14565-47-0

Basic information

• Product Name: LAURIC ACID N-HYDROXY-SUCCINIMIDE ESTER
• Synonyms: 2,5-Pyrrolidinedione, 1-[(1-oxododecyl)oxy]-;2,5-Dioxopyrrolidin-1-Yl Dodecanoate;LAURIC ACID N-HYDROXYSUCCINIMIDE EST;DODECANOIC ACID-N-HYDROXYSUCCINIMIDE ESTER;DODECANOIC ACID-OSU;LAURIC ACID-OSU;LAURIC ACID N-HYDROXY-SUCCINIMIDE ESTER;SUCCINIMIDYL LAURATE
• CAS NO: 14565-47-0
• Molecular Formula: C₁₆H₂₇NO₄
• Molecular Weight: 297.39
• Mol File: 14565-47-0.mol
• Article Data: 35

Chemical Properties

• Melting Point: 76-77 °C
• Boiling Point: 392.3°Cat760mmHg
• Flash Point: 191.1°C
• Appearance: /
• Density: 1.07g/cm³
• Vapor Pressure: 2.31E-06mmHg at 25°C
• Refractive Index: 1.489
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: LAURIC ACID N-HYDROXY-SUCCINIMIDE ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: LAURIC ACID N-HYDROXY-SUCCINIMIDE ESTER(14565-47-0)
• EPA Substance Registry System: LAURIC ACID N-HYDROXY-SUCCINIMIDE ESTER(14565-47-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 14565-47-0(Hazardous Substances Data)

Usage

Biochem/physiol Actions

Lauric acid N-hydroxysuccinimide ester may be used for the synthesis of N-acylamino acids and lipidization of polypeptides or other applications that use N-hydroxysuccinimide ester conjugation chemistry.

InChI:InChI=1/C16H27NO4/c1-2-3-4-5-6-7-8-9-10-11-16(20)21-17-14(18)12-13-15(17)19/h2-13H2,1H3

Upstream product

• 143-07-7 lauric acid 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 112-16-3 n-dodecanoyl chloride 
• 74124-79-1 di(succinimido) carbonate 
• 123-56-8 Succinimide 

Downstream Products

• 14379-56-7 N-Lauroylserine 
• 58725-39-6 N-dodecanoyl-L-proline 
• 1092661-31-8 5'-O-dimethoxytrityl-2'-[(dodecanoyl)amino]-2'-deoxyuridine 
• 1069128-45-5 C₆₉H₁₀₂N₁₂O₁₇S 
• 1352209-30-3 1-(4-fluorophenyl)-1-dodecanone 
• 1428743-62-7 1-(4-[1-(tert-butyl)-1,1-dimethylsilyl]oxyphenyl)-1-dodecanone 

Relevant articles and documents

L-serine and glycine based ceramide analogues as transdermal permeation enhancers: Polar head size and hydrogen bonding

Novel transdermal permeation enhancers related to stratum corneum ceramides were investigated. The synthesis of a series of simple compounds based on two selected amino acids, L-serine and glycine, and their enhancement activities are reported. Glycine derivative 3 enhanced the permeation of theophylline through human skin in vitro 12.5±0.5 times. The relationships between properties of the polar head of the compounds and their activity are discussed.

Glucosamine anchored cancer targeted nano-vesicular drug delivery system of doxorubicin

Background: Efficacy of an anticancer drug is challenged by severe adverse effects persuaded by the drug itself; hence designing a tumour targeted delivery system is chosen as an objective of this research work.Purpose: We propose, glucose transporter targeting ligand, i.e. synthesised N-lauryl glucosamine (NLG) anchored doxorubicin (DOX) in niosomal formulation.Methods: Synthesised NLG was incorporated into niosomal formulation of DOX using Span 60 as surfactant, cholesterol as membrane stabilizer and dicetyl phosphate (DCP) as stabilizer.Results: The formulation was stable with particle size of 110 ± 5 nm, zeta potential -30 ± 5 mV and entrapment efficiency approximately 95%. DSC and XRD pattern of freeze-dried formulation demonstrated encapsulation of DOX in niosomal formulation. Cytotoxicity of targeted niosomal formulation (IC50 = 0.830 ppm) was higher than non-targeted niosomal formulation (IC50 = 1.369 ppm) against B6F10 melanoma cell lines. In vitro cellular internalization revealed that targeted niosomal formulation was internalised more efficiently with higher cellular retention by cancer cells compared to the non-targeted niosomal formulation and free DOX. In vitro receptor binding and docking study of targeted niosomal formulation had shown the comparative association potential with glucose receptor.Conclusion: NLG anchored niosomal formulation of DOX with enhanced cytotoxicity, internalization and receptor binding potential has implication in targeted cancer therapy.

Encapsulation of paclitaxel into lauric acid-O-carboxymethyl chitosan-transferrin micelles for hydrophobic drug delivery and site-specific targeted delivery

Transferrin/PEG/O-carboxymethyl chitosan/fatty acid/paclitaxel (TPOCFP) micelles were tested for suitability as a drug carrier characterized by low cytotoxicity, sustained release, high cellular uptake, and site-specific targeted delivery of hydrophobic drugs. Characterization, drug content, encapsulation efficiency, and in vitro drug release were investigated. When the feeding amount of paclitaxel (PTX) was increased, the drug content increased, but loading efficiency decreased. TPOCFP micelles had a spherical shape, with a particle size of approximately 140-649 nm. In vitro cell cytotoxicity and hemolysis assays were conducted to confirm the safety of the micelles. Anticancer activity and confocal laser scanning microscopy (CLSM) were used to confirm the targeting efficiency of target ligand-modified TPOCFP micelles. Anticancer activity and CLSM results clearly demonstrated that transferrin-modified TPOCFP micelles were quickly taken up by the cell. The endocytic pathway of TPOCFP micelles was analyzed by flow cytometry, revealing transfection via receptor-mediated endocytosis. These results suggest that PTX-encapsulated TPOCFP micelles may be used as an effective cancer-targeting drug delivery system for chemotherapy.

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.

A reagent for analysis of blood and preparation method therof

The present invention relates to a compound for hemanalysis, capable of lysing blood cells except leukocytes without globulolysis of leukocytes. The present invention further relates to a production method thereof. According to various embodiments of the present invention, the compound can lyse every blood cell except the leukocyte without globulolysis of leukocyte, thereby being selectively applicable to various fields. In addition, a kit or a composition for globulolysis using the compound and a kit or a composition for hemanalysis exhibit excellent efficiency compared to conventional counterparts. To this end, the compound is represented by chemical formula 14 or 15.COPYRIGHT KIPO 2018