14398-37-9

Upstream product

• 127-41-3 alpha-ionone 
• 107-21-1 ethylene glycol 

Downstream Products

• 24190-29-2 (R)-α-ionone 
• 14398-36-8 (3E)-4-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-2-one 
• 144-68-3 zeaxanthin 
• 472-70-8 (3R)-cryptoxanthin 
• 116296-75-4 (rac)-(E)-4-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 
• 1200125-02-5 (rac)-(E)-4-(4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-2,2-ethylenedioxy-3-butene 
• 38963-41-6 (rac)-4-(4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one 
• 54165-55-8 (3R)-3-Acetoxy-β-ionon 
• 130696-70-7 <(2Z,4E)-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 

Relevant academic research and scientific papers

Identification of Apocarotenoids as Chemical Markers of in Vitro Anti-Inflammatory Activity for Spirulina Supplements

Identification of chemical markers in food additives and dietary supplements is crucial for quantitative assessment and standardization of their quality and efficacy. Arthrospira platensis, formerly Spirulina platensis and known colloquially as spirulina,

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.

Synthesis of (3S)- and (3R)-3-hydroxy-β-ionone and their transformation into (3S)- and (3R)-β- cryptoxanthin

(3S)- and (3R)-3-Hydroxy-β-ionone and (3S)- and (3R)-3-Hydroxy-β- ionone synthesized in high enantiomeric purity from commercially available () - ionone. These ionones were then transformed into (3R) - cryptoxanthin and (3S) - cryptoxanthin by a C15+C10+C15 Wittig coupling strategy according to known methods. This methodology can considerably simplify the total synthesis of optically active carotenoids with 3-hydroxy - end groups that possess significant biological activities. Georg Thieme Verlag Stuttgart New York.