Nitropentadecene

Nitropentadecene
IUPAC name

(1E)-1-nitropentadec-1-ene
Identifiers
CAS number 53520-53-9 Y
Properties
Molecular formula C15H29NO2
Molar mass 255.396 gmol-1
log P 6.911
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. http://www.springerlink.com/content/h011410868125470/?p=6e995beac5584f5fb5dcc975e692f22b&pi=1. 
  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. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6THS-42HWV7X-2CV&_user=791130&_coverDate=12%2F31%2F1974&_alid=850273264&_rdoc=2&_fmt=high&_orig=search&_cdi=5290&_sort=d&_docanchor=&view=c&_ct=2&_acct=C000043379&_version=1&_urlVersion=0&_userid=791130&md5=b30d307d1296894f05faf404ff08b508.