Erucic acid

Erucic acid

Names
IUPAC name (Z)-Docos-13-enoic acid
Identifiers
CAS Number	112-86-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28792 Y
ChEMBL	ChEMBL1173380 Y
ChemSpider	4444561 Y
ECHA InfoCard	100.003.647
KEGG	C08316 Y
PubChem	5281116
UNII	075441GMF2 Y
InChI 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- Y Key: DPUOLQHDNGRHBS-KTKRTIGZSA-N Y InChI=1/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- Key: DPUOLQHDNGRHBS-KTKRTIGZBD
SMILES O=C(O)CCCCCCCCCCC\C=C/CCCCCCCC
Properties
Chemical formula	C22H42O2
Molar mass	338.58 g·mol−1
Appearance	White waxy solid
Density	0.860 g/cm3
Melting point	33.8 °C (92.8 °F; 306.9 K)
Boiling point	381.5 °C (718.7 °F; 654.6 K) (decomposes)
Solubility in water	Insoluble
Solubility in methanol and ethanol	Soluble
Hazards
Flash point	349.9 °C (661.8 °F; 623.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. It has the formula CH₃(CH₂)₇CH=CH(CH₂)₁₁COOH. It is prevalent in wallflower seed with a reported content of 20 to 54% in high erucic acid rapeseed oil, and 42% in mustard oil. Erucic acid is also known as cis-13-docosenoic acid and the trans isomer is known as brassidic acid.

Erucic acid has many of the same uses as mineral oils, but it is more readily biodegradable than some. It has limited ability to polymerize and dry for use in oil paints. Like other fatty acids, it can be converted into surfactants or lubricants, and can be used as a precursor to biodiesel fuel.

Derivatives of erucic acid have many further uses, such as behenyl alcohol (CH₃(CH₂)₂₁OH), a pour point depressant (enabling liquids to flow at a lower temperature), and silver behenate, for use in photography.

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 colewort, 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 genus. For industrial purposes, a 'low-erucic acid rapeseed' (LEAR) has been developed (canola), which contains fats derived from oleic acid instead of erucic acid.