N-Hydroxysuccinimide

N-Hydroxysuccinimide Basic information
Product Name:N-Hydroxysuccinimide
Synonyms:N-HYDROXY-2,5-PYRROLIDINEDIONE;NHS;N-HYDROXYSUCCINIMDE;N-HYDROXYSUCCINIMIDE;N-HYDROXYSUCCINIMIDE POLYMER-BOUND;NHS N-HYDROXYSUCCINIMIDE,;NHS OR HONSU;HOSu~1-Hydroxy-2,5-pyrrolidinedione
CAS:6066-82-6
MF:C4H5NO3
MW:115.09
EINECS:228-001-3
Product Categories:Zero-Length Crosslinker;heteroXlink;Coupling ReagentsSynthetic Reagents;Coupling;Others;APIS;Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Succinimides;Peptide Synthesis;Supported Reagents;Supported Synthesis;Peptide coupling agents;Medical Intermediates;Heterocycles;Other Reagents;Miscellaneous Reagents;Synthetic Organic Chemistry;bc0001;6066-82-6
Mol File:6066-82-6.mol
N-Hydroxysuccinimide Structure
N-Hydroxysuccinimide Chemical Properties
Melting point 95-98 °C(lit.)
Boiling point 215.33°C (rough estimate)
density 1.4769 (rough estimate)
vapor pressure 0Pa at 25℃
refractive index 1.4080 (estimate)
storage temp. Store at +2°C to +8°C.
solubility DMSO (Soluble), Methanol (Slightly)
pka7.81±0.20(Predicted)
form Liquid or Solid
color Clear yellow-brown to brown
PH5-7 (50g/l, H2O, 20℃)
Water Solubility SOLUBLE
Sensitive Hygroscopic
BRN 113913
Stability:Stable. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, strong bases. Protect from moisture.
InChIKeyNQTADLQHYWFPDB-UHFFFAOYSA-N
LogP-2.01
CAS DataBase Reference6066-82-6(CAS DataBase Reference)
NIST Chemistry ReferenceN-hydroxylsuccinimide(6066-82-6)
EPA Substance Registry System2,5-Pyrrolidinedione, 1-hydroxy- (6066-82-6)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 22-24/25-26-36
WGK Germany 3
Hazard Note Irritant
TSCA Yes
HS Code 29251995
MSDS Information
ProviderLanguage
1-Hydroxy-2,5-pyrrolidinedione English
SigmaAldrich English
ACROS English
ALFA English
N-Hydroxysuccinimide Usage And Synthesis
DescriptionN-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).
Chemical PropertiesWhite to pale yellow
UsesReagent for preparation of active esters of amino acids.
UsesN-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.
UsesN-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.
ApplicationN-Hydroxysuccinimide has been used in the synthesis of intermediates such as:
N-succinimidyl 3-(di-tert-butylfluorosilyl)benzoate
4-[2,2-bis[(p-tolylsulfonyl)-methyl] acetyl]benzoic acid-NHS ester
N-succinimidyl 3-iodobenzoate
It has also been used in a protocol for the surface modification of microchannels of a microfluidic-integrated surface plasmon resonance (SPR) platform for the detection and quantification of bacterial pathogens.
Additive used in the carbodiimide method for improved amidations and peptide couplings.
N-Hydroxysuccinimide can be used in the synthesis of N-hydroxysuccinimide ester via dehydration reaction in the presence of dicyclohexylcarbodiimide in carboxylic acid.
SynthesisN-Hydroxysuccinimide can be synthesized by heating succinic anhydride with hydroxylamine or hydroxylamine hydrochloride.
Purification MethodsRecrystallise the imide from EtOH/ethyl acetate [Manesis & Goodmen J Org Chem 52 5331 1987]. [Beilstein 21/9 V 498.]
N-Chlorosuccinimide N-Iodosuccinimide N-Hydroxysuccinimide O-Phthalimide N-Bromosuccinimide Bismaleimide N-HYDROXYSUCCINIMIDYL ACETOACETATE Succinimide Dispersing agent 155 DIALIFOS 5-CFDA N-succinimidyl ester Diethyl succinosuccinate N-Succinimidyl S-Acetylthioglycolate N-(2-Chlorobenzyloxycarbonyloxy)succinimide 5(6)-CARBOXY-2',7'-DICHLOROFLUORESCEIN DIACETATE N-SUCCINIMIDYL ESTER CHLOROPHOSPHONAZO III BOC-L-ISOLEUCINE HYDROXYSUCCINIMIDE ESTER,BOC-L-ISOLEUCINE N-HYDROXYSUCCINIMIDE ESTER N-(9-Fluorenylmethoxycarbonyloxy)succinimide

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