Showing Compound Card for 3-Hexen-1-ol-acetate (CDB000527)

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Record Information
Version1.0
Created at2020-03-19 00:41:56 UTC
Updated at2020-12-07 19:07:29 UTC
CannabisDB IDCDB000527
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3-Hexen-1-ol-acetate
Description3-Hexenyl acetate also known as 3-Hexen-1-ol-acetate, belongs to the class of organic compounds known as esters. These are carboxylic acid derivatives in which the acid hydrogen atom has been replaced by an alkyl moiety, forming an ester group. 3-Hexenyl acetate is an acetate ester that results from the formal condensation of acetic acid with (Z)-hex-3-en-1-ol or (E)-hex-3-en-1-ol, for this reason there are two 3-hexenyl-acetate isomers, trans- and cis-hexenyl-acetate. Cis-3-hexenyl acetate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Cis-3-hexenyl acetate is a sweet, apple, and banana tasting compound and it is therefore used as a food additive. Cis-3-hexenyl acetate has been detected, but not quantified in, several different foods such as tamarinds, sunburst squash (pattypan squash), carobs, pepper (C. baccatum), and swedes. 3-Hexenyl acetate has also been detected as a volatile component of cannabis samples obtained in police seizures (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Z)-3-Hexen-1-yl acetateChEBI
(Z)-3-Hexenol acetateChEBI
(Z)-3-Hexenyl acetateChEBI
(Z)-Hex-3-enyl acetateChEBI
3Z-Hexenyl acetateChEBI
cis-3-Hexen-1-yl acetateChEBI
cis-3-Hexenyl ethanoateChEBI
(3Z)-Hex-3-en-1-yl acetateKegg
(Z)-3-Hexen-1-yl acetic acidGenerator
(Z)-3-Hexenol acetic acidGenerator
(Z)-3-Hexenyl acetic acidGenerator
(Z)-Hex-3-enyl acetic acidGenerator
3Z-Hexenyl acetic acidGenerator
cis-3-Hexen-1-yl acetic acidGenerator
cis-3-Hexenyl ethanoic acidGenerator
(3Z)-Hex-3-en-1-yl acetic acidGenerator
cis-3-Hexenyl acetic acidGenerator
(3Z)-3-Hexenyl acetateHMDB
(Z)-3-Hexen-1-ol acetateHMDB
(Z)-3-Hexen-1-yl, acetateHMDB
1-Acetate(3Z)-3-hexen-1-olHMDB
3(Z)-Hexenyl acetateHMDB
3-Hexenol acetate, cisHMDB
Acetate(3Z)-3-hexen-1-olHMDB
Acetate(Z)-3-hexen-1-olHMDB
Acetic acid cis-3-hexenyl esterHMDB
cis-3-Hexen-1-ol, acetateHMDB
cis-3-Hexenol acetateHMDB
cis-3-Hexenyl-1-acetateHMDB
cis-Hex-3-enyl acetateHMDB
FEMA 3171HMDB
Hex-3(Z)-enyl acetateHMDB
Z-Hex-3-en-1-yl acetateHMDB
3-HexenylacetateMeSH, HMDB
3-Hexenyl acetateMeSH, HMDB
cis-3-Hexenyl acetateChEBI
(3Z)-Hexen-1-yl acetateHMDB
(Z)-Hex-3-en-1-yl acetateHMDB
3Z-Hexen-1-ol acetateHMDB
cis-3-Hexen-1-ol acetateHMDB
cis-Hex-3-en-1-yl acetateHMDB
Chemical FormulaC8H14O2
Average Molecular Weight142.2
Monoisotopic Molecular Weight142.0994
IUPAC Name(3Z)-hex-3-en-1-yl acetate
Traditional Name(Z)-3-hexenyl acetate
CAS Registry Number3681-71-8
SMILES
CC\C=C/CCOC(C)=O
InChI Identifier
InChI=1S/C8H14O2/c1-3-4-5-6-7-10-8(2)9/h4-5H,3,6-7H2,1-2H3/b5-4-
InChI KeyNPFVOOAXDOBMCE-PLNGDYQASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentCarboxylic acid esters
Alternative Parents
Substituents
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.47ALOGPS
logP1.77ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.6 m³·mol⁻¹ChemAxon
Polarizability16.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00kf-9000000000-b9d062023fc53ab220c02015-03-01View Spectrum
GC-MS3-Hexen-1-ol-acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-92d448bb2099c2ca8a3eSpectrum
GC-MS3-Hexen-1-ol-acetate, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-92d448bb2099c2ca8a3eSpectrum
Predicted GC-MS3-Hexen-1-ol-acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-f0acc67e981853b1d215Spectrum
Predicted GC-MS3-Hexen-1-ol-acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-4900000000-5520b4c1a8e0f15f98a32016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9200000000-0c1cce4833b8fb266c602016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-36ca2a715407a2dd76802016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-7900000000-db796ac26e9c69e965282016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9200000000-289d9b380c452347bbc52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-c8bb62799d02cf5f0d9c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053r-9000000000-a56ff074a6b1befb6aa12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-d9067f1965f70e27bba92021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-2a8e4bb754618aaff1ec2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-9500000000-24eb76b62584688443552021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-1411093172d173726d272021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0040215
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019927
KNApSAcK IDC00048964
Chemspider ID4515742
KEGG Compound IDC19757
BioCyc IDCPD-12846
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5363388
PDB IDNot Available
ChEBI ID61316
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]