Record Information
Version1.0
Creation date2010-04-08 22:10:21 UTC
Update date2019-11-26 03:07:34 UTC
Primary IDFDB012765
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePetroselinic acid
DescriptionPetroselinic acid, also known as (6Z)-petroselinate or octadec-6C-ensaere, 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. Petroselinic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number593-39-5
Structure
Thumb
Synonyms
SynonymSource
(6Z)-Octadecenoic acidChEBI
(6Z)-Petroselinic acidChEBI
(Z)-6-Octadecenoic acidChEBI
cis-6-Octadecenoic acidChEBI
cis-Delta(6)-Octadecenoic acidChEBI
cis-Octadec-6-enoic acidChEBI
cis-Omega-12-octadecenoic acidChEBI
cis-Petroselinic acidChEBI
Octadec-6C-ensaereChEBI
PetroseleninsaeureChEBI
PetroselinsaeureChEBI
(6Z)-OctadecenoateGenerator
(6Z)-PetroselinateGenerator
(Z)-6-OctadecenoateGenerator
cis-6-OctadecenoateGenerator
cis-delta(6)-OctadecenoateGenerator
cis-Δ(6)-octadecenoateGenerator
cis-Δ(6)-octadecenoic acidGenerator
cis-Octadec-6-enoateGenerator
cis-Omega-12-octadecenoateGenerator
cis-PetroselinateGenerator
PetroselinateGenerator
Petroselenic acidMeSH
Petroselinic acid, (Z)-isomerMeSH
Petroselinic acid, (e)-isomerMeSH
Petroselinic acid, sodium salt, (Z)-isomerMeSH
(6Z)-6-Octadecenoatebiospider
(6Z)-6-Octadecenoic acidbiospider
(6Z)-Octadec-6-enoatebiospider
(6Z)-Octadec-6-enoic acidbiospider
6-Octadecenoic acid, (Z)-biospider
6Z-Octadecenoatebiospider
6Z-Octadecenoic acidbiospider
cis-Delta(6)-OctadecenoateChEBI
cis-delta(6)-Octadecenoic acidGenerator
cis-δ(6)-octadecenoateGenerator
cis-δ(6)-octadecenoic acidGenerator
Petroselinic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.00012 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
Polarizability37.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H34O2
IUPAC name(6Z)-octadec-6-enoic acid
InChI IdentifierInChI=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)/b13-12-
InChI KeyCNVZJPUDSLNTQU-SEYXRHQNSA-N
Isomeric SMILESCCCCCCCCCCC\C=C/CCCCC(O)=O
Average Molecular Weight282.4614
Monoisotopic Molecular Weight282.255880332
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 76.54%; H 12.13%; O 11.33%DFC
Melting PointMp 33°DFC
Boiling PointBp0.15 148-152°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0536-9200000000-566b9687fd3f631b2d76Spectrum
GC-MSPetroselinic acid, 1 TMS, GC-MS Spectrumsplash10-015a-5900000000-b74b3a322c8500719900Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0090000000-2974141038ed15c88780Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bi-3690000000-5adf754223a5d1b0454cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-8930000000-46a003c6ec476363e14bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-f0e7bcdc491383b7e254Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1090000000-5c0f89f012fa34d58535Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9230000000-d4a51bb41317cdba5d11Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID4574391
ChEMBL IDNot Available
KEGG Compound IDC08363
Pubchem Compound ID5461010
Pubchem Substance IDNot Available
ChEBI ID28194
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02080
CRC / DFC (Dictionary of Food Compounds) IDGMC63-W:HKR48-P
EAFUS IDNot Available
Dr. Duke IDPETROSELINIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001235
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.