1-Octen-3-ol

Chemical compound From Wikipedia, the free encyclopedia

1-Octen-3-ol, octenol for short and also known as mushroom alcohol, is an organic compound with the formula CH2=CHCH(OH)(CH2)4CH3. It is a chiral secondary alcohol. It is a colorless liquid that occurs widely in nature.[1][2]

Quick facts Names, Identifiers ...
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; Octenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.020.206 Edit this at Wikidata
EC Number
  • 222-226-0
648361
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
  • (R)-(−): Key: VSMOENVRRABVKN-QMMMGPOBSA-N
  • (S)-(+): Key: VSMOENVRRABVKN-MRVPVSSYSA-N
  • CCCCCC(C=C)O
  • (R)-(−): CCCCC[C@@H](O)C=C
  • (S)-(+): CCCCC[C@H](O)C=C
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 Â°C)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 68 ºC
245 ºC
Explosive limits 0.9% (low) to 8% (high)
Lethal dose or concentration (LD, LC):
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 Â°C [77 Â°F], 100 kPa).
checkY verify (what is checkY☒N ?)
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Occurrence

The name "mushroom alcohol" for 1-octen-3-ol comes from it first isolation by S. Murahashi in 1936 and 1938 from crushed matsutake mushrooms.[3][4] A recent study on volatiles of this mushroom has shown this compound is only produced upon tissue disruption.[5] This alcohol is found in many other mushrooms where it may play a role as an antifeedant.[6] In combination with exhaled CO2 and other volatile compounds secreted from the epidermis, it attracts biting insects such as mosquitoes.[7] It is contained in human breath and sweat, and it is believed that the insect repellent DEET works by blocking the insects' octenol odorant receptors.[8][9][10]

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.[11] Octenol is responsible for the moldy odor of damp indoor environments.[12]

It is also a wine fault, defined as a cork taint, occurring in wines made with bunch rot contaminated grape.[13]

Synthesis

It can be prepared by the Grignard reaction of acrolein with the Grignard reagent derived from amyl iodide.[14] It also arises by the selective reduction of 1-octen-3-one

Biosynthesis

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.[15][16]

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.[17]

The name 'mushroom alcohol' is used because octenol is the main flavor component of mushrooms.[18]

Health and safety

Octenol is approved by the U.S. Food and Drug Administration as a food additive.[19] It is of moderate toxicity with an LD50 of 340 mg/kg.[17]

In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism.[20]

See also

References

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