JPH045658B2 - - Google Patents
Info
- Publication number
- JPH045658B2 JPH045658B2 JP62162137A JP16213787A JPH045658B2 JP H045658 B2 JPH045658 B2 JP H045658B2 JP 62162137 A JP62162137 A JP 62162137A JP 16213787 A JP16213787 A JP 16213787A JP H045658 B2 JPH045658 B2 JP H045658B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- singlet
- formula
- spiro
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003205 fragrance Substances 0.000 claims description 15
- -1 formyloxy group Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 125000003003 spiro group Chemical group 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 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 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
- YBUIAJZFOGJGLJ-SWRJLBSHSA-N 1-cedr-8-en-9-ylethanone Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(C)=C(C(C)=O)C2 YBUIAJZFOGJGLJ-SWRJLBSHSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- BGEBZHIAGXMEMV-UHFFFAOYSA-N 5-methoxypsoralen Chemical compound O1C(=O)C=CC2=C1C=C1OC=CC1=C2OC BGEBZHIAGXMEMV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 241000723346 Cinnamomum camphora Species 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000019501 Lemon oil Nutrition 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000019568 aromas Nutrition 0.000 description 2
- 229930008380 camphor Natural products 0.000 description 2
- 229960000846 camphor Drugs 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 239000010501 lemon oil Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 1
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 1
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 description 1
- SSMIFVHARFVINF-UHFFFAOYSA-N 4-amino-1,8-naphthalimide Chemical compound O=C1NC(=O)C2=CC=CC3=C2C1=CC=C3N SSMIFVHARFVINF-UHFFFAOYSA-N 0.000 description 1
- WWJLCYHYLZZXBE-UHFFFAOYSA-N 5-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C2NC(=O)CC2=C1 WWJLCYHYLZZXBE-UHFFFAOYSA-N 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 239000004857 Balsam Substances 0.000 description 1
- DBMJZOMNXBSRED-UHFFFAOYSA-N Bergamottin Natural products O1C(=O)C=CC2=C1C=C1OC=CC1=C2OCC=C(C)CCC=C(C)C DBMJZOMNXBSRED-UHFFFAOYSA-N 0.000 description 1
- HTDNGPLMZDNUCU-UHFFFAOYSA-N C12(CCCC1)CC1(CCC2C1(C)C)C Chemical class C12(CCCC1)CC1(CCC2C1(C)C)C HTDNGPLMZDNUCU-UHFFFAOYSA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 239000005792 Geraniol 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
- 244000018716 Impatiens biflora Species 0.000 description 1
- KGEKLUUHTZCSIP-UHFFFAOYSA-N Isobornyl acetate Natural products C1CC2(C)C(OC(=O)C)CC1C2(C)C KGEKLUUHTZCSIP-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 239000001940 [(1R,4S,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Substances 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010619 basil oil Substances 0.000 description 1
- 229940018006 basil oil Drugs 0.000 description 1
- KGZDKFWCIPZMRK-UHFFFAOYSA-N bergapten Natural products COC1C2=C(Cc3ccoc13)C=CC(=O)O2 KGZDKFWCIPZMRK-UHFFFAOYSA-N 0.000 description 1
- 229960002045 bergapten Drugs 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 229930003642 bicyclic monoterpene Natural products 0.000 description 1
- 150000001604 bicyclic monoterpene derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 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
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/28—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing seven carbon atoms
- C07C35/29—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing seven carbon atoms being a (2.2.1) system
- C07C35/30—Borneol; Isoborneol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0057—Spiro compounds
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)
- Cosmetics (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
- Detergent Compositions (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62162137A JPS649944A (en) | 1987-06-29 | 1987-06-29 | Bornane-3-spiro-1'-cyclopentane derivative and perfume composition containing said derivative |
| DE8888110301T DE3869232D1 (de) | 1987-06-29 | 1988-06-28 | Abkoemmlinge von bornan-3-spiro-l'-cyclopentan und diese enthaltende riechstoffzusammensetzungen. |
| EP88110301A EP0297510B1 (en) | 1987-06-29 | 1988-06-28 | Bornane-3-spiro-1'-cyclopentane derivatives and perfumery compositions containing them |
| US07/213,151 US4839340A (en) | 1987-06-29 | 1988-06-29 | Bornane-3-spiro-1'-cyclopentane derivatives and perfumery compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62162137A JPS649944A (en) | 1987-06-29 | 1987-06-29 | Bornane-3-spiro-1'-cyclopentane derivative and perfume composition containing said derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS649944A JPS649944A (en) | 1989-01-13 |
| JPH045658B2 true JPH045658B2 (cg-RX-API-DMAC7.html) | 1992-02-03 |
Family
ID=15748741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62162137A Granted JPS649944A (en) | 1987-06-29 | 1987-06-29 | Bornane-3-spiro-1'-cyclopentane derivative and perfume composition containing said derivative |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4839340A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0297510B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS649944A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3869232D1 (cg-RX-API-DMAC7.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5196601A (en) * | 1989-12-26 | 1993-03-23 | Kao Corporation | Process for producing alcohol or amine |
| KR19990049068A (ko) * | 1997-12-11 | 1999-07-05 | 우재영 | 신규한 노보넨 알콜 화합물 및 그의 제조방법 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636165A (en) * | 1969-08-18 | 1972-01-18 | Int Flavors & Fragrances Inc | Indanol derivatives and processes for producing same |
| US3860638A (en) * | 1971-05-20 | 1975-01-14 | Inorganic & Metal Treating Che | Bright nickel plating bath addition agents |
| JPS55108829A (en) * | 1979-02-14 | 1980-08-21 | Kao Corp | Tricyclic spiro-alcohol |
| EP0031965A3 (en) * | 1980-01-04 | 1982-01-27 | Roure Bertrand Dupont Société Anonyme | Process for the preparation of tricyclic compounds, intermediates useful in said process, novel tricyclic compounds so prepared and the use thereof as odoriferous agents |
| US4318863A (en) * | 1980-04-29 | 1982-03-09 | International Flavors & Fragrances Inc. | Substituted tricyclodecane derivatives, processes for producing same and organoleptic uses thereof |
| DE3327014A1 (de) * | 1983-07-27 | 1985-02-14 | Hoechst Ag, 6230 Frankfurt | Neue terpenether und verfahren zu ihrer herstellung |
| JPS6216442A (ja) * | 1985-07-12 | 1987-01-24 | Kao Corp | ボルナン−３−スピロ−１′−シクロペンタン類及びそれを含有する香料組成物 |
| JPH0619738A (ja) * | 1992-07-03 | 1994-01-28 | Mitsubishi Heavy Ind Ltd | バスネットワークで結合した電子機器の模擬故障装置 |
-
1987
- 1987-06-29 JP JP62162137A patent/JPS649944A/ja active Granted
-
1988
- 1988-06-28 DE DE8888110301T patent/DE3869232D1/de not_active Expired - Fee Related
- 1988-06-28 EP EP88110301A patent/EP0297510B1/en not_active Expired - Lifetime
- 1988-06-29 US US07/213,151 patent/US4839340A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS649944A (en) | 1989-01-13 |
| EP0297510A2 (en) | 1989-01-04 |
| US4839340A (en) | 1989-06-13 |
| EP0297510A3 (en) | 1989-04-19 |
| DE3869232D1 (de) | 1992-04-23 |
| EP0297510B1 (en) | 1992-03-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH08319250A (ja) | 香 料 | |
| EP0694605B1 (fr) | Diester cyclique et son utilisation à titre d'ingrédient parfumant | |
| EP0045453B1 (de) | Neue Alkenole (I) und Verfahren zu deren Herstellung, Verwendung von (I) als Riech- und/oder Geschmackstoffe sowie Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an (I) | |
| JP2610309B2 (ja) | 新規香料 | |
| US4149020A (en) | Intermediate for preparation of 2,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol | |
| JPH04235940A (ja) | 新規な有香物質 | |
| JPS58134071A (ja) | 新規芳香物質 | |
| JPS648040B2 (cg-RX-API-DMAC7.html) | ||
| JPH045658B2 (cg-RX-API-DMAC7.html) | ||
| US3996169A (en) | Perfume uses of tricyclic alcohols and processes | |
| EP0007486A1 (fr) | Composés oxygénés dérivant du tricyclo(6.2.1.0)undécane, leur utilisation à titre d'ingrédients parfumants respectivement aromatisants, et compositions contenant lesdits composés | |
| JP3040552B2 (ja) | 新規な有香および（または）香味物質 | |
| JPS62298558A (ja) | シクロヘキサン−、シクロヘキセン−およびシクロヘキサジエン−ビシクロ〔２．２．１〕ヘプタン−および−ビシクロ〔２．２．１〕ヘプテンカルボン酸エステル、ならびに香料成分としての利用 | |
| JPH02243638A (ja) | メチル分岐脂肪族化合物を含有する香料組成物 | |
| JPS647978B2 (cg-RX-API-DMAC7.html) | ||
| EP0086944A1 (de) | Neue ungesättigte Aether (I), Verfahren zu deren Herstellung, Verwendung von (I) als Riech- und/oder Geschmackstoffe und Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an (I) | |
| WO1980000839A1 (en) | Novel norcamphanyl-substituted pyrans,method for their synthesis and use thereof in perfumery | |
| US4170577A (en) | 2,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol perfume compositions | |
| JPH045656B2 (cg-RX-API-DMAC7.html) | ||
| JP2754135B2 (ja) | 新規ケトン及びこれを含有する香料組成物 | |
| JP2814182B2 (ja) | 新規エステル化合物及びこれを含有する香料組成物 | |
| JP2630470B2 (ja) | ２―シクロヘキシルプロピルアセテートを含有する香料組成物 | |
| WO1981000204A1 (en) | Novel norbornyl-substituted pyrans,method for their synthesis and use thereof in perfumery | |
| US4147671A (en) | Perfume compositions containing 8 allyl-8-hydroxytricyclo [5,21,02.6 ] | |
| JPH039960B2 (cg-RX-API-DMAC7.html) |