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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:45:09 UTC
Update Date2022-03-07 02:56:31 UTC
HMDB IDHMDB0040215
Secondary Accession Numbers
  • HMDB40215
Metabolite Identification
Common Namecis-3-Hexenyl acetate
Descriptioncis-3-Hexenyl acetate, also known as (Z)-3-hexenol acetic acid or acetate(3Z)-3-hexen-1-ol, is an acetate ester that results from the formal condensation of acetic acid with (Z)-hex-3-en-1-ol. It has a role as a metabolite. It is an acetate ester and an olefinic compound. It derives from a (Z)-hex-3-en-1-ol and an acetic acid. It 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). 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. cis-3-Hexenyl acetate has been detected, but not quantified, in several different foods, such as tamarinds, sunburst squash (pattypan squash), carobs, pepper (Capsicum baccatum), and swedes.
Structure
Data?1588265586
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 Weight142.1956
Monoisotopic Molecular Weight142.099379692
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

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point75.00 to 76.00 °C. @ 23.00 mm HgThe Good Scents Company Information System
Water Solubility0.9 g/L @ 20 °C (exp)The Good Scents Company Information System
LogP2.415 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.98 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.34531661259
DarkChem[M-H]-129.71331661259
DeepCCS[M+H]+136.07130932474
DeepCCS[M-H]-133.10130932474
DeepCCS[M-2H]-169.91130932474
DeepCCS[M+Na]+144.96230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-3-Hexenyl acetateCC\C=C/CCOC(C)=O1380.7Standard polar33892256
cis-3-Hexenyl acetateCC\C=C/CCOC(C)=O994.5Standard non polar33892256
cis-3-Hexenyl acetateCC\C=C/CCOC(C)=O1036.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - cis-3-Hexenyl acetate EI-B (Non-derivatized)splash10-0006-9000000000-92d448bb2099c2ca8a3e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis-3-Hexenyl acetate EI-B (Non-derivatized)splash10-0006-9000000000-92d448bb2099c2ca8a3e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Hexenyl acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-f0acc67e981853b1d2152016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Hexenyl acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00kf-9000000000-b9d062023fc53ab220c02015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl acetate 10V, Positive-QTOFsplash10-0006-4900000000-5520b4c1a8e0f15f98a32016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl acetate 20V, Positive-QTOFsplash10-001i-9200000000-0c1cce4833b8fb266c602016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl acetate 40V, Positive-QTOFsplash10-0006-9000000000-36ca2a715407a2dd76802016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl acetate 10V, Negative-QTOFsplash10-0006-7900000000-db796ac26e9c69e965282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl acetate 20V, Negative-QTOFsplash10-0a4l-9200000000-289d9b380c452347bbc52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl acetate 40V, Negative-QTOFsplash10-0a4l-9000000000-c8bb62799d02cf5f0d9c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl acetate 10V, Positive-QTOFsplash10-053r-9000000000-a56ff074a6b1befb6aa12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl acetate 20V, Positive-QTOFsplash10-0a4i-9000000000-d9067f1965f70e27bba92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl acetate 40V, Positive-QTOFsplash10-0a4i-9000000000-2a8e4bb754618aaff1ec2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl acetate 10V, Negative-QTOFsplash10-0a4l-9500000000-24eb76b62584688443552021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl acetate 20V, Negative-QTOFsplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl acetate 40V, Negative-QTOFsplash10-052f-9000000000-1411093172d173726d272021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1001471
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .