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| | N-Hydroxysuccinimide Basic information |
| | 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) | | pka | 7.81±0.20(Predicted) | | form | Liquid or Solid | | color | Clear yellow-brown to brown | | PH | 5-7 (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. | | InChIKey | NQTADLQHYWFPDB-UHFFFAOYSA-N | | LogP | -2.01 | | CAS DataBase Reference | 6066-82-6(CAS DataBase Reference) | | NIST Chemistry Reference | N-hydroxylsuccinimide(6066-82-6) | | EPA Substance Registry System | 2,5-Pyrrolidinedione, 1-hydroxy- (6066-82-6) |
| 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 |
| | N-Hydroxysuccinimide Usage And Synthesis |
| 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 | | Uses | Reagent for preparation of active esters of amino acids. | | Uses | 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. | | Uses | 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. | | 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. | | 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.] |
| | N-Hydroxysuccinimide Preparation Products And Raw materials |
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