GB2423986A - Fragrance Compound - Google Patents

Fragrance Compound Download PDF

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Publication number
GB2423986A
GB2423986A GB0428295A GB0428295A GB2423986A GB 2423986 A GB2423986 A GB 2423986A GB 0428295 A GB0428295 A GB 0428295A GB 0428295 A GB0428295 A GB 0428295A GB 2423986 A GB2423986 A GB 2423986A
Authority
GB
United Kingdom
Prior art keywords
compound
fragrance
fragrance compound
methyl
oxa
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.)
Withdrawn
Application number
GB0428295A
Other versions
GB0428295D0 (en
Inventor
Fridtjof Schroeder
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.)
Givaudan SA
Original Assignee
Givaudan SA
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.)
Filing date
Publication date
Application filed by Givaudan SA filed Critical Givaudan SA
Priority to GB0428295A priority Critical patent/GB2423986A/en
Publication of GB0428295D0 publication Critical patent/GB0428295D0/en
Publication of GB2423986A publication Critical patent/GB2423986A/en
Withdrawn legal-status Critical Current

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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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0084—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing more than six atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom

Abstract

The compound 3-methyl-6-oxa-bicyclo[13.1.0]hexadecane-7-one and it uses in fragrance applications.

Description

COMPOUND
This invention relates to a novel compound.
The invention provides the compound 3-methyl-6-oxabicyc1o[131O] hexadecafl7one The compound may be made by any convenient method, an especially preferred method being the cyclopropanation of a suitable substituted alkene, comprising the reaction of the alkene with a carbenoide, generated from dibromomethane and a tri-(C2-Cs)-alkylalumjnum compound.
The compound is useful as an ingredient in fragrance applications. The invention therefore also provides the use in a fragrance application of3methyl6oxabicyc1o[131O]hexadecafl7ofle The fragrance application may be in any field of fine or functional fragrance, for example, perfumes, toiletries, cosmetics, soaps, laundry and household products and polishes.
In such applications, it may be combined with other known fragrance materials to provide desirable fragrance properties.
The invention is further described with reference to the following example.
EXAMPLE
Cyclopropanation of cis3methy16oxabjcyc1o[ 13.1.O]hexadecan-7-one.
Anhydrous FeCI3 (0.8 g, 5 mmol) is added under stirring and nitrogen to Z13-methyl- oxacyclopentadec 1 O-en-2-one (NirvanolideTM) (20 g, 84 mmol) in dibromomethane (235 ml, 3.35 mol) at 100 - 20 C, followed by slow addition of neat triisobutylaluminum (100 g, 0. 5 mol) at this temperature. The mixture is stirred for 5 h at 25 C, then cooled to -10 0 C and pumped via double needle onto 25% NaOH at -*10 - 0 C. Under stirring the biphasic mixture is slowly warmed up to room temperature. The phases are separated. The organic phase is washed with 4% oxalic acid, then with conc. NaHCO3 until pH 8, dried over MgSO4 and filtered. After evaporation of the solvents under reduced pressure the oily residue is purified by distillation (bp 100 C / 0.03 Ton) giving 8 g (38%) of the cyclopropanation product as colorless oil. Odour: musky, metallic, powdery. H-NMR (CDCI3, 400 MHz): 4. 2 (m, 2 H), 2.3 (m, 2 H), 1.7(1 H), 1.7- 1.2(1611), 1.0(3 H), 0.8 (m, 1 H), 0.6 (m, I H), -0.3 (m, I H) ppm.
13C-NMR (CDC13, 400 MHz): 174.0 (s), 62.1 (t), 37.4 (t), 36.3 (t), 34.6 (t), 30.2 (d), 28.6 (t), 27.6 (t), 27.5 (t), 27.1 (t), 26.8 (t), 24.8 (t), 18.4 (q), 16.1 (d), 13. 8 (d), 10.9 (t) ppm. GC/MS: 252(1%, M), 237(1%, [M- 15}), 223(1%), 210(1%), 195(1%), 182(1%), 109(20%) , 95 (35%), 81(100%). JR (film): 2924 (m), 2855 (m), 1731 (s), 1458 (m), 1378 (w), 1337 (w), l248(m), 1151 (m), ll20(w), 1091 (w), 1060(m), 1021 (w), 965(w),848(w) * * ..* S S * S S S q S * * S * S S * *SS S S S S S* S S S S *5 S S * S S IS S I S S.. * S 55 S

Claims (3)

Claims.
1. 3-Methyl-6-oxa-bicyclo[ 13.1.O]hexadecan-7..one
2. Use of 3-methyl-6-oxa-bicyclo[1 3.1.O]hexadecan-7..one in a fragrance application.
3. A fragrance application comprising 3-methyl-6-oxa-bicyc!o[ 13.1.O] hexadecan-7-one.
, . ... I. * * * I a S * * S * S S * 555 S S I S5 S * * 5 55 5 5 S * P SI. S I 5* 5 0 *5 0
GB0428295A 2004-12-24 2004-12-24 Fragrance Compound Withdrawn GB2423986A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB0428295A GB2423986A (en) 2004-12-24 2004-12-24 Fragrance Compound

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB0428295A GB2423986A (en) 2004-12-24 2004-12-24 Fragrance Compound

Publications (2)

Publication Number Publication Date
GB0428295D0 GB0428295D0 (en) 2005-01-26
GB2423986A true GB2423986A (en) 2006-09-13

Family

ID=34113217

Family Applications (1)

Application Number Title Priority Date Filing Date
GB0428295A Withdrawn GB2423986A (en) 2004-12-24 2004-12-24 Fragrance Compound

Country Status (1)

Country Link
GB (1) GB2423986A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8217185B2 (en) 2007-09-27 2012-07-10 Givaudan Sa Macrocyclic lactones as fragrances

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4187222A (en) * 1977-07-13 1980-02-05 Bayer Aktiengesellschaft Process for the preparation of cyclopentadecanolide
US4490404A (en) * 1983-07-18 1984-12-25 International Flavors & Fragrances Inc. Flavoring with macrocyclic lactone
US6008185A (en) * 1997-03-05 1999-12-28 Haarmann & Reimer Gmbh Macrocyclic lactones as musk fragrance enhancers
WO2004083357A1 (en) * 2003-03-13 2004-09-30 Flexitral, Inc. Macrocyclic musks

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4187222A (en) * 1977-07-13 1980-02-05 Bayer Aktiengesellschaft Process for the preparation of cyclopentadecanolide
US4490404A (en) * 1983-07-18 1984-12-25 International Flavors & Fragrances Inc. Flavoring with macrocyclic lactone
US6008185A (en) * 1997-03-05 1999-12-28 Haarmann & Reimer Gmbh Macrocyclic lactones as musk fragrance enhancers
WO2004083357A1 (en) * 2003-03-13 2004-09-30 Flexitral, Inc. Macrocyclic musks

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8217185B2 (en) 2007-09-27 2012-07-10 Givaudan Sa Macrocyclic lactones as fragrances

Also Published As

Publication number Publication date
GB0428295D0 (en) 2005-01-26

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WAP Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1)