Surface active N‐acylglutamate: I. Preparation of long chain N‐acylglutamic acid

Abstract

Long chain N-acylglutamic acid was prepared in a high yield by a reaction of glutamic acid with fatty acid chloride in a mixed solvent of water and a water miscible organic solvent such as acetone, methyl ethyl ketone, dioxane, tetrahydrofuran, t-butyl alcohol or cyclohexanone. In this reaction the composition of the mixed solvent influenced the yield of N-acylated glutamic acid and the best yield was obtained when the reaction was carried out in the mixed solvent comprising 30-60% v/v of the organic solvent. Long chain N-acylaspartic acid was also obtained in a high yield by the same method. As the other method to obtain N-lauroyl-DL-glutamic acid, it was examined that N-acyl-ot-aminoglutarodinitrile which was obtained by a reaction of a-aminoglutarodinitrile with fatty acid chloride was hydrolyzed with an aqueous alkaline solution. The salts of long chain N-acylglutamic acid are known as the surface active agents that react mildly on the human skin. 157

The Natural Product N-Palmitoyl-l-leucine Selectively Inhibits Late Assembly of Human Spliceosomes

“…The solvent was removed under reduced pressure and the residue was purified by flash chromatography (SiO 2 , 5-12% (v/v) acetone-CH 2 Cl 2 gradient) to afford N-palmitoyl-D-leucine (700 mg, quant.) as a white solid with spectra matching those previously reported (15,16).…”

A Novel Synthesis of N-Alkoxycarbonyl Amino Acids and Surfactant Properties of Their Sodium Salts

“…Generally, they have been prepared from fatty acid chlorides and amino acids [10][11][12][13][14][15] , where acid halides are used to introduce the hydrophobic groups. However, on the view point of availability of starting materials, it may not be easy to obtain optically active fatty acids compared to the availability of optically active alcohols.…”

“…Among them, sodium salts of Nacyl amino acids are anionic surfactants with good biodegradability [1][2][3] , skin compatibility and antibacterial activity [4][5][6][7][8][9] and have been widely used in detergent, shampoo, cosmetic and food formulations. They are usually prepared from fatty acid chlorides and either pure amino acids or protein hydrolysates [10][11][12][13][14][15] . However, as the acid halides are used to introduce the hydrophobic groups, it may not be easy to vary the hydrophobic groups on the view point of availability.…”

Fabrication of Mesostructured Silica Materials through Co-Structure-Directing Route

“…Moreover, amino acid-derived surfactants can be easily prepared by the reaction of amino acids with alkyl acyl chloride under basic conditions, 39 which allow the rational design of surfactants with specific properties by the combination of various kinds of amino acids and different length of alkyl chains.…”