36577-40-9

Usage

Uses

Used in Pharmaceutical Applications:
1-(1-oxooctadecyl)-L-proline is used as a therapeutic agent for its anti-inflammatory and antioxidant properties, which can be beneficial in the treatment of various conditions associated with inflammation and oxidative stress.
Used in Cosmetics Industry:
In the cosmetics industry, 1-(1-oxooctadecyl)-L-proline is used as an ingredient in skincare products for its potential to provide anti-inflammatory and antioxidant benefits, which may help in reducing signs of aging and promoting skin health.
Used in Surfactant and Emulsifier Development:
Due to its amphiphilic nature, 1-(1-oxooctadecyl)-L-proline is used as a component in the development of surfactants and emulsifiers, which are essential in the formulation of various products such as detergents, cleaners, and personal care items.
Used in Research of Lipid Metabolism and Cellular Signaling:
1-(1-oxooctadecyl)-L-proline is utilized as a research tool in the study of lipid metabolism and cellular signaling pathways, given its structural and functional properties that may provide insights into these biological processes.

InChI:InChI=1/C23H43NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-22(25)24-20-17-18-21(24)23(26)27/h21H,2-20H2,1H3,(H,26,27)

Upstream product

• 56776-02-4 N-hydroxysuccinimide ester of stearic acid 
• 147-85-3 L-proline 
• 14464-32-5 stearic acid N-hydroxysuccinimide ester 
• 112-76-5 Stearoyl chloride 

Relevant academic research and scientific papers

COMPOSITIONS IN THE FORM OF AN INJECTABLE AQUEOUS SOLUTION COMPRISING AMYLIN, AN AMYLIN RECEPTOR AGONIST OR AN AMYLIN ANALOG, AND A CO-POLYAMINO ACID

An injectable aqueous solution, of which the pH is from 6.0 to 8.0, comprising at least: a) amylin, an amylin receptor agonist or an amylin analog; b) a co-polyamino acid bearing carboxylate charges and hydrophobic radicals Hy, said co-polyamino acid consisting of glutamic or aspartic units and said hydrophobic radicals Hy having the following formula I: [in-line-formulae]?GpR?r?GpA?a?GpC)p ??I[/in-line-formulae] wherein the composition does not comprise a basal insulin of which the isoelectric point pI is from 5.8 to 8.5. It also relates to a composition wherein it moreover comprises a prandial insulin.

Compositions in the form of an injectable aqueous solution comprising human glucagon and a co-polyamino acid

An injectable aqueous solution, the pH of which is from 6.0 to 8.0, having at least: a) human glucagon, and b) a co-polyamino acid bearing carboxylate charges and hydrophobic radicals Hy. In an embodiment, the compositions have, in addition, a gastrointestinal hormone.

Synthesis of lipoamino acids and their activity against cerebral ischemic injury

A series of lipoamino acids were synthesized and their neuroprotective effect against brain ischemia induced by oxygen-glucose deprivation (OGD) on rat cerebral slices was evaluated. Among these compounds, N-stearoyl-L-tyrosine (4), N-stearoyl-L-serine (5) and N-stearoyl-L-threonine (6) exhibited good neuroprotective activity. We found that the neuroprotective activity of lipoamino acids depended on the acyl group, the presence of a free carboxylic function and a free hydroxyl group at the branched chain of the amino acids. The results also showed that 5 was the most active compound, protecting rat brain slices against OGD as well as hydrogen peroxide (H2O2) insult at the range of 1-10 M.

Preparation, characterization, and surface and biological properties of N-stearoyl amino acids

Several lipoamino acids were synthesized, in which n-octadecanoic acid (stearic acid) was coupled with the α-amino group of an amino acid. The products were characterized and their identities confirmed by advanced analytical techniques like Fourier transform infrared, 1H nuclear magnetic resonance spectroscopy, and differential scanning calorimetry. Their surface properties, such as critical micelle concentration (CMC) and foaming properties, biodegradability, and antimicrobial activity were also evaluated. The N-stearoyl amino acids (NSA) had low CMC values, and some of them showed good foaming properties. They were screened for antimicrobial activity against the gram-positive bacteria Staphylococcus aureus, Micrococcus luteus, and Bacillus cerceus, the gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa, and the yeast Candida albicans. All the compounds inhibited at least one of these organisms. N-Stearoyl proline was the most effective, the order of antimicrobial activity being aromatic NSA > acidic NSA > basic NSA. However, the effective inhibition by all the compounds indicates the desirability of more thorough investigation and suggests that some of these compounds may have potential utility as biostatic additives in commercial products. All NSA are highly biodegradable and can readily be removed under conditions of normal secondary sewage treatment.

Synthesis of Stearoyl Derivatives of Proline-Containing Peptides

Hydrophobic stearoyl derivatives of proline-containing di- and tripeptides and their deuterated analogs were synthesized.It was shown by NMR spectroscopy that cis-trans-equilibrium around an X-Pro peptide bond is displaced towards trans-conformers for compounds containing a Ste-Pro fragment as opposed to the compounds containing Boc-Pro or Gly-Pro fragments.Key words: proline, proline-containing peptides, cis-trans-isomerism around X-Pro bond, 1H and 13C NMR