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Record Information
Version3.6
Creation Date2006-05-22 14:17:35 UTC
Update Date2016-02-11 01:05:16 UTC
HMDB IDHMDB02068
Secondary Accession NumbersNone
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.
Structure
Thumb
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
ErucateGenerator
(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
13-DocosenoateHMDB
13-Docosenoic acidHMDB
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
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 KeyInChIKey=DPUOLQHDNGRHBS-KTKRTIGZSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Food
  • Plant
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point33.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.27e-05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity105.81 m3·mol-1ChemAxon
Polarizability45.6 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-6900000000-5e6160a7a5341d6f55deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-0009000000-c637d7d9283da6dae58cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-05ur-9100000000-4dfe9f552da0b8ea6e7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0159-9000000000-867fce64ced7de3a289eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a5c-9300000000-53ce9b6b1bd7db601866View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adrenal Gland
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.264 +/- 1.590 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.028 +/- 0.002 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified150.0 (125.0-160.0) uMAdult (>18 years old)BothAdrenomyeloneuropathy 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. [8350883 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB004287
KNApSAcK IDC00001217
Chemspider ID4444561
KEGG Compound IDC08316
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkErucic acid
NuGOwiki LinkHMDB02068
Metagene LinkHMDB02068
METLIN ID6470
PubChem Compound5281116
PDB IDNot Available
ChEBI ID28792
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. [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. [16581239 ]