Showing metabocard for Elaidic acid (BMDB0000573)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:33:00 UTC
Update Date2020-06-04 22:28:40 UTC
MCDB ID BMDB0000573
Secondary Accession Numbers
  • BMDB00573
  • BMDB0063575
  • BMDB63575
Metabolite Identification
Common NameElaidic acid
DescriptionElaidic acid, also known as (9E)-octadecenoic acid, 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. Elaidic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Elaidic 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) 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 (Wikipedia).
Structure
Thumb
MOLSDFPDBSMILESInChI
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)-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
ElaidateGenerator
FA(18:1(9E))HMDB
9-ElaidateHMDB
18:1 N-9HMDB
C18:1 N-9HMDB
Octadec-9-enoic acidHMDB
Octadec-9-enoateHMDB
9,10-OctadecenoateHMDB
9,10-Octadecenoic acidHMDB
Acid, 9-octadecenoicHMDB
9 Octadecenoic acidHMDB
(9E)-9-Octadecenoic acidHMDB
(e)-9-Octadecenoic acidHMDB
9-trans-Oleic acidHMDB
Elaidinic acidHMDB
delta9-trans-Octadecenoic acidHMDB
trans-delta9-Octadecenoic acidHMDB
trans-Δ9-octadecenoic acidHMDB
Δ9-trans-octadecenoic acidHMDB
Elaidic acidKEGG
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
[H]\C(CCCCCCCC)=C(\[H])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
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point42 - 44 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.78Extrapolated
Predicted Properties
PropertyValueSource
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-5900000000-3ba79fbe1b1b3b18c0ff2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00nb-5900000000-3ba79fbe1b1b3b18c0ff2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-3900000000-26468e9cc1331164ac252017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9640000000-29b5681d79890854ef2b2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fe0-9431000000-1879934642ac672cb4012017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001m-9570000000-3794dff1c5c1baa2e7a12021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-4690000000-393df6433d9c0c1e43572021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-07vi-9660000000-38c5c2044b6ae347c0b72021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0090000000-755e8d1537818580a2fd2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-4690000000-ca39c5846217fe0932272016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9830000000-fcb2923d448d11c545592016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-e809fd7222cf63431b772016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1090000000-9c340e3d19cbe7013ccd2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-6e517cda629fcd4df07d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-8b8562cadde7e7a8ba4f2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-1090000000-827ccf4b0fb321cd543d2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9220000000-1a90bd2c4041fc8d39eb2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-3290000000-e57551fac255cafaf4fd2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067j-9410000000-40bef334a898843c3baf2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-9000000000-96ff3dec9c358c726e352021-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-350dc6d7ac541a3c5b672014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected and Quantified10691 uMTotal fatty acid details
Detected and Quantified10691 uMTotal fatty acid details
Detected and Quantified2372 uMTotal fatty acid details
Detected and Quantified3681 uMTotal fatty acid details
Detected and Quantified2372 uMTotal fatty acid details
Detected and Quantified27225 uMTotal fatty acid details
Detected and Quantified26198 uMTotal fatty acid details
Detected and Quantified26198 uMTotal fatty acid details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000573
DrugBank IDDB04224
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002951
KNApSAcK IDC00052377
Chemspider ID553123
KEGG Compound IDC01712
BioCyc IDNot Available
BiGG ID38213
Wikipedia LinkElaidic_acid
METLIN ID3406
PubChem Compound637517
PDB IDNot Available
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. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  2. Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
  3. Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]
  4. van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
  5. Lopez C, Briard-Bion V, Menard O, Rousseau F, Pradel P, Besle JM: Phospholipid, sphingolipid, and fatty acid compositions of the milk fat globule membrane are modified by diet. J Agric Food Chem. 2008 Jul 9;56(13):5226-36. doi: 10.1021/jf7036104. Epub 2008 Jun 4. [PubMed:18522410 ]
  6. Fooddata+, The Technical University of Denmark (DTU) [Link]