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Record Information
Version2.0
Created at2006-05-22 14:17:35 UTC
Updated at2025-02-11 15:42:20 UTC
NP-MRD IDNP0000021
Secondary Accession NumbersNone
Natural Product Identification
Common NameErucic acid
DescriptionErucic acid is a 22-carbon, 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. Erucic acid’s 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. Food-grade rapeseed oil (also known as canola oil) is regulated to a maximum of 2% erucic acid by weight in the US and 5% in the EU, with special regulations for infant food. Canola was bred from rapeseed cultivars of B. Napus and B. Rapa at the University of Manitoba, Canada. Canola oil is derived from a variety of rapeseed that is low in erucic acid.
Structure
Thumb
Synonyms
Chemical FormulaC22H42O2
Average Mass338.5677 Da
Monoisotopic Mass338.31848 Da
IUPAC Name(13Z)-docos-13-enoic acid
Traditional Nameerucic acid
CAS Registry Number112-86-7
SMILES
[H]\C(CCCCCCCC)=C(/[H])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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-14View Spectrum
Species
Species of Origin
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point33.5 °CNot Available
Boiling Point386.15 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility9.5e-05 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP9.459 (est)The Good Scents Company Information System
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
HMDB IDHMDB0002068
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1242821
References
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. Charlton KM, Corner AH, Davey K, Kramer JK, Mahadevan S, Sauer FD: Cardiac lesions in rats fed rapeseed oils. Can J Comp Med. 1975 Jul;39(3):261-9. [PubMed:1170010 ]
  4. Crowther MA, Barr RD, Kelton J, Whelan D, Greenwald M: Profound thrombocytopenia complicating dietary erucic acid therapy for adrenoleukodystrophy. Am J Hematol. 1995 Feb;48(2):132-3. doi: 10.1002/ajh.2830480217. [PubMed:7847331 ]