EP1102832A2 - Odoriferous compounds - Google Patents
Odoriferous compoundsInfo
- Publication number
- EP1102832A2 EP1102832A2 EP99924838A EP99924838A EP1102832A2 EP 1102832 A2 EP1102832 A2 EP 1102832A2 EP 99924838 A EP99924838 A EP 99924838A EP 99924838 A EP99924838 A EP 99924838A EP 1102832 A2 EP1102832 A2 EP 1102832A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- methylcyclohex
- butanal
- enyl
- aldehyde
- 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.)
- Granted
Links
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
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
Definitions
- the invention relates to special fragrance compositions which contain 90-70% by weight of 2-methylene-3- (4-methylcyclohex-3-enyl) butanal and 10-30% by weight of limonaldehyde.
- Limonene whose rational IUPAC name is l-methyl-4-isopropenyl-cyclohex-l-ene, is a well-known natural product.
- the structural formula of limonene (3) is shown below:
- 2-methylene-3- (4-methylcyclohex-3-enyl) butanal (1) can be used as a fragrance according to the information given in DE 29 21 619 C3. However, nothing is disclosed in DE 29 21 619 C3 about the properties of special mixtures of (1) with other olfactory compounds.
- fragrance industry has a constant need for new fragrances with interesting fragrance notes to complement the range of naturally available fragrances and to make the necessary adjustments to changing fashionable flavors as well to meet the ever increasing need for odor improvers for everyday products such as cosmetics and cleaning agents.
- fragrance compositions which contain 90-70% by weight of 2-methylene-3- (4-methylcyclohex-3-enyl) butanal (1) and 10-30% by weight of limonene aldehyde (2) , are characterized by perfume notes of extremely interesting perfume with fine shades.
- the odor profiles of these fragrance compositions according to the invention are qualitatively different, original and novel compared to the individual components (1) and (2).
- the invention relates to fragrance compositions which contain 90-70% by weight of 2-methylene-3- (4-methylcyclohex-3-enyl) butanal (1) and 10-30% by weight of limonene aldehyde (2).
- the fragrance compositions according to the invention contain, in addition to the compulsory components (1) and (2) mentioned, a maximum of 5% by weight of further olfactory components.
- Another object of the invention is the use of aldehyde mixtures as fragrances, the aldehyde mixtures being mixtures which contain 90-70% by weight of 2-methylene-3- (4-methylcyclohex-3-enyl) butanal and 10-30 wt.% Limonenaldehyd contain
- the odor profile of the fragrance compositions according to the invention is original and novel.
- perfume compositions they enhance harmony and charisma as well as adhesion, whereby the dosage is adjusted to the desired fragrance, taking into account the other components of the composition.
- the fragrance compositions according to the invention are particularly suitable for modifying and enhancing known compositions. Their ability to contribute to the refinement of compositions should be particularly emphasized.
- fragrance compositions according to the invention round off and harmonize the olfactory notes of a wide range of known compositions, but without dominating in an unpleasant manner.
- the usable proportions of the fragrance compositions according to the invention in fragrance compositions range from 0.001 to 70% by weight, in each case based on the overall composition.
- the fragrance compositions according to the invention and compositions of this type can be used both for perfuming cosmetic preparations such as lotions, creams, shampoos, soaps, ointments, powders, aerosols, toothpastes, mouthwashes, deodorants and in exquisite perfumery.
- perfuming technical products as well as detergents and cleaning agents, Fabric softener, fabric treatment agent or tobacco.
- the compositions are metered into them in an olfactory effective amount, in particular in a concentration in the range from 0.05 to 2% by weight, based on the entire product.
- these values are not intended to represent any limit values, since the experienced perfumer can also achieve effects with lower concentrations or build new types of complexes with even higher doses.
- a mixture was obtained by mixing 80% by weight of 2-methylene-3- (4-methylcyclohex-3-enyl) butanal (1) and 20% by weight of limonene aldehyde (2) - both statements refer to the entire composition fragrance composition according to the invention produced.
- compositions K-1, K-2 and K-3 listed in Table 1 below were produced.
- the basis of comparison is K-1 (a Muguet composition), according to the invention is K-2, the composition K-3 is used for further comparison.
- Table 1 the details in the columns headed K-1 to K-3 mean parts by weight.
- the components specified in column 1 the following applies to the manufacturers: * Henkel KGaA a) PFW (Perfume Flavors Worldwide) b) Givaudan c) Charabot d) Hüls AG e) Firmenich f) International Flavor and Fragrances
- composition K-2 Compared to Kl, composition K-2 has a significantly fresher green smell of agrumen, which gives the aldehydic floral base and the harmoniously integrated wood base a beautiful appearance and good diffusivity.
- composition K-3 also has a fresh, well-radiating note of agrumen, but the harmony from the balsamic fund is severely impaired and disturbed by an isolated vanilla note.
- Table 1 Table 1:
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19820657 | 1998-05-08 | ||
DE19820657A DE19820657A1 (en) | 1998-05-08 | 1998-05-08 | Aroma composition cosmetics, technical products or alcoholic perfumery |
PCT/EP1999/002902 WO1999058629A2 (en) | 1998-05-08 | 1999-04-29 | Odoriferous compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1102832A2 true EP1102832A2 (en) | 2001-05-30 |
EP1102832B1 EP1102832B1 (en) | 2004-12-22 |
Family
ID=7867124
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99924838A Expired - Lifetime EP1102832B1 (en) | 1998-05-08 | 1999-04-29 | Odoriferous compounds |
Country Status (7)
Country | Link |
---|---|
US (1) | US6451758B1 (en) |
EP (1) | EP1102832B1 (en) |
JP (1) | JP2002514681A (en) |
DE (2) | DE19820657A1 (en) |
ES (1) | ES2233052T3 (en) |
IL (1) | IL139484A0 (en) |
WO (1) | WO1999058629A2 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1054053B1 (en) * | 1999-05-19 | 2004-09-01 | Firmenich S.A. | Utilization of substituted acetaldehydes with a cyclic substituent as perfuming ingredients |
DE10026004A1 (en) * | 2000-05-25 | 2001-11-29 | Cognis Deutschland Gmbh | 3,3-Dimethylcyclohexane derivatives |
DE10206771A1 (en) * | 2002-02-19 | 2003-08-28 | Cognis Deutschland Gmbh | Use of 5-methyl-3-isobutyl-hexenals as fragrances, e.g. in perfumes, cosmetics, toothpastes, mouthwashes, detergents and fabric conditioners |
DE102005061073B4 (en) * | 2005-12-21 | 2020-10-22 | Symrise Ag | Perfume composition with 3- (4-methyl-cyclohex-3-enyl) butyraldehyde and 1,8-p-menthadiene |
GB0622037D0 (en) * | 2006-11-04 | 2006-12-13 | Quest Int Serv Bv | Novel fragrance compounds |
EP1942178B1 (en) * | 2007-01-02 | 2010-03-17 | Symrise GmbH & Co. KG | Mixtures of 3-(4-Methyl-cyclohex-3-enyl)-butyraldehyde and 2,6-Dimethyl-7-octen-2-ol |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2849642A1 (en) * | 1978-11-16 | 1980-06-04 | Henkel Kgaa | NEW ALDEHYDE AND THEIR USE AS A FRAGRANCE |
DE2921619C3 (en) * | 1979-05-28 | 1982-05-19 | Ruhrchemie Ag, 4200 Oberhausen | 2-methylene-3- (4-methylcyclohex-3-enyl) butanal and 2-methylene-3- (4-methylcyclohexyl) butanal and processes for their preparation |
EP0092031B1 (en) * | 1982-04-15 | 1984-12-27 | Firmenich Sa | 1(7)p-menthene-9-al and its use as a perfuming and flavouring agent |
US5068363A (en) | 1990-09-27 | 1991-11-26 | International Flavors & Fragrances Inc. | Cyclohexenylmethloxabicyclooctanes, processes for preparing same, intermediates used in said processes and organoleptic uses of said cyclohexenylmethloxabicyclooctanes and intermediates therefor |
-
1998
- 1998-05-08 DE DE19820657A patent/DE19820657A1/en not_active Withdrawn
-
1999
- 1999-04-29 JP JP2000548423A patent/JP2002514681A/en active Pending
- 1999-04-29 ES ES99924838T patent/ES2233052T3/en not_active Expired - Lifetime
- 1999-04-29 WO PCT/EP1999/002902 patent/WO1999058629A2/en active IP Right Grant
- 1999-04-29 EP EP99924838A patent/EP1102832B1/en not_active Expired - Lifetime
- 1999-04-29 US US09/674,941 patent/US6451758B1/en not_active Expired - Lifetime
- 1999-04-29 DE DE59911336T patent/DE59911336D1/en not_active Expired - Lifetime
- 1999-04-29 IL IL13948499A patent/IL139484A0/en unknown
Non-Patent Citations (1)
Title |
---|
See references of WO9958629A2 * |
Also Published As
Publication number | Publication date |
---|---|
ES2233052T3 (en) | 2005-06-01 |
WO1999058629A2 (en) | 1999-11-18 |
JP2002514681A (en) | 2002-05-21 |
WO1999058629A3 (en) | 2001-03-29 |
DE19820657A1 (en) | 1999-11-11 |
EP1102832B1 (en) | 2004-12-22 |
DE59911336D1 (en) | 2005-01-27 |
IL139484A0 (en) | 2001-11-25 |
US6451758B1 (en) | 2002-09-17 |
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