N-Hydroxysuccinimide

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).

Chemical properties

White to pale yellow

The Uses of N-Hydroxysuccinimide

Reagent for preparation of active esters of amino acids.

The Uses of N-Hydroxysuccinimide

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.

The Uses of N-Hydroxysuccinimide

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.

What are the applications of Application

N-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.

What are the applications of Application

N-Hydroxysuccinimide is useful in the carbodiimide method for improved amidations and peptide couplings

Features

Efficiency of EDC-mediated coupling is increased in the presence of NHS
Amine-reactive NHS esters can be made with any carboxyl-containing molecule
NHS derivatives of typical small molecules (e.g., biotin) are uncharged, organic-soluble (dissolve first in DMSO) and cell membrane-permeable
High-purity, crystalline NHS can be used to create high-quality activated derivatives

Synthesis

N-Hydroxysuccinimide can be synthesized by heating succinic anhydride with hydroxylamine or hydroxylamine hydrochloride.

Purification Methods

Recrystallise the imide from EtOH/ethyl acetate [Manesis & Goodmen J Org Chem 52 5331 1987]. [Beilstein 21/9 V 498.]