Macrocyclic ketones

Details Macrocyclic ketones Macrocyclic ketones

2001-08-02

2004-11-09

Warden, Sr., Robert J. (Department: 1743)

Perfume compositions

Perfume compositions

Oxygen containing active ingredient

C568S303000, C568S338000, C568S341000, C568S343000, C568S347000, C568S361000, C568S365000, C568S366000

Reexamination Certificate

active

06815413

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to novel lower alkyl- and lower alkylidene-substituted, saturated or unsaturated cyclohexadecanones, to their preparation and use in functional perfumery and in fine perfumery.
BACKGROUND OF THE INVENTION
Compounds with a musk odor are sought-after components in the perfume industry. They are characterized both by their property of imparting radiance to perfume compositions and also by their ability to act as fixatives. For this reason, musk fragrances are nowadays used in many perfume compositions.
The class of nature-similar macrocyclic musk fragrances will become more and more important in the future since the synthetic musk compounds of the nitroaromatic and polycyclic series are persistent and lipophilic, meaning that these compounds accumulate in aquatic food chains and fatty tissue (Ernährungs-Umschau 1996, 43, 442 to 449; Ernährungs-Umschau 1997, 44, 4 to 9).
Typical musk fragrances are characterized by a macrocyclic ring having 13 to 17 carbon atoms which carries a ketone or an ester as functional group. As is known, the stability of ketones in acidic and in alkaline media is greater than that of the corresponding lactones. Moreover, an alkyl substitution, preferably a methyl substitution, in the macrocyclic ring is also possible.
A preferred fragrance in perfumery is muscone.
Muscone is one of the most important ingredients of the scent gland of the musk deer and, since its structural determination in 1926 (Helv. Chim. Acta, 9, 230, 1926), numerous syntheses both for racemic muscone, and also for optically pure muscone have been published (Fragrance Chemistry. The Science of the Sense of Smell, ed. E. T. Theimer, Academic Press, 1982, pages 444 to 469). The syntheses involve many reaction stages and require expensive starting materials and/or reaction components. For this reason, the amounts of expensive muscone used in functional perfumery and also in fine perfumery are limited.
SUMMARY OF THE INVENTION
There is, therefore, a pressing need for further macrocyclic compounds with muscone note which can be prepared in an efficient synthesis from cost-effective starting materials and, moreover, extend the perfumer's options with their original scent properties.
The object was therefore to find novel cost-effective macrocyclic ketones with muscone note.
We have found novel macrocyclic ketones of the general formula
in which
R is a lower alkyl or lower alkylidene group,
x=5 and y=7, or
x=6 and y=6, and
the dashed lines are, independently of one another, a C—C single bond or a C═C double bond.


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Fragrance Chemistry: The Science of the Sense of Smell (month unavailable) 1982 pp. 444-469, V. Synthesis of Musk Components, Braja D. Mookherjee and Richard A. Wilson.
Helv. Chem. Acta, 9, (month unavailable) 1926, pp. 230-248, Zur Kenntnis des Kohlenstoffringes I. Uber Die Konstitution des Zibetons, von L. Ruzicka.
Ernahrungs-Umschau 43 pp. 442-449 (month unavailable) 1996, Synthetische Moschusduftstoffe-Anwendung, Anreicherung in der Umwelt und Toxikologie, Gerhard Rimkus, Hubertus Brunn.
Ernahrungs-Umschau 44 pp. 4-9 (month unavailable) 1997, Synthetische Moschusduftstoffe-Anwendung, Anreicherung in der Umwelt und Toxikologie, Hubertus Brunn, Gerhard Rimkus.

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