Record Information
Version1.0
Creation date2015-05-07 20:56:56 UTC
Update date2020-09-17 15:42:26 UTC
Primary IDFDB031070
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameoleate
DescriptionOleic acid, also known as oleate, 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. Oleic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 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 plant oil that is predominantly composed of oleic acid. Oleic acid is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. Fatty acids such as oleic acid occur primarily esters (not as free acids), mostly in the form of triglycerides, which are the greasy materials in many natural oils. Oleic acid is an odorless, colourless oil, although commercial samples may be yellowish. Oleic acid is particularly abundant in plant oils e.g. olive oil (about 80%), almond oil (about 80%) 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, 40% of sesame oil and 14% of poppyseed 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 used in the manufacturing of surfactants, soaps, plasticizers and as an emulsifying agent in foods, lotions, cosmetics and pharmaceuticals. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil . Altered levels of oleic acid have been found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
CAS Number112-80-1
Structure
Thumb
Synonyms
SynonymSource
(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
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H34O2
IUPAC name(9Z)-octadec-9-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/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
InChI KeyZQPPMHVWECSIRJ-KTKRTIGZSA-N
Isomeric SMILESCCCCCCCC\C=C/CCCCCCCC(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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Foods

Fats and oils:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
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)splash10-052f-9100000000-350dc6d7ac541a3c5b67Spectrum
GC-MSoleate, 1 TMS, GC-MS Spectrumsplash10-00vi-9500000000-cdb5366d3ece43c3e166Spectrum
GC-MSoleate, 1 TMS, GC-MS Spectrumsplash10-00nb-5900000000-fc03835c9c8fddb27970Spectrum
GC-MSoleate, non-derivatized, GC-MS Spectrumsplash10-052f-9100000000-7618883a87bd14687fd5Spectrum
GC-MSoleate, non-derivatized, GC-MS Spectrumsplash10-00vi-9500000000-cdb5366d3ece43c3e166Spectrum
GC-MSoleate, non-derivatized, GC-MS Spectrumsplash10-00nb-5900000000-fc03835c9c8fddb27970Spectrum
Predicted GC-MSoleate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f6x-9640000000-29b5681d79890854ef2bSpectrum
Predicted GC-MSoleate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fe0-9431000000-1879934642ac672cb401Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ls-4790000000-d753b2905852ca2a8cbdSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0apm-9100000000-8d5c8ecf0c7a7cc3ccf6Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aou-9000000000-64594906d693e8a08650Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-00l2-4790000000-aefa66e9f83fcb24ead6Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0apm-9100000000-a71c58b95cb65487eeedSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0aou-9000000000-5889cbe3dd606123df50Spectrum
MS/MSLC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negativesplash10-001i-0090000000-89531b488fbe899c09e6Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-052f-9100000000-de078efada08e691dbb8Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-92096c6b229762c5295fSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-5fe8495a19b387bf702cSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090000000-5d40399b1c736b476445Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-45785aeb659bd8a09240Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0091000000-3946ac7663105c7c2700Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0090000000-ce1372cb3b5e84122349Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-92096c6b229762c5295fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0090000000-755e8d1537818580a2fdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-4690000000-ca39c5846217fe093227Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9830000000-fcb2923d448d11c54559Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-e809fd7222cf63431b77Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1090000000-9c340e3d19cbe7013ccdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-6e517cda629fcd4df07dSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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
Flavours
FlavorCitations
fat
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference