14246-60-7

Basic information

• Product Name: N-Octadecanoyl-L-alanine
• Synonyms: N-Octadecanoyl-L-alanine
• CAS NO: 14246-60-7
• Molecular Formula: C21H41NO3
• Molecular Weight: 355.55514
• Mol File: 14246-60-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Octadecanoyl-L-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Octadecanoyl-L-alanine(14246-60-7)
• EPA Substance Registry System: N-Octadecanoyl-L-alanine(14246-60-7)

Safety Data

• Hazardous Substances Data: 14246-60-7(Hazardous Substances Data)

Usage

Uses

suzuki reaction

Upstream product

• 122315-69-9 methyl N-(1-oxo-octadecyl)-L-alaninate 
• 57-11-4 stearic acid 
• 112-76-5 Stearoyl chloride 
• 56-41-7 L-alanin 
• 338-69-2 D-Alanine 

Relevant articles and documents

New N-acylamino acids and derivatives from renewable fatty acids: Gelation of hydrocarbons and thermal properties

This work reports the synthesis of new fatty N-acylamino acids and N-acylamino esters from the C16:0, C18:0, C18:1, and C18:1(OH) fatty acid families and demonstrates the activity of these compounds as organogel agents. Compounds were heated and dissolved in various solvents (n-hexane, toluene, and gasoline). Only saturated C16:0 and C18:0 derived from alanine were able to form gels in toluene, and saturated C16:0 derived from phenylalanine showed gelation in n-hexane. This is the first evidence that fatty N-acylamino esters and N-acylamino acid derivatives of l-serine and fatty acids C16:0, C18:0, and C18:1 are able to form gels with hexane. This observation confirms the importance of the hydroxyl group in the segment derivative of l-serine in forming good gels.

Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids

A variety of fatty acid amides of different naturally occurring l-amino acids have been synthesized and they are found to form gels with various hydrocarbons. The gelation properties of these compounds were studied by a number of physical methods including FTIR spectroscopy, X-ray diffraction, scanning electron microscopy, differential scanning calorimetry, rheology, and it was found that gelation depended critically on the fatty acid chain length and the nature of the amino acid. Among them l-alanine based gelators were found to be the most efficient and versatile gelators as they self-assemble into a layered structure to form the gel network. Mechanisms for the assembly and formation of gels from these molecules are discussed.

Potential anti-inflammatory actions of the elmiric (lipoamino) acids

A library of amino acid-fatty acid conjugates (elmiric acids) was synthesized and evaluated for activity as potential anti-inflammatory agents. The compounds were tested in vitro for their effects on cell proliferation and prostaglandin production, and compared with their effects on in vivo models of inflammation. LPS stimulated RAW 267.4 mouse macrophage cells were the in vitro model and phorbol ester-induced mouse ear edema served as the principal in vivo model. The prostaglandin responses were found to be strongly dependent on the nature of the fatty acid part of the molecule. Polyunsaturated acid conjugates produced a marked increase in media levels of i15-deoxy-PGJ2 with minimal effects on PGE production. It is reported in the literature that prostaglandin ratios in which the J series predominates over the E series promote the resolution of inflammatory conditions. Several of the elmiric acids tested here produced such favorable ratios suggesting that their potential anti-inflammatory activity occurs via a novel mechanism of action. The ear edema assay results were generally in agreement with the prostaglandin assay findings indicating a connection between them.

Self-assembled organogels formed by mono-chain L-alanine derivatives

The mono-chain L-alanine derivatives self-assemble into bilayer aggregates in a number of organic liquids and gelatinize the liquids.

Glutamic acid derivatives

All isomeric forms and mixtures of isomers of glutamic acid compounds of the formula STR1 wherein the glutamic aid is of D- or L- configuration, R1 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, an amino acid, a peptide of 2 to 4 amino acids and an amino acid or a peptide of 2 to 4 amino acids in which the amine is esterified with an optionally unsaturated aliphatic carboxylic acid of 6 to 24 carbon atoms or R1 is selected from the group consisting of a residue of a C6 -C24 optionally unsaturated aliphatic acid. R5 is selected from the group consisting of hydrogen or an alkyl radical of 1 to 5 carbon atoms, R3 is selected from the group consisting of hydroxy, alkoxy of 1 to 5 carbon atoms, an amino acid with the amine optionally substituted with alkyl of 1 to 5 carbon atoms, Z is STR2 R2 is selected from the group consisting of hydrogen, an amino acid and a peptide of 2 to 4 amino acids, R4 is selected from the group consisting of hydroxy, alkoxy 1 to 5 carbon atoms and an amino acid optionally substituted on the amine with alkyl of 1 to 5 carbon atoms, U is selected from the group consisting of STR3 --CH=CH--CH2 -- (E or Z isomer), --CH2 --CH=CH-- (E or Z isomer) and STR4 or U and Y together are =CH--CH2 --CH2 -- (E or Z isomer) and X is hydrogen and their salts with non-toxic, pharmaceutically acceptable acid or bases having immunomodulatory properties.

Glutamic acid derivatives

All isomeric forms and mixtures of isomers of glutamic acid compounds of the formula STR1 wherein the glutamic acid of D- or L- configuration, R1 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, an amino acid, a peptide of 2 to 4 amino acids and an amino acid or a peptide of 2 to 4 amino acids in which the amine is esterified with an optionally unsaturated aliphatic carboxylic acid of 6 to 24 carbon atoms or R1 is selected from the group consisting of a residue of a C6 -C24 optionally unsaturated aliphatic acid, R5 is selected from the group consisting of hydrogen or an alkyl radical of 1 to 5 carbon atoms, R3 is selected from the group consisting of hydroxy, alkoxy of 1 to 5 carbon atoms, an amino acid with the amine optionally substituted with alkyl of 1 to 5 carbon atoms, Z is STR2 R2 is selected from the group consisting of hydrogen, an amino acid and a peptide of 2 to 4 amino acids, R4 is selected from the group consisting of hydroxy, alkoxy 1 to 5 carbon atoms and an amino acid optionally substituted on the amine with alkyl of 1 to 5 carbon atoms, U is selected from the group consisting of STR3 --CH=CH--CH2 -- (E or Z isomer), --CH2 --CH=CH-- (E or Z isomer) and STR4 or U and Y together are =CH--CH2 --CH2 -- (E or Z isomer) and X is hydrogen or U and X together are =CH--CH2 --CH2 -- (E or Z isomer) and Y is hydrogen and their salts with non-toxic, pharmaceutically acceptable acid or bases having immunomodulatory properties.

Dermatological compositions containing an acylamino-carboxylic acid or an alkyl ester thereof

Topical dermatological compositions containing an acylamino-carboxylic acid compound of the formula STR1 wherein R1 is hydrogen, alkyl of 1 to 3 carbon atoms, trifluoromethyl, phenyl, halo-phenyl, nitro-phenyl or biphenylyl, R2 is hydrogen or alkyl of 1 to 3 carbon atoms, R3 is hydrogen, alkyl of 1 to 6 carbon atoms, methylthio-(alkyl of 1 to 6 carbon atoms) or benzyl, R4 is alkyl of 10 to 22 carbon atoms, n is 0, 1 or 2, R5 is alkyl of 8 to 22 carbon atoms, phenyl or biphenylyl, and R6 is hydrogen or alkyl of 1 to 3 carbon atoms; the compositions are useful for the care of the skin.