1-Octen-3-ol

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 is believed that insect repellent DEET works by blocking the insects' octenol odorant receptors.[2][3][4]

"Octenol" redirects here. Not to be confused with octanal, octanol, or octonal.
1-Octen-3-ol
Names
Preferred 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
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 128.215 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 ?)
Infobox references

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.[5]

It is also a wine fault, defined as a cork taint, occurring in wines made with bunch rot contaminated grape.[6]

Properties

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.

The two enantiomers of 1-octen-3-ol

Synthesis

Two possible lab syntheses of 1-octen-3-ol are:[7]

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.[8][9]

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.

Uses

Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electrical devices.[10]

The name 'mushroom alcohol' is used because octenol is the main flavor component of mushrooms.[11]

Health and safety

Octenol is approved by the U.S. Food and Drug Administration as a food additive.[12] It is of moderate toxicity with an LD50 of 340 mg/kg.[10]

In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism.[13]

See also

References
  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. 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.
  5. "Chemical properties of attractants". Archived from the original on 2009-04-27. Retrieved 2010-06-08.
  6. 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.
  7. 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.
  8. 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.
  9. Min Kuo, Tsung; Gardner, Harold W. (2002). Lipid biotechnology. New York: Marcel Dekker. ISBN 0-585-40371-6. OCLC 48691412.
  10. "Biopesticides Fact Sheet for Octenol" (PDF). EPA fact sheet. 2007-07-05. Retrieved 2022-06-28.
  11. "1-octen-3-ol". thegoodscentscompany.com. Retrieved 2015-05-31.
  12. 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.
  13. 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.
  14. 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.
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