Γ-Carotene

γ-Carotene
Names
IUPAC name
β,ψ-Carotene
Systematic IUPAC name
2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E)-3,7,12,16,20,24-Hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaen-1-yl]-1,3,3-trimethylcyclohex-1-ene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C40H56/c1-32(2)18-13-21-35(5)24-15-26-36(6)25-14-22-33(3)19-11-12-20-34(4)23-16-27-37(7)29-30-39-38(8)28-17-31-40(39,9)10/h11-12,14-16,18-20,22-27,29-30H,13,17,21,28,31H2,1-10H3/b12-11+,22-14+,23-16+,26-15+,30-29+,33-19+,34-20+,35-24+,36-25+,37-27+
    Key: HRQKOYFGHJYEFS-BXOLYSJBSA-N
  • InChI=1/C40H56/c1-32(2)18-13-21-35(5)24-15-26-36(6)25-14-22-33(3)19-11-12-20-34(4)23-16-27-37(7)29-30-39-38(8)28-17-31-40(39,9)10/h11-12,14-16,18-20,22-27,29-30H,13,17,21,28,31H2,1-10H3/b12-11+,22-14+,23-16+,26-15+,30-29+,33-19+,34-20+,35-24+,36-25+,37-27+
    Key: HRQKOYFGHJYEFS-BXOLYSJBBV
  • C(/C1=C(/CCCC1(C)C)C)=C\C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(\C=C\C=C(/C)CC\C=C(/C)C)C)C)C)C
Properties
C40H56
Molar mass 536.888 g·mol−1
Melting point 160 to 162 °C (320 to 324 °F; 433 to 435 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

γ-Carotene (gamma-carotene) is a carotenoid, and is a biosynthetic intermediate for cyclized carotenoid synthesis in plants. It is formed from cyclization of lycopene by lycopene cyclase epsilon. Along with several other carotenoids, γ-carotene is a vitamer of vitamin A in herbivores and omnivores. Carotenoids with a cyclized, beta-ionone ring can be converted to vitamin A, also known as retinol, by the enzyme beta-carotene 15,15'-dioxygenase; however, the bioconversion of γ-carotene to retinol has not been well-characterized. γ-Carotene has tentatively been identified as a biomarker for green and purple sulfur bacteria in a sample from the 1.640 ± 0.003-Gyr-old Barney Creek Formation in Northern Australia which comprises marine sediments. Tentative discovery of γ-carotene in marine sediments implies a past euxinic environment, where water columns were anoxic and sulfidic. This is significant for reconstructing past oceanic conditions, but so far γ-carotene has only been potentially identified in the one measured sample.