γ-Carotene

γ-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.[2] 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 gamma-carotene to retinol has not been well-characterized.

γ-Carotene
Names
IUPAC name
β,ψ-Carotene
Preferred 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)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Ruegg, R.; Schwieter, U.; Ryser, G.; Schudel, P.; Isler, O. (1961). "Synthesen in der Carotinoid-Reihe. 17. Mittelung. γ-Carotin sowie d,l-α- und β-Carotin aus Dehydro-β-apo-12′-carotinal(C25)". Helvetica Chimica Acta. 44 (4): 985–93. doi:10.1002/hlca.19610440414.
  2. Rodriguez-Concepcion M, Stange C. Biosynthesis of carotenoids in carrot: an underground story comes to light. Archives of biochemistry and biophysics. 2013;539:110-6.


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