1-Octen-3-ol

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
CAS Number	3391-86-4 Y 3687-48-7 (R)-(–) Y 24587-53-9 (S)-(+) Y
ChEBI	CHEBI:34118 Y
ChemSpider	17778 Y
Jmol 3D model	Interactive image Interactive image
KEGG	C14272 Y
PubChem	18827
UNII	WXB511GE38 Y
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
SMILES CCCCCC(C=C)O OC(C=C)CCCCC
Properties
Chemical formula	C8H16O
Molar mass	128.22 g·mol−1
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

1-Octen-3-ol, octenol for short and also known as mushroom alcohol, is a chemical that attracts biting insects such as mosquitoes. 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. 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.

Natural occurrence

Octenol is produced by several plants and fungi, including edible mushrooms and Lemon balm. Octenol is formed during oxidative breakdown of linoleic acid.

It is also a wine fault, defined as a cork taint, occurring in wines made with bunch rot contaminated grape.

Uses

Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electronic devices.

Its odor has been described as moldy or meaty; it is used in certain perfumes.

Health and safety

Octenol is approved by the U.S. Food and Drug Administration as a food additive. It is of moderate toxicity with an LD 50 of 340 mg/kg.

In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism.

See also

• Olfactory receptor
• Oct-1-en-3-one, the ketone analog that gives blood on skin its typical metallic, mushroom-like smell
• 1-Octen-3-yl acetate, the acetate ester of this compound