# Torulene

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Torulene
> Markdown URL: https://mediated.wiki/source/Torulene.md
> Source: https://en.wikipedia.org/wiki/Torulene
> Source revision: 1293336541
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Chembox
| ImageFile = Torulene.svg
| ImageSize = 
| IUPACName = 3′,4′-Didehydro-β,ψ-carotene
| SystematicName = 2-[(1''E'',3''E'',5''E'',7''E'',9''E'',11''E'',13''E'',15''E'',17''E'',19''E'',21''E'')-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
| OtherNames = 
|Section1={{Chembox Identifiers
| CASNo = 547-23-9 
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7KKR9CWX9P
| PubChem = 5281253
| ChemSpiderID = 4444665
| 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
| StdInChI=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+
| StdInChIKey = AIBOHNYYKWYQMM-MXBSLTGDSA-N
  }}
|Section2={{Chembox Properties
| Formula = C<sub>40</sub>H<sub>54</sub>
| MolarMass = 534.857
| Appearance = 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility =
  }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt =
  }}
}}
'''Torulene''' (3',4'-didehydro-β,γ-carotene) is a [carotene](/source/carotene) (a hydrocarbon [carotenoid](/source/carotenoid)) which is notable for being synthesized by red [pea aphid](/source/pea_aphid)s (''[Acyrthosiphon pisum](/source/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](/source/horizontal_gene_transfer) of a number of genes for carotenoid synthesis, apparently from fungi.<ref>{{cite journal |url=https://www.science.org/doi/abs/10.1126/science.1190417 |title=A Fungal Past to Insect Color |journal=Science |year= 2010|doi= 10.1126/science.1190417|access-date=December 20, 2010|last1= Fukatsu|first1= Takema|volume= 328|issue= 5978|pages= 574–575|pmid= 20431000|bibcode= 2010Sci...328..574F|s2cid= 23686682|url-access= subscription}}</ref> 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).<ref name="moran2010">{{cite journal | author = Nancy A. Moran | author2 = Tyler Jarvik | year = 2010 | title = Lateral Transfer of Genes from Fungi Underlies Carotenoid Production in Aphids | journal = Science | volume = 328 | issue = 5978 | pages = 624–627 | doi = 10.1126/science.1187113 | pmid=20431015|bibcode = 2010Sci...328..624M | s2cid = 14785276 }}</ref>

In 2012, the spider mite ''[Tetranychus urticae](/source/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, [adelgid](/source/adelgid)s and [phylloxerid](/source/phylloxerid)s.<ref>{{cite book |last1=Misawa |first1=N |last2=Takemura |first2=M |last3=Maoka |first3=T |chapter=Carotenoid Biosynthesis in Animals: Case of Arthropods. |title=Carotenoids: Biosynthetic and Biofunctional Approaches|series=Advances in experimental medicine and biology |date=2021 |volume=1261 |pages=217–220 |doi=10.1007/978-981-15-7360-6_19 |pmid=33783744|isbn=978-981-15-7359-0 }}</ref>

== References ==
{{Reflist}}

{{Carotenoids}}

Category:Carotenoids
Category:Plant physiology
Category:Cyclohexenes

{{Photosynthesis-stub}}
{{hydrocarbon-stub}}

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Adapted from the Wikipedia article [Torulene](https://en.wikipedia.org/wiki/Torulene) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Torulene?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.