Compound Summary

General Compound Information

(Z)-3-hexenol

Description
(Z)-hex-3-en-1-ol is a hex-3-en-1-ol in which the double bond adopts a Z-configuration. Also known as leaf alcohol, it is emitted by green plants upon mechanical damage. Used as a flavourant in tea. It has a role as an insect attractant, a plant metabolite and a fragrance.
Synonyms
cis-3-Hexen-1-ol;  928-96-1;  (Z)-Hex-3-en-1-ol;  cis-3-Hexenol;  Leaf alcohol;
FlavorDB ID
2942
PUBCHEM ID
Molecular Weight
100.16
Molecular Formula
C6H12O
Openeye Can Smiles
CCC=CCCO
IUPAC Inchikey
UFLHIIWVXFIJGU-ARJAWSKDSA-N
Compound Classification
  • ClassyFire Ontology
Compound Quality
CATEGORY QUALITY THRESHOLD OCCURENCE REFERENCE
smell green leaves 7.987e-5 µmol/L olive oil details
smell Lettuce-like 3.894e-2 µmol/L details
smell Lettuce-like 1.298e-1 µmol/L details
smell 3.894e-2 µmol/L curry leaf details
smell lettuce-like 3.894e-2 µmol/L green tea details
smell grassy( green, sharp) water details
smell grassy( green, sharp) 6.994e-1 µmol/L water details
Compound Toxicity and Food Additive Safety (OFAS)
Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
IDENTIFICATION AND USE: 3-Hexenol is a colorless liquid. It has a strong, fresh-cut grass odor and a fresh green, fruity taste. It is released to the air from a variety of plants including grass, clover, alfalfa, grapes, onions, peaches and oak trees. It is present in the green parts of nearly all plants. It is reported to be found in several essential oils and in many fruit juices and is a component of tobacco smoke. 3-Hexenol is used as a fragrance in perfumes, household cleaners, and food flavoring.
HUMAN EXPOSURE AND TOXICITY: Tested at 4% in petrolatum, 3-hexenol produced no irritation after a 48 hour closed patch test in humans. Odorization of inert gas can serve to warn workers in an enclosed space. A psychophysical investigation examined 3-hexenol as a candidate for the possible odorization of argon. The detection threshold for 3-hexenol in argon was 19 ppb. 3-Hexenol did not induce any statistically significant increases in the frequency of human lymphocytes with chromosome aberrations in either the absence or presence of a liver enzyme metabolizing system.
ANIMAL STUDIES: The LD50 of 3-hexenol in rats and mice was in the range of 7-10 g/kg by the oral route and 0.4-0.6 g/kg by the intraperitoneal route. No effects were seen at 310 and 1250 ppm, but in males of the 5000-ppm group the intake of drinking water was reduced compared with controls, the relative kidney weight was increased and the urine collected in the first 2 hr after a water load was more concentrated. In females, the only finding was a transitory anemia at this level. In another study, 3-hexanol applied at full strength to rabbit skin for 24 hours produced no irritation. In rats, an analysis of Fos protein was performed as a way of investigating the effects of inhalation of green odor (a mixture of of trans-2-hexenal and 3-hexenol) on the neuronal activations in stress-related forebrain regions induced by acute and repeated stress. Green odor had inhibitory effects on the stress-induced corticosterone response, body-weight loss, and adrenal hypertrophy. In another study, the reproductive toxicity via the oral route was assessed in rats at dose levels of 100, 300 and 1000 mg/kg/day. Based on the results of the study, a NOAEL for general toxicity in males and females was considered to be 1000 mg/kg/day, the highest dose level tested. The potential mutagenicity of 3-hexenol on the thymidine kinase, TK +/-, locus of the L5178Y mouse lymphoma cell line was assessed. 3-Hexenol did not induce any toxicologically significant increases in the mutant frequency at the TK +/- locus in L5178Y cells and is therefore considered to be non-mutagenic under the conditions of the test.
Source: DrugBank or Hazardous Substances Data Bank (HSDB)
Food Additive Safety (OFAS)
CIS-3-HEXEN-1-OL is used for FLAVORING AGENT OR ADJUVANT. More food additive safty information please view GRAS report.
EFSA's chemical Hazards Database : OpenFoodTox
This compound is found in OpenFoodTox with the name: Hex-3(cis)-en-1-ol
Receptors
Receptor REFERENCE EC50 [µM] Effective Concentration [µM]
OR2J3 details Activated
OR2W1 details Activated
Consensus Spectra
Spectrum Type Spectrum View Description Polarity
Experimental GCMS view GCMS positive