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Violaxanthin

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Violaxanthin
Names
IUPAC name (3S,3′S,5R,5′R,6S,6′S)-5,6:5′,6′-Diepoxy-5,5′,6,6′-tetrahydro-β,β-carotene-3,3′-diol
Systematic IUPAC name (1R,1′R,3S,3′S,6S,6′S)-6,6′-bis(1,5,5-trimethyl-7-oxabicycloheptan-3-ol)
Other names
  • Zeaxanthin diepoxide
  • all-trans-Violaxanthin
  • E161e
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
E number E161e (colours)
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1Key: SZCBXWMUOPQSOX-WVJDLNGLSA-N
SMILES
  • C\C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/12C(C(C1(O2)C)O)(C)C)\C=C\C=C(/C)\C=C\34C(C(C3(O4)C)O)(C)C
Properties
Chemical formula C40H56O4
Molar mass 600.884 g·mol
Appearance Orange crystals
Melting point 200 °C (392 °F; 473 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Violaxanthin is a xanthophyll pigment with an orange color found in a variety of plants. Violaxanthin is the product of the epoxidation of zeaxanthin where the oxygen atoms are from reactive oxygen species (ROS). Such ROS's arise when a plant is subject to solar radiation so intense that the light cannot all be absorbed by the chlorophyll.

Food coloring

Violaxanthin is used as a food coloring under the E number E161e and INS number 161e. The coloring is not approved for use in food in the EU or the United States, but is allowed in Australia and New Zealand.

Violaxanthin cycle

Violaxanthin is a participant in the violaxanthin cycle.

The xanthophyll cycle

References

  1. Merck Index, 11th Edition, 9902.
  2. Bassi, Roberto; Dall'Osto, Luca (2021). "Dissipation of Light Energy Absorbed in Excess: The Molecular Mechanisms". Annual Review of Plant Biology. 72: 47–76. doi:10.1146/annurev-arplant-071720-015522. PMID 34143647. S2CID 235480018.
  3. UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.
  4. Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". 8 September 2011. Retrieved 2011-10-27.
Carotenoids
Carotenes (C40)
Xanthophylls (C40)
Apocarotenoids (C<40)
Vitamin A retinoids (C20)
Retinoid drugs
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