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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:08 UTC
HMDB IDHMDB0000392
Secondary Accession Numbers
  • HMDB00392
Metabolite Identification
Common Name2-Octenoic acid
Description2-Octenoic acid, also known as 2-octenoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 2-Octenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752128
Synonyms
ValueSource
2-OctenoateGenerator
cis-2-Octenoic acidHMDB
(Z)-2-Octenoic acidHMDB
2-Octenic acidHMDB
2Z-OctenoateHMDB
2Z-Octenoic acidHMDB
Oct-2-enoateHMDB
Oct-2-enoic acidHMDB
trans-2-OctenoateHMDB
2-Octenoic acidHMDB
Chemical FormulaC8H14O2
Average Molecular Weight142.1956
Monoisotopic Molecular Weight142.099379692
IUPAC Name(2Z)-oct-2-enoic acid
Traditional Namecis-2-octenoic acid
CAS Registry Number1577-96-4
SMILES
CCCCC\C=C/C(O)=O
InChI Identifier
InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6-
InChI KeyCWMPPVPFLSZGCY-SREVYHEPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • 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
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point5 - 6 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.74 g/LALOGPS
logP3.01ALOGPS
logP2.7ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)5.25ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.37 m³·mol⁻¹ChemAxon
Polarizability16.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0096-9000000000-801c8e0537a0c78cb64fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0096-9000000000-801c8e0537a0c78cb64fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054x-9100000000-685aa1c309f4024a258cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05i3-9300000000-009fbcd018a04b967cd1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9200000000-ea14afb080f00f6db329Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0fk9-9000000000-e4e0cfcba513035e593dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-9000000000-ff984717b537e96ab368Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-13db6226b25ca6e887e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003v-9400000000-5c8132b1452fb86685a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9000000000-d964983e7540bbe985aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-bdaae44d4773ffd6a29cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006y-3900000000-f923ee2d24c2c936a395Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9100000000-3f6317b29935f491c0f3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Microsomes
Biospecimen LocationsNot Available
Tissue Locations
  • Liver
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 IDFDB001088
KNApSAcK IDNot Available
Chemspider ID4445840
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID4146
PubChem Compound5282713
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceDupont, Georges; Dulou, Raymond; Pigerol, Charles. Kharasch reactions with 1-heptene. Synthesis of octanoic and 2-octenoic acid. Compt. rend. (1955), 240 628-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Watanabe K, Matsunaga T, Narimatsu S, Yamamoto I, Yoshimura H: Mouse hepatic microsomal oxidation of aliphatic aldehydes (C8 to C11) to carboxylic acids. Biochem Biophys Res Commun. 1992 Oct 15;188(1):114-9. [PubMed:1417834 ]
  3. Libert R, Draye JP, Van Hoof F, Schanck A, Soumillion JP, de Hoffmann E: Study of reactions induced by hydroxylamine treatment of esters of organic acids and of 3-ketoacids: application to the study of urines from patients under valproate therapy. Biol Mass Spectrom. 1991 Feb;20(2):75-86. [PubMed:1883862 ]
  4. Yanagisawa I, Yamane M, Urayama T: Simultaneous separation and sensitive determination of free fatty acids in blood plasma by high-performance liquid chromatography. J Chromatogr. 1985 Dec 13;345(2):229-40. [PubMed:4086594 ]
  5. Tsuchiya H, Hayashi T, Sato M, Tatsumi M, Takagi N: Simultaneous separation and sensitive determination of free fatty acids in blood plasma by high-performance liquid chromatography. J Chromatogr. 1984 Jul 13;309(1):43-52. [PubMed:6480773 ]