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 repellentDEET works by blocking the insects' octenol
odorantreceptors.[2][3][4]
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]
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]
^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.
^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.
PMID17009284.
S2CID45055136.