1-Octen-3-ol

1-Octen-3-ol
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
CAS number	3391-86-4 Y, 3687-48-7 (R)-(-), 24587-53-9 (S)-(+)
PubChem	18827
ChemSpider	17778 Y
UNII	WXB511GE38 Y
KEGG	C14272 Y
ChEBI	CHEBI:34118 Y
Jmol-3D images	Image 1 Image 2
SMILES CCCCCC(C=C)O OC(C=C)CCCCC
InChI InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3 Y Key: VSMOENVRRABVKN-UHFFFAOYSA-N Y InChI=1/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3 Key: VSMOENVRRABVKN-UHFFFAOYAB
Properties
Molecular formula	C8H16O
Molar mass	128.21204
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

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 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. 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

• Olfactory receptor
• Oct-1-en-3-one, the ketone analog that gives blood on skin its typical metallic, mushroom-like smell

References

1. ^ "1-Octen-3-ol, Mushroom alcohol, 3-Octenol, 3391-86-4". http://67.210.99.134/products/3391-86-4.htm. Retrieved 2008-11-14. 
2. ^ Anna Petherick (2008-03-13). "How DEET jams insects' smell sensors". Nature News. http://www.nature.com/news/2008/080313/full/news.2008.672.html. 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. 
4. ^ ^{a b} EPA fact sheet 1-Octen-3-ol
5. ^ "Chemical properties of attractants". http://www.nri.org/tsetse/FAQ/chemprop.html. Retrieved 2010-06-08. 
6. ^ US FDAs Center for Food Safety and Applied Nutrition. "US FDA/CFSAN - EAFUS List". http://vm.cfsan.fda.gov/~dms/eafus.html. Retrieved 2008-03-16.