1-Octen-3-ol

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 Edit this at Wikidata
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 checkYX markN ?)

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.

Occurrence

The name "mushroom alcohol" for 1-octen-3-ol comes from its 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. In combination with exhaled CO2 and other volatile compounds secreted from the epidermis, it attracts biting insects such as mosquitoes. 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.

In nature

Octenol is produced by several plants and fungi, including edible mushrooms and lemon balm. Octenol is formed during oxidative breakdown of linoleic acid. Octenol is responsible for the moldy odor of damp indoor environments.

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.

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.

The enantiopure right-handed isomer known as mushroom alcohol or matsutake alcohol is used in perfumery, because it is the main flavor and odor component of matsutake.

Health and safety

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

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

See also

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. 1 2 "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.