cis-3-Hexen-1-ol

*cis*-3-Hexen-1-ol
Names
	Preferred IUPAC name (3Z)-Hex-3-en-1-ol
Identifiers
CAS Number	928-96-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28857 ;
ChemSpider	21105914 ;
ECHA InfoCard	100.011.994
EC Number	231-192-8;
KEGG	C08492 ;
PubChem CID	5281167;
RTECS number	MP8400000;
UNII	V14F8G75P4 ;
CompTox Dashboard (EPA)	DTXSID6022137 ;
	InChI InChI=1S/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3- Key: UFLHIIWVXFIJGU-ARJAWSKDSA-N ; InChI=1/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3- Key: UFLHIIWVXFIJGU-ARJAWSKDBI;
	SMILES CC\C=C/CCO;
Properties
Chemical formula	C6H12O
Molar mass	100.159 g/mol
Appearance	colorless liquid
Density	0.846 g/cm3
Melting point	−61 °C (−78 °F; 212 K)
Boiling point	156.5 °C (313.7 °F; 429.6 K)
Solubility in water	very slightly soluble
Solubility	soluble in ethanol, ether
Hazards
NFPA 704 (fire diamond)	0 2 0
Flash point	44 °C (111 °F)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	4700 mg/kg (rat, oral)
Safety data sheet (SDS)	External MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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 a very important aroma compound that is used in fruit and vegetable flavors and in perfumes. The yearly production is about 30 tonnes.

cis-3-Hexen-1-ol is an alcohol and 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. However, there is no scientific evidence of its aphrodisiac effects in humans. The popular Mexican alcoholic beverage, mezcal, is found to have enhanced concentrations of this compound when a maguey worm is served in the glass.

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.^[1]

References

^ McRae JF, Mainland JD, Jaeger SR, Adipietro KA, Matsunami H, Newcomb RD (2012). "Genetic Variation in the Odorant Receptor OR2J3 is Associated with the Ability to Detect the "Grassy" Smelling Odor, cis-3-hexen-1-ol". Chemical Senses. 37 (7): 585–593. doi:10.1093/chemse/bjs049. PMC 3408771. PMID 22714804.

External links

[McRae2012-1] McRae JF, Mainland JD, Jaeger SR, Adipietro KA, Matsunami H, Newcomb RD (2012). "Genetic Variation in the Odorant Receptor OR2J3 is Associated with the Ability to Detect the "Grassy" Smelling Odor, cis-3-hexen-1-ol". Chemical Senses. 37 (7): 585–593. doi:10.1093/chemse/bjs049. PMC 3408771. PMID 22714804.

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