Ethanolamides

Lauric acid is the main fatty acid used for producing ethanolamides. Monoethanolamides are used primarily in heavy-duty powder detergents as foam stabilizers and rinse improvers. 

For cosmetic compositions an ether carboxylate is used, derived from a fatty acid monoethanolamide [35]. It is known that the ethoxylation takes place on the OH and not on the NH of the ethanolamide group. Due to the acid H atom a narrow range distribution is obtained. The carboxymethylation is carried out with NaOH and SMCA, followed by a washing step with an aqueous solution of a strong acid at high temperatures. The ether carboxylates have the structure... 

Fatty ethanolamide phosphate surfactants are prepared by the reaction of P4O10 with 0.05-3.0 parts of CI0 16 synthetic fatty ethanolamide and 1.0 part higher alcohol at 20-70°C and neutralization of the product [61],... 

A mixture of monolauryl phosphate sodium salt and triethylamine in H20 was treated with glycidol at 80°C for 8 h to give 98% lauryl 2,3-dihydro-xypropyl phosphate sodium salt [304]. Dyeing aids for polyester fibers exist of triethanolamine salts of ethoxylated phenol-styrene adduct phosphate esters [294], Fatty ethanolamide phosphate surfactant are obtained from the reaction of fatty alcohols and fatty ethanolamides with phosphorus pentoxide and neutralization of the product [295]. A double bond in the alkyl group of phosphoric acid esters alter the properties of the molecule. Diethylethanolamine salt of oleyl phosphate is effectively used as a dispersant for antimony oxide in a mixture of xylene-type solvent and water. The composition is useful as an additive for preventing functional deterioration of fluid catalytic cracking catalysts for heavy petroleum fractions. When it was allowed to stand at room temperature for 1 month it shows almost no precipitation [241]. 

While allowing rapid preparation of a range of polyamides, these resins install a T,A-selective y9-Ala residue at the C-terminus, which places Hmits on the DNA sites that can be targeted ]46]. The shortest tail available from these resins is a propanolamide, obtained by reductive cleavage. Polyamides prepared on Boc-Gly-PAM resin can be reductively cleaved to obtain ethanolamide tails, but it was expected that further truncation of the C-terminus would be necessary for tolerance... 

In addition to anandamide, several other endogenous polyunsaturated fatty acid derivatives were also found to act as cannabimimetics. They are all now collectively referred to as endocannabinoids. Soon after the discovery of anandamide, two more fatty acid ethanolamides were isolated and found to bind to CB1 preparations with affinities similar to that of anandamide (anandamide CB1 binding affinity K = 39.2 nM, according to Hanus et al., 1993). These were the homo-y-linolenylethanol-amide (CB1 K[ = 53.4 nM) and 7,10,13,16-docosatetraenylethanolamide (CB1 K[ = 34.4 nM) (Fig. 2). All three V-acylethanolamide endocannabinoids were found to be CB1 agonists in the MVD test (Pertwee, 1994). 

Hanus L, Gopher A, Almog S, Mechoulam R. Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor. J Med... 

Hillard CJ, Cambell WB. Biochemistry and pharmacology of arachidonyl-ethanolamide, a putative endogenous cannabinoid. J Lip Res 1997 38 2383-2398. 

Pate E, Jarvinsen K, Utri P, Jarho P, Jarvinen, T. Ophthalmic arachidonyl-ethanolamide decreases intraocular pressure in normotensive rabbits. Curr Eye Res 1995 14 791-797. 

Pertwee RG, Griffin G, Hanus L, Mechoulam R. Effects of two endogenous fatty acid ethanolamides on mouse vasa deferentia. Eur J Pharmacol 1994 259 115-120. 

Common antistatic agents for food-contact and medical materials include ethanolamines (ethoxylated amines), ethanolamides, laurylamide and glycerol monostearate. 

Arachidonylethanolamide (anandamide) sn-2-arachidonylglycerol (2-AG) Docosatetraenoyl-ethanolamide Di-homo-y-linolenoyl-ethanolamide... 

Our research group expected that additional polyunsaturated fatty acid ethanolamides may be present in the brain. We also identified in porcine brain another two putative endocannabinoids, namely homo-y-linoleoylethanolamide (K = 53.4 5-5 nM) and 7,10,13,16-docosatetraenoylethanolamide (K = 34.4 3.2 nM). The isolation of these two compounds as constituents of porcine brain that bind to the cannabinoid receptor demonstrated that anandamide is not the sole representative of this class of potential mediators. 

Analogous to the discovery of the endogenous opiates and opiate receptors, the discovery of cannabinoid receptors in 1988 suggested the presence of endogenous cannabimimetic compounds. In 1992 anandamine—the ethanolamide of arachidonic acid was purified from porcine brain and shown to behave... 

CS297 Contassot, E., M. Tenan, V. Schnuriger, M. F. Pelte, and P. Y. Dietrich. Arachidonyl ethanolamide induces apoptosis of uterine cervix cancer cells via aberrantly expressed vanilloid receptor-1. Gynecol Oncol 2004 93(1) 182-188. 

Recently, the ethanolamide of arachidonic acid (anandamide ananda is the Sanskrit word for bliss) (Figure 3.53) has been isolated from animal brain tissue, and has been shown... 

Figure 19.1. Chemical structure of main active ingredient of Cannabis sativa, A9-tetrahydrocannabinol (THC) and the naturally occurring ligand for cannabinoid receptors anandamide (arachidonyl ethanolamide).

Besides serving as biological precursors for fatty acid ethanolamides (FAEs), NAPEs have been recently shown to play a physiological role on their own, reducing food intake and arousal after a fat-containing meal (Gillum et al., 2008). 

Anandamide can be metabolized by cyclooxygenase-2 (COX-2), 12- and 15-lipoxygenase (LOX), and cytochrome P450 (CYP450) to generate prostaglandin ethanolamides (prostamides), hydroperoxide, hydroxide, and epoxide... 

---