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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:46 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 has 8 carbon atoms. 2-Octenoic acid is also known as an olefinic fatty acid carrying a double bond at position 2. It can exist in two isomeric forms, the cis and the trans form, with the trans or 2-E form being more abundant. 2-Octenoic acid is a relatively hydrophobic molecule with a water solubility of approximately 1 g/L. The 2E-isomer has a musty, sour, cheesy aroma and a fatty or waxy taste. 2-Octenoic acid is found in the human body and is naturally produced by hepatic microsomal oxidation of aliphatic aldehydes. 2-Octenoic acid has been detected in human urine and plasma (PMID 1883862 , 8087979 , 4086594 , 1417834 , 6480773 ). 2-Octenoic acid has also been identified as a potential pheromone excreted by the male abdominal glands of the cockroach Leucophaea maderae (PMID: 17200891 ). Outside the human body 2-Octenoic acid has been detected in coffee, cranberries, mushrooms, black tea and strawberries. It is also used as a food flavourant for baked goods and candies.
Structure
Thumb
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point5 - 6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility797.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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 IDFDB022010
KNApSAcK IDC00031683
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 IDNot Available
Good Scents IDrw1621221
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)Not Available
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 ]
  6. 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. [PubMed:17200891 ]