Showing Compound Card for (Z)-3-Hexenyl hexanoate (CDB000179)

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Record Information
Version1.0
Created at2020-03-18 23:27:43 UTC
Updated at2020-12-07 19:07:13 UTC
CannabisDB IDCDB000179
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(Z)-3-Hexenyl hexanoate
Descriptioncis-3-Hexenyl hexanoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. cis-3-Hexenyl hexanoate is very hydrophobic, practically insoluble in water, and relatively neutral. cis-3-Hexenyl hexanoate has a fruity, grassy, and green taste. cis-3-Hexenyl hexanoate has been detected in citrus, fruits, herbs and spices, and tea. This could make cis-3-hexenyl hexanoate a potential biomarker for the consumption of these foods. cis-3-Hexenyl hexanoate is the main volatile compound that gives passion fruit its distinctive aroma ( Ref:DOI ). It is also found in cannabis plants (PMID:6991645 ) and in medical plants such as Chamomile (Matricaria recutita L. ( Ref:DOI 10.1021/bk-1993-0525.ch020).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
cis-3-Hexenyl hexanoic acidGenerator
(3Z)-3-Hexenyl hexanoateHMDB
(Z)-3-Hexen-1-ol, hexanoateHMDB
(Z)-3-Hexenyl hexanoateHMDB
(Z)-Hex-3-enyl hexanoateHMDB
3-Hexen-1-ol hexanoate, cisHMDB
3-Hexenyl ester(Z)-hexanoic acidHMDB
cis-3-Hexenyl caproateHMDB
cis-3-Hexenyl caproate (hexanoate)HMDB
cis-3-Hexenyl hexoateHMDB
cis-3-Hexenyl N-hexanoateHMDB
cis-beta -Hexenyl caproateHMDB
cis-Hexanoic acid, 3-hexenyl esterHMDB
FEMA 3403HMDB
Hexanoate(Z)-3-hexen-1-olHMDB
Hexanoic acid, (3Z)-3-hexen-1-yl esterHMDB
Hexanoic acid, (3Z)-3-hexenyl esterHMDB
Hexanoic acid, 3-hexenyl esterHMDB
N-Caproic acid cis-3-hexenyl esterHMDB
(Z)-3-Hexenyl hexanoic acidGenerator
Chemical FormulaC12H22O2
Average Molecular Weight198.3
Monoisotopic Molecular Weight198.162
IUPAC Name(3Z)-hex-3-en-1-yl hexanoate
Traditional Name(3Z)-hex-3-en-1-yl hexanoate
CAS Registry Number31501-11-8
SMILES
CCCCCC(=O)OCC\C=C/CC
InChI Identifier
InChI=1S/C12H22O2/c1-3-5-7-9-11-14-12(13)10-8-6-4-2/h5,7H,3-4,6,8-11H2,1-2H3/b7-5-
InChI KeyRGACQXBDYBCJCY-ALCCZGGFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • 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:

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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
logP4.41ALOGPS
logP3.81ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity60.03 m³·mol⁻¹ChemAxon
Polarizability24.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(Z)-3-Hexenyl hexanoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001l-9200000000-6b8bf26be0b89f832734Spectrum
Predicted GC-MS(Z)-3-Hexenyl hexanoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-6900000000-60bec3c7e65911e262ea2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-9200000000-4188927f3a46e915411f2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9000000000-0e2ff7ec5d5432598d882016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-7900000000-3b843d69c5d696b4a4e62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-9800000000-16645f3f41eb56d0cd952016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mn-9100000000-aee95e7003d3f74774942016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9300000000-16d125a0b88c2beb43112021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-50a82c936e6d627c174a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-15430215c9611d4361e52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9100000000-7557f7e2d6a690fbe62c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-7ec4d612cc342b3538a12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-9000000000-079f8ad4c0ad555edbc22021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0033378
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011408
KNApSAcK IDC00055585
Chemspider ID4509415
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5352543
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]