Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 21:50:53 UTC
Update Date2024-04-30 20:35:43 UTC
Metabolite IDMMDBc0048107
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
Synonyms
ValueSource
(13Z)-DocosenoateChEBI
(22:1n9)ChEBI
(Z)-13-DocosenoateChEBI
cis-Delta(13)-DocosenoateChEBI
Docos-13C-enoateChEBI
(13Z)-Docosenoic acidGenerator
(Z)-13-Docosenoic acidGenerator
cis-delta(13)-Docosenoic acidGenerator
cis-Δ(13)-docosenoateGenerator
cis-Δ(13)-docosenoic acidGenerator
Docos-13C-enoic acidGenerator
Erucic acidGenerator
Molecular FormulaC22H41O2
Average Mass337.569
Monoisotopic Mass337.31120414
IUPAC Name(13Z)-docos-13-enoate
Traditional Nameerucate
CAS Registry Number112-86-7
SMILES
[H]\C(=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([O-])=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]
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)/p-1/b10-9-
InChI KeyDPUOLQHDNGRHBS-KTKRTIGZSA-M