Spheroidene

all-trans-spheroidene
Spheroidene skeletal formula
Names
IUPAC name
(3E)-1-Methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-ψ,ψ-carotene
Systematic IUPAC name
(6E,10E,12E,14E,16E,18E,20E,22E,24E,26E,28E)-31-methoxy-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,12,14,16,18,20,22,24,26,28-dodecaene
Other names
  • Pigment Y
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH spheroidene
  • Key: FJOCMTHZSURUFA-AXYGSFPTSA-N
  • InChI=1S/C41H60O/c1-34(2)20-14-23-37(5)26-17-29-38(6)27-15-24-35(3)21-12-13-22-36(4)25-16-28-39(7)30-18-31-40(8)32-19-33-41(9,10)42-11/h12-13,15-16,18-22,24-28,30-32H,14,17,23,29,33H2,1-11H3/b13-12+,24-15+,25-16+,30-18+,32-19+,35-21+,36-22+,37-26+,38-27+,39-28+,40-31+
  • CC(=CCC/C(=C/CC/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)OC)/C)/C)/C)C
Properties
C41H60O
Molar mass 568.930 g·mol−1
Melting point 135–138 °C (275–280 °F; 408–411 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Spheroidene is a carotenoid pigment. It is a component of the photosynthetic reaction center of certain purple bacteria of the Rhodospirillaceae family, including Rhodobacter sphaeroides and Rhodopseudomonas sphaeroides.[1][2] Like other carotenoids, it is a tetraterpenoid. In purified form, it is a brick-red solid soluble in benzene.[2]

Spheroidene was discovered by microbiologist C. B. van Niel, who named it "pigment Y". It was renamed by Basil Weedon, who was the first to prepare it synthetically, and to determine its structure, in the mid-1960s.[2]

  1. ^ Harrison, D.M. (1986). "The biosynthesis of carotenoids". Natural Product Reports. 3 (3): 205–215. doi:10.1039/np9860300205. PMID 3534642.
  2. ^ a b c Barber, M.S.; Jackman, L.M.; Manchand, P.S.; Weedon, B.C.L. (1966). "Carotenoids and related compounds. Part XVI. Structural and synthetic studies on spirilloxanthin, chloroxanthin, spheroidene, and spheroidenone". Journal of the Chemical Society C: 2166–2176. doi:10.1039/j39660002166.