Survey with prize
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2020-10-09 21:02:24 UTC
HMDB IDHMDB0002068
Secondary Accession Numbers
  • HMDB02068
Metabolite Identification
Common NameErucic acid
DescriptionErucic acid is a monounsaturated omega-9 fatty acid found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels spouts and broccoli. Some Brassica cultivars can have up to 40 to 50 percent of their oil recovered as erucic acid. Erucic acid is also known as cis-13-docosenoic acid. The trans isomer is known as brassidic acid. Erucic acid occurs in nature only along with bitter-tasting compounds. Erucic acid has many of the same uses as mineral oils but with the advantage that it is more readily bio-degradable. Its high tolerance to temperature makes it suitable for transmission oil. Its ability to polymerize and dry means it can be - and is - used as a binder for oil paints. Increased levels of eicosenoic acid (20:ln9) and erucic acid (22:1n9) have been found in the red blood cell membranes of autistic subjects with developmental regression (PMID: 16581239 ). Erucic acid is broken down long-chain acyl-coenzyme A (CoA) dehydrogenase, which is produced in the liver. This enzyme breaks this long chain fatty acid into shorter-chain fatty acids. human infants have relatively low amounts of this enzyme and because of this, babies should not be given foods high in erucic acid. Erucic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
Structure
Data?1582752227
Synonyms
ValueSource
(13Z)-13-Docosenoic acidChEBI
(13Z)-Docosenoic acidChEBI
(Z)-13-Docosenoic acidChEBI
(Z)-Docos-13-enoic acidChEBI
13-cis-Docosenoic acidChEBI
22:1Omega9ChEBI
C22:1N-9ChEBI
cis-13-Docosenoic acidChEBI
cis-Delta(13)-Docosenoic acidChEBI
cis-Eruic acidChEBI
Docos-13C-enoic acidChEBI
ErucasaeureChEBI
(13Z)-13-DocosenoateGenerator
(13Z)-DocosenoateGenerator
(Z)-13-DocosenoateGenerator
(Z)-Docos-13-enoateGenerator
13-cis-DocosenoateGenerator
cis-13-DocosenoateGenerator
cis-delta(13)-DocosenoateGenerator
cis-Δ(13)-docosenoateGenerator
cis-Δ(13)-docosenoic acidGenerator
cis-EruateGenerator
Docos-13C-enoateGenerator
ErucateGenerator
13-Docosenoic acidHMDB
Erucic acid, (Z)-isomerHMDB
13-DocosenoateHMDB
13-Docosenoic acid (acd/name 4.0)HMDB
cis-Erucic acidHMDB
delta 13-cis-DocosenoateHMDB
delta 13-cis-Docosenoic acidHMDB
Delta.13-cis-docosenoateHMDB
Delta.13-cis-docosenoic acidHMDB
Prifrac 2990HMDB
(Z)-Erucic acidHMDB
13(Z)-Docosenoic acidHMDB
Erucic acidHMDB
FA(22:1(13Z))HMDB
FA(22:1n9)HMDB
cis-13-Erucic acidHMDB
delta13-cis-Docosenoic acidHMDB
Δ13-cis-Docosenoic acidHMDB
Chemical FormulaC22H42O2
Average Molecular Weight338.5677
Monoisotopic Molecular Weight338.318480588
IUPAC Name(13Z)-docos-13-enoic acid
Traditional Nameerucic acid
CAS Registry Number112-86-7
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24)/b10-9-
InChI KeyDPUOLQHDNGRHBS-KTKRTIGZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very 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:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point33.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.3e-05 g/LALOGPS
logP8.97ALOGPS
logP8.56ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity105.81 m³·mol⁻¹ChemAxon
Polarizability45.6 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-6900000000-5e6160a7a5341d6f55deSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00nb-6900000000-5e6160a7a5341d6f55deSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9670000000-abb8d10b97d3c63c8480Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fmv-9452000000-be430773e3b82d00352dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-0009000000-c637d7d9283da6dae58cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-05ur-9100000000-4dfe9f552da0b8ea6e7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0159-9000000000-867fce64ced7de3a289eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-014i-0009000000-a67df2342edb038f0647Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000i-0019000000-0026b53b7b328f5e5154Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00dr-1119000000-fa6979100366edcb2892Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-0fki-5829000000-ff16fd0e5a988fe38fa4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-0apj-9200000000-27116cd4b609b88b4005Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 27V, positivesplash10-0api-9100000000-0f82260b5b86e3b06b2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-0aor-9000000000-0a3061b18adfe4ddad07Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-00di-0129000000-fa49cfc1738521b925d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-000i-0290000000-b4f9a52c100defbf8a39Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-014i-0090000000-02a20bc6ce898cb3824cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-07l5-0950000000-0ca01024ab3b5ad027ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-0udi-0319000000-7b31f345d0546a6c25abSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-00di-2209000000-d03f3b30c822ce8c5e26Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-00di-9608000000-2fc5f27c0bd54f0c003aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-059t-9502000000-8f68c9dbb8e1467805f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-05nb-9300000000-0701894bd7e9b3d37f40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0019000000-c06b5c8f2b9044af1c34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00g3-5695000000-55896e489497235f6a67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9880000000-69f41c34dca989e6c810Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-cfb3c7afc93ecf28f3daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-1039000000-c2dd9360fea23806c313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9131000000-393859815e6c1359d6dfSpectrum
MSMass Spectrum (Electron Ionization)splash10-0a5c-9300000000-53ce9b6b1bd7db601866Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Adrenal Gland
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.264 +/- 1.590 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.028 +/- 0.002 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified20.2 +/- 6.8 uMAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified150.0 (125.0-160.0) uMAdult (>18 years old)BothAdrenomyeloneuropathy details
BloodDetected and Quantified3.4 +/- 2.2 uMAdult (>18 years old)Not Specified
Isovaleric acidemia
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Adrenomyeloneuropathy
  1. Aubourg P, Adamsbaum C, Lavallard-Rousseau MC, Rocchiccioli F, Cartier N, Jambaque I, Jakobezak C, Lemaitre A, Boureau F, Wolf C, et al.: A two-year trial of oleic and erucic acids ("Lorenzo's oil") as treatment for adrenomyeloneuropathy. N Engl J Med. 1993 Sep 9;329(11):745-52. [PubMed:8350883 ]
Isovaleric acidemia
  1. Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004287
KNApSAcK IDC00001217
Chemspider ID4444561
KEGG Compound IDC08316
BioCyc IDCPD-14292
BiGG IDNot Available
Wikipedia LinkErucic_acid
METLIN ID6470
PubChem Compound5281116
PDB IDNot Available
ChEBI ID28792
Food Biomarker OntologyNot Available
VMH IDDOCO13AC
MarkerDB IDMDB00000374
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rizzo WB, Leshner RT, Odone A, Dammann AL, Craft DA, Jensen ME, Jennings SS, Davis S, Jaitly R, Sgro JA: Dietary erucic acid therapy for X-linked adrenoleukodystrophy. Neurology. 1989 Nov;39(11):1415-22. [PubMed:2682348 ]
  2. Bu B, Ashwood P, Harvey D, King IB, Water JV, Jin LW: Fatty acid compositions of red blood cell phospholipids in children with autism. Prostaglandins Leukot Essent Fatty Acids. 2006 Apr;74(4):215-21. [PubMed:16581239 ]
  3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]