Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
2000-05-17
2001-05-01
Owens, Amelia (Department: 1625)
Perfume compositions
Perfume compositions
Ring containing active ingredient
C549S266000
Reexamination Certificate
active
06225281
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a process for manufacturing cis-isoambrettolide in a very high degree of purity.
2. Description of the Prior 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 hon-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 a process for manufacturing 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 process which is the subject of the present invention lies in the fact that it gives cis-isoambrettolide in a degree of purity of greater than 99.5%, this advantage being combined with the one above.
cis-16-Hydroxy-9-hexadecenoic acid is an essential chemical compound as a starting material for the synthesis of the macrocyclic lactone cis-isoambrettolide, of which it is the direct precursor.
The present invention thus relates to a process for manufacturing cis-16-hydroxy-9-hexadecenoic acid in order subsequently to obtain cis-isoambrettolide by the usual macrolactonization methods.
The present invention relates more particularly to a process for manufacturing cis-isoambrettolide, using the following chemical reaction steps:
a) trans-epoxidation of trans-16-hydroxy-9-hexadecenoic acid, of formula (5), which may or may not be esterified, to give the epoxide of formula (6);
b) opening of the epoxide bridge, to give erythro-aleuritic acid, or an ester of this acid, of formula (7);
c) action of an ortho ester of formula HC(OR
3
)
3
on erythro-aleuritic acid, or its ester, to give the dioxolane of formula (9);
d) pyrolysis of the dioxolane to give cis-16-hydroxy-9-hexadecenoic arid, or an ester of this acid, of formula (10), in a purity of greater than 99%;
e) macrolactonization of the above acid, or its ester, resulting in cis-isoambrettolide.
A subject of the present invention is also, as a variant, a process for manufacturing cis-isoambrettolide, using the following chemical reaction steps:
a) trans-epoxidation of trans-16-hydroxy-9-hexadecenoic acid, of formula (5), which may or may not be esterified, to give the epoxide of formula (6);
b) opening of the epoxide bridge to give a mixture of &bgr;-hydroxy ethers of formula (8);
c) action of an ortho ester of formula HC(OR
3
)
3
on the mixture of &bgr;-hydroxy ethers, to give the dioxolane of formula (9);
d) pyrolysis of the dioxolane to give cis-16-hydroxy-9-hexadecenoic acid, or an ester of this acid, of formula (10), in a purity of greater than 99%;
e) macrolactonization of the above acid, or its ester, resulting in cis-isoambrettolide.
In the above formulae:
R
1
represents a hydrogen atom or an acetyl radical,
R
2
represents a hydrogen atom or a methyl radical,
R represents a hydrogen atom or a methyl radical,
R′ represents a methyl radical or an ethyl radical,
R
3
represents a methyl radical or an ethyl radical.
The examples which follow, which are given as guides, of one embodiment will further illustrate the process for manufacturing cis-isoambrettolide according to the invention, without, however, limiting its scope.
REFERENCES:
patent: 2417151 (1947-03-01), Colluad et al.
patent: 4014902 (1977-03-01), Tseng
Chemical Abstracts, vol. 98, 1983 #13 98-10754 w.
Preatwich, J. Agric Food Chemicals, 1981, 29 10 18-1022.
Owens Amelia
Perman & Green LLP
Synarome
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