Antheraxanthin

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Antheraxanthin
Names
IUPAC name
(3S,5R,6S,3R)-5,6-Epoxy-5,6-dihydro-β,β-carotene-3,3-diol
Systematic IUPAC name
(1S,4S,6R)-4-Hydroxy-1-{(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl}-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane
Identifiers
3D model (JSmol)
101042
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35+,39-,40+/m1/s1
    Key: OFNSUWBAQRCHAV-OYQUVCAXSA-N
  • InChI=1/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35+,39-,40+/m1/s1
    Key: OFNSUWBAQRCHAV-OYQUVCAXBE
  • O[C@H]1CC(C(=C(/C)C1)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/[C@@]32O[C@@]3(C[C@@H](O)CC2(C)C)C)C)C)C)C)(C)C
Properties
C40H56O3
Molar mass 584.885 g·mol−1
Appearance Yellow solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Antheraxanthin (from ánthos, Greek for "flower" and xanthos, Greek for "yellow") is a bright yellow accessory pigment found in many organisms that perform photosynthesis. It is a xanthophyll cycle pigment, an oil-soluble alcohol within the xanthophyll subgroup of carotenoids. Antheraxanthin is both a component in and product of the cellular photoprotection mechanisms in photosynthetic green algae, red algae, euglenoids, and plants.[1][2]

Antheraxanthin has been found in high levels in sun-exposed dandelions (Taraxacum officinale).

Antheraxanthin is an intermediate molecule of the xanthophyll cycle in most photosynthetic eukaryotes, namely plants, and some bacteria. In the xanthophyll cycle, specific carotenoid pigments are transformed via enzymatic reactions into either more or less photoprotective biological pigments.[3]

A plant can increase its capacity for non-photochemical quenching (NPQ) and excess heat dissipation by converting the orange pigment violaxanthin to antheraxanthin and then to light-yellow pigment zeaxanthin.[4] The xanthophyll pool, or total xanthophyll cycle pigment levels are sometimes abbreviated as "VAZ" in scientific literature.[5]

"VAZ" is an abbreviation of the cycle's main pigments in order of lowest to highest photoprotection each pigment provides. Antheraxanthin is denoted by the "A" in the middle, between violaxanthin (V) and zeaxanthin (Z).[6]

Location in thylakoid membrane

Enzymes and reactions

References

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