1-Octen-3-ol

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1-Octen-3-ol
(RS)-1-Octen-3-ol FormulaV1.svg
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
KEGG
UNII
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).
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Infobox references

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]

Uses[edit]

Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electronic devices.[8]

The name 'mushroom alcohol' is used because octenol is the main flavour component of mushrooms.[9]

Health and safety[edit]

Octenol is approved by the U.S. Food and Drug Administration as a food additive.[10] It is of moderate toxicity with an LD 50 of 340 mg/kg.[8]

In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism.[11]

See also[edit]

References[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.
  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: S0960982219311674. doi:10.1016/j.cub.2019.09.007. 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. ^ a b "1-Octen-3-ol". EPA fact sheet.
  9. ^ "1-octen-3-ol". thegoodscentscompany.com. Retrieved 2015-05-31.
  10. ^ 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.
  11. ^ 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.
  12. ^ 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.