16417-38-2

Basic information

• Product Name: N-Palmitoyl-L-serine
• Synonyms: N-HEXADECANOYL-SERINE;N-palmitoyl-L-serine;2-(Hexadecanoylamino)-3-hydroxypropanoic acid;N-(1-Oxohexadecyl)-L-serine;Einecs 240-466-4
• CAS NO: 16417-38-2
• Molecular Formula: C₁₉H₃₇NO₄
• Molecular Weight: 343.5
• EINECS: 240-466-4
• Mol File: 16417-38-2.mol

Chemical Properties

• Melting Point: 96-99 °C
• Boiling Point: 540 °C at 760 mmHg
• Flash Point: 280.4 °C
• Appearance: /
• Density: 1.008g/cm³
• Vapor Pressure: 6.5E-14mmHg at 25°C
• Refractive Index: 1.479
• PKA: 3.28±0.10(Predicted)
• CAS DataBase Reference: N-Palmitoyl-L-serine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Palmitoyl-L-serine(16417-38-2)
• EPA Substance Registry System: N-Palmitoyl-L-serine(16417-38-2)

Safety Data

• Hazardous Substances Data: 16417-38-2(Hazardous Substances Data)

Usage

Uses

Used in Skincare and Cosmetic Industry:
N-Palmitoyl-L-serine is used as a moisturizing and protective ingredient for its potential to enhance skin hydration and provide a protective barrier against environmental stressors.
Used in Anti-Aging and Wrinkle-Reducing Formulations:
N-Palmitoyl-L-serine is used as an anti-aging and wrinkle-reducing agent for its potential to improve skin elasticity and reduce the appearance of fine lines and wrinkles.
Used in Drug Delivery Systems:
N-Palmitoyl-L-serine is studied for its potential use in drug delivery systems, aiming to improve the delivery and efficacy of pharmaceutical agents for the treatment of certain skin conditions.
Used in Pharmaceutical Industry:
N-Palmitoyl-L-serine demonstrates its versatility and potential applications in the pharmaceutical industry, particularly in the development of treatments for specific skin conditions, due to its anti-inflammatory and protective properties.

InChI:InChI=1/C19H37NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(22)20-17(16-21)19(23)24/h17,21H,2-16H2,1H3,(H,20,22)(H,23,24)/t17-/m0/s1

Upstream product

• 56-45-1 L-serin 
• 1492-30-4 4-nitrophenyl palmitate 
• 114134-57-5 N-hexadecanoyl-L-serine methyl ester 
• 56776-06-8 N-(palmitoyloxy)succinimide 
• 57-10-3 1-hexadecylcarboxylic acid 
• 14464-31-4 palmitic acid N-succinimide ester 
• 112-67-4 n-hexadecanoyl chloride 

Downstream Products

• 947325-41-9 2-(S)-hexadecanoylamino-3-hydroxythiopropionic acid S-phenyl ester 
• 947325-42-0 3-(tert-butyldimethylsilanyloxy)-2-(S)-hexadecanoylaminothiopropionic acid S-phenyl ester 

Relevant articles and documents

N-acyl-O-phosphocholineserines: Structures of a novel class of lipids that are biomarkers for Niemann-Pick C1 disease

Niemann-Pick disease type C1 (NPC1) is a fatal, neurodegenerative, cholesterol storage disorder. With new therapeutics in clinical trials, there is an urgency to improve diagnostics and monitor therapeutic efficacy with biomarkers. In this study, we sought to define the structure of an unknown lipid biomarker for NPC1 with [M + H]+ ion at m/z 509.3351, previously designated as lysoSM-509. The structure of N-palmitoyl-O-phosphocholineserine (PPCS) was proposed for the lipid biomarker based on the results from mass spectrometric analyses and chemical derivatizations. As no commercial standard is available, authentic PPCS was chemically synthesized, and the structure was confirmed by comparison of endogenous and synthetic compounds as well as their derivatives using liquid chromatographytandem mass spectrometry (LC-MS/MS). PPCS is the most abundant species among N-acyl-O-phosphocholineserines (APCS), a class of lipids that have not been previously detected in biological samples. Further analysis demonstrated that all APCS species with acyl groups ranging from C14 to C24 were elevated in NPC1 plasma. PPCS is also elevated in both central and peripheral tissues of the NPC1 cat model. Identification of APCS structures provide an opportunity for broader exploration of the roles of these novel lipids in NPC1 disease pathology and diagnosis.-Sidhu, R., Y. Mondjinou, M. Qian, H. Song, A. B. Kumar, X. Hong, F-F. Hsu, D. J. Dietzen, N. M. Yanjanin, F. D. Porter, E. Berry- Kravis, C. H. Vite, M. H. Gelb, J. E. Schaffer, D. S. Ory, and X. Jiang. N-acyl-O-phosphocholineserines: structures of a novel class of lipids that are biomarkers for Niemann-Pick C1 disease. J. Lipid Res. 2019. 60: 1410-1424.

The relationship between the structure and properties of amino acid surfactants based on glycine and serine

Two series of surfactants based on glycine and serine were synthesized with aproic acid, octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid and hexadecanoic acid. All the surfactants were characterized by MS and 1H NMR, the structures of the synthesized surfactants are correct and the signals in MS and 1H NMR can be explained. The reaction conditions, surface properties and foam properties were studied. For the two series of surfactants, critical micelle concentration (CMC) and γ CMC (surface tension at CMC) decrease and surface activity is enhanced as the length of carbon chain increases. The surfactants with tetradecanoyl and hexadecanoyl groups show a good foaming property and especially, the long-chain acyl-serine performs better. These are all related to the hydromethyl group in the serine.

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.

Chiral surfaces in micelles of enantiomeric N-palmitoyl- and N-stearoylserine

Circular dichroism (CD) spectra were recorded with micellar aggregates of a series of N-palmitoyl and N-stearoyl derivatives of amino acid enantiomers. N-Palmitoyl- and N-stearoyl-L- (or -D-) serine in the micelle form (10-4 M in aqueous 0.01 M KOH) exhibited a strong CD band centered at 213-215 nm which could be completely abolished by disintegrating the micelles in 50% ethanol. Analogous CD spectra of enantiomeric N-palmitoyl derivatives of tyrosine or proline did not display any exclusive band for the micellar form. The CD spectra of the enantiomeric N-palmitoyl- or N-stearoylserine micelles presumably originated from a repetitive arrangement of the amide planes on the micellar surface. Computer modeling suggested an alternating tilt of the amide planes associated with the formation of parallel spines of -NH?OC- intermolecular hydrogen bonds which cover the micellar surface. Each of such spines has a supramolecular chirality, which is presumably the origin of the observed CD band. The network of such chiral spines forms a unique chiral surface which may bear important implications for surface recognition and catalysis.

HIGHER N-ACYL-L-AMINO ACID DERIVATIVES

A preparative method is proposed for obtaining higher N-acylamino acids by reaction of free amino acids with fatty acid nitrophenyl esters.It was shown that these acids can transport positive ions through a liquid lipophilic medium.A direct method is proposed for obtaining fatty acid 4-nitrophenyl esters by boiling 4-nitrophenol and the fatty acid in xylene in a Soxhlet apparatus in the presence of an acid catalyst.