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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2018-05-20 19:06:04 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
Thumb
Synonyms
ValueSource
18:1N-6ChEBI
6-OctadecensaeureChEBI
C18:1N-6ChEBI
Octadec-6-ensaeureChEBI
Octadec-6-enoateGenerator
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
DescriptionThis compound 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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationNot 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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID11144
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11634
PDB IDNot Available
ChEBI ID36022
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 ]