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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2017-12-07 01:47:02 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
(6Z)-OctadecenoateChEBI
(6Z)-PetroselinateChEBI
(Z)-6-OctadecenoateChEBI
cis-Delta(6)-OctadecenoateChEBI
cis-Octadec-6-enoateChEBI
cis-Omega-12-octadecenoateChEBI
cis-PetroselinateChEBI
(6Z)-Octadecenoic acidGenerator
PetroselinateGenerator
(6Z)-Petroselinic acidGenerator
(Z)-6-Octadecenoic acidGenerator
cis-delta(6)-Octadecenoic acidGenerator
cis-δ(6)-octadecenoateGenerator
cis-δ(6)-octadecenoic acidGenerator
cis-Octadec-6-enoic acidGenerator
cis-Omega-12-octadecenoic acidGenerator
cis-Petroselinic acidGenerator
(6Z)-6-OctadecenoateHMDB
(6Z)-6-Octadecenoic acidHMDB
(6Z)-Octadec-6-enoateHMDB
(6Z)-Octadec-6-enoic acidHMDB
cis-6-OctadecenoateHMDB
cis-6-Octadecenoic acidHMDB
Chemical FormulaC18H33O2
Average Molecular Weight281.4534
Monoisotopic Molecular Weight281.2480553
IUPAC Name(6Z)-octadec-6-enoate
Traditional Namepetroselinate
CAS Registry Number593-39-5
SMILES
CCCCCCCCCCC\C=C/CCCCC([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)/p-1/b13-12-
InChI KeyCNVZJPUDSLNTQU-SEYXRHQNSA-M
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Carboxylic acid salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

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
logP7.75ALOGPS
logP6.78ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity98.24 m³·mol⁻¹ChemAxon
Polarizability36.36 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-e258d2b6ea17cffea226View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-0090000000-5b0f98e625b1928fed12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4390000000-51f8a672b2a06711e56eView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012765
KNApSAcK IDC00001235
Chemspider ID4574391
KEGG Compound IDC08363
BioCyc IDCPD-8477
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6476
PubChem Compound5461010
PDB IDNot Available
ChEBI ID32375
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 ]