Torulene
Names
IUPAC name
3′,4′-Didehydro-β,ψ-carotene
Systematic IUPAC name
2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E,21E)-3,7,12,16,20,24-Hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,21,23-dodecaen-1-yl]-1,3,3-trimethylcyclohex-1-ene
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C40H54/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/h11-16,18-27,29-30H,17,28,31H2,1-10H3/b12-11+,21-13+,22-14+,23-16+,26-15+,30-29+,33-19+,34-20+,35-24+,36-25+,37-27+
    Key: AIBOHNYYKWYQMM-MXBSLTGDSA-N
  • 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=C\C=C(/C)C)C)C)C)C)C
Properties
C40H54
Molar mass 534.857
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Torulene (3',4'-didehydro-β,γ-carotene) is a carotene (a hydrocarbon carotenoid) which is notable for being synthesized by red pea aphids (Acyrthosiphon pisum), imparting the natural red color to the aphids, which aids in their camouflage and escape from predation. The aphids have gained the ability to synthesize torulene by horizontal gene transfer of a number of genes for carotenoid synthesis, apparently from fungi.[1] Plants, fungi, and microorganisms can synthesize carotenoids, but torulene made by pea aphids is the only carotenoid known to be synthesized by an organism in the animal kingdom.[2]

References

  1. ^ Fukatsu, Takema (2010). "A Fungal Past to Insect Color". Science. 328 (5978): 574–575. Bibcode:2010Sci...328..574F. doi:10.1126/science.1190417. PMID 20431000. S2CID 23686682. Retrieved December 20, 2010.
  2. ^ Nancy A. Moran; Tyler Jarvik (2010). "Lateral Transfer of Genes from Fungi Underlies Carotenoid Production in Aphids". Science. 328 (5978): 624–627. Bibcode:2010Sci...328..624M. doi:10.1126/science.1187113. PMID 20431015. S2CID 14785276.


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