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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2020-02-26 21:23:47 UTC
HMDB IDHMDB0002080
Secondary Accession Numbers
  • HMDB02080
Metabolite Identification
Common NamePetroselinic acid
DescriptionPetroselinic acid is a cis-monoenoic fatty acid, and is present as a major component in parsley seeds (and many other species of the Umbelliferae family), described first in 1909 (Vongerichten, E. Kohler, A. Petroselic Acid, a New Oleic Acid. Berichte der Deutschen Chemischen Gesellschaft (1909), 42 1638-9.). Petroselinic acid is an important oleochemical material for the food, cosmetics, chemistry and pharmaceutical (PMID: 16604360 ).
Structure
Data?1582752227
Synonyms
ValueSource
18:1N-6ChEBI
6-OctadecensaeureChEBI
C18:1N-6ChEBI
Octadec-6-ensaeureChEBI
PetroselinateGenerator
Octadec-6-enoateHMDB
Petroselinic acid, (e)-isomerHMDB
Petroselinic acid, sodium salt, (Z)-isomerHMDB
Petroselenic acidHMDB
Petroselinic acid, (Z)-isomerHMDB
Petroselinic acidMeSH
Chemical FormulaC18H34O2
Average Molecular Weight282.468
Monoisotopic Molecular Weight282.255880335
IUPAC Nameoctadec-6-enoic acid
Traditional Name6-octadecenoic acid
CAS Registry Number593-39-5
SMILES
CCCCCCCCCCCC=CCCCCC(O)=O
InChI Identifier
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20)
InChI KeyCNVZJPUDSLNTQU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point29.8 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.9e-05 g/LALOGPS
logP7.72ALOGPS
logP6.78ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.4 m³·mol⁻¹ChemAxon
Polarizability37.64 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-015a-5900000000-b74b3a322c8500719900Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-92eaf2fd267975519c73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-3590000000-a09c373d95774671d77aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9830000000-5407ff71f907bbcff81eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-1b80c5a75129c09b94aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-0090000000-594a087f3d32d156a36bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9130000000-ca75de66449608dc0999Spectrum
MSMass Spectrum (Electron Ionization)splash10-0536-9200000000-566b9687fd3f631b2d76Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2010 +/- 530 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2170 +/- 600 uMAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012765
KNApSAcK IDNot Available
Chemspider ID11144
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPetroselinic acid
METLIN IDNot Available
PubChem Compound11634
PDB IDNot Available
ChEBI ID36022
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceChobanov, D.; Agova, M.; Chuparova, E.; Chalukova, R. Preparation of pure petroselinic acid. Journal of the American Oil Chemists' Society (1966), 43(11), 625-6.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Metzger JO, Bornscheuer U: Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. Appl Microbiol Biotechnol. 2006 Jun;71(1):13-22. Epub 2006 Apr 8. [PubMed:16604360 ]