Drug – bio-affecting and body treating compositions – Topical body preparation containing solid synthetic organic... – Skin cosmetic coating
Reexamination Certificate
2002-03-20
2003-06-24
Lilling, Herbert J. (Department: 1651)
Drug, bio-affecting and body treating compositions
Topical body preparation containing solid synthetic organic...
Skin cosmetic coating
C424S725000, C424S757000, C424S769000, C426S051000
Reexamination Certificate
active
06582688
ABSTRACT:
The present invention relates to a novel process for extracting furan lipid compounds and polyhydroxylated fatty alcohols from avocado, and also to a pharmaceutical or cosmetic composition based on these compounds and to the use of these compounds for manufacturing a medicinal product, in a cosmetic treatment method and as a food additive.
Avocado comprises, as is known, particular lipids of furan type, the main component of which is a linoleic furan:
The furan derivatives of avocado oil have been described in particular in Farines, M. et al., 1995, J. of Am. Oil Chem. Soc. 72, 473.
It is currently well established that the presence of these furan compounds in the leaves or the fruit depends not only on the variety (the varieties Hass and Fuerte being the richest in furan compounds), but also on the method for obtaining the oil or another plant extract of avocado (ethanolic or hexane extract of avocado leaves).
Specifically, it is known that these furan lipids are metabolites of compounds that are initially present in the fruit and the leaves, which, due to the effect of heat, become dehydrated and cyclize into furan derivatives.
For example, linoleic furan is derived from the thermal transformation of the following precursor:
Moreover, certain compounds initially present in avocado fruit and leaves may be in the form of nonacetylated polyhydroxylated fatty alcohols, such as the following compound:
The polyhydroxylated fatty alcohol content in the fruit depends mainly on the climatic conditions, the quality of the soil, the season and the maturity of the fruit on harvesting.
In general, the furan lipids of avocado are compounds that are unique in the plant kingdom and are desired above all for their pharmacological, cosmetic or even nutritional properties.
However, the known techniques for obtaining these specific compounds from avocado fruit or from the oil of avocado fruit amount either to preparative chromatography or to industrial processes that allow these furan lipids to be obtained only as a mixture with the other unsaponifiable compounds of avocado, in a maximum content of furan lipids that is at best between 50% and about 65% by weight only.
In addition, the known industrial processes require a preliminary step of molecular distillation of the oil of the fruit to obtain the furan lipids in contents that are nevertheless still unsatisfactory. This preliminary step requires the use of high temperatures, such as temperatures above 180° C. for pressures of the order of 10
−3
mmHg, which, in industrial terms, involves a large consumption of energy.
More particularly, the production of furan lipids of higher purity by molecular distillation of the oil of the fruit (“crude pressed oil”) is industrially difficult given the very acidic nature of the oil (acid number of about 6 to 10 mg KOH/g), necessitating a preliminary neutralization by at least partially refining the oil. Furthermore, such a refining operation, even partial, entails a consequent loss of furan lipids and thus a reduction in the final yield of these desired compounds.
It has now been found, entirely surprisingly and unexpectedly, that the drawbacks of the prior art described above can be overcome by carrying out a specific process for obtaining a selective extraction of the furan lipids of avocado with a content of more than 80% by weight of furan lipids, or even close to 98%.
Moreover, according to one particular embodiment of the process according to the invention, a selective extraction is advantageously obtained not only of the furan lipids, but also of the polyhydroxylated fatty alcohols of avocado.
What is more, the process according to the invention comprises a step of molecular distillation in which the temperature and pressure settings may be markedly lower than those of the abovementioned prior art.
One subject of the present invention is thus a process for selectively extracting the furan lipids and polyhydroxylated fatty alcohols of avocado, characterized in that it comprises the steps consisting in preparing an unsaponifiable material from avocado, and then in subjecting the unsaponifiable material from avocado to a step of molecular distillation using temperature and pressure means that are adjusted so as to obtain either a distillate mainly comprising furan lipids of avocado, or a distillate mainly comprising furan lipids and polyhydroxylated fatty alcohols of avocado.
According to the invention, the expression “furan lipids of avocado” means the compounds corresponding to the formula:
in which R is a saturated C
11
-C
19
and preferably C
13
-C
17
linear hydrocarbon-based chain or a chain comprising one or more ethylenic or acetylenic unsaturations.
According to the invention, the expression “polyhydroxylated fatty alcohol of avocado” means a polyol in the form of a saturated C
17
-C
21
linear hydrocarbon-based main chain or a chain comprising one or more ethylenic or acetylenic unsaturations, and comprising at least two hydroxyl groups, the hydroxyl groups being mainly located on one portion of the main chain, preferably toward one of the two ends of the main chain, the other portion of this main chain thus constituting the “fatty” chain (hydrophobic portion) of the polyol.
The unsaponifiable material is the fraction of a fatty substance which, after the prolonged action of an alkaline base, remains insoluble in water and may be extracted with an organic solvent. Five major groups of substances are present in the majority of the unsaponifiable materials from plant oils: saturated or unsaturated hydrocarbons, aliphatic or terpenic alcohols, sterols, tocopherols, carotenoid and xanthophilic pigments.
A comparison of the contents of unsaponifiable materials from various plant oils: soybean, cotton, coconut, olive and avocado, shows a very large content of unsaponifiable material from avocado oil obtained by extraction according to various known processes. Typically, the contents obtained range from 2 to 7% of unsaponifiable material in avocado oil, compared with 0.5% in coconut oil, 1% in soybean oil and 1% in olive oil. The unsaponifiable material from avocado may be prepared by extraction starting with avocado oil.
The known processes for obtaining avocado oil are mainly the following:
either the fresh pulp is pressed in the presence of a water-absorbing intermediary fibrous substance such as coffee husk in a cage press, and the emulsion of oil and water obtained is then separated out by settling and/or centrifugation;
or the fresh pulp is ground and is placed in contact with a suitable organic solvent (for example a methanol/chloroform mixture) and the oil is then recovered by evaporating off the solvent.
The avocado oil thus obtained is then subjected to an extraction of the unsaponifiable material, in a known manner.
Several processes have been described for extracting the unsaponifiable material from a plant oil. All preferably adopt saponification with potassium hydroxide or sodium hydroxide in alcoholic medium, preferably ethanolic medium, followed by one or more extractions with a suitable organic solvent, for example petroleum ether, ethyl ether or any other suitable solvent that is immiscible with the aqueous-alcoholic solution.
The extraction solution obtained is then preferably centrifuged, filtered and then washed with water to remove the residual traces of alkalinity. Next, the extraction solvent is carefully evaporated off to recover the unsaponifiable material. Needless to say, additional operations known to those skilled in the art, such as a deodorization step, may also be included.
Preferably, the unsaponifiable material from avocado is prepared from the fruit that has been heat-treated beforehand, before extraction of the oil and saponification, as described in particular in patent application FR-91/08301.
This heat treatment consists of a controlled drying of the fruit, which is preferably fresh, for at least four hours, advantageously at least 10 hours and preferably between about 24 and about 48 hours, at a temperature preferably of at least about 80° C. and
Broutin Nicole
Legrand Jacques
Piccirilli Antoine
Lilling Herbert J.
Pharmascience
LandOfFree
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