FComEx: Erucic acid (PC000766)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:35 UTC

Update date

2017-01-19 02:36:35 UTC

FoodComEx ID

PC000766

FoodDB Record

FDB004287

Chemical Information

Name

Erucic acid

Description

Before genetic engineering, plant breeders were aiming to produce a less-bitter-tasting multi-purpose oil from rapeseed that would appeal to a larger market by making it more palatable for cattle and other livestock. While it was possible to breed out much of the pungent-tasting glucosinolates, one of the dominant erucic acid genes would get stripped out of the genome as well, greatly reducing its valuable erucic acid content. Studies on rats show lipodosis problems when fed high quantities of erucic acid, however, so this did not hinder saleability. Later trials showed that rats had the same problems with other vegetable fatty acids, because rats are poor at metabolising some fats. The plant breeding industry later changed "low erucic acid" to be its unique selling proposition over that of its competitors.; Erucic 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.; Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1 ?-9. It is prevalent in rapeseed, wallflower seed, and mustard seed, making up 40-50% of their oils. Erucic acid is also known as cis-13-docosenoic acid and the trans isomer is known as brassidic acid.; The name erucic means: of or pertaining to eruca; which is a genus of flowering plants in the family Brassicaceae. It is also the Latin for coleworth, which today is better known as kale. Erucic acid is produced naturally (together with other fatty acids) across a great range of green plants, but especially so in members of the brassica family. It is highest in some of the rapeseed varieties of brassicas, kale and mustard being some of the highest, followed by Brussels spouts and broccoli. For industrial purposes, a High-Erucic Acid Rapeseed (HEAR) has been developed. These cultivars can yield 40% to 60% of the total oil recovered as erucic acid.

CAS Number

112-86-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(13Z)-13-Docosenoate	biospider
(13Z)-13-Docosenoic acid	biospider
(13Z)-Docosenoate	biospider
(13Z)-Docosenoic acid	ChEBI
(Z)-13-Docosenoate	biospider
(Z)-13-Docosenoic acid	biospider
(Z)-Docos-13-enoate	Generator
(Z)-Docos-13-enoic acid	ChEBI
«delta»13-cis-Docosenoic acid	biospider
13-cis-Docosenoate	Generator
13-cis-Docosenoic acid	ChEBI
13-docosenoate	biospider
13-Docosenoic acid	biospider
13-Docosenoic acid (acd/name 4.0)	HMDB
13-Docosenoic acid, (Z)-	biospider
22:1Omega9	ChEBI
Brassidic acid	biospider
C22:1N-9	ChEBI
cis -13-Docosenoic acid	biospider
cis-13-Docosenoate	biospider
cis-13-Docosenoic acid	ChEBI
cis-delta(13)-Docosenoate	Generator
cis-Delta(13)-Docosenoic acid	ChEBI
cis-Eruate	Generator
cis-Erucic acid	HMDB
cis-Eruic acid	ChEBI
cis-δ(13)-docosenoate	Generator
cis-δ(13)-docosenoic acid	Generator
delta 13-cis-Docosenoate	biospider
delta 13-cis-Docosenoic acid	biospider
delta.13-cis-Docosenoate	biospider
delta.13-cis-Docosenoic acid	biospider
Docos-13c-enoate	Generator
Docos-13c-enoic acid	ChEBI
Erucasaeure	ChEBI
Erucate	Generator
Erucic acid, pract	biospider
Prifrac 2990	biospider
trans -13-Docosenoic acid	biospider

Chemical Formula

C22H42O2

IUPAC name

docos-13-enoic acid

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

Isomeric SMILES

CCCCCCCCC=CCCCCCCCCCCCC(O)=O

Average Molecular Weight

338.5677

Monoisotopic Molecular Weight

338.318480588

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents