Chemistry:1-Octen-3-ol

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

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

  1. ↑ "1-Octen-3-ol, Mushroom alcohol". https://www.hmdb.ca/metabolites/HMDB0031299. 
  2. ↑ "Fungal Volatile Organic Compounds: More Than Just a Funky Smell?". Annual Review of Microbiology 74: 101–116. 2020. doi:10.1146/annurev-micro-012420-080428. PMID 32905756. 
  3. ↑ Murahashi, S.. "Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 34, 155". Chemical Abstracts 31: 21617. 
  4. ↑ Murahashi, S.. "Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 30, 263". Chemical Abstracts 32: 27078. 
  5. ↑ 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. doi:10.1016/j.bse.2007.03.001. Bibcode: 2007BioSE..35..634W. 
  6. ↑ 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. doi:10.1016/s0305-1978(00)00076-4. PMID 11274773. Bibcode: 2001BioSE..29..531W. 
  7. ↑ Takken, W; Kline, D L (1989-09-01). "Carbon dioxide and 1-octen-3-ol as mosquito attractants". Journal of the American Mosquito Control Association 5 (3): 311–316. ISSN 1943-6270. PMID 2573687. https://europepmc.org/article/med/2573687. 
  8. ↑ Petherick, Anna (2008-03-13). "How DEET jams insects' smell sensors". Nature News. doi:10.1038/news.2008.672. http://www.nature.com/news/2008/080313/full/news.2008.672.html. 
  9. ↑ "Insect odorant receptors are molecular targets of the insect repellent DEET". Science 319 (5871): 1838–42. March 2008. doi:10.1126/science.1153121. PMID 18339904. Bibcode: 2008Sci...319.1838D. 
  10. ↑ "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. doi:10.1073/pnas.0805312105. PMID 18711137. 
  11. ↑ "Chemical properties of attractants". http://www.nri.org/tsetse/FAQ/chemprop.html. 
  12. ↑ "Are Some Fungal Volatile Organic Compounds (VOCs) Mycotoxins?". Toxins 7 (9): 3785–3804. 2015. doi:10.3390/toxins7093785. PMID 26402705. 
  13. ↑ "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. doi:10.1021/jf400641r. PMID 23675852. Bibcode: 2013JAFC...61.5189S. 
  14. ↑ 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. doi:10.1002/food.19830270523. ISSN 0027-769X. PMID 6684212. 
  15. ↑ 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. doi:10.1271/bbb.67.2280. ISSN 0916-8451. PMID 14586122. 
  16. ↑ Min Kuo, Tsung; Gardner, Harold W. (2002). Lipid biotechnology. New York: Marcel Dekker. ISBN 0-585-40371-6. OCLC 48691412. 
  17. ↑ 17.0 17.1 "Biopesticides Fact Sheet for Octenol". EPA fact sheet. 2007-07-05. https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_G-126_05-Jul-07.pdf. 
  18. ↑ "1-octen-3-ol". https://www.thegoodscentscompany.com/data/rw1024051.html. 
  19. ↑ US FDAs Center for Food Safety and Applied Nutrition. "US FDA/CFSAN – EAFUS List". http://vm.cfsan.fda.gov/~dms/eafus.html. 
  20. ↑ "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. doi:10.1073/pnas.1318830110. PMID 24218591. Bibcode: 2013PNAS..11019561I. 
  21. ↑ "The two odors of iron when touched or pickled: (skin) carbonyl compounds and organophosphines". Angewandte Chemie 45 (42): 7006–9. October 2006. doi:10.1002/anie.200602100. PMID 17009284. Bibcode: 2006ACIE...45.7006G. 



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