26927-07-1

Basic information

• Product Name: 9cViol
• Synonyms: (3S,3'S,5R,5'R,6S,6'S,9Z)-5,6:5',6'-Bisepoxy-5,5',6,6'-tetrahydro-β,β-carotene-3,3'-diol;(3S,3'S,5R,5'R,6S,6'S,9Z)-5,6:5',6'-Diepoxy-5,6,5',6'-tetrahydro-β,β-carotene-3,3'-diol;(3S,3'S,5R,5'R,6S,6'S,9Z)-5,6:5',6'-Diepoxy-β,β-carotene-3,3'-diol;(9Z)-Violaxanthin;9cViol;Violeoxanthin
• CAS NO: 26927-07-1
• Molecular Formula: C₄₀H₅₆O₄
• Molecular Weight: 600.87024
• Mol File: 26927-07-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 9cViol(CAS DataBase Reference)
• NIST Chemistry Reference: 9cViol(26927-07-1)
• EPA Substance Registry System: 9cViol(26927-07-1)

Safety Data

• Hazardous Substances Data: 26927-07-1(Hazardous Substances Data)

Upstream product

• 122346-90-1 15,15'-Didehydroviolaxanthin 
• 23069-07-0 4,4-(Ethylendioxy)-2,6,6-trimethyl-1-cyclohexen-1-methanol 
• 23069-06-9 4,4-(Ethylendioxy)-2,6,6-trimethyl-1-cyclohexen-1-carbonsaeure-ethylester 
• 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 
• 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 
• 122346-84-3 (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 
• 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 
• 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

• 122203-82-1 <2R-<1R*(E),2α,4β>>-5-(2,4-Dihydroxy-2,6,6-trimethylcyclohexylidene)-3-methylpenta-2,4-dienal 
• 8066-07-7 (1'S,2'R,4'S,2Z,4E)-(1',2'-epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methylpenta-2,4-dienal 
• 62777-81-5 5,6-epoxy-3-hydroxy-5,6-dihydro-12'-apo-β-caroten-12'-al 
• 62839-95-6 9'-cis-5',6'-epoxy-3'-hydroxy-5',6'-dihydro-10-apo-β-caroten-10-al 
• 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 
• 62713-23-9 9'-cis-5',6'-epoxy-3'-hydroxy-5',6'-dihydro-12-apo-β-caroten-12-al 
• 17237-68-2 5,6-epoxy-3-hydroxy-5,6-dihydro-10'-apo-β-caroten-10'-al 
• 126-29-4 Violaxanthin 
• 11011-41-9 auroxanthin 

Relevant articles and documents

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.

NATURALLY OCURING DI-CIS-VIOLAXANTHINS FROM VIOLA TRICOLOR: ISOLATION AND IDENTIFICATION BY 1H NMR SPECTROSCOPY OF FOUR DI-CIS-ISOMERS

From blossoms of Viola tricolor, four new naturally occuring geometrical isomers of violaxanthin (5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-β,β-carotene-3,3'-diol) have been isolated in the crystalline state.By two-dimensional 1H NMR methods, the new pigments are shown to be the 9,9'-, 9,13'-,9,15-and 9,13-di-cis isomers.Thermal and iodine-catalysed photochemical stereomutations of the new natural pigments have also been studied.Key Word Index-Viola tricolor; Violaceae; 9,9'-, 9,13'-, 9,15- and 9,13-di-cis-violaxanthins.