[(1s)-2,2,3-trimethylcyclopentyl]methyl]cyclopropyl]ethanol Chemical compound CC(O)C1(C)CC1C[C@H]1C(C)(C)C(C)CC1 DHFSQQGEXRKGSP-IDTBKSBVSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
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- 239000000284 extract Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- NGYMOTOXXHCHOC-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CC(O)C(C)CCC1CC=C(C)C1(C)C NGYMOTOXXHCHOC-UHFFFAOYSA-N 0.000 description 3
- YDUQIQJDISZACN-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopentyl)pent-3-en-2-ol Chemical compound CC(O)C(C)=CCC1CCC(C)C1(C)C YDUQIQJDISZACN-UHFFFAOYSA-N 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
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- WNFFALOIJUMLCA-UHFFFAOYSA-N 2-methyl-4-(2,2,3-trimethylcyclopentyl)but-2-en-1-ol Chemical compound CC1CCC(CC=C(C)CO)C1(C)C WNFFALOIJUMLCA-UHFFFAOYSA-N 0.000 description 2
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- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
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- CPFYMRIASYWZLF-FUWMQMHUSA-N [1-methyl-2-[[(1r)-2,2,3-trimethylcyclopentyl]methyl]cyclopropyl]methanol Chemical compound CC1(C)C(C)CC[C@@H]1CC1C(CO)(C)C1 CPFYMRIASYWZLF-FUWMQMHUSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
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- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 2
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- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
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- 241000220317 Rosa Species 0.000 description 1
- 238000006932 Simmons-Smith cyclopropanation reaction Methods 0.000 description 1
- 244000025271 Umbellularia californica Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QZNUYOQPHYUXKE-UHFFFAOYSA-N [1-ethyl-2-[(2,2,3-trimethylcyclopentyl)methyl]cyclopropyl]methanol Chemical compound CCC1(CO)CC1CC1C(C)(C)C(C)CC1 QZNUYOQPHYUXKE-UHFFFAOYSA-N 0.000 description 1
- CPFYMRIASYWZLF-UHFFFAOYSA-N [1-methyl-2-[(2,2,3-trimethylcyclopentyl)methyl]cyclopropyl]methanol Chemical compound CC1(C)C(C)CCC1CC1C(CO)(C)C1 CPFYMRIASYWZLF-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
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- YPZUZOLGGMJZJO-UHFFFAOYSA-N ambrofix Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 description 1
- YPZUZOLGGMJZJO-LQKXBSAESA-N ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 description 1
- 239000001138 artemisia absinthium Substances 0.000 description 1
- 239000012752 auxiliary agent 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
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- WTYGAUXICFETTC-UHFFFAOYSA-N cyclobarbital Chemical compound C=1CCCCC=1C1(CC)C(=O)NC(=O)NC1=O WTYGAUXICFETTC-UHFFFAOYSA-N 0.000 description 1
- 229960004138 cyclobarbital Drugs 0.000 description 1
- 150000001940 cyclopentanes Chemical class 0.000 description 1
- 238000005888 cyclopropanation reaction Methods 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
- 238000011161 development Methods 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940093468 ethylene brassylate Drugs 0.000 description 1
- 229960002217 eugenol Drugs 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
- 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
- 239000000499 gel Substances 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- 239000010656 jasmine oil Substances 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 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
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- 229940116411 terpineol Drugs 0.000 description 1
- LFSYLMRHJKGLDV-UHFFFAOYSA-N tetradecanolide Natural products O=C1CCCCCCCCCCCCCO1 LFSYLMRHJKGLDV-UHFFFAOYSA-N 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/13—Monohydroxylic alcohols containing saturated 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
- C11B9/0026—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
- 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
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Led Devices (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0621805.1A GB0621805D0 (en) | 2006-11-03 | 2006-11-03 | Organic compounds |
| GB0621805.1 | 2006-11-03 | ||
| PCT/CH2007/000545 WO2008052379A2 (en) | 2006-11-03 | 2007-11-02 | Organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0717878A2 BRPI0717878A2 (pt) | 2013-10-29 |
| BRPI0717878B1 true BRPI0717878B1 (pt) | 2017-02-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0717878A BRPI0717878B1 (pt) | 2006-11-03 | 2007-11-02 | derivados de 2,2,3-trimetilciclopentano, composição de fragrância, uso da mesma e métodos de fabricação da referida composição e para melhorar, intensificar ou modificar a fragrância de uma composição de fragrância ou aplicação de fragrância |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8030524B2 (enExample) |
| EP (1) | EP2076481B9 (enExample) |
| JP (1) | JP5399908B2 (enExample) |
| CN (1) | CN101528652B (enExample) |
| AT (1) | ATE501103T1 (enExample) |
| BR (1) | BRPI0717878B1 (enExample) |
| DE (1) | DE602007013077D1 (enExample) |
| ES (1) | ES2362945T3 (enExample) |
| GB (1) | GB0621805D0 (enExample) |
| MX (1) | MX2009004343A (enExample) |
| WO (1) | WO2008052379A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8410042B2 (en) | 2009-11-02 | 2013-04-02 | Firmenich Sa | Odorants with anisic notes |
| CN103562167B (zh) * | 2011-05-25 | 2015-07-29 | 奇华顿股份有限公司 | 用于香料组合物和香味产品的萜烯醇 |
| WO2012159223A1 (en) * | 2011-05-25 | 2012-11-29 | Givaudan Sa | Trimethyloctadienol and derivatives thereof used as fragrance ingredient |
| CN105073698B (zh) * | 2013-03-12 | 2017-03-15 | 高砂香料工业株式会社 | 具有环丙烷环的化合物及包含其的香料组合物和/或芳香组合物 |
| EP3042891B1 (en) | 2013-09-06 | 2018-08-15 | Takasago International Corporation | Fragrance composition |
| WO2015163023A1 (ja) | 2014-04-21 | 2015-10-29 | 高砂香料工業株式会社 | 新規化合物及び該化合物を含有する香料組成物 |
| GB2528480A (en) * | 2014-07-23 | 2016-01-27 | Givaudan Sa | Improvements in or relating to organic compounds |
| CN107735389A (zh) * | 2015-05-29 | 2018-02-23 | 巴斯夫欧洲公司 | 具有1,2,2‑三甲基环戊烷‑1‑基结构部分的新型芳香化学品 |
| ES2774937T3 (es) | 2015-07-27 | 2020-07-23 | Givaudan Sa | 2,4,7-trimetiloct-6-en-1-ol como ingrediente de fragancia |
| WO2020249222A1 (en) | 2019-06-13 | 2020-12-17 | Symrise Ag | Sandalwood-type fragrance compounds |
| EP4139270B1 (en) | 2020-04-20 | 2025-03-05 | Symrise AG | Oxa-sandalwood-type fragrance compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US5288701A (en) | 1990-07-12 | 1994-02-22 | Givaudan-Roure Corporation | Derivatives of dihydrocampholenic aldehyde |
| EP0838451B1 (en) * | 1996-03-05 | 2001-11-28 | Kao Corporation | Process for producing unsaturated alcohols |
| EP0801049B1 (en) | 1996-04-09 | 2001-11-21 | Givaudan SA | Cyclopentanebutanol derivatives as odorants |
| ES2166928T3 (es) * | 1996-04-09 | 2002-05-01 | Givaudan Sa | Derivados de ciclopentanbutanol como odorantes. |
| JP3400291B2 (ja) * | 1996-09-17 | 2003-04-28 | 高砂香料工業株式会社 | （ｅ）−（ｒ）−２−アルキル−４−（２，２，３−トリメチルシクロペント−３−エン−１−イル）−２−ブテン−１−オール誘導体、その製造方法および用途 |
| DE602005011481D1 (de) * | 2004-12-24 | 2009-01-15 | Givaudan Sa | Cyclopropanierungsverfahren |
| GB0506263D0 (en) | 2005-03-29 | 2005-05-04 | Givaudan Sa | Skin lightening methods, composition and products |
-
2006
- 2006-11-03 GB GBGB0621805.1A patent/GB0621805D0/en not_active Ceased
-
2007
- 2007-11-02 EP EP07816228A patent/EP2076481B9/en active Active
- 2007-11-02 DE DE602007013077T patent/DE602007013077D1/de active Active
- 2007-11-02 AT AT07816228T patent/ATE501103T1/de not_active IP Right Cessation
- 2007-11-02 JP JP2009534975A patent/JP5399908B2/ja active Active
- 2007-11-02 MX MX2009004343A patent/MX2009004343A/es active IP Right Grant
- 2007-11-02 US US12/513,263 patent/US8030524B2/en active Active
- 2007-11-02 CN CN2007800404380A patent/CN101528652B/zh active Active
- 2007-11-02 WO PCT/CH2007/000545 patent/WO2008052379A2/en not_active Ceased
- 2007-11-02 ES ES07816228T patent/ES2362945T3/es active Active
- 2007-11-02 BR BRPI0717878A patent/BRPI0717878B1/pt active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008052379A2 (en) | 2008-05-08 |
| ATE501103T1 (de) | 2011-03-15 |
| US8030524B2 (en) | 2011-10-04 |
| CN101528652A (zh) | 2009-09-09 |
| WO2008052379A3 (en) | 2008-06-19 |
| US20100069508A1 (en) | 2010-03-18 |
| JP5399908B2 (ja) | 2014-01-29 |
| BRPI0717878A2 (pt) | 2013-10-29 |
| EP2076481B9 (en) | 2011-07-06 |
| DE602007013077D1 (de) | 2011-04-21 |
| EP2076481A2 (en) | 2009-07-08 |
| CN101528652B (zh) | 2012-11-28 |
| GB0621805D0 (en) | 2006-12-13 |
| MX2009004343A (es) | 2009-05-05 |
| ES2362945T3 (es) | 2011-07-15 |
| EP2076481B1 (en) | 2011-03-09 |
| JP2010508310A (ja) | 2010-03-18 |
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Legal Events
| Date | Code | Title | Description |
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| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |