CIS-3-HEXEN-1-OL (CHEM005145)

Record Information
Version1.0
Creation Date2016-05-19 01:58:36 UTC
Update Date2026-03-27 01:02:49 UTC
Accession NumberCHEM005145
Identification
Common NameCIS-3-HEXEN-1-OL
ClassSmall Molecule
Description
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.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3Z)-3-Hexen-1-olChEBI
(3Z)-Hex-3-en-1-olChEBI
(Z)-3-Hexen-1-olChEBI
BlatteralkoholChEBI
cis-3-Hexen-1-olChEBI
Leaf alcoholChEBI
(Z)-3-Hexeno1MeSH
3-Hexen-1-ol, (Z)-isomerMeSH
cis-3-HexenolMeSH
3-Hexen-1-olMeSH, KEGG
(3Z)-HexenolHMDB
(Z)-3-HexenolHMDB
(Z)-Hex-3-en-1-olHMDB
1-Hydroxy-3-hexeneHMDB
3Z-Hexen-1-olHMDB
beta-gamma-HexenolHMDB
cis-1-Hydroxy-3-hexeneHMDB
cis-3-Hexene-1-olHMDB
cis-3-Hexenyl alcoholHMDB
β-γ-HexenolHMDB
Folic alcoholPhytoBank
Green leaf alcoholPhytoBank
cis-Hex-3-en-1-olPhytoBank
Chemical FormulaC6H12O
Average Molecular Mass100.159 g/mol
Monoisotopic Mass100.089 g/mol
CAS Registry Number928-96-1
IUPAC Name(3Z)-hex-3-en-1-ol
Traditional Namecis-3-hexenol
SMILESCC\C=C/CCO
InChI IdentifierInChI=1S/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3-
InChI KeyUFLHIIWVXFIJGU-ARJAWSKDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentFatty alcohols
Alternative Parents
Substituents
  • Fatty alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.2 g/LALOGPS
logP1.69ALOGPS
logP1.33ChemAxon
logS-0.79ALOGPS
pKa (Strongest Acidic)16.79ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.45 m³·mol⁻¹ChemAxon
Polarizability12.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0030003
FooDB IDFDB008091
Phenol Explorer IDNot Available
KNApSAcK IDC00000356
BiGG IDNot Available
BioCyc IDCIS-3-HEXENOL
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCis-3-Hexen-1-ol
Chemspider ID21105914
ChEBI ID28857
PubChem Compound ID5281167
Kegg Compound IDC08492
YMDB IDYMDB01420
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16132223
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21628908
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22714804
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23001219
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23678819
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23749439
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23923622
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24301200
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=27717473
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=5351709
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16. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
17. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
18. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
19. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
20. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
21. The lipid handbook with CD-ROM