Erucamide is also known as 13-Docosenamide or Erucylamide. It is in the form of white flakes or beads. It is soluble in isopropanol, slightly soluble in alcohol and acetone.1 In industry, cis-13-docosenoamide is used in the formulations of anti-adhesive agents, lubricants, and lubricant additives to reduce their friction coefficient and to make films easier to handle.2 It is used as a standard to determine fatty acid amides in polyethylene packaging film by GC/MS.3
Erucamide is a fatty acid amide derived from erucic acid, which is found in vegetable oil. It is a odorless waxy solid that can dissolve in isopropanol and has low solubility in alcohol and acetone. It is also combustible. Its molecular structure consists of a long unsaturated C22 chain and a polar amine group, which gives it strong surface polarity, a high melting point, and good thermal stability. Because of these properties, it finds extensive applications in industries such as plastics, rubber, printing, and machinery.
Erucamide is primarily used as a polymer additive, with plastic additive 21 is a plasticizer; used in preparation of natural mineral modified degradable polymer flame-retardant composite material.
Erucamide is prepared by reaction of erucic acid with anhydrous ammonia. The reaction of erucic acid with anhydrous ammonia is as follows: C22H42O2 + NH3 → C22H43NO2.
ChEBI: Erucamide is a primary fatty amide resulting from the formal condensation of the carboxy group of erucic acid with ammonia. It is commonly used as a slip additive in the plastic manufacturing industry. It has a role as a human metabolite, a rat metabolite, a mammalian metabolite, a plant metabolite and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is functionally related to an erucic acid.
Erucamide is a migratory additive that is commonly placed in polyolefin films to reduce their coefficient of friction (COF), a good attribute for high speed packaging operations.
13-Docosenamide is the amide of docosenoic acid. It was first identified in the cerebrospinal fluid of sleep-deprived cats. It has also been detected in the cerebrospinal fluid of rats and humans. 13-Docosenamide causes reduced mobility and slightly lessened awareness in rats, whereas 9-octadecenamide induces physiological sleep.
[1] MIAO-MIAO LI . Antidepressant and anxiolytic-like behavioral effects of erucamide, a bioactive fatty acid amide, involving the hypothalamus–pituitary–adrenal axis in mice[J]. Neuroscience Letters, 2017, 640: Pages 6-12. DOI:
10.1016/j.neulet.2016.12.072.
[2] LIEROP B V, CASTLE L, FEIGENBAUM A, et al. Spectra for the Identification of Additives in Food Packaging[C]. 1998: 0. DOI:
10.1007/978-94-011-5222-8.
[3] https://pubchem.ncbi.nlm.nih.gov/compound/Erucylamide#section=Use-and-Manufacturing
[4] https://www.sigmaaldrich.com/catalog/product/aldrich/280577?lang=de®ion=DE
[5] I. QUIJADA-GARRIDO. Desorption of Erucamide Vapor in Vacuum from Erucamide/Isotactic Polypropylene Films 1[J]. Macromolecules, 1996, 29 27: 8791-8797. DOI:
10.1021/ma961065i.
