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N-Hydroxysuccinimide

Base Information Edit
  • Chemical Name:N-Hydroxysuccinimide
  • CAS No.:6066-82-6
  • Molecular Formula:C4H5NO3
  • Molecular Weight:115.089
  • Hs Code.:29251995
  • European Community (EC) Number:228-001-3
  • NSC Number:74335
  • UNII:MJE3791M4T
  • DSSTox Substance ID:DTXSID7064102
  • Nikkaji Number:J26.034G
  • Wikipedia:N-Hydroxysuccinimide
  • Wikidata:Q408833
  • ChEMBL ID:CHEMBL403753
  • Mol file:6066-82-6.mol
N-Hydroxysuccinimide

Synonyms:N-hydroxysuccinimide

Suppliers and Price of N-Hydroxysuccinimide
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • N-Hydroxysuccinimide
  • 25g
  • $ 85.00
  • TRC
  • N-Hydroxysuccinimide
  • 100g
  • $ 120.00
  • TCI Chemical
  • N-Hydroxysuccinimide >98.0%(T)
  • 25g
  • $ 33.00
  • TCI Chemical
  • N-Hydroxysuccinimide >98.0%(T)
  • 500g
  • $ 188.00
  • TCI Chemical
  • N-Hydroxysuccinimide [Coupling Reagent for Peptide] >98.0%(GC)(T)
  • 25g
  • $ 83.00
  • TCI Chemical
  • N-Hydroxysuccinimide >98.0%(T)
  • 100g
  • $ 62.00
  • SynQuest Laboratories
  • N-Hydroxysuccinimide 97%
  • 500 g
  • $ 75.00
  • SynQuest Laboratories
  • N-Hydroxysuccinimide 97%
  • 25 g
  • $ 10.00
  • SynQuest Laboratories
  • N-Hydroxysuccinimide 97%
  • 100 g
  • $ 20.00
  • Sigma-Aldrich
  • N-Hydroxysuccinimide 98%
  • 5kg
  • $ 2250.00
Total 297 raw suppliers
Chemical Property of N-Hydroxysuccinimide Edit
Chemical Property:
  • Appearance/Colour:white to pale yellow 
  • Vapor Pressure:0.00155mmHg at 25°C 
  • Melting Point:95-98 °C(lit.) 
  • Refractive Index:1.599 
  • Boiling Point:262.4 °C at 760 mmHg 
  • PKA:7.81±0.20(Predicted) 
  • Flash Point:112.5 °C 
  • PSA:57.61000 
  • Density:1.649 g/cm3 
  • LogP:-0.53750 
  • Storage Temp.:2-8°C 
  • Sensitive.:Hygroscopic 
  • Solubility.:DMSO (Soluble), Methanol (Slightly) 
  • Water Solubility.:SOLUBLE 
  • XLogP3:-1.4
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:3
  • Rotatable Bond Count:0
  • Exact Mass:115.026943022
  • Heavy Atom Count:8
  • Complexity:126
Purity/Quality:

99% *data from raw suppliers

N-Hydroxysuccinimide *data from reagent suppliers

Safty Information:
  • Pictogram(s): IrritantXi 
  • Hazard Codes:Xi 
  • Statements: 36/37/38 
  • Safety Statements: 22-24/25-26-36 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Nitrogen Compounds -> Succinimides
  • Canonical SMILES:C1CC(=O)N(C1=O)O
  • Description N-hydroxysuccinimide is a synthetic ingredient used in cosmetics as an ester to soften and condition skin. It's also a reagent, a substance used to trigger a reaction that leads to a new substance, such as peptides and polymers.N-Hydroxysuccinimide is used in cosmetics and beauty products as an ester often seen in eye creams. N-hydroxysuccinimide activates the elimination of blood originated pigments responsible for dark color and inflammation that causes under eye circles. "Infra-orbital shadows are due to the accumulation of hemoglobin and its coloured degradation products - biliverdin, bilirubin and iron - in the dermis and epidermis ... N-hydroxysuccinimide renders the iron soluble for natural elimination" (source).
  • Uses Reagent for preparation of active esters of amino acids. N-Hydroxysuccinimide is used for improved amidations in the carbodiimide method. It is also used to activate a carboxyl group and reacts with amine to form amide. It is involved in the preparation of N-hydroxymaleimide-styrene copolymer. Further, it finds use in analytical chemistry. As an additive, it is used in the carbodiimide method for improved amidations and peptide couplings. N-hydroxysuccinimide (NHS) is often used to assist carbodiimide-mediated peptide coupling by forming an active ester intermediate via condensation of the surface carboxyl group and NHS. The NHS-reactive ester intermediate is susceptible to nucleophilic attack by primary amines and results in the formation of stable amide bonds between the biomaterial surface and the N-terminus of the peptide.
Technology Process of N-Hydroxysuccinimide

There total 63 articles about N-Hydroxysuccinimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate; isobutylamine; In dichloromethane; at 20 ℃; for 4h;
girard's reagent T; In methanol; dichloromethane;
DOI:10.1021/co400003d
Guidance literature:
2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate; 6-amino-3,4-benzodioxane; In dichloromethane; at 20 ℃; for 4h;
girard's reagent T; In methanol; dichloromethane;
DOI:10.1021/co400003d
Guidance literature:
With chitosan; In aq. phosphate buffer; dichloromethane; at 50 ℃; for 5h; Solvent; Temperature; Microwave irradiation;
Refernces Edit

Dendrimeric-containing nitronyl nitroxides as spin traps for nitric oxide: Synthesis, kinetic, and stability studies

10.1021/ma021292m

The research focuses on the synthesis, kinetic, and stability studies of dendrimeric-containing nitronyl nitroxides as spin traps for nitric oxide (NO?). The purpose of this study was to develop a family of dendrimers that could effectively trap NO?, a free radical with a long lifetime in biological environments, and to overcome the limitations of traditional spin traps, such as iron chelates, which are unstable in biological milieus. The researchers synthesized a series of dendrimers with terminal nitronyl nitroxide groups and evaluated their reaction rates with NO?, their spin-trapping capacity, and their stability under various experimental conditions. The key chemicals used in the synthesis process included 2-(4-carboxyphenyl)-4,4,5,5-tetramethylimidazoline 3-oxide, N-hydroxysuccinimide, 1,3-dicyclohexylcarbodiimide, and various dendrimers like poly(propyleneimine tetraamine) dendrimers (DAB-Am).

ω-AMINOALKYL β-GLYCOSIDES OF N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE, AND THEIR CONJUGATES WITH MENINGOCOCCAL GROUP C POLYSACCHARIDE

10.1016/0008-6215(83)88218-4

The research focuses on the synthesis of w-aminoalkyl β-glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) and their conjugates with meningococcal group C polysaccharide, aiming to enhance the immunogenicity of the polysaccharide antigen. Key chemicals involved in the study include 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline, 6-(benzyloxycarbonylamino)-1-hexanol, L-alanyl-D-isoglutamine benzyl ester hydrochloride, and N-hydroxysuccinimide. The researchers synthesized the 6-aminohexyl β-glycoside of MDP and its spacer-arm-linked analog (3.8 nm) and coupled these with meningococcal group C polysaccharide. The resulting conjugates exhibited enhanced antigenicity in vitro but did not show enhanced immunogenicity in vivo.

TOTAL SYNTHESIS OF AMAUROMINE

10.1016/S0040-4020(01)96070-3

The research describes the successful total synthesis of the dimeric alkaloid amauromine, a compound of interest due to its unique structure and biological activity as a vasodilator. The purpose of the study was to achieve the first total synthesis of amauromine using a convergent synthetic route based on the thio-Claisen rearrangement reaction through a sulphonium salt, starting from L-tryptophan. Key chemicals used in the synthesis include L-tryptophan, phosphorus pentasulfide, methyl iodide, dicyclohexylcarbodiimide (DCC), N-hydroxysuccinimide (HOSu), potassium carbonate, prenyl bromide, titanium tetrachloride, and lithium aluminium hydride. The synthesis involved multiple steps, including oxidation, esterification, introduction of methylthio function, formation of the key intermediate diketopiperazine, thio-Claisen rearrangement, catalytic reduction, and reductive desulphurization. The final step involved concurrent cyclization and reductive desulphurization using TiCl4-LiAlH4 to obtain amauromine. The study concluded that the total synthesis was achieved with a yield of 15%, and the synthesized amauromine was identical to the natural compound in all respects, confirming the success of the synthetic route. This achievement supports the hypothesis on the mode of introduction of the inverted isoprene unit in related indole alkaloids and provides a potential pathway for the biosynthesis of amauromine.

General method for the preparation of active esters by palladium-catalyzed alkoxycarbonylation of aryl bromides

10.1021/jo5025464

The research focuses on the development of a general method for the preparation of active esters through palladium-catalyzed alkoxycarbonylation of aryl bromides. The study explores the use of various oxygen nucleophiles, including N-hydroxysuccinimide (NHS), pentafluorophenol (PFP), hexafluoroisopropanol (HFP), 4-nitrophenol, and N-hydroxyphthalimide, to synthesize active esters with high functional group tolerance and good to excellent isolated yields. The methodology was further extended to access a synthetic precursor to the HIV-protease inhibitor, saquinavir. The experiments involved the use of a Pd catalyst, ligands, and carbon monoxide (CO) under specific conditions to achieve the desired transformations. The analyses used to characterize the products included 1H NMR, 13C NMR, 19F NMR, and HRMS, providing detailed spectral data to confirm the structures of the synthesized active esters.

Facile and universal immobilization of l-lysine inspired by mussels

10.1039/c2jm16598h

The study presents the synthesis and application of a novel molecule, lysine-dopamine (LDA), which was inspired by the adhesive properties of mussels and the bio-functionality of L-lysine. LDA serves as a universal modifier for various surfaces to enhance their biocompatibility, cell adhesion, and promote cell growth. The chemicals used in the study include L-lysine, N-hydroxysuccinimide (NHS), di-t-butyl dicarbonate ((Boc)2O), dopamine hydrochloride (DA-HCl), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCl) for the synthesis of LDA. These chemicals were utilized in a series of reactions to create LDA, which was then applied to different substrates through a simple dip-coating process. The purpose of these chemicals was to create a functional molecule that could mimic the strong adhesion properties of mussel proteins and improve the biocompatibility of surfaces for biomedical applications.

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