80629-24-9

Upstream product

• 23069-07-0 4,4-(Ethylendioxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol 
• 122346-90-1 15,15'-Didehydroviolaxanthin 
• 115406-45-6 (all-E,3R,3'R)-β,β-carotene-3,3'-diol 3,3'-diacetate 
• 122346-84-3 (1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-pivaloyloxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-diensaeure-methylester 
• 122346-80-9 (1R,2R,4S)-Essigsaeure-(1,2-epoxy-4-pivaloyloxy-2,6,6-trimethylcyclohexan-1-methyl)ester 
• 122346-82-1 (1R,2R,4S)-1,2-Epoxy-4-pivaloyloxy-2,6,6-trimethylcyclohexan-1-carbaldehyd 
• 118205-56-4 (2E,4E)-5-[(1'S,2'R,4'S)-4'-hydroxy-1',2'-epoxy-2',6',6'-trimethylcyclohexa-1'-yl]-3-methylpenta-2,4-diene-1-ol 
• 122346-81-0 (1R,2R,4S)-1,2-Epoxy-4-pivaloyloxy-2,6,6-trimethylcyclohexan-1-methanol 
• 122346-77-4 (1R,2R)-Essigsaeure-(1,2-epoxy-2,6,6-trimethyl-4-oxocyclohexan-1-methyl)ester 
• 122346-88-7 (1'S,2'R,2E,4E)-5-(1',2'-Epoxy-2',6',6'-trimethyl-4'-oxocyclohexyl)-3-methyl-2,4-pentadiensaeure-methylester 
• 122346-75-2 (+)-(1R,2R)-1,2-Epoxy-4,4-(ethylendioxy)-2,6,6-trimethylcyclohexan-1-methanol 
• 28874-44-4 (1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal 
• 122346-85-4 (-)-(1S,2R)-1,2-Epoxy-4,4-(ethylendioxy)-2,6,6-trimethylcyclohexan-1-carbaldehyd 
• 23068-96-4 ethyl 2,6,6-trimethyl-4-oxocyclohex-2-ene-1-carboxylate 

Downstream Products

• 11011-41-9 auroxanthin 
• 126-29-4 Violaxanthin 

Relevant academic research and scientific papers

Preparation and (E/Z)-Isomerization of the Diastereoisomers of Violaxanthin

Violaxanthin A (=(all-E,3S,5S,6R,3′S,5′S,6′ R)-5,6:5′,6′-diepoxy-5,6,5′,6′-tetrahydro-β, β-carotene-3,3′-diol = syn,syn-violaxanthin; 5) and violaxanthin B (=(all-E,3S,5S,6R,3′S,5′R,6′S)-5,6:5′, 6′-diepoxy-5,6,5′,6′-tetrahydro-β,β-carotene-3, 3′-diol = syn,anti-violaxanthin; 6) were prepared by epoxidation of zeaxanthin diacetate (1) with monoperphthalic acid. Violaxanthins 5 and 6 were submitted to thermal isomerization and I2-catalyzed photoisomerization. The structure of the main products, i.e., (9Z)-5, (13Z)-5, (9Z)-6, (9′Z)-6, (13Z)-6, and (13′Z)-6, was determined by their UV/VIS, CD, 1H-NMR, 13C-NMR, and mass spectra.

Syntheses of Enantiomerically Pure Violaxanthins and Related Compounds

The epoxides 16 and ent-16, prepared by Sharpless-Katsuki oxidation of 15 in excellent yield and very high enantiomeric purity, were used as synthons for the preparation of (+)-(S)-didehydrovomifoliol (45), (+)-(6S,7E,9E)-abscisic ester 46, (+)-(6S,7E,9Z)-abscisic ester 47, (-)-(3S,7E,9E)-xanthoxin (49), (-)-(3R,7E,9E)-xanthoxin (50), (3S,5R,6S,3'S,5'R,6'S,all-E)-violaxanthin (1), (3R,5R,6S,3'R,5'R,6'S,all-E)-violaxanthin (55) and their (9Z) (see 53, 57), (13Z) (see 54, 58), and (15Z) (see 60) isomers.The novel violadione (61) was prepared from 1 by oxidation with DMSO/Ac2O.By base treatment, 61 was converted into violadienedione (62), a potential precursor of carotenoids with phenolic end groups.