From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
(RS)-1-Octen-3-ol FormulaV1.svg
Preferred IUPAC name
Other names
Amyl vinyl carbinol; 1-Vinylhexanol; Matsutake alcohol; Vinyl amyl carbinol; Vinyl hexanol; Matsuica alcohol; Mushroom alcohol; 3-Hydroxy-1-octene
3D model (JSmol)
ECHA InfoCard 100.020.206 Edit this at Wikidata
  • InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3 checkY
  • InChI=1/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3
Molar mass 128.215 g·mol−1
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 and also known as mushroom alcohol,[1] 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 worked by blocking the insects' octenol odorant receptors.[2][3] Recent evidence in Anopheles gambiae and Culex quequinfasciatius mosquitoes suggest DEET reduces the volatility of 1-octen-3-ol which can result in a reduction in human attraction.[4][5] 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[edit]

Octenol is produced by several plants and fungi, including edible mushrooms and lemon balm. Octenol is formed during oxidative breakdown of linoleic acid.[6]

It is also a wine fault, defined as a cork taint, occurring in wines made with bunch rot contaminated grape.[7]


Two possible lab syntheses of 1-octen-3-ol are:[8]

Biochemically, 1-octen-3-ol is generated from the peroxidation of linoleic acid, catalyzed by a lipoxygenase, followed by cleavage of the resulting hydroperoxide with the help of a hydroperoxide lyase. This reaction takes place in cheese and is used in biotechnology to produce the (R)-isomer.[9][10]

Biosynthesis of (R)-1-octen-3-ol: 1) linoleic acid, 2) (8E,12Z)-10-hydroperoxyoctadecadienoic acid, 3) (R)-1-octen-3-ol, 4) (8E)-10-oxodecenoic acid, 5) lipoxygenase, 6) hydroperoxide lyase.


Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electrical devices.[11]

The name 'mushroom alcohol' is used because octenol is the main flavour component of mushrooms.[12]

Health and safety[edit]

Octenol is approved by the U.S. Food and Drug Administration as a food additive.[13] It is of moderate toxicity with an LD50 of 340 mg/kg.[11]

In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism.[14]

See also[edit]


  1. ^ "1-Octen-3-ol, Mushroom alcohol". Retrieved 2019-08-29.
  2. ^ Petherick A (2008-03-13). "How DEET jams insects' smell sensors". Nature News. doi:10.1038/news.2008.672. Archived from the original on 15 March 2008.
  3. ^ Ditzen M, Pellegrino M, Vosshall LB (March 2008). "Insect odorant receptors are molecular targets of the insect repellent DEET". Science. 319 (5871): 1838–42. Bibcode:2008Sci...319.1838D. doi:10.1126/science.1153121. PMID 18339904. S2CID 18499590.
  4. ^ Afify A, Betz JF, Riabinina O, Lahondère C, Potter CJ (October 2019). "Commonly Used Insect Repellents Hide Human Odors from Anopheles Mosquitoes". Current Biology. 29 (21): 3669–3680.e5. doi:10.1016/j.cub.2019.09.007. PMC 6832857. PMID 31630950.
  5. ^ Syed Z, Leal WS (September 2008). "Mosquitoes smell and avoid the insect repellent DEET". Proceedings of the National Academy of Sciences of the United States of America. 105 (36): 13598–603. doi:10.1073/pnas.0805312105. PMC 2518096. PMID 18711137.
  6. ^ "Chemical properties of attractants". Archived from the original on 2009-04-27. Retrieved 2010-06-08.
  7. ^ Steel CC, Blackman JW, Schmidtke LM (June 2013). "Grapevine bunch rots: impacts on wine composition, quality, and potential procedures for the removal of wine faults". Journal of Agricultural and Food Chemistry. 61 (22): 5189–206. doi:10.1021/jf400641r. PMID 23675852.
  8. ^ Wnuk, S.; Kinastowski, S.; Kamiński, E. (1983). "Synthesis and analysis of 1-octen-3-ol, the main flavour component of mushrooms". Die Nahrung. 27 (5): 479–486. doi:10.1002/food.19830270523. ISSN 0027-769X. PMID 6684212.
  9. ^ Matsui, Kenji; Sasahara, Satomi; Akakabe, Yoshihiko; Kajiwara, Tadahiko (2003). "Linoleic acid 10-hydroperoxide as an intermediate during formation of 1-octen-3-ol from linoleic acid in Lentinus decadetes". Bioscience, Biotechnology, and Biochemistry. 67 (10): 2280–2282. doi:10.1271/bbb.67.2280. ISSN 0916-8451. PMID 14586122. S2CID 46173472.
  10. ^ Lipid biotechnology. Tsung Min Kuo, Harold W. Gardner. New York: Marcel Dekker. 2002. ISBN 0-585-40371-6. OCLC 48691412.{{cite book}}: CS1 maint: others (link)
  11. ^ a b "Biopesticides Fact Sheet for Octenol" (PDF). EPA fact sheet. 2007-07-05. Retrieved 2022-06-28.
  12. ^ "1-octen-3-ol". thegoodscentscompany.com. Retrieved 2015-05-31.
  13. ^ US FDAs Center for Food Safety and Applied Nutrition. "US FDA/CFSAN – EAFUS List". Archived from the original on 2008-02-21. Retrieved 2008-03-16.
  14. ^ Inamdar AA, Hossain MM, Bernstein AI, Miller GW, Richardson JR, Bennett JW (November 2013). "Fungal-derived semiochemical 1-octen-3-ol disrupts dopamine packaging and causes neurodegeneration". Proceedings of the National Academy of Sciences of the United States of America. 110 (48): 19561–6. Bibcode:2013PNAS..11019561I. doi:10.1073/pnas.1318830110. PMC 3845153. PMID 24218591.
  15. ^ Glindemann D, Dietrich A, Staerk HJ, Kuschk P (October 2006). "The two odors of iron when touched or pickled: (skin) carbonyl compounds and organophosphines". Angewandte Chemie. 45 (42): 7006–9. doi:10.1002/anie.200602100. PMID 17009284.