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Record Information
Version1.0
Creation Date2016-07-13 19:42:12 UTC
Update Date2016-07-20 20:50:30 UTC
LmdbLMDB00093
Secondary Accession NumbersNone
Metabolite Identification
Common NameOleic acid
DescriptionOleic acid is an unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed) Biological Source: Major constituent of plant oils e.g. olive oil (about 80%), almond oil (about 80%) and many others, mainly as glyceride. Constituent of tall oil and present in fruits Use/Importance: Food additive. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. Emulsifying agent in foods and pharmaceuticals. Biological Use/Importance: Skin penetrant. Herbicide, insecticide, fungicide (Dictionary of Organic Compounds). Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colourless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. The term "oleic" means related to, or derived from, oil or olive, the oil that is predominantly composed of oleic acid. (Wiki).
Structure
Thumb
Synonyms
ValueSource
(9Z)-Octadecenoic acidChEBI
(Z)-Octadec-9-enoic acidChEBI
18:1 N-9ChEBI
18:1DElta9cisChEBI
C18:1 N-9ChEBI
cis-9-Octadecenoic acidChEBI
cis-Delta(9)-Octadecenoic acidChEBI
cis-Oleic acidChEBI
FA 18:1ChEBI
Octadec-9-enoic acidChEBI
OelsaeureChEBI
OleateChEBI
(9Z)-OctadecenoateGenerator
(Z)-Octadec-9-enoateGenerator
cis-9-OctadecenoateGenerator
cis-delta(9)-OctadecenoateGenerator
cis-Δ(9)-octadecenoateGenerator
cis-Δ(9)-octadecenoic acidGenerator
cis-OleateGenerator
Octadec-9-enoateGenerator
(9Z)-9-OctadecenoateHMDB
(9Z)-9-Octadecenoic acidHMDB
(Z)-9-OctadecanoateHMDB
(Z)-9-Octadecanoic acidHMDB
9,10-OctadecenoateHMDB
9,10-Octadecenoic acidHMDB
9-(Z)-OctadecenoateHMDB
9-(Z)-Octadecenoic acidHMDB
9-OctadecenoateHMDB
9-Octadecenoic acidHMDB
Century CD fatty acidHMDB
cis-Octadec-9-enoateHMDB
cis-Octadec-9-enoic acidHMDB
DistolineHMDB
Emersol 210HMDB
Emersol 211HMDB
Emersol 213HMDB
Emersol 220 white oleateHMDB
Emersol 220 white oleic acidHMDB
Emersol 221 low titer white oleateHMDB
Emersol 221 low titer white oleic acidHMDB
Emersol 233LLHMDB
Emersol 6321HMDB
Emersol 6333 NFHMDB
Emersol 7021HMDB
Glycon roHMDB
Glycon woHMDB
Groco 2HMDB
Groco 4HMDB
Groco 5lHMDB
Groco 6HMDB
Industrene 104HMDB
Industrene 105HMDB
Industrene 205HMDB
Industrene 206HMDB
L'acide oleiqueHMDB
MetauponHMDB
OelsauereHMDB
Oleic acid extra pureHMDB
OleinateHMDB
Oleinic acidHMDB
PamolynHMDB
Pamolyn 100HMDB
Pamolyn 100 FGHMDB
Pamolyn 100 FGKHMDB
Pamolyn 125HMDB
Priolene 6900HMDB
Red oilHMDB
Tego-oleic 130HMDB
Vopcolene 27HMDB
Wecoline ooHMDB
Z-9-OctadecenoateHMDB
Z-9-Octadecenoic acidHMDB
Acid, 9-octadecenoicHMDB
Acid, oleicHMDB
9 Octadecenoic acidHMDB
Acid, cis-9-octadecenoicHMDB
cis 9 Octadecenoic acidHMDB
FA(18:1(9Z))HMDB
FA(18:1n9)HMDB
Chemical FormulaC18H34O2
Average Molecular Weight282.4614
Monoisotopic Molecular Weight282.255880332
IUPAC Name(9Z)-octadec-9-enoic acid
Traditional Nameoleic acid
CAS Registry Number112-80-1
SMILES
CCCCCCCC\C=C/CCCCCCCC(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/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
InChI KeyZQPPMHVWECSIRJ-KTKRTIGZSA-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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.68ALOGPS
logP6.78ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.4 m³·mol⁻¹ChemAxon
Polarizability37.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00vi-9500000000-cdb5366d3ece43c3e166Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-5900000000-fc03835c9c8fddb27970Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9100000000-7618883a87bd14687fd5Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00vi-9500000000-cdb5366d3ece43c3e166Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00nb-5900000000-fc03835c9c8fddb27970Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9640000000-29b5681d79890854ef2bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fe0-9431000000-1879934642ac672cb401Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-00l2-4790000000-aefa66e9f83fcb24ead6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0apm-9100000000-a71c58b95cb65487eeedSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0aou-9000000000-5889cbe3dd606123df50Spectrum
LC-MS/MSLC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negativesplash10-001i-0090000000-89531b488fbe899c09e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-92096c6b229762c5295fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-5fe8495a19b387bf702cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090000000-5d40399b1c736b476445Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-45785aeb659bd8a09240Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0091000000-3946ac7663105c7c2700Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0090000000-ce1372cb3b5e84122349Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-92096c6b229762c5295fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-5fe8495a19b387bf702cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-5d40399b1c736b476445Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-58579e8fd3d4191bcfadSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-d495e7abd2148c8c3582Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0090000000-18d19c433b2ebed71fcfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ls-4790000000-d753b2905852ca2a8cbdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0apm-9100000000-8d5c8ecf0c7a7cc3ccf6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aou-9000000000-64594906d693e8a08650Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-052f-9100000000-de078efada08e691dbb8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00l6-9450000000-10bf11713f51451a3797Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-350dc6d7ac541a3c5b67Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Follicular Fluid
  • Milk
  • Muscle
  • Oocyte
  • Oocyte (zona-intact oocytes)
  • Plasma
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Follicular FluidDetected but not QuantifiedNot ApplicableNot AvailablePorcine
    • Warzych, E., Cies...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Lawrence K. Cream...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MuscleDetected but not QuantifiedNot ApplicableNot AvailableBovine details
OocyteDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Oocyte (zona-intact oocytes)Detected but not QuantifiedNot ApplicableNot AvailableBovine details
Oocyte (zona-intact oocytes)Detected but not QuantifiedNot ApplicableNot AvailablePorcine details
Oocyte (zona-intact oocytes)Detected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified1.1 +/- 0.3 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0000207
FooDB IDFDB012858
Phenol Explorer IDNot Available
KNApSAcK IDC00001232
BiGG IDNot Available
BioCyc IDOLEATE-CPD
METLIN ID190
PDB IDNot Available
Wikipedia LinkOleic_acid
Chemspider ID393217
ChEBI ID16196
PubChem Compound ID445639
Kegg Compound IDC00712
YMDB IDYMDB00131
ECMDB IDECMDB21423
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available