38963-41-6

Basic information

• Product Name: 3-Buten-2-one, 4-(4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-
• CAS NO: 38963-41-6
• Molecular Formula: C13H20O2
• Molecular Weight: 208.301
• Mol File: 38963-41-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-Buten-2-one, 4-(4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Buten-2-one, 4-(4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-(38963-41-6)
• EPA Substance Registry System: 3-Buten-2-one, 4-(4-hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-(38963-41-6)

Safety Data

• Hazardous Substances Data: 38963-41-6(Hazardous Substances Data)

Upstream product

• 14398-37-9 (E)-4-<2',6',6'-trimethylcyclohex-2'-enyl>but-3-en-2-one ethylene ketal 
• 127-41-3 alpha-ionone 

Downstream Products

• 50281-38-4 (3R)-3-hydroxy-β-ionone 
• 76686-31-2 [(2E,4E)-(R)-5-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]-triphenylphosphonium chloride 
• 1200446-88-3 all-E-(3S)-β-cryptoxanthin 
• 54165-55-8 (3R)-3-Acetoxy-β-ionon 
• 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 
• 1200124-92-0 (3S)-3-hydroxy-vinyl-β-ionol 

Relevant articles and documents

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.