2002
DOI: 10.1351/pac200274112213
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Recent advances in industrial carotenoid synthesis

Abstract: Symmetrical C 40 -carotenoids are efficiently produced by double Wittig olefination of the corrresponding C 15 -phosphonium salts with C 10 -dialdehyde. Industrial syntheses of lycopene-, astaxanthin-, and (3R,3′R)-zeaxanthin-C 15 -phosphonium salts are discussed. An efficient route to a monoprotected C 10 -dialdehyde for the synthesis of unsymmetrical C 40 -carotenoids is presented. Primary polyene allyl alcohols can be converted to the corresponding aldehydes by "TEMPO" oxidation. A high-yield synthesis of m… Show more

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Cited by 88 publications
(38 citation statements)
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“…The presence of stereoisomer by-products, in addition to the naturally occurring 3S,3'S, may have an inhibitory effect on the biological activity of astaxanthin, and synthetic astaxanthin may be contaminated by other reaction by-products or intermediates 18 . The obtainment of enantiopure compounds for the development of pharmaceutical products requires chirality to be introduced at a very early stage of its synthesis and maintained throughout a scalable, reproducible, and economically viable manufacturing process 19 .…”
Section: Chemical Structure Of Astaxanthinmentioning
confidence: 99%
See 1 more Smart Citation
“…The presence of stereoisomer by-products, in addition to the naturally occurring 3S,3'S, may have an inhibitory effect on the biological activity of astaxanthin, and synthetic astaxanthin may be contaminated by other reaction by-products or intermediates 18 . The obtainment of enantiopure compounds for the development of pharmaceutical products requires chirality to be introduced at a very early stage of its synthesis and maintained throughout a scalable, reproducible, and economically viable manufacturing process 19 .…”
Section: Chemical Structure Of Astaxanthinmentioning
confidence: 99%
“…Nowadays, a large proportion of commercial astaxanthin is produced synthetically 18 . This synthesis starts with a C-9 unit, ketoisophorone, which is obtained from petroleum feedstocks 19,20 . However, the growing demand for natural feeds and the high cost of synthetic pigments have led to the search of natural sources of astaxanthin, such as microalgae, yeasts and crustacean by-products [13][14][15]17,21,22 .…”
Section: Introductionmentioning
confidence: 99%
“…Currently, xanthophylls are mainly produced by solvent-based extraction procedures from natural sources or by multistep chemical synthesis (Bhosale and Bernstein 2005). Naturally occurring xanthophylls such as zeaxanthin, canthaxanthin, and astaxanthin are produced synthetically on an industrial scale (Ernst 2002). Commercial production of carotenoids using microorganisms has been achieved in the case of astaxanthin, which is produced by fermentation using the red yeast X. dendrorhous or in culturally manipulated open ponds using the alga H. pluvialis (Jacobson et al 2000;Lorenz and Cysewski 2000;Olaizola 2000).…”
Section: Biosynthesis Of Astaxanthinmentioning
confidence: 99%
“…Carotenoids are used commercially as food colorants, feed supplements, nutraceuticals and for cosmetic and pharmaceutical purposes. Of the more than 600 different carotenoids identified in nature, only a small number can be synthesized in useful quantities by chemical synthesis (Ernst, 2002), extraction from their natural sources or microbial fermentation (Lee and Schmidt-Dannert, 2002;Valla et al, 2004).…”
Section: Introductionmentioning
confidence: 99%