NL8020236A - Bicyclische alkoholen en de toepassing daarvan als parfumbestanddelen. - Google Patents

Bicyclische alkoholen en de toepassing daarvan als parfumbestanddelen. Download PDF

Info

Publication number: NL8020236A
Authority: NL; Netherlands
Prior art keywords: formula; enyl; trimethylcyclopent; ethylidene; cyclopentanol
Prior art date: 1979-08-14

Application number

NL8020236A

Other languages

English (en)

Dutch (nl)

Original Assignee

Firmenich & Cie

Priority date (The priority date 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 date listed.)

1979-08-14

Filing date

1980-07-10

Publication date

1981-07-01

1980-07-10 Application filed by Firmenich & Cie filed Critical Firmenich & Cie

1981-07-01 Publication of NL8020236A publication Critical patent/NL8020236A/nl

Links

239000004615 ingredient Substances 0.000 title claims description 4
-1 2,2,3-trimethylcyclopent-3-enyl Chemical group 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 8
150000002576 ketones Chemical class 0.000 claims description 8
239000002304 perfume Substances 0.000 claims description 6
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims description 5
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
238000005882 aldol condensation reaction Methods 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
150000001299 aldehydes Chemical class 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000000203 mixture Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000284 extract Substances 0.000 description 5
238000000034 method Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000470 constituent Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000003205 fragrance Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
238000011282 treatment Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
HQKQRXZEXPXXIG-VJOHVRBBSA-N chembl2333940 Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1[C@@](OC(C)=O)(C)CC2 HQKQRXZEXPXXIG-VJOHVRBBSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000003599 detergent Substances 0.000 description 2
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
FACFHHMQICTXFZ-UHFFFAOYSA-N 2-(2-phenylimidazo[1,2-a]pyridin-3-yl)ethanamine Chemical compound N1=C2C=CC=CN2C(CCN)=C1C1=CC=CC=C1 FACFHHMQICTXFZ-UHFFFAOYSA-N 0.000 description 1
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 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000218645 Cedrus Species 0.000 description 1
235000002548 Cistus Nutrition 0.000 description 1
241000984090 Cistus Species 0.000 description 1
244000183685 Citrus aurantium Species 0.000 description 1
235000007716 Citrus aurantium Nutrition 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
244000178870 Lavandula angustifolia Species 0.000 description 1
235000010663 Lavandula angustifolia Nutrition 0.000 description 1
235000019501 Lemon oil Nutrition 0.000 description 1
244000179970 Monarda didyma Species 0.000 description 1
235000010672 Monarda didyma Nutrition 0.000 description 1
235000010676 Ocimum basilicum Nutrition 0.000 description 1
240000007926 Ocimum gratissimum Species 0.000 description 1
240000002505 Pogostemon cablin Species 0.000 description 1
235000011751 Pogostemon cablin Nutrition 0.000 description 1
240000000513 Santalum album Species 0.000 description 1
235000008632 Santalum album Nutrition 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000001387 apium graveolens Substances 0.000 description 1
235000013709 carrot oil Nutrition 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000012459 cleaning agent Substances 0.000 description 1
239000010634 clove oil Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
YFPCLQKFNXUAAK-UHFFFAOYSA-N cyclopentyl acetate Chemical compound CC(=O)OC1CCCC1 YFPCLQKFNXUAAK-UHFFFAOYSA-N 0.000 description 1
QLBKLJFKEUBMGH-UHFFFAOYSA-N cyclopentyl formate Chemical compound O=COC1CCCC1 QLBKLJFKEUBMGH-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000001299 ferula galbaniflua resinoid Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000001102 lavandula vera Substances 0.000 description 1
235000018219 lavender Nutrition 0.000 description 1
239000010501 lemon oil Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229940067137 musk ketone Drugs 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
WYMSBXTXOHUIGT-UHFFFAOYSA-N paraoxon Chemical compound CCOP(=O)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 WYMSBXTXOHUIGT-UHFFFAOYSA-N 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
238000003822 preparative gas chromatography Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000001385 rosmarinus officinalis l. absolute Substances 0.000 description 1
239000010671 sandalwood oil Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000004753 textile Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 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
- C11B9/0026—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
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- 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
- C07C35/21—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 non-condensed ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
- C07C49/653—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring polycyclic
- 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)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Fats And Perfumes (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

NL8020236A 1979-08-14 1980-07-10 Bicyclische alkoholen en de toepassing daarvan als parfumbestanddelen. NL8020236A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH742279		1979-08-14
CH742279		1979-08-14

Publications (1)

Publication Number	Publication Date
NL8020236A true NL8020236A (nl)	1981-07-01

Family

ID=4324883

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8020236A NL8020236A (nl)	1979-08-14	1980-07-10	Bicyclische alkoholen en de toepassing daarvan als parfumbestanddelen.

Country Status (6)

Country	Link
BR (1)	BR8008796A (fr)
CH (1)	CH640208A5 (fr)
DE (1)	DE3049802C1 (fr)
GB (1)	GB2071101B (fr)
NL (1)	NL8020236A (fr)
WO (1)	WO1981000561A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4289658A (en) *	1979-09-19	1981-09-15	Fritzsche Dodge & Olcott Inc.	2-[-(2'2'3'-Trimethyl-3'-cyclopenten-1'-yl)-ethyliden]-and ethyl]-cyclopentanols
US5128317A (en) *	1990-09-27	1992-07-07	International Flavors And Fragrances Inc.	Camphonyl spirocyclooxaoctane-containing compositions, organoleptic uses thereof and process for preparing same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1922391A1 (de) *	1968-05-08	1970-08-27	Chem Fab Miltitz Veb	Riechstoffe und Riechstoffkompositionen
US4052341A (en) *	1976-04-29	1977-10-04	Givaudan Corporation	3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol compound and perfume compositions
US4173585A (en) *	1978-08-10	1979-11-06	International Flavors & Fragrances Inc.	2,2,3-Trimethyl-3-cyclopenten-1-ylalkenyl- and alkylidene-cycloalkanones

1980
- 1980-07-10 GB GB8109133A patent/GB2071101B/en not_active Expired
- 1980-07-10 WO PCT/CH1980/000084 patent/WO1981000561A1/fr not_active Ceased
- 1980-07-10 NL NL8020236A patent/NL8020236A/nl not_active Application Discontinuation
- 1980-07-10 DE DE3049802T patent/DE3049802C1/de not_active Expired
- 1980-07-10 BR BR8008796A patent/BR8008796A/pt unknown
- 1980-07-10 CH CH253381A patent/CH640208A5/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB2071101A (en)	1981-09-16
CH640208A5 (fr)	1983-12-30
BR8008796A (pt)	1981-06-23
DE3049802C1 (de)	1984-11-22
WO1981000561A1 (fr)	1981-03-05
GB2071101B (en)	1984-02-22

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1985-03-01	BV	The patent application has lapsed

Publication	Publication Date	Title
EP0908455A1 (fr)	1999-04-14	Macrocycles
ES2553646T3 (es)	2015-12-10	Derivados de 2,3,3-trimotilciclopent-3-enocarboaldehído útiles como substancias odoríferas
US4100110A (en)	1978-07-11	Isolongifolene Prins reaction compounds in perfumery
EP0137419B1 (fr)	1987-08-12	Compositions parfumées contenant des éthers benzyliques
DE602005003937T2 (de)	2008-12-18	Alicyclische carbonsäureoxycarbonylmethylester und deren verwendung als riechstoffen
EP0002510B1 (fr)	1981-02-11	Cyclohexanes, procédé de leur préparation, leur utilisation et compositions les contenant
NL8020236A (nl)	1981-07-01	Bicyclische alkoholen en de toepassing daarvan als parfumbestanddelen.
US4572795A (en)	1986-02-25	Odorant substances
DE2652452A1 (de)	1977-05-18	Cyclohexenester, verfahren zu ihrer herstellung und ihre verwendung in riechstoff-kompositionen
DE2812288C2 (fr)	1988-03-31
DE2036936B2 (de)	1973-10-25	Hydrierte Indanon Derivate, Ver fahren zu ihrer Herstellung und ihre Ver Wendung als Riechstoffe
US4132677A (en)	1979-01-02	Perfume compositions containing 2-(2-cyanoethylidene)-2-methyl-bicyclo(2.2.1)hept-5-enes
DE1902074A1 (de)	1969-09-04	Sauerstoffhaltige Derivate acyclischer Olefine
DE69803429T2 (de)	2002-09-05	Von 3-Isopropenyl-1,2-dimethyl-1-cyclopentanol abgeleitete Nitrile und Aldehyde und ihre Verwendung in der Parfümerie
DE2617816A1 (de)	1977-11-10	Verwendung von epoxynitrilen als riechstoffe sowie diese enthaltende riechstoffkompositionen
US3557188A (en)	1971-01-19	4,7-methanoindene derivatives
EP0073771B1 (fr)	1985-09-18	Nouveaux composes odoriferants
US4322559A (en)	1982-03-30	4(5)-Acetyl-9,9-dimethyltricyclo-[4,4,0,18,10 ]-undec-1-ene, its preparation and use in perfumery compositions and as an odorant
DE69204660T2 (de)	1996-04-18	Pinane.
CH642612A5 (de)	1984-04-30	1,5-dimethyl-bicyclo(3,2,1)octan-derivate, verfahren zu ihrer herstellung und ihre verwendung.
US4187243A (en)	1980-02-05	Novel 2-(2-cyanoethylidene)-bicyclo[2.2.1]hept-5-enes and hydrogenated derivatives thereof
DE1811289B2 (de)	1974-12-19	eis- 1,7,7-Trimethyl-bicyclo eckige Klammer auf 4,4,0 eckige Klammer zu decanon- (3), Verfahren zu dessen Herstellung und dessen Verwendung als Riechstoff
DE2461605A1 (de)	1975-10-02	5-acetyl-1,2,6-trimethyltricyclo eckige klammer auf 5,3,2,0 hoch 2,7 eckige klammer zu dodeca-5-en, verfahren zu seiner herstellung und seine verwendung als riechstoff
JPS62501008A (ja)	1987-04-23	発明の名称なし
DE3049802T5 (de)	1982-02-25	Bicyclic alcohols and use thereof as perfuming ingredients