1-octen-3-ol
1-Octen-3-ol
Chemical compound
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]
| 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; Octenol | |
| Identifiers | |
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3D model (JSmol) |
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| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.020.206  |
| KEGG |
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PubChem CID |
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| UNII |
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CompTox Dashboard (EPA) |
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| Properties | |
| C8H16O | |
| Molar mass | 128.215 g·mol−1 |
| Density | 0.837 g/mL |
| Boiling point | 174 ºC at 1 atm |
| Vapor pressure | 0.3 kPa (at 50 °C) |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| NFPA 704 (fire diamond) | |
| Flash point | 68 ºC |
| 245 ºC | |
| Explosive limits | 0.9% (low) to 8% (high) |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
340 mg/kg (rat) |
| Safety data sheet (SDS) | Fisher Scientific |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The name “mushroom Alcohol” for 1-octen-3-ol comes from it first isolation by Murahashi in 1936 and 1938 from crushed matsutake mushrooms. [5][6]A recent study on volatiles of this mushroom has shown this compound is only produced upon tissue disruption.[7] This alcohol is found in many other mushrooms where it may play a role as an antifeedant.[8]
Octenol is produced by several plants and fungi, including edible mushrooms and lemon balm. Octenol is formed during oxidative breakdown of linoleic acid.[9]
It is also a wine fault, defined as a cork taint, occurring in wines made with bunch rot contaminated grape.[10]
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.
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Two possible lab syntheses of 1-octen-3-ol are:[11]
- by the Grignard reaction of acrolein and amyl iodide
- by the selective reduction of 1-octen-3-one
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.[12][13]
Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electrical devices.[14]
The name 'mushroom alcohol' is used because octenol is the main flavor component of mushrooms.[15]
Octenol is approved by the U.S. Food and Drug Administration as a food additive.[16] It is of moderate toxicity with an LD50 of 340 mg/kg.[14]
In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism.[17]
- Olfactory receptor
- Oct-1-en-3-one, the ketone analog that gives blood on skin its typical metallic, mushroom-like smell[18]
- 1-Octen-3-yl acetate, the acetate ester of this compound
- "1-Octen-3-ol, Mushroom alcohol". Retrieved 2019-08-29.
- 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.
- 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.
- 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.
- Murahashi S. "Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 34, 155". Chemical Absracts. 31: 21617.
- Murahashi S. "Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 30, 263". Chemical Absracts. 32: 27078.
- Wood W. F., Lefevre C. K. (2007). "Changing volatile compounds from mycelium and sporocarp of American matsutake mushroom, Tricholoma magnivelare". Biochemical Systematics and Ecology. 35 (9): 634–636. Bibcode:2007BioSE..35..634W. doi:10.1016/j.bse.2007.03.001.
- Wood WF, Archer CL, Largent DL (2001). "1-Octen-3-ol, a banana slug antifeedant from mushrooms". Biochemical Systematics and Ecology. 29 (5): 531–533. Bibcode:2001BioSE..29..531W. doi:10.1016/s0305-1978(00)00076-4. PMID 11274773.
- "Chemical properties of attractants". Archived from the original on 2009-04-27. Retrieved 2010-06-08.
- 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.
- 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.
- Matsui K, Sasahara S, Akakabe Y, Kajiwara T (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.
- Min Kuo T, Gardner HW (2002). Lipid biotechnology. New York: Marcel Dekker. ISBN 0-585-40371-6. OCLC 48691412.
- "Biopesticides Fact Sheet for Octenol" (PDF). EPA fact sheet. 2007-07-05. Retrieved 2022-06-28.
- "1-octen-3-ol". thegoodscentscompany.com. Retrieved 2015-05-31.
- 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.
- 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.