1-Octen-3-ol

"Octenol" redirects here. Not to be confused with octanal, octanol, or octonal.

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]

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
CAS Number	3391-86-4 Y (R)-(−): 3687-48-7 Y (S)-(+): 24587-53-9 Y
3D model (JSmol)	Interactive image (R)-(−): Interactive image (S)-(+): Interactive image
ChEBI	CHEBI:34118 Y (R)-(−): CHEBI:39932 (S)-(+): CHEBI:46735
ChEMBL	ChEMBL3183573 (R)-(−): ChEMBL1230177
ChemSpider	17778 Y (R)-(−): 5360388.html : 5360388 (S)-(+): 2007013.html : 2007013
DrugBank	(S)-(+): DB03025
ECHA InfoCard	100.020.206
EC Number	222-226-0
Gmelin Reference	648361
KEGG	C14272 Y
PubChem CID	18827 (R)-(−): 6992244
UNII	WXB511GE38 Y (R)-(−): BYV0MEV7V1 Y (S)-(+): 07D31239FH Y
CompTox Dashboard (EPA)	DTXSID3035214
InChI InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3 Y Key: VSMOENVRRABVKN-UHFFFAOYSA-N Y 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
SMILES CCCCCC(C=C)O (R)-(−): CCCCC[C@@H](O)C=C (S)-(+): CCCCC[C@H](O)C=C
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
NFPA 704 (fire diamond)	2 2 0
Flash point	68 ºC
Autoignition temperature	245 ºC
Explosive limits	0.9% (low) to 8% (high)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	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). Y verify (what is YN ?) Infobox references

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.^[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.

The two enantiomers of 1-octen-3-ol

Synthesis

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

• by the Grignard reaction of acrolein and amyl iodide
• by the selective reduction of 1-octen-3-one

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]

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.^[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

• Olfactory receptor
• Oct-1-en-3-one, the ketone analog that gives blood on skin its typical metallic, mushroom-like smell^[19]
• 1-Octen-3-yl acetate, the acetate ester of this compound

References

1. "1-Octen-3-ol, Mushroom alcohol". Retrieved 2019-08-29.
2. 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.
3. 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.
4. 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.
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. 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.
8. 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.
9. "Chemical properties of attractants". Archived from the original on 2009-04-27. Retrieved 2010-06-08.
10. 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.
11. 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. doi:10.1021/jf400641r. PMID 23675852.
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. doi:10.1002/food.19830270523. ISSN 0027-769X. PMID 6684212.
13. 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.
14. Min Kuo T, Gardner HW (2002). Lipid biotechnology. New York: Marcel Dekker. ISBN 0-585-40371-6. OCLC 48691412.
15. "Biopesticides Fact Sheet for Octenol" (PDF). EPA fact sheet. 2007-07-05. Retrieved 2022-06-28.
16. "1-octen-3-ol". thegoodscentscompany.com. Retrieved 2015-05-31.
17. 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.
18. 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.
19. 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. PMID 17009284. S2CID 45055136.