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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:29:35 UTC
HMDB IDHMDB0000573
Secondary Accession Numbers
  • HMDB00573
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
Data?1584717281
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
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
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point42 - 44 °CNot Available
Boiling Point360.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.012 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.78Extrapolated
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available175.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00002144
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP10(7.68) g/LALOGPS
logP10(6.78) g/LChemAxon
logS10(-6.4) g/LALOGPS
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
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]+176.24631661259
DarkChem[M-H]-178.04131661259
AllCCS[M+H]+179.56932859911
AllCCS[M-H]-179.42832859911

Predicted Kovats Retention Indices

Underivatized

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

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Elaidic acid,1TMS,isomer #1CCCCCCCC/C=C/CCCCCCCC(=O)O[Si](C)(C)C2217.5Semi standard non polar33892256
Elaidic 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 - Elaidic acid GC-MS (1 TMS)splash10-00nb-5900000000-3ba79fbe1b1b3b18c0ff2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Elaidic acid GC-MS (Non-derivatized)splash10-00nb-5900000000-3ba79fbe1b1b3b18c0ff2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Elaidic acid GC-EI-TOF (Non-derivatized)splash10-00mk-3900000000-26468e9cc1331164ac252017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Elaidic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9640000000-29b5681d79890854ef2b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Elaidic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0fe0-9431000000-1879934642ac672cb4012017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Elaidic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Elaidic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-350dc6d7ac541a3c5b672014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Elaidic acid 20V, Positive-QTOFsplash10-001m-9570000000-3794dff1c5c1baa2e7a12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Elaidic acid 10V, Positive-QTOFsplash10-001i-4690000000-393df6433d9c0c1e43572021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Elaidic acid 40V, Positive-QTOFsplash10-07vi-9660000000-38c5c2044b6ae347c0b72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Elaidic acid 10V, Positive-QTOFsplash10-00lr-0090000000-755e8d1537818580a2fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Elaidic acid 20V, Positive-QTOFsplash10-00y0-4690000000-ca39c5846217fe0932272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Elaidic acid 40V, Positive-QTOFsplash10-0596-9830000000-fcb2923d448d11c545592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Elaidic acid 10V, Negative-QTOFsplash10-001i-0090000000-e809fd7222cf63431b772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Elaidic acid 20V, Negative-QTOFsplash10-001r-1090000000-9c340e3d19cbe7013ccd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Elaidic acid 40V, Negative-QTOFsplash10-0a4l-9230000000-6e517cda629fcd4df07d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Elaidic acid 10V, Negative-QTOFsplash10-001i-0090000000-8b8562cadde7e7a8ba4f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Elaidic acid 20V, Negative-QTOFsplash10-01q9-1090000000-827ccf4b0fb321cd543d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Elaidic acid 40V, Negative-QTOFsplash10-0006-9220000000-1a90bd2c4041fc8d39eb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Elaidic acid 10V, Positive-QTOFsplash10-00lr-3290000000-e57551fac255cafaf4fd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Elaidic acid 20V, Positive-QTOFsplash10-067j-9410000000-40bef334a898843c3baf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Elaidic acid 40V, Positive-QTOFsplash10-0a5c-9000000000-96ff3dec9c358c726e352021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
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 QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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 IDDB04224
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDELAID
MarkerDB IDNot Available
Good Scents IDrw1242511
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 ]