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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:57 UTC
HMDB IDHMDB00573
Secondary Accession NumbersNone
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
(9E)-Octadecenoic acidChEBI
(e)-Oleic acidChEBI
9-OCTADECENOIC ACIDChEBI
9-trans-Octadecenoic acidChEBI
Acide elaidiqueChEBI
D9-trans-Octadecenoic acidChEBI
ElaidinsaureChEBI
ElaidinsaeureChEBI
trans-9-Octadecenoic acidChEBI
trans-D9-Octadecenoic acidChEBI
trans-Delta(9)-Octadecenoic acidChEBI
trans-Elaidic acidChEBI
trans-Oleic acidChEBI
(9E)-OctadecenoateGenerator
(e)-Octadec-9-enoateGenerator
(e)-OleateGenerator
9-OCTADECENOateGenerator
9-trans-OctadecenoateGenerator
D9-trans-OctadecenoateGenerator
trans-9-OctadecenoateGenerator
trans-D9-OctadecenoateGenerator
trans-delta(9)-OctadecenoateGenerator
trans-δ(9)-octadecenoateGenerator
trans-δ(9)-octadecenoic acidGenerator
trans-ElaidateGenerator
trans-OleateGenerator
ElaidateHMDB
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 KeyInChIKey=ZQPPMHVWECSIRJ-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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point42 - 44 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.78Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility0.000121 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.4 m3·mol-1ChemAxon
Polarizability37.64 Å3ChemAxon
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
MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-350dc6d7ac541a3c5b67View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
Tissue Location
  • Adipose Tissue
  • Fibroblasts
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified100.00 (42.20 - 128.08) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothColorectal cancer details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothColorectal cancer details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002951
KNApSAcK IDNot Available
Chemspider ID553123
KEGG Compound IDC00712
BioCyc IDNot Available
BiGG ID38213
Wikipedia LinkElaidic acid
NuGOwiki LinkHMDB00573
Metagene LinkHMDB00573
METLIN ID3406
PubChem Compound445639
PDB IDOLA
ChEBI ID27997
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. [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. [15309454 ]