Phytoene

Phytoene (/ˈfaɪtoʊiːn/) is a 40-carbon intermediate in the biosynthesis of carotenoids. The synthesis of phytoene is the first committed step in the synthesis of carotenoids in plants. Phytoene is produced from two molecules of geranylgeranyl pyrophosphate (GGPP) by the action of the enzyme phytoene synthase. The two GGPP molecules are condensed together followed by removal of diphosphate and proton shift leading to the formation of phytoene.

Phytoene
Names
IUPAC name
15-cis-7,8,11,12,7′,8′,11′,12′-Octahydro-ψ,ψ-carotene
Systematic IUPAC name
(6E,10E,14E,16Z,18E,22E,26E)-2,6,10,14,19,23,27,31-Octamethyldotriaconta-2,6,10,14,16,18,22,26,30-nonaene
Other names
15-cis-Phytoene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C40H64/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,19-22,27-30H,13-18,23-26,31-32H2,1-10H3/b12-11-,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+ N
    Key: YVLPJIGOMTXXLP-BHLJUDRVSA-N N
  • CC(=CCC/C(=C/CC/C(=C/CC/C(=C/C=C\C=C(/C)\CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C)/C)/C)/C)C
Properties
C40H64
Molar mass 544.952 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Dietary phytoene and phytofluene are found in a number of human tissues including the liver, lung, breast, prostate, colon, and skin. Accumulation of these carotenoids in the skin may protect the skin by several mechanisms: acting as UV absorbers, as antioxidants, and as anti-inflammatory agents.

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