Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-08-10
2001-09-04
Owens, Amelia (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06284900
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a cis-isoambrettolide in a very high degree of isomer purity and the use thereof.
2. Description of Related Art
It is known that substances with a musk odor are commonly used in the perfume industry in the broad sense, where they have a primary advantage, both in the perfumes sector and in that of washing products such as soaps and detergents, on account of their persistent effect.
These molecules are represented by 4 families: the non-nitro aromatic musks, the nitro aromatic musks, the macrocyclic ketones and the macrocyclic lactones. The lactones are important aromatic agents on account of their abundance in natural products.
Among the macrocyclic lactones of natural origin, derived from the plant kingdom, mention may be made of exaltolide, of formula (1) and ambrettolide, of formula (2).
Ambrettolide is obtained from the essential oil and the resinoids of ambrette, whose round, warm, musk note is highly appreciated in perfumery. This plant is Hibiscus abelmoschus 4, which is grown in South America, Indonesia and the West Indies.
An unsaturated macrocyclic lactone is already known: trans-isoambrettolide of formula (3), which is obtained industrially, this being a geometrical and positional isomer of natural ambrettolide. A process for obtaining the trans lactone is described in U.S. Pat. No. 4,014,902.
SUMMARY OF THE INVENTION
The present invention relates, however, to an another geometrical and positional isomer of natural ambrettolide: cis-isoambrettolide of formula (4), which has the advantage of being much more powerful than trans-isoambrettolide in olfactory terms, thereby allowing it to be used in the perfume industry at much lower concentrations, resulting in considerable savings which make it all the more appreciated.
In addition, the advantage of the present invention lies in the fact that the cis-isoambrettolide used has a geometrical isomer purity of at least 90%, more preferably about 95% and most preferably at least greater than 97%.
REFERENCES:
patent: 4014902 (1977-03-01), Tseng
Chemical Abstracts, vol. 98, No. 13, 1983 “Synthesis of Trans Delta9-Isoambrettolide” Majee et al., p. 578.
Owens Amelia
Perman & Green LLP
Synarome
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