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The chemistry of novel xanthophyll carotenoids.
Am J Cardiol. 2008 May 22; 101(10A):50D-57D.AJ

Abstract

Natural product isolates are typically not developed as drug candidates because of the difficulty in obtaining the desired stable molecular orientation (ie, stereochemistry), purity, and scale required to meet pharmaceutical industry standards. Recent advances in medicinal and process chemistry have played key roles in transforming a class of dietary natural products-carotenoids-into potential medical therapeutics. Carotenoids are natural pigments derived from the acyclic C40 isoprenoid lycopene, which can also be classified as a tetraterpene. Carotenoids are classified on their chemical composition as either carotenes or xanthophylls. There are 5 C40 carotenoids manufactured synthetically on an industrial scale, including lycopene, ss,ss-carotene, and canthaxanthin (which are achiral compounds); zeaxanthin (produced in enantiopure form, as the 3R,3'R enantiomer); and astaxanthin (produced as mixture of configurational isomers) for use as nutritional supplements and for animal feed additives in poultry farming and aquaculture that are essential for the animals' growth, health and reproduction. The xanthophyll astaxanthin shows pharmaceutical potential, but the configurational complexity has thus far made it difficult to synthesize an enantiopure form on a large scale. Astaxanthin has 2 identical asymmetric carbon atoms (position 3 and 3') and can therefore exist in 4 different configurations, providing 3 different configurational isomers: (3S,3'S) and (3R,3'R), which are enantiomers, and (3R,3'S) and (3S,3'R), which are identical (a meso form). An enantiopure industrial scale synthesis of astaxanthin (3S,3'S) has recently been developed by BASF AG. The desired stereochemistry (chirality) is introduced early in the synthetic process by a proprietary catalytic reaction using an intermediate of the existing technical astaxanthin production process as a substrate. By controlling this essential process, it is possible to produce pharmaceutical quality astaxanthin in quantities large enough to support drug development programs for medical therapies.

Authors+Show Affiliations

Cardax Pharmaceuticals, 99-193 Aeia Heights Drive, Aiea, HI 96701, USA.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Review

Language

eng

PubMed ID

18474275

Citation

Jackson, Henry, et al. "The Chemistry of Novel Xanthophyll Carotenoids." The American Journal of Cardiology, vol. 101, no. 10A, 2008, 50D-57D.
Jackson H, Braun CL, Ernst H. The chemistry of novel xanthophyll carotenoids. Am J Cardiol. 2008;101(10A):50D-57D.
Jackson, H., Braun, C. L., & Ernst, H. (2008). The chemistry of novel xanthophyll carotenoids. The American Journal of Cardiology, 101(10A), 50D-57D. https://doi.org/10.1016/j.amjcard.2008.02.008
Jackson H, Braun CL, Ernst H. The Chemistry of Novel Xanthophyll Carotenoids. Am J Cardiol. 2008 May 22;101(10A):50D-57D. PubMed PMID: 18474275.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The chemistry of novel xanthophyll carotenoids. AU - Jackson,Henry, AU - Braun,Cristi L, AU - Ernst,Hansgeorg, PY - 2008/6/24/pubmed PY - 2008/7/3/medline PY - 2008/6/24/entrez SP - 50D EP - 57D JF - The American journal of cardiology JO - Am. J. Cardiol. VL - 101 IS - 10A N2 - Natural product isolates are typically not developed as drug candidates because of the difficulty in obtaining the desired stable molecular orientation (ie, stereochemistry), purity, and scale required to meet pharmaceutical industry standards. Recent advances in medicinal and process chemistry have played key roles in transforming a class of dietary natural products-carotenoids-into potential medical therapeutics. Carotenoids are natural pigments derived from the acyclic C40 isoprenoid lycopene, which can also be classified as a tetraterpene. Carotenoids are classified on their chemical composition as either carotenes or xanthophylls. There are 5 C40 carotenoids manufactured synthetically on an industrial scale, including lycopene, ss,ss-carotene, and canthaxanthin (which are achiral compounds); zeaxanthin (produced in enantiopure form, as the 3R,3'R enantiomer); and astaxanthin (produced as mixture of configurational isomers) for use as nutritional supplements and for animal feed additives in poultry farming and aquaculture that are essential for the animals' growth, health and reproduction. The xanthophyll astaxanthin shows pharmaceutical potential, but the configurational complexity has thus far made it difficult to synthesize an enantiopure form on a large scale. Astaxanthin has 2 identical asymmetric carbon atoms (position 3 and 3') and can therefore exist in 4 different configurations, providing 3 different configurational isomers: (3S,3'S) and (3R,3'R), which are enantiomers, and (3R,3'S) and (3S,3'R), which are identical (a meso form). An enantiopure industrial scale synthesis of astaxanthin (3S,3'S) has recently been developed by BASF AG. The desired stereochemistry (chirality) is introduced early in the synthetic process by a proprietary catalytic reaction using an intermediate of the existing technical astaxanthin production process as a substrate. By controlling this essential process, it is possible to produce pharmaceutical quality astaxanthin in quantities large enough to support drug development programs for medical therapies. SN - 0002-9149 UR - https://www.unboundmedicine.com/medline/citation/18474275/The_chemistry_of_novel_xanthophyll_carotenoids_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0002-9149(08)00218-X DB - PRIME DP - Unbound Medicine ER -