High cis beta-carotene composition

Chemistry of hydrocarbon compounds – Alicyclic compound synthesis – Carotene or derivative

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

585 1, 585 3, C07C40300, C07C 720, C10M10502

Patent

active

056124856

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The invention relates to a carotenoid composition derived from a natural source, with a high cis beta-carotene concentration and its preparation from natural sources, and more preferably a high 9 cis beta-carotene composition and its preparation from natural sources.


BACKGROUND OF THE INVENTION

In this specification it is to be understood that the natural sources of carotene include fruits, vegetables and other plant tissue, and animal tissue. A particularly important commercial source of carotene is certain types of algae.
Beta-carotene occurs in a number of different chemical isomer forms. Some of these are geometrical isomers which have a different orientation around one of the double bonds In the conjugated double bond structure of the molecule.
This can occur in a number of positions along the conjugated backbone to make a range of different geometrical isomers. In some cases there can even be more than one double bond where change of orientation occurs.
The most common geometrical isomer is the all trans isomer with a structure occurring as shown as follows where the main carbon chain of the molecule occurs in a trans (across) or straight configuration. ##STR1##
However, there are cis forms of beta-carotene which occur naturally, and can be produced by chemical synthesis, or formed by physical processes like heat on the all trans isomers, where the main carbon chain of the molecule takes a bend (cis) or sideways configuration. Naturally occurring cis forms of beta-carotene are not known to occur over a weight percentage of approximately 30% to less than 50% of the total carotenoid content.
Associated with the different geometric isomers are different properties and possible functions and for this reason there are potential benefits in relatively concentrated forms of the cis isomers.
In natural products such as fruit, vegetables, algae and other plant and animal material the carotenoids are stabilized as part of the cell structure in small micron or sub-micron sized particles in the cell organelles or even by association with other molecules which stabilize the isomeric forms produced by the biochemical pathways of the organism. However, in the preparation of concentrated forms of these materials for commercial products desired from the natural sources, the natural stabilising capacity of the cellular structure may be removed or reduced in the extraction and concentration of the carotenoids.
In addition, as the carotenoid products are concentrated to increase their beta-carotene concentrations and to remove the other cell material which is not desired in the product, there is a natural tendency for certain isomers to crystallize out.
Crystallisation is a problem in certain applications since the crystalline form may not be available for efficient use in the application because of its relative insolubility. Crystallisation occurs particularly with all trans beta-carotene and as a result it is not, for example, readily available for biological use.
Cis isomers, on the other hand are much less likely to crystallise and as a consequence are much more soluble than the trans isomers. For this reason, it is often more desirable to use beta-carotene containing compositions with higher concentrations of cis isomers for various applications. For example, the 9 cis isomer is much more readily soluble in oils than the all trans form. In fact, it is very difficult to get the 9 cis isomer to crystallize out from naturally derived oils, thus making it difficult or expensive to purify on a large scale.
Unlike trans isomers, cis isomers have a number of applications, including use in water dispersible food colourants and in tabletting powders. The cis isomers are also useful in a water dispersible form as emulsions for colouring and in beverages. They can also be used in special vitamin supplements in concentrates for direct supplementation or as part of food.
In naturally occurring products the proportion of cis isomers is rather small, but one of the highest proportions occurs in the halo

REFERENCES:
patent: 3039877 (1962-06-01), Borenstein
patent: 3367985 (1968-02-01), Surmatis
patent: 3441623 (1969-04-01), Surmatis
patent: 3492202 (1970-01-01), Bohinski
patent: 3989757 (1976-11-01), Surmatis
patent: 4199895 (1980-04-01), Avron et al.
patent: 4439629 (1984-03-01), R uegg
patent: 4713398 (1987-12-01), Nonomura
patent: 4851339 (1989-07-01), Hills
patent: 5019668 (1991-05-01), Keat et al.
patent: 5206025 (1993-04-01), Courteille et al.
patent: 5245095 (1993-09-01), Graves et al.
patent: 5310554 (1994-05-01), Haigh
patent: 5382732 (1995-01-01), Frank et al.
patent: 5453447 (1995-09-01), Evod et al.
Ami Ben-Amotz et al., Stereoisomers of .beta.-Carotene and Phytoene in the Alga Dunaliella Bardawil, 86 Plant Physiol. 1286 (1988).
Ami Ben-Amotz & Mordhay Avron, The Wavelength Dependence of Massive Carotene Synthesis in Dunaliella Bardawill (Chlorophyceae), 25 J. Phycol. 175 (1989).
Ami Ben-Amotz et al., Bioavailability of a Natural Isomer Mixture as Compared with Synthetic all-trans-.beta.Carotene in Rats and Chicks, 119 J. Nutr. 1013 (1989).
O. Isler, ed. Carotenoids, Birk h auser Verlag, Basel, 1971, pp. 195, 198, 236, 237, 239, 251, 268-275, 281, 284-287, 328, 474-482, 489, 545, 682, 761.
T. Movinobu et al., "Changes in .beta.-Carotene Levels by Long-Term Administration of Natural .beta.-Carotene Derived from Dunaliella bardawil in Humans", J. Nutri. Sci. Vitamind., vol. 90, pp. 421-430, 1994.
R. Bushvay, "Separation of Carotenoids in Fruits and Vegetables by High Performance Liquid Chromatography", J. Liquid Chromatography, vol. 8, No. 8, pp. 1527-1547, 1985.
F. Quackenbush, "Reverse Phase HPLC Separation of CIS-and Trans-Carotenoids And its Application To .beta.Carotenes in Food Materials", J. Liquid Chromatography, vol. 10, No. 4, pp. 643-653, 1987.
J. Bieri et al., "Determination of Individual Carotenoids in Human Plasma by High Performance Liquid Chromatography", J. Liquid Chromatography, vol. 8, No. 3, pp. 473-484, 1985.
B. Borenstein et al., "Carotenoids: Properties, Occurrence, and Utilization in Foods", Food Res., vol. 15, pp. 195-276, 1966.
A. Ben-Amotz et al., "Photosynthetic Activities of the Halophilic Alga Dunaliella parva", Plant Physiol., vol. 49, No. 2, pp. 240-244, 1972.
R. Evans et al., "Lipid composition of halophilic species of Dunaliella from the dead sea", Archives of Microbiology, vol. 140, pp. 50-56, 1984.
A. Ben-Amotz et al., "Accumulation of .beta.-carotene in halotolerant algae: purification and characterization of .beta.-carotene-rich globules from Dunaliella bardawil (Chlorophyceae)", J. Phycol., pp. 529-537, 1982.
A. Shaish et al., "Effect of Inhibitors on the Formation of Stereoisomers in the Biosynthesis of .beta.-Carotene in Dunaliella bardawil", Plant Cell Physiol., vol. 31, No. 5, pp. 689-696, 1990.
A. Ben-Amotz, et al., "Use of the .beta.-carotene rich alga Dunaliella bardawil as a source of retinol", British Poultry Science, vol. 27, pp. 613-619, 1986.
A. Gillam et al., "The Isomerization of Carotenes by Chromatographic Adsorption. II.Neo-.alpha.-Carotene", Biochem. J., vol. 31, pp. 1605-1610, 1937.
L. Zechmeister et al., "Isomerization of Carotenoids", Biochem. J., vol. 32, pp. 1305-1311, 1938.
A. Gillam et al., "The Isomerization of Carotenes by Chromatographic Adsorption. I. Pseudo.alpha.-Carotene", Biochem. J., vol. 30, pp. 1735-1742, 1936.
D. M. Snodderly et al., "Plasma Carotenoids of Monkeys (Macaca fascicularis and Saimiri sciureus) Fed a Nonpurified Diet", J. Nutr., vol. 120, pp. 1663-1671, 1990.
C. Jensen et al., "Observations on the Effects of Ingesting CIS-and trans-beta-carotene Isomers on Human Serum Concentrations", Nutrition Reports International, vol. 35, No. 2, pp. 413-422, 1987.
H. Nagasawa, et al., "Inhibition by Beta-Carotene--Rich Algae Dunaliella of Spontaneous Mammary Tumourigenesis in Mice", Anticancer Research, vol. 9, pp. 71-76, 1989.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

High cis beta-carotene composition does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with High cis beta-carotene composition, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and High cis beta-carotene composition will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1707464

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.