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1-Octen-3-ol

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This is an old revision of this page, as edited by Zaphraud (talk | contribs) at 04:27, 16 January 2013 (Clarify with sometimes. Reference: personal; the bug-zapper I bought at Home Depot did not contain any carbon dioxide attractant, but it did come with a little package of this chemical suspended in a gel.). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

1-Octen-3-ol
Names
IUPAC name
Oct-1-en-3-ol
Other names
Amyl vinyl carbinol, 1-vinylhexanol, matsutake alcohol, vinyl amyl carbinol, vinyl hexanol, matsuica alcohol, mushroom alcohol, 3-hydroxy-1-octene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.020.206 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3 checkY
    Key: VSMOENVRRABVKN-UHFFFAOYSA-N checkY
  • InChI=1/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3
    Key: VSMOENVRRABVKN-UHFFFAOYAB
  • CCCCCC(C=C)O
  • OC(C=C)CCCCC
Properties
C8H16O
Molar mass 128.21204
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

1-Octen-3-ol, octenol for short (also known as mushroom alcohol[1]), is a chemical that attracts biting insects such as mosquitos. It is contained in human breath and sweat, and it was once believed that insect repellent DEET works by blocking the insects' octenol odorant receptors.[2][3] Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electronic devices.[4]

1-Octen-3-ol is a secondary alcohol derived from 1-octene. It exists in the form of two enantiomers, (R)-(–)-1-octen-3-ol and (S)-(+)-1-octen-3-ol. Octenol is formed during oxidative breakdown of linoleic acid.[5]

Octenol is produced by several plants and fungi, including edible mushrooms and Lemon balm. Its odor has been described as green and moldy or meaty; it is used in certain perfumes.[citation needed] It is approved by the U.S. Food and Drug Administration as a food additive.[6] It is of moderate toxicity with an LD 50 of 340 mg/kg.[4]

See also

References

  1. ^ "1-Octen-3-ol, Mushroom alcohol, 3-Octenol, 3391-86-4". Retrieved 2008-11-14.
  2. ^ Anna Petherick (2008-03-13). "How DEET jams insects' smell sensors". Nature News. Archived from the original on 15 March 2008. Retrieved 2008-03-16.
  3. ^ Mathias Ditzen, Maurizio Pellegrino, Leslie B. Vosshall (2008). "Insect Odorant Receptors Are Molecular Targets of the Insect Repellent DEET". Sciencexpress. 319 (5871): 1838–42. doi:10.1126/science.1153121. PMID 18339904.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ a b EPA fact sheet 1-Octen-3-ol
  5. ^ "Chemical properties of attractants". Retrieved 2010-06-08.
  6. ^ US FDAs Center for Food Safety and Applied Nutrition. "US FDA/CFSAN - EAFUS List". Archived from the original on 21 February 2008. Retrieved 2008-03-16.
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