(9Z)-5α,6α-Epoxy-5,6-dihydro-β,β-carotene-3β,3'β-diol
- CAS No.
- 68831-78-7
- Chemical Name:
- (9Z)-5α,6α-Epoxy-5,6-dihydro-β,β-carotene-3β,3'β-diol
- Synonyms
- Antherxanthin;cis-Antheraxanthin;(9Z)-5α,6α-Epoxy-5,6-dihydro-β,β-carotene-3β,3'β-diol;(3S,3'R,5R,6S,9Z)-5,6-Epoxy-5,6-dihydro-β,β-carotene-3,3'-diol;β,β-Carotene-3,3'-diol, 5,6-epoxy-5,6-dihydro-, (3S,3'R,5R,6S,9-cis)-
- CBNumber:
- CB42262927
- Molecular Formula:
- C40H56O3
- Molecular Weight:
- 584.89
- MDL Number:
- MOL File:
- 68831-78-7.mol
(9Z)-5α,6α-Epoxy-5,6-dihydro-β,β-carotene-3β,3'β-diol Chemical Properties,Uses,Production
Uses
Antheraxanthin is a carotenoid pigment in the xanthophyll-cycle. Antheraxanthin levels were found to be higher in plants during depressions of photosystem II (PSII) efficiency.
Definition
ChEBI: Antheraxanthin is an epoxycarotenol that is beta-carotene-3,3'-diol in which one of the one of the endocyclic double bonds has been oxidised to the corresponding epoxide. It is a neutral yellow plant pigment found in Euglenophyta. It has a role as a biological pigment, a plant metabolite and a marine metabolite.
Purification Methods
Likely impurities are violaxanthin (see later) and mutatoxanthin (which contains a dihydrofuran ring derived from the epoxy group of antheraxanthin). Purify it by chromatography on columns of Ca(OH)2 and of ZnCO3. It crystallises from *C6H6/MeOH as needles or thin plates. Store it in the dark, under N2 or Ar at -20o. In CHCl3/SbCl2 it gives a blue colour with max at 587nm and gives a stable blue colour with conc HCl. [Karrer & Oswald Helv Chim Acta 18 1303 1935, Karrer & Jucker Helv Chim Acta 28 300