Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1997-12-22
1999-12-07
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C07C 3521
Patent
active
059986786
DESCRIPTION:
BRIEF SUMMARY
This application is the national phase of PCT/ES97/00049 filed Feb. 25, 1997 now, WO97/3189.
TECHNICAL SCOPE OF THE INVENTION
This report describes a new procedure for the preparation of formula I carotenoid (Scheme 1) and the pigments that have this compound as a basic component. ##STR1##
The objective that is proposed is, as described below, that of improving the pigmenting power of natural products obtained by extractive processes through the chemical transformation of one of their general formula II (Scheme 2) components in the formula I (Scheme 1) compound.
Chemical transformation of the general formula II compounds is also an objective of the present invention, when these do not come from a natural source but are obtained synthetically. ##STR2## where R and R' are similar or different and may be H, lower acyl, fatty acyl or a hydroxyl protector group.
The name lower acyl refers to an acyl group with a branched or unbranched hydrocarbonated chain of 2 to 5 carbon atoms. The term fatty acyl refers to an acyl remainder coming from a fatty acid.
The compounds that are the subject of the present invention are part of a broad family of compounds called Carotenoids, within which are differentiated two big groups, the hydrocarbons or CAROTENES and their oxygenated by-products or XANTHOPHYLLS. The products herein described are part of this latter group.
The carotenoids are made up of eight isoprenoid units linked such that they are inverted in the exact center of the molecule, since the two central methyl groups remain in relative position 1,6, while the other non-terminal methyls remain in relative position 1,5.
All carotenoids can be derived formally from an acyclic C.sub.40 H.sub.36 structure made up of a large central chain of conjugated double links, which was subjected to hydrogenation, dehydrogenation, cyclation, oxidation processes or a combination of the same.
Some carotenoids have a biological activity, such as provitamins A, that is, they generate "in vivo", through an enzymatic process, the respective vitamin A. This function is more common in those carotenes in which there is no substitution in the beta-ionone ring and, hence, they have a greater structural similarity with vitamin A. There are exceptions to this general rule and, thus, certain carotene epoxides have been described that have a high activity as provitamins.
However, most carotenoids do not have great activity as propharmacons and are therefore not useful as provitamins.
The extended conjugation of the double links that make up their hydrocarbonated structure give to the carotenoids a generally intense color, a quality for which they are highly valued, especially in the food industry.
The carotenoids are broadly distributed in nature, being responsible for the color of fruits, flowers and even birds and marine animals. They are produced by a multitude of plants and microorganisms. However, even though they can metabolize them, animals are not capable of synthesizing them
Generally, they appear mixed among themselves, some or others predominating, depending on the natural source from where they come, and they customarily appear as the respective fatty acids.
OBJECTIVE OF THE INVENTION
One of the most broadly distributed xanthophylls in nature is Lutein (R.dbd.R.dbd.H. Scheme 2). This carotenoid is the main constituent of marigold resin (Tagetes erecta L.), an extractive product that constitutes one of the most important natural sources of xanthophyll. Together with Lutein, marigold resin has small quantities of other xanthophylls, mainly Zeaxanthin (I, Scheme 1).
The natural product has a high proportion of Lutein of around 85-90% as compared to a proportion of Zeaxanthin of around 4-5% of total xanthophylls.
An important number of pigmentation tests have been performed on chickens, eggs, . . . , comparing the pigmenting power of these two xanthophylls, lutein (or basically the extractive natural product from the marigold) and zeaxanthin (also of natural origin, from sources other than the marigold).
The result, as collected in
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De Bloos De Clercq Mildred
Fernandez Martin Juan A.
Ferrater Martorell Joan Carles
Sanroma Virgili Nuria
Geist Gary
Investigaciones Quimicas y Farmaceutics, S.A.
Vollano Jean F
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