Nitropentadecene

Nitropentadecene

Names
IUPAC name (1E)-1-nitropentadec-1-ene
Identifiers
CAS Number	53520-53-9
ChemSpider	26949125
Jmol interactive 3D	Image
InChI InChI=1S/C15H29NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h14-15H,2-13H2,1H3/b15-14+ Key: VXUKZOXLZJQOHU-CCEZHUSRSA-N InChI=1/C15H29NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h14-15H,2-13H2,1H3/b15-14+ Key: VXUKZOXLZJQOHU-CCEZHUSRBB
SMILES CCCCCCCCCCCCC/C=C/[N+](=O)[O-]
Properties
Chemical formula	C15H29NO2
Molar mass	255.396 gmol^−1
log P	6.911
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Nitropentadecene, or more precisely (E)-1-nitropentadec-1-ene, is a highly toxic unsaturated nitroalkene, the only aliphatic nitro compound known to be synthesized by insects. It is produced by termite soldiers of Prorhinotermes genus (Isoptera, Rhinotermitidae) as a defensive chemical.^[1][2] Nitropentadecene is biosynthesized and stored in one of the exocrine glands, a frontal gland, of termite soldiers, and it is released upon attack of enemy.

References

1. Piskorski R, Hanus R, Vašíčková S, Cvačka J, Šobotník J, Svatoš A, Valterová I (2007). "Nitroalkenes and sesquiterpene hydrocarbons from the frontal gland of three Prorhinotermes termite species". Journal of Chemical Ecology 33 (9): 1787–94. doi:10.1007/s10886-007-9341-y. PMID 17665266.
2. Vrkoč J, Ubik K. (1974). "1-Nitro-trans-1-pentadecene as the defensive compound of termites". Tetrahedron Letters 15 (15): 1463–1464. doi:10.1016/S0040-4039(01)82519-3.