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| Erucic Acid Chemical Properties |
| Melting point | 28-32 °C (lit.) | | Boiling point | 358 °C/400 mmHg (lit.) | | density | 0,86 g/cm3 | | refractive index | nD45 1.4534; nD65 1.44794 | | Fp | 265°C/15mm | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 4.78±0.10(Predicted) | | form | Solid | | color | White to Off-White Low-Melting | | Merck | 14,3674 | | BRN | 1728049 | | CAS DataBase Reference | 112-86-7(CAS DataBase Reference) | | NIST Chemistry Reference | Erucic acid(112-86-7) | | EPA Substance Registry System | 13-Docosenoic acid, (13Z)- (112-86-7) |
| Erucic Acid Usage And Synthesis |
| Description | Erucic acid also known as cis-13-Docosenoic acid is a monounsaturated omega-9 fatty acid. It occurs at high concentrations mainly in the seeds of species of the Brassicaceae (e.g. rape seed or mustard seed, and seeds from vegetable crops such as kales, cabbages and turnips).
High-erucic acid oils are used either directly as lubricants (e.g. in the manufacture of rubber additives) or in formulations. They are used as spinning lubricants in the textile, steel, and shipping industries; as cutting, metal-forming, rolling, fabricating, and drilling oils; and as marine lubes. Erucic acid can also be oxidatively cleaved to brassylic acid for use in the production of polyesters. The oxidative cleavage of erucic acid can be performed via ozonolysis or by reaction with hydrogen peroxide in the presence of an inorganic oxide catalyst. Erucic acid can be used to prepare useful nitrogen derivatives: behenyl amine is used in a corrosion inhibitor; disubstituted amides are effective plasticizers and erucamide is an excellent slip and antiblocking agent for plastic films.
| | References | [1] J.M. Vargas-Lopez, D. Wiesenborna, K. Tostenson , L. Cihacek (1999) Processing of Crambe for Oil and Isolation of Erucic Acid, JAOCS, 76, 801-809
[2] H. J. Nieschlag, I. A. Wolff (1971) Industrial uses of high erucic oils, JAOCS, 48, 723-727
| | Description | 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, makes up 4.1% of rapeseed oil, and makes up 42% of mustard oil. Erucic acid is also known as cis-13- docosenoic acid and the trans isomer is known as brassidic acid. | | Chemical Properties | White crystalline | | Uses | 13(Z)-Docosenoic acid is a 22-carbon monounsaturated fatty acid. It is found predominantly in canola oil. 13(Z)-Docosenoic acid is metabolized to oleic acid in vivo. Diets rich in 13(Z)-docosenoic acid were shown to cause heart lipidosis in experimental animals. The C-1 amide of docosenoic acid has been identified as one of the anandamide-related neurotransmitters associated with sleep. | | Uses | 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 bio-diesel 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. It is also used as an ingredient in appetite suppressants. | | Uses | Erucic acid is a long-chain alcohol that acts as an inhibitor of fatty acid oxidation in the heart. Erucic acid originates in rapeseed plants, and is the major fatty acid constituent of rapeseed plant oil extracts and canola oil. | | Definition | ChEBI: A docosenoic acid having a cis- double bond at C-13. It is found particularly in brassicas - it is a major component of mustard and rapeseed oils and is produced by broccoli, Brussels sprouts, kale, and wallflowers. | | Biotechnological Applications | Erucic acid is produced by elongation of oleic acid via oleoylcoenzyme A and malonyl- CoA. Erucic acid is broken down into shorter- chain fatty acids in the human liver by the long - chain Acyl CoA dehydrogenase enzyme. | | Purification Methods | Crystallise erucic acid from MeOH. [Beilstein 2 IV 1676.] |
| Erucic Acid Preparation Products And Raw materials |
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