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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:48:59 UTC
HMDB IDHMDB0000207
Secondary Accession Numbers
  • HMDB0002066
  • HMDB00207
  • HMDB02066
Metabolite Identification
Common NameOleic acid
DescriptionOleic acid (or 9Z)-Octadecenoic acid) is an unsaturated C-18 or an omega-9 fatty acid that is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. The name derives from the Latin word oleum, which means oil. Oleic acid is the most abundant fatty acid in human adipose tissue, and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils. Triglycerides of oleic acid represent the majority of olive oil (about 70%). Oleic acid triglycerides also make up 59-75% of pecan oil, 61% of canola oil, 36-67% of peanut oil, 60% of macadamia oil, 20-80% of sunflower oil, 15-20% of grape seed oil, sea buckthorn oil, 40% of sesame oil, and 14% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80%) and canola oil (70%) also have been developed. consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, the ability of oleic acid to raise HDL is still debated. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. It is also used as an emulsifying agent in foods and pharmaceuticals. Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent.
Structure
Data?1600188291
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
Physiological effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point13.4 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg173.87530932474
[M-H]-Not Available175.2http://allccs.zhulab.cn/database/detail?ID=AllCCS00000183
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.56531661259
DarkChem[M-H]-177.26531661259
AllCCS[M+H]+179.56932859911
AllCCS[M-H]-179.42832859911
DeepCCS[M+H]+180.77130932474
DeepCCS[M-H]-176.75230932474
DeepCCS[M-2H]-213.90330932474
DeepCCS[M+Na]+189.82830932474
AllCCS[M+H]+179.632859911
AllCCS[M+H-H2O]+176.632859911
AllCCS[M+NH4]+182.332859911
AllCCS[M+Na]+183.132859911
AllCCS[M-H]-179.432859911
AllCCS[M+Na-2H]-181.032859911
AllCCS[M+HCOO]-182.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Oleic acidCCCCCCCC\C=C/CCCCCCCC(O)=O3141.2Standard polar33892256
Oleic acidCCCCCCCC\C=C/CCCCCCCC(O)=O2093.8Standard non polar33892256
Oleic acidCCCCCCCC\C=C/CCCCCCCC(O)=O2150.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oleic acid,1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[Si](C)(C)C2217.5Semi standard non polar33892256
Oleic acid,1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2477.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Oleic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00vi-9500000000-cdb5366d3ece43c3e1662014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oleic acid GC-MS (1 TMS)splash10-00nb-5900000000-fc03835c9c8fddb279702014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oleic acid EI-B (Non-derivatized)splash10-052f-9100000000-7618883a87bd14687fd52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oleic acid GC-EI-TOF (Non-derivatized)splash10-00vi-9500000000-cdb5366d3ece43c3e1662017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oleic acid GC-MS (Non-derivatized)splash10-00nb-5900000000-fc03835c9c8fddb279702017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9640000000-29b5681d79890854ef2b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0fe0-9431000000-1879934642ac672cb4012017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-350dc6d7ac541a3c5b672018-05-25Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-00l2-4790000000-aefa66e9f83fcb24ead62012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0apm-9100000000-a71c58b95cb65487eeed2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0aou-9000000000-5889cbe3dd606123df502012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negative-QTOFsplash10-001i-0090000000-89531b488fbe899c09e62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid ESI-TOF 10V, Negative-QTOFsplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid ESI-TOF 20V, Negative-QTOFsplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid ESI-TOF 30V, Negative-QTOFsplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid ESI-TOF , Negative-QTOFsplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid ESI-TOF 10V, Negative-QTOFsplash10-001i-0090000000-92096c6b229762c5295f2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid ESI-TOF 20V, Negative-QTOFsplash10-001i-0090000000-5fe8495a19b387bf702c2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid ESI-TOF 30V, Negative-QTOFsplash10-001i-0090000000-5d40399b1c736b4764452017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid ESI-TOF , Negative-QTOFsplash10-001i-0090000000-45785aeb659bd8a092402017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid ESI-TOF 10V, Negative-QTOFsplash10-001i-0091000000-3946ac7663105c7c27002017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid LC-ESI-IT , negative-QTOFsplash10-001i-0090000000-ce1372cb3b5e841223492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid LC-ESI-TOF , negative-QTOFsplash10-001i-0090000000-92096c6b229762c5295f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid LC-ESI-TOF , negative-QTOFsplash10-001i-0090000000-5fe8495a19b387bf702c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid LC-ESI-TOF , negative-QTOFsplash10-001i-0090000000-5d40399b1c736b4764452017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid 20V, Negative-QTOFsplash10-001i-0090000000-58579e8fd3d4191bcfad2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid 10V, Negative-QTOFsplash10-001i-0090000000-d495e7abd2148c8c35822021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid 35V, Negative-QTOFsplash10-001i-0090000000-18d19c433b2ebed71fcf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00ls-4790000000-d753b2905852ca2a8cbd2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0apm-9100000000-8d5c8ecf0c7a7cc3ccf62012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0aou-9000000000-64594906d693e8a086502012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid EI-B (Unknown) , Positive-QTOFsplash10-052f-9100000000-de078efada08e691dbb82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oleic acid 20V, Positive-QTOFsplash10-00l6-9450000000-10bf11713f51451a37972021-09-20HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Epidermis
  • Intestine
  • Liver
  • Pancreas
  • Placenta
  • Prostate
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.42 +/- 1.67 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified122 +/- 56 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified346.950 +/- 38.943 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified332.789 +/- 49.564 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified339.869 +/- 42.484 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified339.869 +/- 31.863 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified130 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified131 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified158 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified191 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified202 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified236 uMAdult (>18 years old)BothNormal