EP0586442A1 - Use of isomeric 1,1,1-trialkyl-2-phenylethane derivatives as odoriferous substances, and fragrances containing these substances. - Google Patents
Use of isomeric 1,1,1-trialkyl-2-phenylethane derivatives as odoriferous substances, and fragrances containing these substances.Info
- Publication number
- EP0586442A1 EP0586442A1 EP92910449A EP92910449A EP0586442A1 EP 0586442 A1 EP0586442 A1 EP 0586442A1 EP 92910449 A EP92910449 A EP 92910449A EP 92910449 A EP92910449 A EP 92910449A EP 0586442 A1 EP0586442 A1 EP 0586442A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- phenyl
- trialkyl
- fragrances
- isomeric
- carbon atoms
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
Definitions
- the invention relates to the use of isomeric l, l, l-trialkyl-2-phenylethane derivatives as fragrances.
- fragrance industry has a constant need for new fragrances with interesting fragrances to complement the range of naturally available fragrances and make the necessary adjustments to changing modern tastes and the ever increasing need for odor improvers for products of daily use such as To be able to cover cosmetics and cleaning agents.
- Acetic acid (1-phenyl-2,2,2-trichloroethyl) ester is a known, commercially available fragrance which has a mild, floral, rosy odor.
- halogenated compounds are increasingly viewed critically by the consumer, so that there is a need for suitable substitutes.
- the subject of the invention is therefore the use of isomeric 1,1,1 trialkyl-2-phenylethane derivatives of the general formula (I) in which the radicals R * to R3 independently of one another are alkyl groups with 1 to C atoms and the radical R 4 is an alkyl or an acyl group with 1 to 5 carbon atoms or an alkoxycarbonyl or an alkoxyalkyl group with 2 to 5 carbon atoms mean as fragrances.
- the C atom directly adjacent to the phenyl radical in the compounds of the general formula (I) represents a chiral center, so that these compounds can exist in different spatial forms.
- the compounds according to the invention are obtained as a mixture of the corresponding isomers and are as such as a fragrance used. If desired, however, the enantiomeric compounds can be used alone as a fragrance.
- the products to be used as fragrances according to the invention are produced by methods known per se in preparative organic chemistry. For example, Convert pivalinaldehyde by Grignard reaction with phenyl magnesium bromide to give 2,2-dimethyl-l-phenyl-propanol (II), which is e.g. by reaction with acetic anhydride in pyridine or dimethylaminopyridine to give the acetate (la), with dimethyl carbonate to the carbonate (Ib) or with ethyl vinyl ether in the presence of an acidic catalyst to give the acetal (Ic).
- acetic acid (2,2-dimethyl-1-phenyl-propyl) ester (Ia) is particularly preferred.
- the compound (la) in particular has remarkable olfactory properties that are very much in demand in perfumery, namely rosy-wood with complex shades and great charisma.
- This particular olfactory characteristic of the rose type is original and novel and softly differs from the olfactory characteristic of the acetic acid (l-phenyl-2,2,2-trichloroethyl) ester known as a fragrance, which is particularly surprising.
- the compound (la) enhances the harmony and charisma as well as the adhesion, whereby the dosage can be adjusted to the desired fragrance note taking into account the other components of the composition.
- fragrances such as acetic acid (l-phenyl-2,2,2-trichloroethyl) ester can be used as a fragrance or as a component of fragrance compositions.
- the compounds of the formula (I) are particularly suitable for modifying and enhancing known compositions. It should be emphasized in particular their extraordinary smell strength, which contributes in general to the refinement of the composition.
- the compounds of formula (I) can be used with numerous known fragrance ingredients, e.g. combine other fragrances of natural, synthetic or partially synthetic origin, essential oils and plant extracts.
- the range of natural fragrances can include both volatile, medium and low volatile components and those of synthetic fragrances include representatives from practically all classes of substances. Examples are:
- Natural products such as tree absolute, basil oil, agricultural oils such as bergaot oil, mandarin oil, etc., mastic absolute, myrtle oil, palmarosa oil, patchouli oil, petitgrain oil, Paraguay, wormwood oil,
- Alcohols such as farnesol, geraniol, linalool, nerol, phenylethyl alcohol, rhodinol, cinnamon alcohol, Sandalore [3-methyl-5- (2.2.3-trimethylcyclopent-3-en-1-yl) pentan-2-ol ], Sandela [3-isocamphyl- (5) -cyclohexanol],
- aldehydes such as citral, helional, o-hexylcinnamaldehyde, hydroxycitronellal, lilial R [p-tert-butyl- ⁇ -methyldihydrocinnamaldehyde], methylnonyl acetaldehyde,
- Ketones such as allyl ionone, ⁇ -ionone, ⁇ -ionone, methyl ionone.
- esters such as allylphenoxyacetate, benzylsalicylate, cinnamylpropionate, citronellyl acetate, citronellylethoxylate, decyl acetate, dimethylbenzylcarbinylacetate, ethylacetoacetate, hexenylisobutyrate, linalyl acetate, methyldihydrojasmonate, vetivery1 acetate, (f) Lactones such as Undecalactone, l-0xaspiro [4.4] nonan-2-one and various other components often used in perfumery w
- the usable proportions of the compounds according to the invention or their mixtures in fragrance compositions range from 1 to 70 percent by weight, based on the mixture as a whole.
- Mixtures of the compounds (I) according to the invention and compositions of this type can be used for perfuming cosmetic preparations such as lotions, creams, shampoos, be fen, ointments, powders, aerosols, toothpastes, mouthwashes, deodorants and also in alcoholic perfumery (e.g. Eau de Cologne, Eau de toilet te, tincts) can be used.
- perfuming technical products such as washing and cleaning agents, fabric softeners and textile treatment agents or tobacco.
- compositions are added to them in an olfactory effective amount, in particular in a concentration of 0.05 to percent by weight, based on the entire product.
- this value should not represent any limit values, since the experienced perfumer can also achieve effects with even lower concentrations or build new types of complexes with higher doses.
Abstract
L'invention concerne l'utilisation, comme parfums, de dérivés isomères 1,1,1-trialkyl-2-phényl-éthane de formule générale (I), dans laquelle les restes R1 à R3 désignent, indépendamment les uns des autres, des groupes alkyle de 1 à 3 atomes de carbone, le reste R4 est un hydrogène ou un groupe alkyle, un groupe acyle, un groupe alkoxycarbonyle ou un groupe alkoxyalkyle ayant au total de 2 à 5 atomes de carbone. Ces composés, notamment le (2,2-diméthyl-1-phényl-propyl)-ester de l'acide acétique, ont la particularité de présenter un profil odorant boisé-rosé de nature complexe et d'une grande exhalaison et peuvent être mélangés entre eux ou avec d'autres parfums dans les proportions les plus diverses pour donner de nouvelles compositions de parfums, généralement dans une proportion de 1 à 70 % en poids, par rapport à la composition totale. Ces compositions peuvent être utilisées pour parfumer des préparations cosmétiques et des produits industriels, ainsi qu'en parfumerie alcoolisée.The invention relates to the use, as perfumes, of 1,1,1-trialkyl-2-phenylethane isomer derivatives of general formula (I), in which the residues R1 to R3 denote, independently of one another, alkyl groups of 1 to 3 carbon atoms, the remainder R4 is hydrogen or an alkyl group, an acyl group, an alkoxycarbonyl group or an alkoxyalkyl group having in total from 2 to 5 carbon atoms. These compounds, in particular the (2,2-dimethyl-1-phenyl-propyl) -ester of acetic acid, have the particularity of presenting a woody-pink odorous profile of complex nature and of a great exhalation and can be mixed with each other or with other perfumes in the most diverse proportions to give new perfume compositions, generally in a proportion of 1 to 70% by weight, relative to the total composition. These compositions can be used to perfume cosmetic preparations and industrial products, as well as in alcoholic perfumery.
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19914117669 DE4117669A1 (en) | 1991-05-29 | 1991-05-29 | USE OF ISOMERIC 1,1,1-TRIALKYL-2-PHENYL-ETHANE DERIVATIVES AS A FRAGRANCE, AND THEIR COMPOSITIONS CONTAINING THESE |
DE4117669 | 1991-05-29 | ||
PCT/EP1992/001118 WO1992021738A1 (en) | 1991-05-29 | 1992-05-20 | Use of isomeric 1,1,1-trialkyl-2-phenylethane derivatives as odoriferous substances, and fragrances containing these substances |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0586442A1 true EP0586442A1 (en) | 1994-03-16 |
EP0586442B1 EP0586442B1 (en) | 1995-01-04 |
Family
ID=6432762
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92910449A Expired - Lifetime EP0586442B1 (en) | 1991-05-29 | 1992-05-20 | Use of isomeric 1,1,1-trialkyl-2-phenylethane derivatives as odoriferous substances, and fragrances containing these substances |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0586442B1 (en) |
JP (1) | JPH06507659A (en) |
DE (2) | DE4117669A1 (en) |
WO (1) | WO1992021738A1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008285422A (en) * | 2007-05-15 | 2008-11-27 | Maruzen Pharmaceut Co Ltd | Dna damage inhibitor and glutathione production promoter |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1293747B (en) * | 1965-08-27 | 1969-04-30 | Universal Oil Prod Co | Process for the preparation of allyl-ª ‰ -phenylpropionates |
US4490284A (en) * | 1982-09-29 | 1984-12-25 | Dragoco Gerberding & Co. Gmbh | 1,1-Di(C1 -C6 -alkyl)-2-phenyl-ethane derivatives as perfuming ingredients |
-
1991
- 1991-05-29 DE DE19914117669 patent/DE4117669A1/en not_active Withdrawn
-
1992
- 1992-05-20 DE DE59201157T patent/DE59201157D1/en not_active Expired - Fee Related
- 1992-05-20 WO PCT/EP1992/001118 patent/WO1992021738A1/en active IP Right Grant
- 1992-05-20 JP JP4510420A patent/JPH06507659A/en active Pending
- 1992-05-20 EP EP92910449A patent/EP0586442B1/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
See references of WO9221738A1 * |
Also Published As
Publication number | Publication date |
---|---|
DE59201157D1 (en) | 1995-02-16 |
DE4117669A1 (en) | 1992-12-03 |
JPH06507659A (en) | 1994-09-01 |
WO1992021738A1 (en) | 1992-12-10 |
EP0586442B1 (en) | 1995-01-04 |
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