135589-15-0

Upstream product

• 49817-17-6 [(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienyl]-triphenyl-phosphonium; bromide 
• 62285-98-7 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide 
• 260244-86-8 (2E,4E)-5-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]-3-methylpenta-2,4-dienal 
• 50281-38-4 (3R)-3-hydroxy-β-ionone 
• 83021-07-2 (S,E)-4-[4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one 
• 121468-88-0 (-)-(2E,4E)-5-[(R)-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3-methylpenta-2,4-dienal 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 260244-85-7 C₄₉H₄₇NO₁₀ 
• 260244-82-4 C₄₇H₄₆O₁₁ 
• 76686-48-1 all-trans-(7-Formyl-2-methyl-2,4,6-octatrienyl)triphenylphosphoniumchlorid 
• 104707-00-8 methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Carotenoids and related polyenes. Part 9. Total synthesis of thermozeaxanthin and thermocryptoxanthin and the stabilizing effect of thermozeaxanthin on liposomes

Thermozeaxanthin and thermocryptoxanthin are efficiently synthesized via β-selective glucosidation of (3R)-3-hydroxy-β-ionone 7, and the stabilizing effects of zeaxanthin 5, its glucoside 3 and thermozeaxanthin-15 1a on liposomes are also examined.

Synthesis of zeaxanthin- and cryptoxanthin-β-D-glucopyranosides

β-Glucosidation of (3R)-3-hydroxy-β-ionone (6) was achieved in a reasonable yield by use of tetra-O-benzoyl-α-D-glucopyranosyl bromide (8 c) as a glycosyl donor and silver triflate as an activator. The resulting glucoside (9) was transformed into the β-apo-12'-carotenal (18), which was condensed with the Wittig salt (19) or (20) to provide zeaxanthin-mono-β-D- glucopyranoside (3) or cryptoxanthin-β-D-glucopyranoside (4).