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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:05:40 UTC
Update Date2019-07-23 06:13:16 UTC
HMDB IDHMDB0033378
Secondary Accession Numbers
  • HMDB33378
Metabolite Identification
Common Namecis-3-Hexenyl hexanoate
Descriptioncis-3-Hexenyl hexanoate is found in citrus. cis-3-Hexenyl hexanoate is a constituent of tabasco peppers (Capsicum frutescens). Aroma component of green tea. Also present in orange peel oil, guava fruit, feijoa fruit, purple passion fruit and other fruits. cis-3-Hexenyl hexanoate is a flavouring agent.
Structure
Data?1563862396
Synonyms
ValueSource
(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
Chemical FormulaC12H22O2
Average Molecular Weight198.3019
Monoisotopic Molecular Weight198.161979948
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
DescriptionThis compound 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:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9200000000-6b8bf26be0b89f832734JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-6900000000-60bec3c7e65911e262eaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-9200000000-4188927f3a46e915411fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9000000000-0e2ff7ec5d5432598d88JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-7900000000-3b843d69c5d696b4a4e6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-9800000000-16645f3f41eb56d0cd95JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mn-9100000000-aee95e7003d3f7477494JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • 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
FoodDB IDFDB011408
KNApSAcK IDNot Available
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
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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. [PubMed:16902246 ]
  3. 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. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.