14464-32-5

Basic information

• Product Name: Stearic acid-N-hydroxysuccinimide ester
• Synonyms: STEARIC ACID-N-HYDROXYSUCCINIMIDE ESTER;OCTADECANOIC ACID-NHSE;N-SUCCINIMIDYL STEARATE;N-HYDROXY SUCCINIMIDO STEARIC ACID ESTER;2,5-PYRROLIDINEDIONE, 1-[(1-OXOOCTADECYL)OXY]-;stearicacid-n-hydroxysuccinimideesterstearicacid-nhs;1-[(1-Oxooctadecyl)oxy]-2,5-pyrrolidinedione;Stearic Acid Hydroxysuccinimide Ester
• CAS NO: 14464-32-5
• Molecular Formula: C₂₂H₃₉NO₄
• Molecular Weight: 381.55
• Product Categories: Medical Intermediates;Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Intermediates;Glucuronides;Metabolites;Nicotine Derivatives
• Mol File: 14464-32-5.mol
• Article Data: 35

Chemical Properties

• Melting Point: 92-93°C
• Boiling Point: 473.06 °C at 760 mmHg
• Flash Point: 239.898 °C
• Appearance: Colourless shiny leaflets
• Density: 1.019 g/cm³
• Vapor Pressure: 4.06E-09mmHg at 25°C
• Refractive Index: 1.487
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Stearic acid-N-hydroxysuccinimide ester(CAS DataBase Reference)
• NIST Chemistry Reference: Stearic acid-N-hydroxysuccinimide ester(14464-32-5)
• EPA Substance Registry System: Stearic acid-N-hydroxysuccinimide ester(14464-32-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 14464-32-5(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Shiny Leaflets

Uses

Different sources of media describe the Uses of 14464-32-5 differently. You can refer to the following data:
1. Stearic Acid derivative.
2. A Nicotine metabolite. Carcinogen.
3. N-Succinimidyl Stearate (cas# 14464-32-5) is a compound useful in organic synthesis.

General Description

Stearic acid N-hydroxysuccinimide ester is an N-Hydroxysuccinimide ester of fatty acid. They are used in the synthesis of N-acyl amino acids and fatty acyl CoA. They are also used in the direct N-acylation of sphingenine or sphinganine thus leading to the formation of ceramides.

InChI:InChI=1/C22H39NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(26)27-23-20(24)18-19-21(23)25/h2-19H2,1H3

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 57-11-4 stearic acid 
• 112-80-1 cis-Octadecenoic acid 

Downstream Products

• 54336-64-0 (2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol 
• 86216-27-5 benzyl 2-deoxy-4,6-O-isopropylidene-2-(octadecanoylamino)-α-D-glucopyranoside 
• 1393355-27-5 2-deoxy-2-fluoro-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->1)-(2S,3R,E)-2-octadecanamido-3-O-benzyl-4-octadecene-1,3-diol 
• 14379-33-0 N-octadecanoyl-L-valine 
• 6162-69-2 N-(2-mercaptoethyl)stearamide 
• 1389347-69-6 (S)-2,3-distearamidopropanoic acid 
• 1204614-75-4 4'-O-stearoyl-resveratrol 
• 1325147-13-4 N-((2S,3R,4S,5S)-3,4,5-tris(benzyloxy)-6-(dodecyloxy)-1-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexan-2-yl)stearamide 
• 105955-10-0 N-stearoyldopamine 
• 21400-91-9 N-stearoyl-L-tryptophan 
• 36577-40-9 N-stearoyl-L-proline 
• 57993-25-6 N-stearoyl-L-tyrosine 
• 37571-95-2 N-n-octadecanoyl (L)-phenylalanine 
• 133849-18-0 N-stearoyl-DL-phenylalanine 

Relevant articles and documents

MALDI-TOF mass spectrometric analysis of enzyme activity and lectin trapping on an array of N-glycans

Active arrays: Complex lipid-tagged oligosaccharides, including large multiantennary species, can be efficiently immobilized on self-assembled monolayers of alkyl mercaptans . These arrays can be used to follow the action of a galactosyltransferase (GalT) and a hydrolase. The utility of the system for the selective trapping and identification of a lectin from a complex mixture was also demonstrated.

Chemically Reactive Liposomes as a New Type of Sensor for Proteins

A new type of sensor for proteins has been developed by utilizing a liposome which contains molecules chemically reactive with protein on the membrane surface of the liposome.The covalently bound aggregation of proteins with liposomes has been observed by a quasi-elastic light scattering measurement at the concentration down to about 1E-8 mol dm-3.

Hemoglobin Derivative Co-conjugated with Fatty Acid-linked PEG and Alkoxy PEG as a Blood Substitute

The invention relates to hemoglobin derivative, particularly hemoglobin which is co-conjugated with both fatty acid-linked polyethylene glycol (FA-PEG) derivatives and alkoxy polyethylene glycol (alkoxy-PEG) derivatives, and a method for making such hemoglobin derivative. Various embodiments of the invention include crosslinked hemoglobin which is co-conjugated with both FA-PEG derivatives and alkoxy-PEG derivatives. Such hemoglobin derivative according to the invention exhibit non-toxicity and extended intravascular retention time.

Development of small-molecule inhibitors of fatty acyl-AMP and fatty acyl-CoA ligases in Mycobacterium tuberculosis

Lipid metabolism in Mycobacterium tuberculosis (Mtb) relies on 34 fatty acid adenylating enzymes (FadDs) that can be grouped into two classes: fatty acyl-CoA ligases (FACLs) involved in lipid and cholesterol catabolism and long chain fatty acyl-AMP ligases (FAALs) involved in biosynthesis of the numerous essential and virulence-conferring lipids found in Mtb. The precise biochemical roles of many FACLs remain poorly characterized while the functionally non-redundant FAALs are much better understood. Here we describe the systematic investigation of 5′-O-[N-(alkanoyl)sulfamoyl]adenosine (alkanoyl adenosine monosulfamate, alkanoyl-AMS) analogs as potential multitarget FadD inhibitors for their antitubercular activity and biochemical selectivity towards representative FAAL and FACL enzymes. We identified several potent compounds including 12-azidododecanoyl-AMS 28, 11-phenoxyundecanoyl-AMS 32, and nonyloxyacetyl-AMS 36 with minimum inhibitory concentrations (MICs) against M. tuberculosis ranging from 0.098 to 3.13 μM. Compound 32 was notable for its impressive biochemical selectivity against FAAL28 (apparent Ki = 0.7 μM) versus FACL19 (Ki > 100 μM), and uniform activity against a panel of multidrug and extensively drug-resistant TB strains with MICs ranging from 3.13 to 12.5 μM in minimal (GAST) and rich (7H9) media. The SAR analysis provided valuable insights for further optimization of 32 and also identified limitations to overcome.

Synthesis and Characterization of Fatty Acid Grafted Chitosan Polymer and Their Nanomicelles for Nonviral Gene Delivery Applications

The aim of this study was to synthesize and characterize fatty acid-grafted-chitosan (fatty acid-g-CS) polymer and their nanomicelles for use as carriers for gene delivery. CS was hydrophobically modified using saturated fatty acids of increasing fatty acyl chain length. Carbodiimide along with N-hydroxysuccinimide was used for coupling carboxyl group of fatty acids with amine groups of CS. Proton nuclear magnetic resonance and Fourier transform infrared spectroscopy were used to quantify fatty acyl substitution onto CS backbone. The molecular weight distribution of the synthesized polymers was determined using size exclusion high performance liquid chromatography and was found to be in range of the parent CS polymer (～50 kDa). The critical micelle concentration (cmc) of the polymers was determined using pyrene as a fluorescent probe. The cmc was found to decrease with an increase in fatty acyl chain length. The amphiphilic fatty acid-g-CS polymers self-assembled in an aqueous environment to form nanomicelles of ～200 nm particle size and slightly positive net charge due to the cationic nature of free primary amino groups on CS molecule. These polymeric nanomicelles exhibited excellent hemo- and cytocompatibility, as evaluated by in vitro hemolysis and MTT cell viability assay, respectively, and showed superior transfection efficiency compared to unmodified chitosan and naked DNA. The surface of these nanomicelles can be further modified with ligands allowing for selective targeting, enhanced cell binding, and internalization. These nanomicelles can thus be exploited as potential nonviral gene delivery vectors for safe and efficient gene therapy.