130696-70-7

Upstream product

• 91739-51-4 <(2Z,4Z)-5-<(R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl>-3-methylpenta-2,4-dienyl>triphenylphosphonium chloride 
• 50281-38-4 (3R)-3-hydroxy-β-ionone 
• 54165-55-8 (3R)-3-Acetoxy-β-ionon 
• 1200125-02-5 (rac)-(E)-4-(4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-2,2-ethylenedioxy-3-butene 
• 14398-37-9 (E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal 
• 127-41-3 alpha-ionone 
• 15647-89-9 triphenylphosphine hydrochloride 
• 91662-50-9 [(Z)-5-((R)-4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-pent-2-en-4-ynyl]-triphenyl-phosphonium; chloride 

Downstream Products

• 72580-10-0 (9Z,9'Z,3R,3'R)-zeaxanthin 
• 62741-99-5 (9Z,3R)-3-hydroxy-12'-apo-β-carotin-12'-al 
• 144-68-3 zeaxanthin 
• 472-70-8 (3R)-cryptoxanthin 

Relevant academic research and scientific papers

Process or synthesis of (3S)- and (3R)-3-hydroxy-beta-ionone, and their transformation to zeaxanthin and beta-cryptoxanthin

Disclosed is a process for the synthesis of (3R)-3-hydroxy-β-ionone and its (3S)-enantiomer in high optical purity from commercially available (rac)-α-ionone. The key intermediate for the synthesis of these hydroxyionones is 3-keto-α-ionone ketal that was prepared from (rac)-α-ionone after protection of this ketone as a 1,3-dioxolane. Reduction of 3-keto-α-ionone ketal followed by deprotection, lead to 3-hydroxy-α-ionone that was transformed into (rac)-3-hydrox-β-ionone by base-catalyzed double bond isomerization in 46% overall yield from (rac)-α-ionone. The racemic mixture of these hydroxyionones was then resolved by enzyme-mediated acylation in 96% ee. (3R)-3-Hydroxy-β-ionone and its (3S)-enantiomer were respectively transformed to (3R)-3-hydroxy-(β-ionylideneethyl)triphenylphosphonium chloride [(3R)-C15-Wittig salt] and its (3S)-enantiomer [(3S)-C15-Wittig salt] according to known procedures. Double Wittig condensation of these Wittig salts with commercial available 2,5- dimethtylocta-2,4,6-triene-1,8-dial provided all 3 stereoisomers of zeaxanthin. Similarly, (3R)-C15-Wittig and its (3S)-enantiomer were each coupled with β-apo-12′-carotenal.

91. Synthesis, Isolation, and Full Spectroscopic Characterization of Eleven (Z)-Isomers of (3R,3'R)-Zeaxanthin

Developmental efforts to improve the yield of the chemical synthesis of (3R,3'R)-zeaxanthin resulted in the isolation, partly by chromatography from reaction mixtures, and full spectroscopic characterization by 1H NMR, UV/VIS, and CD spectroscopy of eleven (Z/E)-isomers of zeaxanthin: (7Z)-, (9Z)-, (13Z)-, (15Z)-, (7Z,7'Z)-, (9Z,9'Z)-, (7Z,9Z,7'Z)-, (7Z,11Z,7'Z)-, (9Z,13Z,9'Z)-, (7Z,9Z,7'Z,9'Z)-, and (7Z,9Z,11Z,7'Z,9'Z)-zeaxanthin.Five of these isomers were obtained by specific synthesis, namely the (7Z)-, (7Z,7'Z)-, (9Z,9'Z)-, (7Z,9Z,7'Z)-, and (7Z,9Z,7'Z,9'Z)-isomers.