ChemFOnt: Showing chemical card for Erucic acid (CFc000001388)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:00 UTC

Chemfont ID

CFc000001388

Molecule Identification

Common Name

Erucic acid

Definition

Erucic 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‚Äôs 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Erucate	Generator
Erucic acid, (e)-isomer	MeSH
Erucic acid, (Z)-isomer	MeSH
Erucic acid, potassium salt, (Z)-isomer	MeSH
Erucic acid, sodium salt, (Z)-isomer	MeSH
13-Docosenoic acid	MeSH

Chemical Formula

C₂₂H₄₂O₂

Average Molecular Weight

338.5677

Monoisotopic Molecular Weight

338.318480588

IUPAC Name

docos-13-enoic acid

Traditional Name

13-docosenoic acid

CAS Registry Number

112-86-7

SMILES

CCCCCCCCC=CCCCCCCCCCCCC(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)

InChI Key

DPUOLQHDNGRHBS-UHFFFAOYSA-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.

Showing chemical card for Erucic acid (CFc000001388)

MOL for CFc000001388 (Erucic acid)

3D MOL for CFc000001388 (Erucic acid)

3D SDF for CFc000001388 (Erucic acid)

3D-SDF for CFc000001388 (Erucic acid)

PDB for CFc000001388 (Erucic acid)

3D PDB for CFc000001388 (Erucic acid)

SMILES for CFc000001388 (Erucic acid)

INCHI for CFc000001388 (Erucic acid)

Structure for CFc000001388 (Erucic acid)

3D Structure for CFc000001388 (Erucic acid)