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1-Octen-3-ol

April 12, 2024

"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
  • 3391-86-4 Y
  • 3687-48-7 (R)-(−) Y
  • 24587-53-9 (S)-(+) Y
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:34118 Y
ChemSpider
  • 17778 Y
ECHA InfoCard 100.020.206
KEGG
  • C14272 Y
  • 18827
UNII
  • WXB511GE38 Y
  • BYV0MEV7V1 (R)-(−) Y
  • 07D31239FH (S)-(+) Y
  • DTXSID3035214
  • 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
  • CCCCCC(C=C)O
  • OC(C=C)CCCCC
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:
Warning
NFPA 704 (fire diamond)
Health 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).
Y verify (what is YN ?)

The name “mushroom Alcohol” for 1-octen-3-ol comes from it first isolation by 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 edit

Octenol is produced by several plants and fungi, including edible mushrooms and lemon balm. Octenol is formed during oxidative breakdown of linoleic acid.[9]

It is also a wine fault, defined as a cork taint, occurring in wines made with bunch rot contaminated grape.[10]

Properties edit

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 edit

Two possible lab syntheses of 1-octen-3-ol are:[11]

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.[12][13]

 
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 edit

Octenol is used, sometimes in combination with carbon dioxide, to attract insects in order to kill them with certain electrical devices.[14]

The name 'mushroom alcohol' is used because octenol is the main flavor component of mushrooms.[15]

Health and safety edit

Octenol is approved by the U.S. Food and Drug Administration as a food additive.[16] It is of moderate toxicity with an LD50 of 340 mg/kg.[14]

In an animal study, octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism.[17]

See also edit

References edit

  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. 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. ^ . Archived from the original on 2009-04-27. Retrieved 2010-06-08.
  10. ^ 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.
  11. ^ 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.
  12. ^ 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.
  13. ^ Min Kuo T, Gardner HW (2002). Lipid biotechnology. New York: Marcel Dekker. ISBN 0-585-40371-6. OCLC 48691412.
  14. ^ a b "Biopesticides Fact Sheet for Octenol" (PDF). EPA fact sheet. 2007-07-05. Retrieved 2022-06-28.
  15. ^ "1-octen-3-ol". thegoodscentscompany.com. Retrieved 2015-05-31.
  16. ^ US FDAs Center for Food Safety and Applied Nutrition. . Archived from the original on 2008-02-21. Retrieved 2008-03-16.
  17. ^ 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.
  18. ^ 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.

April 12, 2024
octen, octenol, redirects, here, confused, with, octanal, octanol, octonal, octenol, short, also, known, mushroom, alcohol, chemical, that, attracts, biting, insects, such, mosquitoes, contained, human, breath, sweat, believed, that, insect, repellent, deet, w. 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 NamesPreferred IUPAC name Oct 1 en 3 olOther names Amyl vinyl carbinol 1 Vinylhexanol Matsutake alcohol Vinyl amyl carbinol Vinyl hexanol Matsuica alcohol Mushroom alcohol 3 Hydroxy 1 octene OctenolIdentifiersCAS Number 3391 86 4 Y3687 48 7 R Y24587 53 9 S Y3D model JSmol Interactive imageInteractive imageChEBI CHEBI 34118 YChemSpider 17778 YECHA InfoCard 100 020 206KEGG C14272 YPubChem CID 18827UNII WXB511GE38 YBYV0MEV7V1 R Y07D31239FH S YCompTox Dashboard EPA DTXSID3035214InChI InChI 1S C8H16O c1 3 5 6 7 8 9 4 2 h4 8 9H 2 3 5 7H2 1H3 YKey VSMOENVRRABVKN UHFFFAOYSA N YInChI 1 C8H16O c1 3 5 6 7 8 9 4 2 h4 8 9H 2 3 5 7H2 1H3Key VSMOENVRRABVKN UHFFFAOYABSMILES CCCCCC C C OOC C C CCCCCPropertiesChemical formula C 8H 16OMolar mass 128 215 g mol 1Density 0 837 g mLBoiling point 174 ºC at 1 atmVapor pressure 0 3 kPa at 50 C HazardsGHS labelling PictogramsSignal word WarningNFPA 704 fire diamond 220Flash point 68 ºCAutoignitiontemperature 245 ºCExplosive 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 ScientificExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references The name mushroom Alcohol for 1 octen 3 ol comes from it first isolation by 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 Contents 1 Natural occurrence 2 Properties 3 Synthesis 4 Uses 5 Health and safety 6 See also 7 ReferencesNatural occurrence editOctenol is produced by several plants and fungi including edible mushrooms and lemon balm Octenol is formed during oxidative breakdown of linoleic acid 9 It is also a wine fault defined as a cork taint occurring in wines made with bunch rot contaminated grape 10 Properties edit1 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 nbsp The two enantiomers of 1 octen 3 olSynthesis editTwo possible lab syntheses of 1 octen 3 ol are 11 by the Grignard reaction of acrolein and amyl iodide by the selective reduction of 1 octen 3 oneBiochemically 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 12 13 nbsp 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 editOctenol is used sometimes in combination with carbon dioxide to attract insects in order to kill them with certain electrical devices 14 The name mushroom alcohol is used because octenol is the main flavor component of mushrooms 15 Health and safety editOctenol is approved by the U S Food and Drug Administration as a food additive 16 It is of moderate toxicity with an LD50 of 340 mg kg 14 In an animal study octenol has been found to disrupt dopamine homeostasis and may be an environmental agent involved in parkinsonism 17 See also editOlfactory receptor Oct 1 en 3 one the ketone analog that gives blood on skin its typical metallic mushroom like smell 18 1 Octen 3 yl acetate the acetate ester of this compoundReferences edit 1 Octen 3 ol Mushroom alcohol Retrieved 2019 08 29 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 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 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 Murahashi S Sci Pap Inst Phys Chem Res Jpn 34 155 Chemical Absracts 31 21617 Murahashi S Sci Pap Inst Phys Chem Res Jpn 30 263 Chemical Absracts 32 27078 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 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 Chemical properties of attractants Archived from the original on 2009 04 27 Retrieved 2010 06 08 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 Wnuk S Kinastowski S Kaminski 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 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 Min Kuo T Gardner HW 2002 Lipid biotechnology New York Marcel Dekker ISBN 0 585 40371 6 OCLC 48691412 a b Biopesticides Fact Sheet for Octenol PDF EPA fact sheet 2007 07 05 Retrieved 2022 06 28 1 octen 3 ol thegoodscentscompany com Retrieved 2015 05 31 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 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 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 Retrieved from https en wikipedia org w index php title 1 Octen 3 ol amp oldid 1214148598, wikipedia, wiki, book, books, library,

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