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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:05:43 UTC
Update Date2023-02-21 17:23:17 UTC
HMDB IDHMDB0033379
Secondary Accession Numbers
  • HMDB33379
Metabolite Identification
Common Namecis-3-Hexenyl benzoate
Descriptioncis-3-Hexenyl benzoate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. cis-3-Hexenyl benzoate is a balsam, fatty, and floral tasting compound. cis-3-Hexenyl benzoate has been detected, but not quantified in, several different foods, such as green tea, fruits, cauliflowers (Brassica oleracea var. botrytis), black tea, and red tea. This could make cis-3-hexenyl benzoate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on cis-3-Hexenyl benzoate.
Structure
Data?1677000197
Synonyms
ValueSource
cis-3-Hexenyl benzoic acidGenerator
(3Z)-3-Hexenyl benzoateHMDB
(Z)-3-Hexen-1-ol benzoateHMDB
(Z)-3-Hexen-1-yl benzoateHMDB
(Z)-3-Hexen-1-yl-benzoateHMDB
3-Hexenyl ester(Z)-benzoic acidHMDB
Benzoic acid cis-3-hexenyl esterHMDB
cis-3-HEXENYLBENZOATEHMDB
cis-Hexenyl-3-benzoateHMDB
FEMA 3688HMDB
Hex-3(Z)-enyl benzoateHMDB
Z-Hex-3-en-1-yl benzoateHMDB
(3Z)-Hex-3-en-1-yl benzoic acidGenerator
Chemical FormulaC13H16O2
Average Molecular Weight204.2649
Monoisotopic Molecular Weight204.115029756
IUPAC Name(3Z)-hex-3-en-1-yl benzoate
Traditional Name(3Z)-hex-3-en-1-yl benzoate
CAS Registry Number25152-85-6
SMILES
CC\C=C/CCOC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C13H16O2/c1-2-3-4-8-11-15-13(14)12-9-6-5-7-10-12/h3-7,9-10H,2,8,11H2,1H3/b4-3-
InChI KeyBCOXBEHFBZOJJZ-ARJAWSKDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Benzoyl
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point105.00 °C. @ 1.00 mm HgThe Good Scents Company Information System
Water Solubility13.95 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.241 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP4.01ALOGPS
logP3.83ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity62.28 m³·mol⁻¹ChemAxon
Polarizability23.5 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.131661259
DarkChem[M-H]-147.87931661259
DeepCCS[M+H]+151.13730932474
DeepCCS[M-H]-148.77930932474
DeepCCS[M-2H]-183.59130932474
DeepCCS[M+Na]+158.51530932474
AllCCS[M+H]+147.432859911
AllCCS[M+H-H2O]+143.532859911
AllCCS[M+NH4]+151.032859911
AllCCS[M+Na]+152.032859911
AllCCS[M-H]-151.532859911
AllCCS[M+Na-2H]-152.132859911
AllCCS[M+HCOO]-152.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-3-Hexenyl benzoateCC\C=C/CCOC(=O)C1=CC=CC=C12218.5Standard polar33892256
cis-3-Hexenyl benzoateCC\C=C/CCOC(=O)C1=CC=CC=C11544.2Standard non polar33892256
cis-3-Hexenyl benzoateCC\C=C/CCOC(=O)C1=CC=CC=C11609.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - cis-3-Hexenyl benzoate EI-B (Non-derivatized)splash10-0arr-9200000000-81473c0496fc70351f742017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis-3-Hexenyl benzoate EI-B (Non-derivatized)splash10-0arr-9200000000-81473c0496fc70351f742018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Hexenyl benzoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-5900000000-24ce24a8a400301321f12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Hexenyl benzoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Hexenyl benzoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl benzoate 10V, Positive-QTOFsplash10-0a4i-4590000000-c298928447b5a209f0c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl benzoate 20V, Positive-QTOFsplash10-053r-9510000000-b14533d3e60c2e0986562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl benzoate 40V, Positive-QTOFsplash10-0pb9-9400000000-73f1d324b8e569da50032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl benzoate 10V, Negative-QTOFsplash10-0udi-2390000000-6a51e4dc0ebb2b14427b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl benzoate 20V, Negative-QTOFsplash10-0fmi-4920000000-8faaff6228db81dd742e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl benzoate 40V, Negative-QTOFsplash10-004i-9500000000-aa7ab13bab5a978c797d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl benzoate 10V, Negative-QTOFsplash10-0udi-2290000000-a447828716a58558249d2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl benzoate 20V, Negative-QTOFsplash10-004i-9400000000-439f09e35f1256bc4ba42021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl benzoate 40V, Negative-QTOFsplash10-004i-9000000000-45e282b3ab3faf17eda72021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl benzoate 10V, Positive-QTOFsplash10-0a4i-6930000000-c1bbdcd8df87eee6ff0a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl benzoate 20V, Positive-QTOFsplash10-0a4i-8900000000-a983e11ecd6fb207d0c02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl benzoate 40V, Positive-QTOFsplash10-0a4i-9800000000-a8c09a6fa2c563a4bfec2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB011409
KNApSAcK IDC00029345
Chemspider ID4519192
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5367706
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1001382
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.. .