1-Octen-3-ol explained

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]

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] Octenol is responsible for the moldy odor of damp indoor environments.[10]

It is also a wine fault, defined as a cork taint, occurring in wines made with bunch rot contaminated grape.[11]

Properties

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.

Synthesis

Two possible lab syntheses of 1-octen-3-ol are:[12]

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.[13] [14]

Uses

Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electrical devices.[15]

The name 'mushroom alcohol' is used because octenol is the main flavor component of mushrooms.[16]

Health and safety

Octenol is approved by the U.S. Food and Drug Administration as a food additive.[17] It is of moderate toxicity with an LD50 of 340 mg/kg.[15]

In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism.[18]

See also

Notes and References

  1. Web site: 1-Octen-3-ol, Mushroom alcohol . 2019-08-29 .
  2. Anna . Petherick . How DEET jams insects' smell sensors . Nature News . 2008-03-13 . https://web.archive.org/web/20080315162356/http://www.nature.com/news/2008/080313/full/news.2008.672.html . 15 March 2008 . live . 10.1038/news.2008.672 . free .
  3. Ditzen M, Pellegrino M, Vosshall LB . Insect odorant receptors are molecular targets of the insect repellent DEET . Science . 319 . 5871 . 1838–42 . March 2008 . 18339904 . 10.1126/science.1153121 . 2008Sci...319.1838D . 18499590 . Leslie B. Vosshall .
  4. Syed Z, Leal WS . 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 . September 2008 . 18711137 . 2518096 . 10.1073/pnas.0805312105 . free .
  5. Murahashi . S. . Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 34, 155 . Chemical Absracts . 31 . 21617 .
  6. Murahashi . S. . Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 30, 263 . Chemical Absracts . 32 . 27078 .
  7. Biochemical Systematics and Ecology . 35 . 2007 . Changing volatile compounds from mycelium and sporocarp of American matsutake mushroom, Tricholoma magnivelare . Wood W. F. . Lefevre C. K. . 9 . 10.1016/j.bse.2007.03.001 . 634–636. 2007BioSE..35..634W .
  8. Wood . William F. . Archer . Cynthia L. . Largent . David L. . 2001 . 1-Octen-3-ol, a banana slug antifeedant from mushrooms . Biochemical Systematics and Ecology . 29 . 5 . 531–533. 10.1016/s0305-1978(00)00076-4. 11274773 . 2001BioSE..29..531W .
  9. Web site: Chemical properties of attractants . 2010-06-08 . https://web.archive.org/web/20090427113618/http://www.nri.org/tsetse/FAQ/chemprop.html . 2009-04-27 . dead.
  10. Bennett JW, Inamdar AA . Are Some Fungal Volatile Organic Compounds (VOCs) Mycotoxins? . Toxins . 2015 . 7 . 9 . 3785–3804 . 10.3390/toxins7093785 . free . 4591661. 26402705 .
  11. Steel CC, Blackman JW, Schmidtke LM . 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 . June 2013 . 23675852 . 10.1021/jf400641r .
  12. 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. 10.1002/food.19830270523. 0027-769X. 6684212.
  13. Matsui. Kenji. Sasahara. Satomi. Akakabe. Yoshihiko. Kajiwara. Tadahiko. 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. 10.1271/bbb.67.2280. 0916-8451. 14586122. 46173472 . free.
  14. Book: Min Kuo . Tsung . Lipid biotechnology . Gardner . Harold W. . 2002 . Marcel Dekker . 0-585-40371-6 . New York . 48691412.
  15. Web site: 2007-07-05 . Biopesticides Fact Sheet for Octenol . 2022-06-28 . EPA fact sheet.
  16. Web site: 1-octen-3-ol. thegoodscentscompany.com. 2015-05-31.
  17. Web site: US FDAs Center for Food Safety and Applied Nutrition . US FDA/CFSAN – EAFUS List . 2008-03-16 . https://web.archive.org/web/20080221184706/http://vm.cfsan.fda.gov/~dms/eafus.html . 2008-02-21 . dead.
  18. Inamdar AA, Hossain MM, Bernstein AI, Miller GW, Richardson JR, Bennett JW . 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 . November 2013 . 24218591 . 3845153 . 10.1073/pnas.1318830110 . 2013PNAS..11019561I . free .
  19. Glindemann D, Dietrich A, Staerk HJ, Kuschk P . The two odors of iron when touched or pickled: (skin) carbonyl compounds and organophosphines . Angewandte Chemie . 45 . 42 . 7006–9 . October 2006 . 17009284 . 10.1002/anie.200602100 . 45055136 .

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