GB2448180A - Spiro compound and its use in fragrance applications - Google Patents
Spiro compound and its use in fragrance applications Download PDFInfo
- Publication number
- GB2448180A GB2448180A GB0706694A GB0706694A GB2448180A GB 2448180 A GB2448180 A GB 2448180A GB 0706694 A GB0706694 A GB 0706694A GB 0706694 A GB0706694 A GB 0706694A GB 2448180 A GB2448180 A GB 2448180A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fragrance
- compound
- spiro compound
- fragrance applications
- application
- 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- Withdrawn
Links
- 239000003205 fragrance Substances 0.000 title claims description 12
- 150000003413 spiro compounds Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- -1 for example Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
- C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
- C07C49/623—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two 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
- C11B9/0042—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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Description
COMPOUND
This invention relates to a novel compound.
The invention provides the compound 7,9-dimethylSpirO[5.5jundeC-8-efl-3-Ofle 1. S...
S S...
The molecule has a chiral centre at the 7-methyl position and is thus available as the S...
*. enantiomers la ((7R)7,9.ditnethY1sPir0[5.5)un..8--3-one) and lb ((7S)-7,9-dimethy1spirO[5.5)fldeC8e33o1) S... Ia lb
The enantiomers may be separated by conventional techniques, but this adds to the expense and complexity of the process. Moreover, for some purposes, it may not be necessary and the molecule may be used as a racemic mixture.
The compound may be made by any convenient method, an especially preferred method being the selective hydrogenation of the conjugated double bond of Spirodiene 2. The conjugated double bond is situated in the ct,-positiofl of the keto group. 2
The compound has an odour described as leathery, floral, green, powdery, and it is useful as an ingredient in fragrance applications. 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 therefore also provides a method of providing a fragrance to a fragrance application, comprising the addition to the application of 7,9dimethylSpirO[5.5JUfldecSe130 There is known to the art the compound 3 * *I.1 S...
***** 10 produced by the hydrogenation of Spirodiene 2 (El' 0074 693). The depicted relative stereochemistry refers to the main diastereomer of the racemate. Because of the relatively high GC threshold of this compound (22 ng), a relatively high dosage has to be used in perfumery *.** bases. *5S*S * .
Synthesis and use of the compound 1 offers several advantages over this art, namely: a) Hydrogenation of substrate 2 can be done under less drastic conditions; b) A lower threshold (9 ng) allows the use of less material to achieve the same or a better olfactory effect in perfumery bases; and c) A different olfactory profile -the olfactory profile of compound 1 was described as more floral, more powdery and more elegant, compared to the green, leathery and woody compound 3, which has also fruity, spicy and iris notes.
The invention is further described with reference to the following example:
EXAMPLE 1
MonohydrogeflatiOn of Diene 2: 7,9dimethylspirO[5.53Ufldec8 n-3-one 1.
j p*oi 16g of 2 (84 mmol) was hydrogenated in 0.3M KOH / ethanol (300 ml) over 10% Pd / C (0.4 g) at 2 bar and 25 C for 6 hours. After filtration of the catalyst the filtrate was neutralized with acetic acid and about 90% of the solvent was evaporated in vacuo. The residue was a.
a..., diluted with water (100 ml) and the mixture extracted with n-hexane (1 x 100,2 x 50 ml). The * : organic layer was dried over sodium sulphate. After filtration the solvent was evaporated in "I vacuo. The residue (15,0 g, yellow oil, OC-purity 88%) was fractionated twice in vacuo (h.p. **S
98-100 C / 237 mbar) to provide 11.7 g (72% yield) of 1 (96% GC-purity) as a pale yellow oil, * S..
which crystallizes slowly at room temperature. H-NMR (CDCI3, 400 MHz): 5.25 (1 H), 2.25 -*S * 2.4(4 H, CH2(CO)CH2), 2.1 (1 H), 1.95(1 H), 1.8-1.9(3 H), 1.6-1.7(2 H), 1.65(3 H), 1.4 (1 H), 0.9 (d, 3 H, CH-cLb) ppm. 3C-NMR (CDCI3, 400 MHz): 212.9 (s, CO), 132.2 (s), 126.3 (d), 37.3 (2 t), 37.1 (d), 34.0 (t), 33.0 (s), 32.0 (t), 27.8 (t), 27.3 (t), 23.2 (q), 16.3 (q) ppm. GCIMS: 192(10%, M4), 177 (1%, [M -15]), 159 (1%, [M -15 -H20f), 107 (5%), 91 (6%), 82 (100%), 67 (25%). IR (film): 2800 -3000 (m), 1713 (s), 1448 (m), 1148 (w), 1116 (w), 838 (w), 754 (w). Odour: Leathery, floral, green, powdery. OC-threshold: 8.6 ng.
Olfactometer threshold: 8 ng.
Claims (7)
- Claims: 1. 7,9.dimethylspirOE5.51UfldeCSefl30e.
- 2.
- 3. (7S)7,9dimethylsPirO[5.5]UfldeC830ne.
- 4. Use of 7,9dimethylSpirO[5.51UfldecS_e13011e in a fragrance application. S.. *5*SS *5S5
- 5. A fragrance application comprising 7,9dimethylSpirO[5.51Uec_8e3_0ne.SS
- 6. A fragrance application according to claim 5, selected from perfumes, toiletries, *5IS cosmetics, soaps, laundry and household products and polishes. * S
- 7. Method of providing a fragrant odour to a fragrance application, comprising the addition to the application of 7,9dimethYlSPirO[5.51Ufld8e30ht
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0706694A GB2448180A (en) | 2007-04-05 | 2007-04-05 | Spiro compound and its use in fragrance applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0706694A GB2448180A (en) | 2007-04-05 | 2007-04-05 | Spiro compound and its use in fragrance applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB0706694D0 GB0706694D0 (en) | 2007-05-16 |
| GB2448180A true GB2448180A (en) | 2008-10-08 |
Family
ID=38090939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0706694A Withdrawn GB2448180A (en) | 2007-04-05 | 2007-04-05 | Spiro compound and its use in fragrance applications |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2448180A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0074693A1 (en) * | 1981-09-16 | 1983-03-23 | Naarden International N.V. | Perfume compositions and perfumed articles containing spiro-undecanones and -undecenones as perfume base |
| US4562293A (en) * | 1984-10-15 | 1985-12-31 | Ethyl Corporation | Spiroketone process |
| US4622172A (en) * | 1985-12-06 | 1986-11-11 | International Flavors & Fragrances Inc. | Alkyl-substituted spiroundecenone derivatives, organoleptic utility thereof and processes for preparing same |
| WO2000037117A1 (en) * | 1998-12-22 | 2000-06-29 | Quest International B.V. | Improvements in or relating to reduction of malodour |
| EP1411110A1 (en) * | 2002-10-14 | 2004-04-21 | Firmenich Sa | Spiro compounds as perfuming ingredients |
-
2007
- 2007-04-05 GB GB0706694A patent/GB2448180A/en not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0074693A1 (en) * | 1981-09-16 | 1983-03-23 | Naarden International N.V. | Perfume compositions and perfumed articles containing spiro-undecanones and -undecenones as perfume base |
| US4562293A (en) * | 1984-10-15 | 1985-12-31 | Ethyl Corporation | Spiroketone process |
| US4622172A (en) * | 1985-12-06 | 1986-11-11 | International Flavors & Fragrances Inc. | Alkyl-substituted spiroundecenone derivatives, organoleptic utility thereof and processes for preparing same |
| WO2000037117A1 (en) * | 1998-12-22 | 2000-06-29 | Quest International B.V. | Improvements in or relating to reduction of malodour |
| EP1411110A1 (en) * | 2002-10-14 | 2004-04-21 | Firmenich Sa | Spiro compounds as perfuming ingredients |
Also Published As
| Publication number | Publication date |
|---|---|
| GB0706694D0 (en) | 2007-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4200094B2 (en) | A cycloalkanecarboxylic acid derivative as a fragrant fragrance | |
| CN101528652B (en) | Organic compounds | |
| CA2249843A1 (en) | Macrocyclen | |
| JP2011526252A (en) | Isolongifolanil derivatives suitable as odorants | |
| RU2482108C2 (en) | Substituted octan(ene)nitriles, method for production thereof and use thereof in perfumery | |
| EP1743013B1 (en) | Alicyclic carboxylic acid oxycarbonylmethyl esters and their use as odorants | |
| EP2904080B1 (en) | Flavor and fragrance formulation (i) | |
| JP4518957B2 (en) | Aliphatic compounds as perfumes with pepper properties | |
| WO2009056756A1 (en) | Substituted octane(ene) nitriles, methods for the synthesis thereof and uses thereof in perfumery | |
| GB2448180A (en) | Spiro compound and its use in fragrance applications | |
| US9845443B2 (en) | Synthesis of a novel odorant | |
| JPS63264477A (en) | Perfume composition | |
| WO2008017183A1 (en) | Cyclopentane/cyclopentene aldehyde or ketone derivatives and their use as odorants | |
| MX2008003072A (en) | Oxygen containing tri- or tetra-cyclic terpenoid compounds. | |
| FR2651496A1 (en) | PROCESS FOR THE PREPARATION OF ALPHA-ALKYL-LACTONES FROM ALPHA-ACYL-LACTONES AND PERFUME CONTAINING THEM | |
| KR20070085865A (en) | Organic compounds | |
| CN111448299B (en) | Odorants and compositions comprising odorants | |
| JP4859826B2 (en) | Tri-substituted furan suitable for the manufacture of fragrance compositions | |
| JP3642860B2 (en) | 5-Benzylhexanol-2 and perfume composition containing the same | |
| DE3203977A1 (en) | NEW CYCLOPROPANCARBONIC ACID DERIVATIVES SUBSTITUTED IN 3-POSITION BY A VINYL CHAIN, THEIR PRODUCTION, THE USE THEREOF AS A FRAGRANT, AND THE COMPOSITIONS CONTAINING THEM | |
| WO2014064716A1 (en) | (5h)-1 -benzopyran-5-one derivatives and formulations for perfumery and flavor applications | |
| JP2002519396A (en) | Preparation of macrocyclic ketones utilizing addition of ketones to alkenes | |
| WO2010125100A1 (en) | 2-oxaspiro [5, 5] undec-8-ene derivatives useful in fragrance compositions | |
| EP0189581A1 (en) | 2,3-Disubstituted bicyclo[2,2,1]heptanes and heptenes, their preparation and their use as perfumes | |
| JP2014141436A (en) | Bicyclo compounds and perfume compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |