Torulene

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
CAS Number	547-23-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	4444665;
PubChem CID	5281253;
UNII	7KKR9CWX9P ;
CompTox Dashboard (EPA)	DTXSID901029634 ;
	InChI 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;
	SMILES 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
Chemical formula	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). Infobox references

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 at the time of its discovery (2010).^[2]

In 2012, the spider mite Tetranychus urticae was found to produce its own caretinoids using homologous genes, likely derived from similar fungi. In 2013, the Acyrthosiphon caretinoid synthesis genes were found to be present in aphid relatives, adelgids and phylloxerids.^[3]

^ 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.
^ 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.
^ Misawa, N; Takemura, M; Maoka, T (2021). "Carotenoid Biosynthesis in Animals: Case of Arthropods.". Carotenoids: Biosynthetic and Biofunctional Approaches. Advances in experimental medicine and biology. Vol. 1261. pp. 217–220. doi:10.1007/978-981-15-7360-6_19. PMID 33783744.

[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.

[moran2010-2] 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.

[3] Misawa, N; Takemura, M; Maoka, T (2021). "Carotenoid Biosynthesis in Animals: Case of Arthropods.". Carotenoids: Biosynthetic and Biofunctional Approaches. Advances in experimental medicine and biology. Vol. 1261. pp. 217–220. doi:10.1007/978-981-15-7360-6_19. PMID 33783744.

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