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 meso-zeaxanthin as an example for syntheses of unsymmetrical carotenoids is presented.

Introductory Chapter: Carotenoids - A Brief Overview on Its Structure, Biosynthesis, Synthesis, and Applications

“…Apart from β, β-carotene, the other synthetically produced carotenoids are manufactured mostly by the companies Hoffmann-La Roche and BASF [47].…”

“…cally at industrial level. Between them C40 carotenoids: lycopene, β, β-carotene, (3R,3′R)zeaxanthin, canthaxanthin, and astaxanthin; and three apocarotenoids: ß-apo-8′-carotenal, ethyl ß-apo-8′-carotenoate, and citranaxanthin[47].For the chemical synthesis, several building concepts are possible. However, on industrial scale, only few of them have been applied successfully.…”

“We Create Chemistry for a Sustainable Future”: Chemistry Creates Sustainable Solutions for a Growing World Population

“…Using citral as as tarting point, the tomato pigment and dietary supplement lycopene,w hich acts as an antioxidant, has been produced on industrial scale since 2005. [34] Over the last few years,anew citral-based value chain for enantiomerically pure l-menthol has been established, and in 2012, aproduction facility with the largest capability for continuous asymmetric hydrogenation worldwide commenced operation.…”

Metathesis of renewable polyene feedstocks – Indirect evidences of the formation of catalytically active ruthenium allylidene species

“…7 The synthesis of polyenes was carried out mainly by the Wittig reaction in the past. 8 The longest polyene synthetized so far contains eighty carbon atoms and twenty-seven conjugated double bonds. 9 However, research on polyenes and -conjugated oligomers has dramatically expanded by the development of transition metal catalysed cross-coupling reactions and analytical techniques, allowing the well-designed synthesis of linear, conjugated molecular rods with accurate characterisation.…”