DE10022971B4 - Use of 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal as fragrance - Google Patents

Abstract

Use of 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal as fragrance.

Description

Field of the invention

The The present invention relates to the use of 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal as a fragrance.

State of the art

Lots natural Fragrances are available in a completely inadequate amount, measured on demand. For example For the production of 1 kg of rose oil 5000 kg of rose petals are necessary. The consequences are a very limited world annual production as well as a high price. It is therefore clear that the fragrance industry a permanent one Need has new fragrances with interesting fragrance notes. On the one hand This can make the range of course available Perfumes added On the other hand, this makes it possible to make the necessary adjustments to be able to make changing fashion tastes. Furthermore is it possible in this way the constantly increasing demand for odoriferous serers for everyday products To be able to cover requirements such as cosmetics and detergents.

Otherwise exists generally a constant need Synthetic fragrances that are cheap and consistent high quality make and original olfactory properties to have. In particular, they should be pleasant, as close to nature and qualitatively possess novel odor profiles of sufficient intensity and be able to benefit the scent of cosmetic and consumer goods to influence. In other words, there is a constant need at compounds that have characteristic new odor profiles at the same time high adhesive strength, odor intensity and radiance.

DE 195 20 103 A1 describes a process for preparing alkyl-substituted butenols of specific structure. These compounds are fragrances that have a sandal odor.

DE 69512579 T2 discloses 2-methyl-4- (2,2,3-trimethyl-cyclopenten-1-yl) -4-penten-1-al. This compound unfolds a woody sandalwood-like, slightly aldehydic note, which is combined with a distinct marine and ozone character. Furthermore, the compound 4- (2,2,3-trimethylcyclopenten-1-yl) -4-penten-1-al is described which has an ozone-sea-like note instead of a sandalwood.

EP 0466019 A2 discloses derivatives of dihydro-campholenaldehyde which have fruity notes rather than sandalwood notes. Examples of these are 3-methyl-5- (2,2,3-trimethylcyclopenten-1-yl) -pent-3-en-2-one, 3,3-dimethyl-5- (2,2,3-trimethylcyclopentene) 1-yl) -pent-4-en-2-one and 3,3-dimethyl-5- (2,2,3-trimethylcyclopenten-1-yl) -pent-4-en-2-ol.

Description of the invention

It it has been found that the compounds of general formula (I) meet the above requirements perfectly in every respect and advantageously as fragrances with different nuanced Odor notes with good adhesion can be used.

object The present invention contemplates the use of 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal as a fragrance.

4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal has the following chemical structural formula:

4- (2,2,3-trimethylcyclopentane-1-yl) -2-methylbutanal is characterized by an odor characteristic, in the melon notes and marine notes dominate. The compound has excellent stability in formulations of cosmetics and utility perfumery on.

The Preparation of 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal can be done according to known synthetic methods of organic chemistry.

In Perfume compositions reinforced 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal the Harmony and charisma as well as the naturalness and also the adhesion, taking into account the dosage the rest Components of the composition to the intended fragrance is agreed.

The fact that 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal has the abovementioned odor notes was unpredictable and thus further confirms the general experience that the olfactory properties of known fragrances are not necessarily conclusive allow the properties of structurally related compounds, because neither the mechanism of scent perception nor the influence of the chemical structure on the scent perception are adequately researched and thus therefore normally can not be foreseen whether a modified structure of known fragrances ever leads to change the olfactory properties and whether these Än be judged positively or negatively by the person skilled in the art.

4- (2,2,3-trimethylcyclopentane-1-yl) -2-methylbutanal is suitable due to its odor profile especially for Modification and reinforcement known compositions. Should be highlighted in particular its extraordinary odor strength, which is generally used to Refining the composition contributes.

4- (2,2,3-trimethylcyclopentane-1-yl) -2-methylbutanal let yourself with numerous known fragrance ingredients, for example other fragrances natural, synthetic or partial-synthetic origin, essential oils and Combine plant extracts. The range of natural fragrances can handle both light, medium and low volatility components include. The range of synthetic fragrances can be representative from virtually all substance classes.

• (a) Naturprodukte wie Baummoos-Absolue, Basilikumöl, Agrumenöle wie Bergamotteöl, Mandarinenöl, usw., Mastix-Absolue, Myrtenöl, Palmarosaöl, Patchouliöl, Petitgrainöl, Wermutöl, Myrrheöl, Olibanumöl
• (b) Alkohole wie Farnesol, Geraniol, Linalool, Nerol, Phenylethylalkohol, Rhodinol, Zimtalkohol, Sandalore [3-Methyl-5-(2.2.3-trimethylcyclopent-3-en-1-yl)pentan-2-ol], Sandela [3-Isocamphyl-(5)-cyclohexanol],
• (c) Aldehyde wie Citral, Helional^R, α-Hexylzimtaldehyd, Hydroxycitronellal, Lilial^R [p-tert.-Butyl-α-methyldihydrozimtaldehyd], Methylnonylacetaldehyd,
• (d) Ketone wie Allylionon, α-Ionon, β-Ionon, Isoraldein, Methylionon,
• (e) Ester wie Allylphenoxyacetat, Benzylsalicylat, Cinnamylpropionat, Citronellylacetat, Decylacetat, Dimethylbenzylcarbinylacetat, Ethylacetoacetat, Hexenylisobutyrat, Linalylacetat, Methyldihydrojasmonat, Vetiverylacetat, Cyclohexylsalicylat,
• (f) Lactone wie gamma-Undecalacton, 1-Oxaspiro[4.4]nonan-2-on, sowie verschiedene weitere in der Parfümerie oft benutzte Komponenten wie Moschus- und Sandelholz-Riechstoffe, Indol, p-Menthan-8-thiol-3-on, Methyleugenol und Ambroxan.

Examples of suitable substances with which 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal can be combined are in particular:

• (a) Natural products such as tree moss absolute, basil oil, coconut oils such as bergamot oil, tangerine oil, etc., mastic absolute, myrtle oil, palmarosa oil, patchouli oil, petitgrain oil, wormwood oil, myrrh oil, olibanum oil
• (b) Alcohols such as farnesol, geraniol, linalool, nerol, phenylethyl alcohol, rhodinol, cinnamyl alcohol, Sandalore [3-methyl-5- (2,2,3-trimethylcyclopent-3-en-1-yl) pentan-2-ol], Sandela [3-Isocamphyl- (5) -cyclohexanol],
• (c) aldehydes such as citral, helional ^R , α-hexylcinnamaldehyde, hydroxycitronellal, Lilial ^R [p-tert-butyl-α-methyldihydrocinnamaldehyde], methylnonylacetaldehyde,
• (d) ketones such as allylionone, α-ionone, β-ionone, isoraldein, methylionone,
• (e) esters such as allylphenoxyacetate, benzylsalicylate, cinnamylpropionate, citronellylacetate, decylacetate, dimethylbenzylcarbinylacetate, ethylacetoacetate, hexenylisobutyrate, linalylacetate, methyldihydrojasmonate, vetiverylacetate, cyclohexylsalicylate,
• (f) lactones such as gamma undecalactone, 1-oxaspiro [4.4] nonan-2-one, as well as various other perfumery-frequently used components such as musk and sandalwood fragrances, indole, p-menthane-8-thiol-3 on, methyleugenol and ambroxan.

Remarkable Further, the manner in which 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal round off the odor notes of a wide range of well-known compositions and harmonizes, but without dominating in an unpleasant way.

The usable proportions of 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal in fragrance compositions are from about 1-70% by weight, based on the entire mix. 4- (2,2,3-trimethylcyclopentane-1-yl) -2-methylbutanal can be used both for perfuming cosmetic preparations such as lotions, creams, shampoos, soaps, ointments, powders, aerosols, Toothpaste, mouthwash, Deodorants as well as in alcoholic perfumery (eg Eau de Cologne, Eau de Toilette, Extraits). There is also one possible use for perfuming technical products such as detergents and cleaners, softeners and Textile treatment agents. To perfume these different products These compositions become effective in an olfactory manner Amount, in particular in a concentration of 0.05-2 wt .-% - related added to the entire product. These values are not restrictive Limits, as the experienced perfumer even with even lower Concentrations still achieve effects or with even higher dosages can build novel complexes.

Examples

• 1) 150 g (0,78 mol) 4-(2,2,3-Trimethylcyclopent-3-en-1-yl)-2-methylbut-2-en-1-al (96%ig hergestellt nach DE-A-195 20 103 )
• 2) 10 g 5% Palladium/Kohle
• 3) 200 ml Ethanol

Preparation of 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal Approach:

• 1) 150 g (0.78 mol) of 4- (2,2,3-trimethylcyclopent-3-en-1-yl) -2-methyl-but-2-en-1-al (96% prepared according to DE-A-195 20 103 )
• 2) 10 g of 5% palladium / carbon
• 3) 200 ml of ethanol

Apparatus:

• 1-1 steel autoclave insert, high pressure stir-stroke autoclave

Execution:

The Components 1), 2) and 3) were successively under nitrogen in Weighed the autoclave insert, placed in the autoclave and purged with nitrogen. At room temperature, 40 bar of hydrogen were injected and within 2 hours at 100 ° C heated. Every 45 minutes, hydrogen became constant (reaches after 3 hours) to 50 bar and then further Held under 100 bar hydrogen at 100 ° C for 4 hours. The sales control reported a product content of 78.7%, in addition to a 7.3% starting material.

Work-up:

After cooling to room temperature and venting, the hydrogenation catalyst was filtered off and the reaction mixture was concentrated on a rotary evaporator. 142 g of crude product were distilled on a 20 cm Vigreux column. 80.5 g main run were at boiling temperatures of 72-73 ° C / 0.08 mbar with a gas chromatographically determined purity of 94.8%. Of these, 26.5 g were fractionated on a rotating column, with purities of 98.5% were achieved at boiling points of 64-65 ° C / 0.04 mbar.

Yield:

• 53.7% of theory

analytics:

The IR spectrum (film between NaCl) showed characteristic vibrational bands at 1727 (C = O) and 2702 cm ^-1 .

¹ H NMR (280 MHz, in CDCl ₃ ) showed signals for 2 methyl groups (singlets) at 0.5 and 0.9 ppm, for 2 methyl groups at 0.8 and 1.1 ppm (doublets) and for 4 CH ₂ groups between 1.0 and 1.9 ppm (3 wide multiplets). The proton adjacent to the aldehyde group gave 2 superimposed multiplets at 2.3 ppm (1H) and the aldehyde proton appeared as 2 superimposed doublets at 9.6 ppm.

Odor characteristic:

in the Smell of melon, ozone, aniseed, canthoxal; in the afterglow (after 24 hours on the smelling strip) melon, nitrile, ozone.

Claims (2)

Use of 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal as a fragrance. Fragrance compositions containing 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal, wherein 4- (2,2,3-trimethylcyclopentan-1-yl) -2-methylbutanal in the compositions in an amount of 1 to 70 wt .-% - based on the total composition - included is.