112-86-7 Usage
Description
Erucic acid, also known as cis-13-docosenoic acid, is a monounsaturated omega-9 fatty acid with the formula CH3(CH2)7CH=CH(CH2)11COOH. It is predominantly found in the seeds of species belonging to the Brassicaceae family, such as rapeseed, mustard seed, and seeds from vegetable crops like kales, cabbages, and turnips. Erucic acid is characterized by its white crystalline appearance and is produced through the elongation of oleic acid via oleoylcoenzyme A and malonyl-CoA. In the human liver, it is broken down into shorter-chain fatty acids by the long-chain Acyl CoA dehydrogenase enzyme.
Uses
Used in Lubricants:
Erucic acid is used as a lubricant in various industries, including textile, steel, and shipping. It serves as a spinning lubricant and is also utilized in cutting, metal-forming, rolling, fabricating, and drilling oils. Additionally, it is employed as a marine lubricant.
Used in Oil Paints:
Erucic acid has limited ability to polymerize and dry, making it suitable for use in oil paints.
Used in Surfactants and Lubricants:
Like other fatty acids, erucic acid can be converted into surfactants or lubricants.
Used in Bio-diesel Fuel:
Erucic acid can be used as a precursor to bio-diesel fuel.
Used in Appetite Suppressants:
Erucic acid is also used as an ingredient in appetite suppressants.
Used in Corrosion Inhibitors:
Behenyl amine, a derivative of erucic acid, is used in corrosion inhibitors.
Used in Plasticizers:
Disubstituted amides, derived from erucic acid, are effective plasticizers.
Used in Plastic Films:
Erucic acid-derived erucamide is an excellent slip and anti-blocking agent for plastic films.
Used in Polyesters:
Erucic acid can be oxidatively cleaved to brassylic acid for use in the production of polyesters. The oxidative cleavage can be performed via ozonolysis or by reaction with hydrogen peroxide in the presence of an inorganic oxide catalyst.
Used in Rubber Additives:
High-erucic acid oils are used directly as lubricants in the manufacture of rubber additives.
Used in Pharmaceutical Applications:
The C-1 amide of docosenoic acid, a derivative of erucic acid, has been identified as one of the anandamide-related neurotransmitters associated with sleep.
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
Purification Methods
Crystallise erucic acid from MeOH. [Beilstein 2 IV 1676.]
Check Digit Verification of cas no
The CAS Registry Mumber 112-86-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 2 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 112-86:
(5*1)+(4*1)+(3*2)+(2*8)+(1*6)=37
37 % 10 = 7
So 112-86-7 is a valid CAS Registry Number.
InChI: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-
112-86-7Relevant articles and documents
Alteration of Chain Length Selectivity of Candida antarctica Lipase A by Semi-Rational Design for the Enrichment of Erucic and Gondoic Fatty Acids
Zorn, Katja,Oroz-Guinea, Isabel,Brundiek, Henrike,D?rr, Mark,Bornscheuer, Uwe T.
, p. 4115 - 4131 (2018/10/02)
Biotechnological strategies using renewable materials as starting substrates are a promising alternative to traditional oleochemical processes for the isolation of different fatty acids. Among them, long chain mono-unsaturated fatty acids are especially interesting in industrial lipid modification, since they are precursors of several economically relevant products, including detergents, plastics and lubricants. Therefore, the aim of this study was to develop an enzymatic method in order to increase the percentage of long chain mono-unsaturated fatty acids from Camelina and Crambe oil ethyl ester derivatives, by using selective lipases. Specifically, the focus was on the enrichment of gondoic (C20:1 cisΔ11) and erucic acid (C22:1 cisΔ13) from Camelina and Crambe oil derivatives, respectively. The pursuit of this goal entailed several steps, including: (i) the choice of a suitable lipase scaffold to serve as a protein engineering template (Candida antarctica lipase A); (ii) the identification of potential amino acid targets to disrupt the binding tunnel at the adequate location; (iii) the design, creation and high-throughput screening of lipase mutant libraries; (iv) the study of the selectivity towards different chain length p-nitrophenyl fatty acid esters of the best hits found, as well as the analysis of the contribution of each amino acid change and the outcome of combining several of the aforementioned residue alterations and, finally, (v) the selection and application of the most promising candidates for the fatty acid enrichment biocatalysis. As a result, enrichment of C22:1 from Crambe ethyl esters was achieved either, in the free fatty acid fraction (wt, 78%) or in the esterified fraction (variants V1, 77%; V9, 78% and V19, 74%). Concerning the enrichment of C20:1 when Camelina oil ethyl esters were used as substrate, the best variant was the single mutant V290W, which doubled its content in the esterified fraction from approximately 15% to 34%. A moderately lower increase was achieved by V9 and its two derived triple mutant variants V19 and V20 (27%). (Figure presented.).