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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2021-10-13 04:37:22 UTC
HMDB IDHMDB0002080
Secondary Accession Numbers
  • HMDB02080
Metabolite Identification
Common NamePetroselinic acid
DescriptionPetroselinic acid, also known as (6Z)-Octadecenoic acid, is an 18-carbon unsaturated fatty acid that occurs naturally in several animal and vegetable fats and oils. It is a white powder and is commercially available. In chemical terms, petroselinic acid is classified as a monounsaturated omega-12 fatty acid, abbreviated as 18:1 cis-6. Petroselinic acid is a positional isomer of oleic acid. The term "petroselinic" means related to, or derived from, oil of Petroselinum, or oil of parsley. Petroselinic acid was first isolated from parsley seed oil in 1909. Petroselinic acid occurs in high amounts in plants in the Apiaceae family (a family of mostly aromatic flowering plants named after the genus Apium and commonly known as the celery, carrot or parsley family), Araliaceae (a family of flowering plants composed of about 43 genera and around 1500 species consisting of primarily woody plants and some herbaceous plants), Griselinia (Griseliniaceae) and in Garryaceae. The occurrence of petroselinic acid as the major fatty acid is used in chemosystematics as a proof of a close relationship of several families within the Apiales as well as within the Garryales. Petroselonic acid has been found in coriander (Coriandrum sativum) and cumin (Cuminum cyminum) and caraway seeds. In addition, petroselinic acid has been found in minor amounts in several fats of plant and animal origin, including in human sources. Petroselinic acid is an important oleochemical material for the food, cosmetics, chemistry and pharmaceutical industry (PMID: 16604360 ) as it can be easily processed into lauric and adipinic acid.
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point29.8 °CNot Available
Boiling Point399.00 to 400.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.012 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP7.481 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.9e-05 g/LALOGPS
logP10(7.72) g/LALOGPS
logP10(6.78) g/LChemAxon
logS10(-6.4) g/LALOGPS
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
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Petroselinic acid,1TMS,#1CCCCCCCCCCCC=CCCCCC(=O)O[Si](C)(C)C2216.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Petroselinic acid,1TBDMS,#1CCCCCCCCCCCC=CCCCCC(=O)O[Si](C)(C)C(C)(C)C2470.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Petroselinic acid GC-MS (1 TMS)splash10-015a-5900000000-b74b3a322c85007199002018-05-25HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Petroselinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Petroselinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0536-9200000000-566b9687fd3f631b2d762018-05-25Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petroselinic acid 10V, Positive-QTOFsplash10-014i-0090000000-92eaf2fd267975519c732019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petroselinic acid 20V, Positive-QTOFsplash10-014r-3590000000-a09c373d95774671d77a2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petroselinic acid 40V, Positive-QTOFsplash10-006x-9830000000-5407ff71f907bbcff81e2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petroselinic acid 10V, Negative-QTOFsplash10-001i-0090000000-1b80c5a75129c09b94ae2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petroselinic acid 20V, Negative-QTOFsplash10-01qi-0090000000-594a087f3d32d156a36b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petroselinic acid 40V, Negative-QTOFsplash10-0a4l-9130000000-ca75de66449608dc09992019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petroselinic acid 10V, Negative-QTOFsplash10-001i-0090000000-8b8562cadde7e7a8ba4f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petroselinic acid 20V, Negative-QTOFsplash10-01q9-1090000000-594ebc89873b9a07daab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petroselinic acid 40V, Negative-QTOFsplash10-0006-9120000000-53ca828fdedf1b6b53542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petroselinic acid 10V, Positive-QTOFsplash10-00lr-2290000000-b0d2eeeebe9b395823a62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petroselinic acid 20V, Positive-QTOFsplash10-05nb-9520000000-a105cfcc2e8bdbf85fe62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Petroselinic acid 40V, Positive-QTOFsplash10-0a4m-9000000000-4f913ba39936bf42fbe32021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDC00001235
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
MarkerDB IDNot Available
Good Scents IDrw1589961
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 ]