1-Octen-3-ol

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. A recent study on volatiles of this mushroom has shown this compound is only produced upon tissue disruption. This alcohol is found in many other mushrooms where it may play a role as an antifeedant. It attracts biting insects such as mosquitoes.reference? 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.

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.{{ cite web |access-date = 2010-06-08 |archive-url = https://web.archive.org/web/20090427113618/http://www.nri.org/tsetse/FAQ/chemprop.html |archive-date = 2009-04-27 |url-status = dead

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

Synthesis

It can be prepared by the Grignard reaction of acrolein with the Grignard reagent derived from amyl iodide. 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.

Uses

Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electrical devices.

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

Health and safety

Octenol is approved by the U.S. Food and Drug Administration as a food additive.{{cite web |access-date = 2008-03-16 |archive-url = https://web.archive.org/web/20080221184706/http://vm.cfsan.fda.gov/~dms/eafus.html |archive-date = 2008-02-21 |url-status = dead

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

References

References

1. (2020). "Fungal Volatile Organic Compounds: More Than Just a Funky Smell?". Annual Review of Microbiology.
2. "Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 34, 155". Chemical Abstracts.
3. "Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 30, 263". Chemical Abstracts.
4. (2007). "Changing volatile compounds from mycelium and sporocarp of American matsutake mushroom, ''Tricholoma magnivelare''". Biochemical Systematics and Ecology.
5. (2001). "1-Octen-3-ol, a banana slug antifeedant from mushrooms". Biochemical Systematics and Ecology.
6. Petherick, Anna. (2008-03-13). "How DEET jams insects' smell sensors". Nature News.
7. (March 2008). "Insect odorant receptors are molecular targets of the insect repellent DEET". Science.
8. (September 2008). "Mosquitoes smell and avoid the insect repellent DEET". Proceedings of the National Academy of Sciences of the United States of America.
9. (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.
10. (1983). "Synthesis and analysis of 1-octen-3-ol, the main flavour component of mushrooms". Die Nahrung.
11. (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.
12. (2002). "Lipid biotechnology". Marcel Dekker.
13. (2007-07-05). "Biopesticides Fact Sheet for Octenol". EPA fact sheet.
14. "1-octen-3-ol".
15. (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.