Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1998-05-08
1999-08-03
Wilson, James O.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568338, 568376, C07C33100, C07C 4500
Patent
active
059327715
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
This invention relates to special carbonyl compounds with the structure shown below and to their use as perfumes.
DISCUSSION OF RELATED ART
Judging by demand, many natural perfumes are available in totally inadequate quantities. For example, 5,000 kg of rose blossoms are required to produce 1 kg of rose oil. The consequences are a seriously limited annual world production and a high price. Accordingly, it is clear that the perfume industry has a constant need for new perfumes with interesting notes in order to add to the range of naturally available perfumes, to make the necessary adaptations to changing fashion trends and to be able to cover the constantly increasing demand for improvements in the odor of products of everyday use, such as cosmetics and cleaners.
Accordingly, it is clear that the perfume industry has a constant need for new perfumes with interesting notes in order to add to the range of naturally available perfumes and to make the necessary adaptations to changing fashion trends and to be able to meet the steadily growing demand for odour enhancers for products of everyday use, such as cosmetics and cleaners.
In addition, there is generally a constant demand for synthetic perfumes which can be favorably produced in a consistent quality and which have desirable olfactory properties, i.e. pleasant, close-to-nature and--qualitatively--novel odor profiles of sufficient intensity, and which are capable of favorably influencing the smell of cosmetic products and consumer goods. In other words, there is a constant need for compounds which have characteristic new odor profiles and, at the same time, high staying power, intensity of odor and emanative power.
DESCRIPTION OF THE INVENTION
It has been found that compounds corresponding to general formula (1a) and/or (1b) meet the requirements stated above in every respect and may advantageously be used as perfumes with differently nuanced odor notes characterized by high staying power: ##STR2##
Accordingly, the present invention relates to carbonyl compounds corresponding to formula (1a) and/or (1b).
The present invention also relates to the use of the carbonyl compounds (1a) and/or (1b) as perfumes.
The carbonyl compounds according to the invention are distinguished by an odor characteristic dominated by fruity, green notes reminiscent of ionone. They show excellent stability in formulations used for cosmetics and inexpensive perfumes.
The compounds (I) are produced by known synthesis methods of organic chemistry. The compounds (I) are preferably produced from the corresponding allyl alcohols by the socalled Carroll reaction. These alcohols are perilla alcohol and/or isoperilla alcohol ##STR3##
In the context of the present invention, the Carroll reaction is understood to be the conversion of allyl alcohols into .omega.,.delta.-unsaturated ketones. In a first variant of the reaction, the allyl alcohol is converted by reaction with acetoacetic ester into the corresponding acetoacetic acid allyl ester, from which .alpha.-allyl acetoacetic acid is after thermal decarboxylation, gives the required .omega.,.delta.-unsaturated ketone (I). The acetoacetic acid allyl ester may be used as such or may be formed in situ.
In a second variant of the Carroll reaction which is discussed, for example, in a synoptic article by G. B. Bennet (see Synthesis 1977, pages 589-606), the allyl alcohol is reacted with a vinyl ether or an alkoxyalkene. Where vinyl ethers are used, aldehydes are formed; where alkoxyalkenes are used, aldehydes or ketones are formed according to the nature of the alkoxyalkene used. For example, the reaction of cinnamic alcohol with 1-methoxypropene gives an aldehyde while the reaction of cinnamic alcohol with 2-methoxypropene gives a ketone. Acetals or allyl vinyl ether may be assumed to be formed as intermediate compounds in these reactions.
In one preferred embodiment of the invention, perilla and/or isoperilla alcohol is reacted with 2-methoxypropene in the Carroll reaction. The intermediate allyl vinyl ether
REFERENCES:
patent: 3993604 (1976-11-01), Thomas et al.
Faber Werner
Markert Thomas
Pierik Theo ten
Porrmann Volker
Schaper Ulf-Armin
Hall Linda E.
Kinzig Charles M.
SmithKline Beecham Corporation
Venetianer Stephen A.
Wilson James O.
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