1-Octen-3-ol

"Octenol" redirects here; not to be confused with octanal, octanol, or octonal.
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
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 °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 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

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]

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

  • Olfactory receptor
  • Oct-1-en-3-one, the ketone analog that gives blood on skin its typical metallic, mushroom-like smell[21]
  • 1-Octen-3-yl acetate, the acetate ester of this compound

References

  1. ^ "1-Octen-3-ol, Mushroom alcohol". Retrieved 2019-08-29.
  2. ^ Inamdar AA, Morath S, Bennett JW (2020). "Fungal Volatile Organic Compounds: More Than Just a Funky Smell?". Annual Review of Microbiology. 74: 101–116. 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. Bibcode:2007BioSE..35..634W. doi:10.1016/j.bse.2007.03.001.
  6. ^ Wood WF, Archer CL, Largent DL (2001). "1-Octen-3-ol, a banana slug antifeedant from mushrooms". Biochemical Systematics and Ecology. 29 (5): 531–533. Bibcode:2001BioSE..29..531W. doi:10.1016/s0305-1978(00)00076-4. PMID 11274773.
  7. ^ Takken W, Kline DL (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.
  8. ^ Petherick A (2008-03-13). "How DEET jams insects' smell sensors". Nature News. doi:10.1038/news.2008.672. Archived from the original on 15 March 2008.
  9. ^ Ditzen M, Pellegrino M, Vosshall LB (March 2008). "Insect odorant receptors are molecular targets of the insect repellent DEET". Science. 319 (5871): 1838–42. Bibcode:2008Sci...319.1838D. doi:10.1126/science.1153121. PMID 18339904. S2CID 18499590.
  10. ^ Syed Z, Leal WS (September 2008). "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. doi:10.1073/pnas.0805312105. PMC 2518096. PMID 18711137.
  11. ^ "Chemical properties of attractants". Archived from the original on 2009-04-27. Retrieved 2010-06-08.
  12. ^ Bennett JW, Inamdar AA (2015). "Are Some Fungal Volatile Organic Compounds (VOCs) Mycotoxins?". Toxins. 7 (9): 3785–3804. doi:10.3390/toxins7093785. PMC 4591661. PMID 26402705.
  13. ^ Steel CC, Blackman JW, Schmidtke LM (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. 61 (22): 5189–206. Bibcode:2013JAFC...61.5189S. doi:10.1021/jf400641r. PMID 23675852.
  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 K, Sasahara S, Akakabe Y, Kajiwara T (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. S2CID 46173472.
  16. ^ Min Kuo T, Gardner HW (2002). Lipid biotechnology. New York: Marcel Dekker. ISBN 0-585-40371-6. OCLC 48691412.
  17. ^ a b "Biopesticides Fact Sheet for Octenol" (PDF). EPA fact sheet. 2007-07-05. Retrieved 2022-06-28.
  18. ^ "1-octen-3-ol". thegoodscentscompany.com. Retrieved 2015-05-31.
  19. ^ US FDAs Center for Food Safety and Applied Nutrition. "US FDA/CFSAN – EAFUS List". Archived from the original on 2008-02-21. Retrieved 2008-03-16.
  20. ^ Inamdar AA, Hossain MM, Bernstein AI, Miller GW, Richardson JR, Bennett JW (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. 110 (48): 19561–6. Bibcode:2013PNAS..11019561I. doi:10.1073/pnas.1318830110. PMC 3845153. PMID 24218591.
  21. ^ 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. Bibcode:2006ACIE...45.7006G. doi:10.1002/anie.200602100. PMID 17009284. S2CID 45055136.
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