Record Information
Version1.0
Creation Date2016-05-19 02:20:23 UTC
Update Date2016-11-09 01:09:50 UTC
Accession NumberCHEM007004
Identification
Common NameOLEIC ACID, FROM TALL OIL FATTY ACIDS
ClassSmall Molecule
DescriptionMajor constituent of plant oils e.g. olive oil (ca. 80%), almond oil (ca. 80%) and many others, mainly as glyceride. Constituent of tall oiland is also present in apple, melon, raspberry oil, tomato, banana, roasted peanuts, black tea, rice bran, cardamon, plum brandy, peated malt, dairy products and various animal fats. Component of citrus fruit coatings. Emulsifying agent in foods Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable fats. The trans isomer of oleic acid is called elaidic acid.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical 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 Mass282.461 g/mol
Monoisotopic Mass282.256 g/mol
CAS Registry Number977047-39-4
IUPAC Name(9Z)-octadec-9-enoic acid
Traditional Nameoleic acid
SMILESCCCCCCCC\C=C\CCCCCCCC(O)=O
InChI IdentifierInChI=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-MDZDMXLPSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
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
Bioavailability0ChemAxon
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, 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 - 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 - EI-B (Unknown) , Positivesplash10-052f-9100000000-de078efada08e691dbb8Spectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0090000000-755e8d1537818580a2fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-4690000000-ca39c5846217fe093227Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9830000000-fcb2923d448d11c54559Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-e809fd7222cf63431b77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1090000000-9c340e3d19cbe7013ccdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-6e517cda629fcd4df07dSpectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-350dc6d7ac541a3c5b67Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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
MSDSNot Available
General References
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3. Jensen MD: Gender differences in regional fatty acid metabolism before and after meal ingestion. J Clin Invest. 1995 Nov;96(5):2297-303.
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15. Vinggaard AM, Provost JJ, Exton JH, Hansen HS: Arf and RhoA regulate both the cytosolic and the membrane-bound phospholipase D from human placenta. Cell Signal. 1997 Feb;9(2):189-96.
16. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69.
17. Mittendorfer B, Liem O, Patterson BW, Miles JM, Klein S: What does the measurement of whole-body fatty acid rate of appearance in plasma by using a fatty acid tracer really mean? Diabetes. 2003 Jul;52(7):1641-8.
18. Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4.
19. Bajaj M, Suraamornkul S, Romanelli A, Cline GW, Mandarino LJ, Shulman GI, DeFronzo RA: Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients. Diabetes. 2005 Nov;54(11):3148-53.
20. Andersen TC, Pedersen JF, Nordentoft T, Olsen O: Fat and mesenteric blood flow. Scand J Gastroenterol. 1999 Sep;34(9):894-7.
21. Ayala-Bravo HA, Quintanar-Guerrero D, Naik A, Kalia YN, Cornejo-Bravo JM, Ganem-Quintanar A: Effects of sucrose oleate and sucrose laureate on in vivo human stratum corneum permeability. Pharm Res. 2003 Aug;20(8):1267-73.
22. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
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27. https://www.ncbi.nlm.nih.gov/pubmed/?term=18772370
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=19761868
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=23844805
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32. https://www.ncbi.nlm.nih.gov/pubmed/?term=25794012
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=5332408
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=6205897