MUSHROOM ALCOHOL

1-Octen-3-ol, octenol for short and also known as mushroom alcohol,[1] is a chemical that attracts biting insects such asmosquitoes. It is contained in human breath and sweat, and it was once believed that insect repellent DEET works by blocking the insects’ octenol odorant receptors.[2][3] 1-Octen-3-ol is a secondary alcohol derived from 1-octene. It exists in the form of twoenantiomers, (R)-(–)-1-octen-3-ol and (S)-(+)-1-octen-3-ol.

NMR……..https://www.jstage.jst.go.jp/article/cl1972/6/8/6_8_975/_pdf

IR(film):3350(OH)and 920cm-1(CH2=);NMR(CCl4)δ 0.90(t,3H,CH3CH2-),1.36
(m,8H,-(CH2)4-),1.96(s,1H,-OH),4.07(m,1H, CHOH),4.90-5.40(m,2H, CH2=),
and 5.55-6.20 (m, 1H, -CH=).

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.[4]

It is also a wine fault, defined as a cork taint, occurring in wines made with bunch rot contaminated grape.[5]

Uses

Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electronic devices.[6]

Its odor has been described as green and moldy or meaty; it is used in certain perfumes.[citation needed]

Health and safety

Octenol is approved by the U.S. Food and Drug Administration as a food additive.[7] It is of moderate toxicity with an LD 50 of 340 mg/kg.[6]

In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved inparkinsonism.[8]

See also

1-Octen-3-ol
Octenol.png
Identifiers
CAS number 3391-86-4 Yes, 3687-48-7 (R)-(–), 24587-53-9 (S)-(+)
PubChem 18827
ChemSpider 17778 Yes
UNII WXB511GE38 Yes
KEGG C14272 Yes
ChEBI CHEBI:34118 Yes
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C8H16O
Molar mass 128.21 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)

References

  1.  “1-Octen-3-ol, Mushroom alcohol, 3-Octenol, 3391-86-4”. Retrieved 2008-11-14.
  2.  Anna Petherick (2008-03-13). “How DEET jams insects’ smell sensors”. Nature News. Archived from the original on 15 March 2008. Retrieved 2008-03-16.
  3.  Mathias Ditzen, Maurizio Pellegrino, Leslie B. Vosshall (2008). “Insect Odorant Receptors Are Molecular Targets of the Insect Repellent DEET”. Sciencexpress 319 (5871): 1838–42.doi:10.1126/science.1153121. PMID 18339904.
  4.  “Chemical properties of attractants”. Retrieved 2010-06-08.
  5.  Grapevine bunch rots: impacts on wine composition, quality, and potential procedures for the removal of wine faults. Steel CC, Blackman JW and Schmidtke LM, J Agric Food Chem., 5 June 2013, volume 61, issue 22, pages 5189-5206, doi:10.1021/jf400641r
  6.  EPA fact sheet 1-Octen-3-ol
  7.  US FDAs Center for Food Safety and Applied Nutrition. “US FDA/CFSAN – EAFUS List”. Archived from the original on 21 February 2008. Retrieved 2008-03-16.
  8.  Inamdar, A. A.; Hossain, M. M.; Bernstein, A. I.; Miller, G. W.; Richardson, J. R.; Bennett, J. W. (2013). “Fungal-derived semiochemical 1-octen-3-ol disrupts dopamine packaging and causes neurodegeneration”. Proceedings of the National Academy of Sciences 110 (48): 19561. doi:10.1073/pnas.1318830110.
  9.  D. Glindemann, A. Dietrich, H. Staerk, P. Kuschk, (2006). “The Two Odors of Iron when Touched or Pickled: (Skin) Carbonyl Compounds and Organophosphines”. Angewandte Chemie International Edition 45 (42): 7006–7009. doi:10.1002/anie.200602100. PMID 17009284.
H-NMR spectral analysis
1-Octen-3-ol NMR spectra analysis, Chemical CAS NO. 3391-86-4 NMR spectral analysis, 1-Octen-3-ol H-NMR spectrum
CAS NO. 3391-86-4, 1-Octen-3-ol H-NMR spectral analysis
C-NMR spectral analysis
1-Octen-3-ol NMR spectra analysis, Chemical CAS NO. 3391-86-4 NMR spectral analysis, 1-Octen-3-ol C-NMR spectrum
CAS NO. 3391-86-4, 1-Octen-3-ol C-NMR spectral analysis

Synthesis Route for 3391-86-4

88738-33-4
3-(2-methoxyetho…
~99%
3391-86-4
1-Octen-3-ol

Reference:

Monti, H.; Leandri, G.; Klos-Ringuet, M.; Corriol, C. Synthetic Communications, 1983 , vol. 13, # 12 p. 1021 – 1026

Synthesis Route for 3391-86-4

818-72-4
1-Octyn-3-ol
~99%
3391-86-4
1-Octen-3-ol

Reference:

Yoon, Nung Min; Park, Kyung Bae; Lee, Hyun Ju; Choi, Jaesung Tetrahedron Letters, 1996 , vol. 37, # 47 p. 8527 – 8528

Synthesis Route for 3391-86-4

4312-99-6
oct-1-en-3-one

~91%
3391-86-4
1-Octen-3-ol

Reference:

Ferreira, Hercules V.; Rocha, Lenilson C.; Severino, Richele P.; Porto, Andre L. M. Molecules, 2012 , vol. 17, # 8 p. 8955 – 8967,13 Title/Abstract Full Text Show Details Ferreira, Hercules V.; Rocha, Lenilson C.; Severino, Richele P.; Porto, Andre L.M. Molecules, 2012 , vol. 17, # 8 p. 8955 – 8967

Synthesis Route for 3391-86-4

1826-67-1
Vinylmagnesium b…
66-25-1
hexanal
~90%
3391-86-4
1-Octen-3-ol

Reference:

Yadav; Pandurangam; Suman Kumar; Adi Narayana Reddy; Prasad; Reddy, B.V. Subba; Rajendraprasad; Kunwar Tetrahedron Letters, 2012 , vol. 53, # 45 p. 6048 – 6050

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