Chemistry: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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28857 Y
ChemSpider	21105914 Y
EC Number	231-192-8
KEGG	C08492 Y
PubChem CID	5281167
RTECS number	MP8400000
UNII	V14F8G75P4 Y
InChI InChI=1S/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3- Y Key: UFLHIIWVXFIJGU-ARJAWSKDSA-N Y 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
Safety data sheet	External MSDS
NFPA 704 (fire diamond)	2 0 0
Flash point	44 °C (111 °F)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	4700 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tracking categories (test):

• SizeSet

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.

External links

• Pheromone database
• Molecule of the Month: Hexenal
• That Worm at the Bottom of Your Mezcal Isn’t a Total Lie