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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-09-07 20:56:21 UTC
HMDB IDHMDB0000573
Secondary Accession Numbers
  • HMDB00573
Metabolite Identification
Common NameElaidic acid
DescriptionElaidic acid is the major trans fat found in hydrogenated vegetable oils and occurs in small amounts in caprine and bovine milk (very roughly 0.1 % of the fatty acids) [1] and some meats. It is the trans isomer of oleic acid. The name of the elaidinization reaction comes from elaidic acid. Elaidic acid increases CETP activity, which in turn raises VLDL and lowers HDL cholesterol. (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
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-octadecenoicMeSH
Acid, oleicMeSH
9 Octadecenoic acidMeSH
Acid, cis-9-octadecenoicMeSH
cis 9 Octadecenoic acidMeSH
Chemical FormulaC18H34O2
Average Molecular Weight282.4614
Monoisotopic Molecular Weight282.255880332
IUPAC Name(9E)-octadec-9-enoic acid
Traditional Nameelaidic acid
CAS Registry Number112-79-8
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-MDZDMXLPSA-N
Chemical Taxonomy
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point42 - 44 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.78Extrapolated
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
Polarizability37.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-5900000000-3ba79fbe1b1b3b18c0ffView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00nb-5900000000-3ba79fbe1b1b3b18c0ffView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-3900000000-26468e9cc1331164ac25View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9640000000-29b5681d79890854ef2bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fe0-9431000000-1879934642ac672cb401View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0090000000-755e8d1537818580a2fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-4690000000-ca39c5846217fe093227View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9830000000-fcb2923d448d11c54559View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-e809fd7222cf63431b77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1090000000-9c340e3d19cbe7013ccdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-6e517cda629fcd4df07dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-350dc6d7ac541a3c5b67View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Adipose Tissue
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified100.00 (42.20 - 128.08) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
FecesDetected but not Quantified Newborn (0-30 days old)Not Specified
Premature neonates
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ]
  2. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  3. Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012858
KNApSAcK IDC00001232
Chemspider ID393217
KEGG Compound IDC00712
BioCyc IDOLEATE-CPD
BiGG IDNot Available
Wikipedia LinkOleic_acid
METLIN ID190
PubChem Compound445639
PDB IDOLA
ChEBI ID16196
References
Synthesis ReferenceVitagliano, Michele. Formation of elaidic acid. Oli, Grassi, Derivati (1967), 111(12), 77-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Andrei G, Snoeck R, Neyts J, Sandvold ML, Myhren F, De Clercq E: Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. Antiviral Res. 2000 Mar;45(3):157-67. [PubMed:10771080 ]
  2. Stachowska E, Dolegowska B, Chlubek D, Wesolowska T, Ciechanowski K, Gutowski P, Szumilowicz H, Turowski R: Dietary trans fatty acids and composition of human atheromatous plaques. Eur J Nutr. 2004 Oct;43(5):313-8. Epub 2004 Jan 27. [PubMed:15309454 ]