Record Information
Version1.0
Creation date2015-10-09 22:32:35 UTC
Update date2017-01-19 02:36:35 UTC
FoodComEx IDPC000766
FoodDB RecordFDB004287
Chemical Information
NameErucic acid
DescriptionBefore 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 Number112-86-7
Structure
Thumb
Synonyms
SynonymSource
(13Z)-13-Docosenoatebiospider
(13Z)-13-Docosenoic acidbiospider
(13Z)-Docosenoatebiospider
(13Z)-Docosenoic acidChEBI
(Z)-13-Docosenoatebiospider
(Z)-13-Docosenoic acidbiospider
(Z)-Docos-13-enoateGenerator
(Z)-Docos-13-enoic acidChEBI
«delta»13-cis-Docosenoic acidbiospider
13-cis-DocosenoateGenerator
13-cis-Docosenoic acidChEBI
13-docosenoatebiospider
13-Docosenoic acidbiospider
13-Docosenoic acid (acd/name 4.0)HMDB
13-Docosenoic acid, (Z)-biospider
22:1Omega9ChEBI
Brassidic acidbiospider
C22:1N-9ChEBI
cis -13-Docosenoic acidbiospider
cis-13-Docosenoatebiospider
cis-13-Docosenoic acidChEBI
cis-delta(13)-DocosenoateGenerator
cis-Delta(13)-Docosenoic acidChEBI
cis-EruateGenerator
cis-Erucic acidHMDB
cis-Eruic acidChEBI
cis-δ(13)-docosenoateGenerator
cis-δ(13)-docosenoic acidGenerator
delta 13-cis-Docosenoatebiospider
delta 13-cis-Docosenoic acidbiospider
delta.13-cis-Docosenoatebiospider
delta.13-cis-Docosenoic acidbiospider
Docos-13c-enoateGenerator
Docos-13c-enoic acidChEBI
ErucasaeureChEBI
ErucateGenerator
Erucic acid, practbiospider
Prifrac 2990biospider
trans -13-Docosenoic acidbiospider
Chemical FormulaC22H42O2
IUPAC namedocos-13-enoic acid
InChI IdentifierInChI=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 KeyDPUOLQHDNGRHBS-UHFFFAOYSA-N
Isomeric SMILESCCCCCCCCC=CCCCCCCCCCCCC(O)=O
Average Molecular Weight338.5677
Monoisotopic Molecular Weight338.318480588
Chemical Taxonomy
ClassificationNot classified
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting Point33.5 oC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 100 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci 2227AA
Cayman Chemical 90175
MetaSci HMDB0002068
Toronto Research Chemicals E649900
Toronto Research Chemicals HMDB0002068