US3745131A - Perfumery compositions - Google Patents

Perfumery compositions Download PDF

Info

Publication number: US3745131A
Authority: US; United States
Prior art keywords: longifolene; perfumery; composition; hydroxymethyl; derivatives
Prior art date: 1968-03-21
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

Application number

US00808665A

Other languages

English (en)

Inventor

A Curtis

J Janes

B Jaggers

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bush Boake Allen Ltd

Original Assignee

Bush Boake Allen Ltd

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.)

1968-03-21

Filing date

1969-03-19

Publication date

1973-07-10

1969-03-19 Application filed by Bush Boake Allen Ltd filed Critical Bush Boake Allen Ltd

1973-07-10 Application granted granted Critical

1973-07-10 Publication of US3745131A publication Critical patent/US3745131A/en

1990-07-10 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title abstract description 68
ZPUKHRHPJKNORC-UHFFFAOYSA-N Longifolene Natural products CC1(C)CCCC2(C)C3CCC1(C3)C2=C ZPUKHRHPJKNORC-UHFFFAOYSA-N 0.000 abstract description 13
PDSNLYSELAIEBU-UHFFFAOYSA-N Longifolene Chemical compound C1CCC(C)(C)C2C3CCC2C1(C)C3=C PDSNLYSELAIEBU-UHFFFAOYSA-N 0.000 abstract description 11
238000002156 mixing Methods 0.000 abstract description 7
239000000834 fixative Substances 0.000 abstract description 6
239000003795 chemical substances by application Substances 0.000 abstract description 3
230000002708 enhancing effect Effects 0.000 abstract description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
239000000463 material Substances 0.000 description 20
150000004192 longifolene derivatives Chemical class 0.000 description 17
150000001875 compounds Chemical class 0.000 description 15
230000000694 effects Effects 0.000 description 14
239000012141 concentrate Substances 0.000 description 13
239000004615 ingredient Substances 0.000 description 10
239000002304 perfume Substances 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000001738 pogostemon cablin oil Substances 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical class CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
GLZPCOQZEFWAFX-UHFFFAOYSA-N KU0063794 Natural products CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
239000010627 cedar oil Substances 0.000 description 4
239000000470 constituent Substances 0.000 description 4
-1 hydroxymethyl compound Chemical class 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000000758 substrate Substances 0.000 description 4
239000001724 (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulen-6-yl) acetate Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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 3
229930002839 ionone Natural products 0.000 description 3
150000002499 ionone derivatives Chemical class 0.000 description 3
238000000034 method Methods 0.000 description 3
229940067107 phenylethyl alcohol Drugs 0.000 description 3
239000010671 sandalwood oil Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
239000010679 vetiver oil Substances 0.000 description 3
OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 description 2
NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
239000005792 Geraniol Substances 0.000 description 2
GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
229930040373 Paraformaldehyde Natural products 0.000 description 2
238000010478 Prins reaction Methods 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
239000002537 cosmetic Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000002781 deodorant agent Substances 0.000 description 2
239000003599 detergent Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000004744 fabric Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
229940113087 geraniol Drugs 0.000 description 2
150000002596 lactones Chemical class 0.000 description 2
239000006210 lotion Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000000344 soap Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
LQKRYVGRPXFFAV-UHFFFAOYSA-N Phenylmethylglycidic ester Chemical compound CCOC(=O)C1OC1(C)C1=CC=CC=C1 LQKRYVGRPXFFAV-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
241000220317 Rosa Species 0.000 description 1
241000109329 Rosa xanthina Species 0.000 description 1
235000004789 Rosa xanthina Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
241000779819 Syncarpia glomulifera Species 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis 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
238000010348 incorporation Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000035800 maturation Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000001739 pinus spp. Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000007670 refining Methods 0.000 description 1
238000007127 saponification reaction Methods 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
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000516 sunscreening agent Substances 0.000 description 1
229940036248 turpentine Drugs 0.000 description 1
239000003643 water by type Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 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

Definitions

composition according to claim 6 containing said longifolene derivative or derivatives in a concentration of from 0.1% to 20% by weight based on the total composition.

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Fats And Perfumes (AREA)
Cosmetics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

US00808665A 1968-03-21 1969-03-19 Perfumery compositions Expired - Lifetime US3745131A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB1375668		1968-03-21
GB3103368		1968-06-28

Publications (1)

Publication Number	Publication Date
US3745131A true US3745131A (en)	1973-07-10

Family

ID=26249981

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US00808665A Expired - Lifetime US3745131A (en)	1968-03-21	1969-03-19	Perfumery compositions

Country Status (5)

Country	Link
US (1)	US3745131A (de)
CH (1)	CH512580A (de)
DE (1)	DE1913691A1 (de)
FR (1)	FR2004426A1 (de)
NL (1)	NL6904363A (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3839233A (en) *	1970-05-14	1974-10-01	Int Flavors & Fragrances Inc	Perfume compositions
US4100110A (en) *	1974-08-09	1978-07-11	Bush Boake Allen Limited	Isolongifolene Prins reaction compounds in perfumery
US9399078B2 (en)	2009-12-17	2016-07-26	The Procter & Gamble Company	Unscented and low scented malodor control compositions and methods thereof
US11110196B2 (en)	2013-08-01	2021-09-07	The Procter & Gamble Company	Articles comprising malodor reduction compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2281100A1 (fr) *	1974-08-12	1976-03-05	Bush Boake Allen Ltd	Nouveaux produits de parfumerie

1969
- 1969-03-18 DE DE19691913691 patent/DE1913691A1/de active Pending
- 1969-03-19 US US00808665A patent/US3745131A/en not_active Expired - Lifetime
- 1969-03-20 CH CH421769A patent/CH512580A/de not_active IP Right Cessation
- 1969-03-20 FR FR6908218A patent/FR2004426A1/fr not_active Withdrawn
- 1969-03-21 NL NL6904363A patent/NL6904363A/xx unknown

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3839233A (en) *	1970-05-14	1974-10-01	Int Flavors & Fragrances Inc	Perfume compositions
US4100110A (en) *	1974-08-09	1978-07-11	Bush Boake Allen Limited	Isolongifolene Prins reaction compounds in perfumery
US9399078B2 (en)	2009-12-17	2016-07-26	The Procter & Gamble Company	Unscented and low scented malodor control compositions and methods thereof
US9642927B2 (en)	2009-12-17	2017-05-09	The Procter & Gamble Company	Unscented and low scented malodor control compositions and methods thereof
US11110196B2 (en)	2013-08-01	2021-09-07	The Procter & Gamble Company	Articles comprising malodor reduction compositions

Also Published As

Publication number	Publication date
DE1913691A1 (de)	1969-11-06
FR2004426A1 (de)	1969-11-21
CH512580A (de)	1971-09-15
NL6904363A (de)	1969-09-23

Publication	Publication Date	Title
US3959185A (en)	1976-05-25	Perfume blend including 2-keto-6-substituted-dioxanes-(1,4)
US3480677A (en)	1969-11-25	Novel ionone
US3952016A (en)	1976-04-20	2-Keto-6-substituted dioxane-(1,4) compounds
US4308179A (en)	1981-12-29	Perfumed compositions
US4460498A (en)	1984-07-17	Unsaturated alicyclic ethers and their utilization as perfuming and flavoring ingredients
EP0137419A2 (de)	1985-04-17	Riechstoffkompositionen mit einem Gehalt an Benzyläthern
JPS58134071A (ja)	1983-08-10	新規芳香物質
EP0004968B1 (de)	1981-10-21	Norbornen(-an)Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Riechstoffe
CA1136552A (en)	1982-11-30	Acetyl trimethyl bicyclo non-ene as perfume
EP0007486B1 (de)	1981-08-26	Sauerstoff enthaltende Abkömmlinge des Tricyclo(6.2.1.0)-undecans, ihre Verwendung als Riech- und Aromastoffe und sie enthaltende Zusammensetzungen
US3673120A (en)	1972-06-27	Perfumery compositions containing patchouli oil and 8-camphene carbinol
US3258400A (en)	1966-06-28	Isopropyl and diisopropyl-3, 4-dihydrocoumarins in perfume compositions
US4028279A (en)	1977-06-07	Novel fragrance compositions containing 2,6,6 trimethyl-1-cyclohexen-1-yl acetaldehyde and phenyl C6 ketone
US3942761A (en)	1976-03-09	4-(2'-Norbornyl)-2-butanones
JPS62298558A (ja)	1987-12-25	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
EP0053979B1 (de)	1985-07-10	Cyclopentanol-Derivate, deren Herstellung, deren Verwendung als Riechstoffe, Gemische, in denen diese Produkte einverleibt werden, und erhaltene Zwischenprodukte
DE2015865A1 (de)	1971-03-04	Cyclische Ester und Verwendung (der selben) in der Parfumene
JPS61178944A (ja)	1986-08-11	４−（２，２，３−トリメチルシクロペント−３−エン−１−イル）−ブト−３−エン−１−オル、それらの製造方法および芳香剤としての用途
US4113664A (en)	1978-09-12	2,4-Dioxa-spiro(5,5)undec-8-ene perfume compositions
US4294727A (en)	1981-10-13	Perfume composition containing 4,5-dioxa-5-alkyl-tricyclo[7.2.1.0 2,8 ]dodec-10-enes and its use as an odorant
US4267075A (en)	1981-05-12	Perfume compositions containing esters of 3,5,5-trimethylhexanoic acid
DE1913691A1 (de)	1969-11-06	Parfuemeriezusammensetzungen
US3557188A (en)	1971-01-19	4,7-methanoindene derivatives
US4132676A (en)	1979-01-02	Perfume compositions containing ethyl 3,4-dichloro-5-isothiazolecarboxylate
US4545930A (en)	1985-10-08	Terpene derivatives and perfume compositions containing them