Cis-3-Hexen-1-ol

{{DISPLAYTITLE:''cis''-3-Hexen-1-ol}} {{chembox | Watchedfields = changed | verifiedrevid = 446436268 | Name = ''cis''-3-Hexen-1-ol | ImageFile = Cis-3-Hexenol.svg | ImageSize = 150px | ImageFile1 = Cis-hex-3-en-1-ol-from-xtal-3D-bs-17.png | ImageSize1 = 150px | PIN = (3''Z'')-Hex-3-en-1-ol | OtherNames = |Section1={{Chembox Identifiers | UNII_Ref = {{fdacite|correct|FDA}} | UNII = V14F8G75P4 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C08492 | InChI = 1/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3- | InChIKey = UFLHIIWVXFIJGU-ARJAWSKDBI | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3- | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = UFLHIIWVXFIJGU-ARJAWSKDSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=928-96-1 | PubChem=5281167 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 28857 | SMILES=CC\C=C/CCO | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 21105914 | RTECS = MP8400000 | EINECS = 231-192-8 }} |Section2={{Chembox Properties | Formula=C6H12O | MolarMass=100.159 g/mol | Appearance=colorless liquid | Density=0.846 g/cm3 | MeltingPtC=-61 | BoilingPtC=156.5 | Solubility=very slightly soluble | SolubleOther = soluble in ethanol, ether }} |Section3={{Chembox Hazards | ExternalSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=PL&language=EN-generic&productNumber=W256307&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2Fw256307%3Flang%3Dpl External MSDS] | MainHazards= | NFPA-H = 0 | NFPA-F = 2 | NFPA-R = 0 | FlashPt={{convert|44|C|F}} | AutoignitionPt = | LD50 = 4700 mg/kg (rat, oral) }} }}

'''''cis''-3-Hexen-1-ol''', also known as '''(''Z'')-3-hexen-1-ol''' and '''leaf alcohol''', is a colorless oily liquid with an intense grassy-green odor of freshly cut green grass and leaves. It is produced in small amounts by most plants and it acts as an attractant to many predatory insects. ''cis''-3-Hexen-1-ol is an important aroma compound that is used in fruit and vegetable flavors and in perfumes. The yearly production is about 30 tonnes. Its esters are also important flavor and fragrance raw materials.

The related aldehyde ''cis''-3-hexenal (leaf aldehyde) has a similar and even stronger smell but is relatively unstable and isomerizes into the conjugated ''trans''-2-hexenal.

This compound has been recognized as a semiochemical involved in mechanisms and behaviors of attraction in diverse animals such as insects and mammals.

==Human odor perception== A pair of two single-nucleotide polymorphisms, both in the gene for the OR2J3 odor receptor, strongly reduce sensitivity to this odorant.<ref name="McRae2012">{{cite journal |vauthors=McRae JF, Mainland JD, Jaeger SR, Adipietro KA, Matsunami H, Newcomb RD | title = Genetic Variation in the Odorant Receptor OR2J3 is Associated with the Ability to Detect the "Grassy" Smelling Odor, cis-3-hexen-1-ol | journal = Chemical Senses | volume = 37 | issue = 7 | pages = 585–593 | year = 2012 | pmid = 22714804 | pmc = 3408771 | doi = 10.1093/chemse/bjs049 }}</ref>

==References== <references/>

==External links== * [https://web.archive.org/web/20050429182138/http://www.pherobase.com/database/compounds-detail-Z3-6OH.html Pheromone database] * [http://www.chm.bris.ac.uk/motm/hexenal/hexenalh.htm Molecule of the Month: Hexenal] * [https://www.vice.com/en/article/that-worm-at-the-bottom-of-your-mezcal-isnt-a-lie-1/ That Worm at the Bottom of Your Mezcal Isn’t a Total Lie]

{{DEFAULTSORT:Hex-1-ol, cis-3-}} Category:Flavors Category:Alkenols