1-Octen-3-ol
Names | |
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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
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Identifiers | |
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3D model (
JSmol ) |
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ChEBI | |
ChemSpider | |
ECHA InfoCard
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100.020.206 |
KEGG | |
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: | |
Warning | |
NFPA 704 (fire diamond) | |
Flash point | 68 ºC |
245 ºC | |
Explosive limits
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0.9% (low) to 8% (high) |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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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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1-Octen-3-ol, octenol for short and also known as mushroom alcohol,
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]
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.[9]
It is also a wine fault, defined as a cork taint, occurring in wines made with bunch rot contaminated grape.[10]
Properties
1-octen-3-ol is a
Synthesis
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]
Uses
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]
Health and safety
Octenol is approved by the
In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism.[17]
See also
- 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
References
- ^ "1-Octen-3-ol, Mushroom alcohol". Retrieved 2019-08-29.
- from the original on 15 March 2008.
- S2CID 18499590.
- 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.
- .
- PMID 11274773.
- ^ "Chemical properties of attractants". Archived from the original on 2009-04-27. Retrieved 2010-06-08.
- PMID 23675852.
- PMID 6684212.
- S2CID 46173472.
- OCLC 48691412.
- ^ a b "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.
- PMID 24218591.
- S2CID 45055136.