(E)-2-OCTENOIC ACID (CHEM006967)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:19:58 UTC
Update Date2016-11-09 01:09:50 UTC
Accession NumberCHEM006967
Identification
Common Name(E)-2-OCTENOIC ACID
ClassSmall Molecule
Description2-Octenoic acid is a normal organic acid produced by hepatic microsomal oxidation of aliphatic aldehydes and is a metabolite naturally found in the urine and plasma. (PMID 1883862, 8087979, 4086594, 1417834, 6480773) [HMDB]
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass142.196 g/mol
Monoisotopic Mass142.099 g/mol
CAS Registry Number1871-67-6
IUPAC Name(2Z)-oct-2-enoic acid
Traditional Namecis-2-octenoic acid
SMILESCCCCC\C=C\C(O)=O
InChI IdentifierInChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6+
InChI KeyCWMPPVPFLSZGCY-VOTSOKGWSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9100000000-35fbf6036a26b499b040Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-a8d30352fd0b19afc3f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-45f40a1dbaae13a04daeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-0900000000-e92c8d4ba859e2c18a1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0596-0900000000-15af8a5dc0356cd2f4b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-5f0acc9c148a535551fdSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000392
FooDB IDFDB022010
Phenol Explorer IDNot Available
KNApSAcK IDC00031683
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID4146
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4445840
ChEBI IDNot Available
PubChem Compound ID5282713
Kegg Compound IDNot Available
YMDB IDYMDB16141
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Dupont, Georges; Dulou, Raymond; Pigerol, Charles. Kharasch reactions with 1-heptene. Synthesis of octanoic and 2-octenoic acid. Compt. rend. (1955), 240 628-9.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. Farine JP, Sirugue D, Abed-Vieillard D, Everaerts C, Le Quere JL, Bonnard O, Brossut R: The male abdominal glands of Leucophaea maderae: chemical identification of the volatile secretion and sex pheromone function. J Chem Ecol. 2007 Feb;33(2):405-15. doi: 10.1007/s10886-006-9224-7. Epub 2007 Jan 3.