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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2022-03-07 02:49:12 UTC
HMDB IDHMDB0002068
Secondary Accession Numbers
  • HMDB02068
Metabolite 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
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
FA(22:1(13Z))HMDB
FA(22:1n9)HMDB
cis-13-Erucic acidHMDB
delta13-cis-Docosenoic acidHMDB
Δ13-cis-docosenoic acidHMDB
Erucic 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 effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process