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Revision as of 16:44, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 453633385 of page 1-Octen-3-ol for the Chem/Drugbox validation project (updated: '').  Latest revision as of 13:21, 2 November 2024 edit Trasheater Midir (talk | contribs)Extended confirmed users3,648 edits →top 
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{{cs1 config|name-list-style=vanc}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Redirect-distinguish|Octenol|octanal|octanol|Octonal (disambiguation){{!}}octonal}}
{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 443480026
| verifiedrevid = 477208406
|ImageFile=Octenol.png
| ImageFile=Oct-1-en-3-ol.svg
|ImageSize=200px
| ImageSize=200px
|IUPACName=Oct-1-en-3-ol
| PIN=Oct-1-en-3-ol
|OtherNames=Amyl vinyl carbinol, 1-vinylhexanol, matsutake alcohol, vinyl amyl carbinol, vinyl hexanol, matsuica alcohol, mushroom alcohol, 3-hydroxy-1-octene
| OtherNames=Amyl vinyl carbinol; 1-Vinylhexanol; Matsutake alcohol; Vinyl amyl carbinol; Vinyl hexanol; Matsuica alcohol; Mushroom alcohol; 3-Hydroxy-1-octene; Octenol
|Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 34118 | ChEBI = 34118
| ChEBI1 = 39932
| ChEBI2 = 46735
| ChEMBL = 3183573
| ChEMBL1 = 1230177
| ChemSpiderID = 17778 | ChemSpiderID = 17778
| ChemSpiderID1 = : 5360388
| ChemSpiderID2 = : 2007013
| DrugBank2 = DB03025
| EC_number = 222-226-0
| Gmelin = 648361
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14272 | KEGG = C14272
| InChI = 1/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3 | InChI = 1/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3
| SMILES1 = OC(C=C)CCCCC
| InChIKey = VSMOENVRRABVKN-UHFFFAOYAB | InChIKey = VSMOENVRRABVKN-UHFFFAOYAB
| InChIKey1 =VSMOENVRRABVKN-QMMMGPOBSA-N
| InChIKey2 =VSMOENVRRABVKN-MRVPVSSYSA-N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3 | StdInChI = 1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3
Line 22: Line 34:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo= 3391-86-4 | CASNo= 3391-86-4
| CASNo1_Ref = {{cascite|correct|??}}
| CASNo1 = 3687-48-7 | CASNo1 = 3687-48-7
| CASNo1_Comment = (R)-(-) | index1_label = (''R'')-(−)
| CASNo2_Comment = (S)-(+) | index2_label = (''S'')-(+)
| CASNo2_Ref = {{cascite|correct|??}}
| CASNo2 = 24587-53-9 | CASNo2 = 24587-53-9
| PubChem=18827 | PubChem=18827
| UNII_Ref = {{fdacite|correct|FDA}} | PubChem1 = 6992244
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = WXB511GE38 | UNII = WXB511GE38
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = BYV0MEV7V1
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = 07D31239FH
| SMILES=CCCCCC(C=C)O | SMILES=CCCCCC(C=C)O
| SMILES1 = CCCCC(O)C=C
| SMILES2 = CCCCC(O)C=C
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=8 | H=16 | O=1
| Formula=C<sub>8</sub>H<sub>16</sub>O
| Appearance=
| MolarMass=128.21204
| Density= 0.837 g/mL
| Appearance=
| Density= | MeltingPt=
| BoilingPt= 174 ºC at 1 atm
| MeltingPt=
| VaporPressure = 0.3 kPa (at 50&nbsp;°C)
| BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt= 68 ºC
| AutoignitionPt = 245 ºC
| Autoignition=
| ExploLimits = 0.9% (low) to 8% (high)
|GHSPictograms = {{GHS07}}
|GHSSignalWord = Warning
|NFPA-H = 2
|NFPA-F = 2
|NFPA-R = 0
|LD50 = 340 mg/kg (rat)
|ExternalSDS =
}} }}
}} }}

'''1-Octen-3-ol''', '''octenol''' for short and also known as '''mushroom alcohol''',<ref>{{cite web
|title = 1-Octen-3-ol, Mushroom alcohol
|access-date = 2019-08-29
|url = http://www.hmdb.ca/metabolites/HMDB0031299
}}</ref> is a chemical that attracts biting insects such as ]es. It is contained in human breath and sweat, and it is believed that ] ] works by blocking the insects' octenol ] ]s.<ref name=petherick>{{cite journal |first=Anna |last=Petherick |title=How DEET jams insects' smell sensors |journal=Nature News |date=2008-03-13 |url= http://www.nature.com/news/2008/080313/full/news.2008.672.html |archive-url=https://web.archive.org/web/20080315162356/http://www.nature.com/news/2008/080313/full/news.2008.672.html | archive-date=15 March 2008 |url-status=live |doi=10.1038/news.2008.672 |doi-access=free }}</ref><ref>{{cite journal | vauthors = Ditzen M, Pellegrino M, Vosshall LB | title = Insect odorant receptors are molecular targets of the insect repellent DEET | journal = Science | volume = 319 | issue = 5871 | pages = 1838–42 | date = March 2008 | pmid = 18339904 | doi = 10.1126/science.1153121 | bibcode = 2008Sci...319.1838D | s2cid = 18499590 | author3-link = Leslie B. Vosshall }}</ref><ref>{{cite journal | vauthors = Syed Z, Leal WS | title = Mosquitoes smell and avoid the insect repellent DEET | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 105 | issue = 36 | pages = 13598–603 | date = September 2008 | pmid = 18711137 | pmc = 2518096 | doi = 10.1073/pnas.0805312105 | doi-access = free }}</ref>

The name "mushroom alcohol" for 1-octen-3-ol comes from it first isolation by S. Murahashi in 1936 and 1938 from crushed ] mushrooms.<ref>{{cite journal | last1 = Murahashi | first1 = S. | title = Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 34, 155 | journal = Chemical Absracts | volume = 31 | page = 21617 }}</ref><ref>{{cite journal | last1 = Murahashi | first1 = S. | title = Sci. Pap. Inst. Phys. Chem. Res. (Jpn.) 30, 263 | journal = Chemical Absracts | volume = 32 | page = 27078 }}</ref> A recent study on volatiles of this mushroom has shown this compound is only produced upon tissue disruption.<ref>{{cite journal |journal= Biochemical Systematics and Ecology |volume=35 | year=2007 |title= Changing volatile compounds from mycelium and sporocarp of American matsutake mushroom, ''Tricholoma magnivelare'' |author1=Wood W. F. |author2=Lefevre C. K. |issue=9 | doi= 10.1016/j.bse.2007.03.001 |pages=634–636|bibcode=2007BioSE..35..634W }}</ref>
This alcohol is found in many other mushrooms where it may play a role as an ].<ref>{{cite journal | last1 = Wood | first1 = William F. | last2 = Archer | first2 = Cynthia L. | last3 = Largent | first3 = David L. | year = 2001 | title = 1-Octen-3-ol, a banana slug antifeedant from mushrooms | journal = Biochemical Systematics and Ecology | volume = 29 | issue = 5 | pages = 531–533| doi=10.1016/s0305-1978(00)00076-4| pmid = 11274773 | bibcode = 2001BioSE..29..531W }}</ref>

== Natural occurrence==
Octenol is produced by several plants and fungi, including ]s and ]. Octenol is formed during oxidative breakdown of ].<ref>{{ cite web
|title = Chemical properties of attractants
|access-date = 2010-06-08
|url = http://www.nri.org/tsetse/FAQ/chemprop.html
|archive-url = https://web.archive.org/web/20090427113618/http://www.nri.org/tsetse/FAQ/chemprop.html
|archive-date = 2009-04-27
|url-status = dead
}}</ref> Octenol is responsible for the moldy odor of damp indoor environments.<ref>{{cite journal | vauthors = Bennett JW, Inamdar AA | title = Are Some Fungal Volatile Organic Compounds (VOCs) Mycotoxins? | journal = Toxins | year = 2015 | volume = 7 | issue = 9 | pages = 3785–3804 | doi = 10.3390/toxins7093785 | doi-access = free | pmc = 4591661
| pmid = 26402705 }}</ref>

It is also a ], defined as a ], occurring in wines made with ] contaminated grape.<ref name="pmid23675852">{{cite journal | vauthors = Steel CC, Blackman JW, Schmidtke LM | title = Grapevine bunch rots: Impacts on wine composition, quality, and potential procedures for the removal of wine faults | journal = Journal of Agricultural and Food Chemistry | volume = 61 | issue = 22 | pages = 5189–206 | date = June 2013 | pmid = 23675852 | doi = 10.1021/jf400641r }}</ref>

==Properties==
1-octen-3-ol is a ] derived from ]. It exists in the form of two ]s, (''R'')-(−)-1-octen-3-ol and (''S'')-(+)-1-octen-3-ol.
:]{{clear-left}}

== Synthesis ==
Two possible lab syntheses of 1-octen-3-ol are:<ref>{{cite journal|last1=Wnuk|first1=S.|last2=Kinastowski|first2=S.|last3=Kamiński|first3=E.|date=1983|title=Synthesis and analysis of 1-octen-3-ol, the main flavour component of mushrooms|url=https://pubmed.ncbi.nlm.nih.gov/6684212/|journal=Die Nahrung|volume=27|issue=5|pages=479–486|doi=10.1002/food.19830270523|issn=0027-769X|pmid=6684212}}</ref>

* by the Grignard reaction of ] and amyl iodide
* by the selective reduction of ]

Biochemically, 1-octen-3-ol is generated from the ] of ], catalyzed by a ], followed by cleavage of the resulting hydroperoxide with the help of a ]. This reaction takes place in cheese and is used in biotechnology to produce the ''(R)''-isomer.<ref>{{cite journal|last1=Matsui|first1=Kenji|last2=Sasahara|first2=Satomi|last3=Akakabe|first3=Yoshihiko|last4=Kajiwara|first4=Tadahiko|date=2003|title=Linoleic acid 10-hydroperoxide as an intermediate during formation of 1-octen-3-ol from linoleic acid in Lentinus decadetes|journal=Bioscience, Biotechnology, and Biochemistry|volume=67|issue=10|pages=2280–2282|doi=10.1271/bbb.67.2280|issn=0916-8451|pmid=14586122|s2cid=46173472 |doi-access=free}}</ref><ref>{{cite book |last1=Min Kuo |first1=Tsung |url=https://www.worldcat.org/oclc/48691412 |title=Lipid biotechnology |last2=Gardner |first2=Harold W. |date=2002 |publisher=Marcel Dekker |isbn=0-585-40371-6 |location=New York |oclc=48691412}}</ref>

]

==Uses==
Octenol is used, sometimes in combination with ], to attract insects in order to kill them with certain electrical devices.<ref name="epa">{{cite web |date=2007-07-05 |title=Biopesticides Fact Sheet for Octenol |url=https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_G-126_05-Jul-07.pdf |access-date=2022-06-28 |work=EPA fact sheet}}</ref>

The name 'mushroom alcohol' is used because octenol is the main flavor component of ]s.<ref>{{cite web|url=http://www.thegoodscentscompany.com/data/rw1024051.html|title=1-octen-3-ol|date=|website=thegoodscentscompany.com|access-date=2015-05-31}}</ref>

==Health and safety==
Octenol is approved by the ] as a ].<ref>{{cite web
|author = US FDAs Center for Food Safety and Applied Nutrition
|title = US FDA/CFSAN – EAFUS List
|access-date = 2008-03-16
|url = http://vm.cfsan.fda.gov/~dms/eafus.html
|archive-url = https://web.archive.org/web/20080221184706/http://vm.cfsan.fda.gov/~dms/eafus.html
|archive-date = 2008-02-21
|url-status = dead
}}</ref> It is of moderate ]ity with an ] of 340&nbsp;mg/kg.<ref name=epa/>

In an animal study, octenol has been found to disrupt ] ] and may be an environmental agent involved in ].<ref>{{cite journal | vauthors = Inamdar AA, Hossain MM, Bernstein AI, Miller GW, Richardson JR, Bennett JW | title = Fungal-derived semiochemical 1-octen-3-ol disrupts dopamine packaging and causes neurodegeneration | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 110 | issue = 48 | pages = 19561–6 | date = November 2013 | pmid = 24218591 | pmc = 3845153 | doi = 10.1073/pnas.1318830110 | bibcode = 2013PNAS..11019561I | doi-access = free }}</ref>

== See also ==
* ]
* ], the ketone analog that gives blood on skin its typical metallic, mushroom-like smell<ref>{{cite journal | vauthors = Glindemann D, Dietrich A, Staerk HJ, Kuschk P | title = The two odors of iron when touched or pickled: (skin) carbonyl compounds and organophosphines | journal = Angewandte Chemie | volume = 45 | issue = 42 | pages = 7006–9 | date = October 2006 | pmid = 17009284 | doi = 10.1002/anie.200602100 | doi-access = | s2cid = 45055136 }}
</ref>
* ], the acetate ester of this compound

== References ==
{{Reflist}}

{{Alcohols}}
{{Authority control}}

{{DEFAULTSORT:Octen-3-ol, 1-}}
]
]
]