N-Hydroxysuccinimide

HCID 80170CAS 6066-82-6

Basic information

Standard SMILES
O=C1CCC(=O)N1O
InChIKey
NQTADLQHYWFPDB-UHFFFAOYSA-N
Molecular formula
C4H5NO3
Average molar mass
115.09 g/mol
Monoisotopic mass
115.02694302

Names & identifiers

Preferred name
N-Hydroxysuccinimide
IUPAC
1-hydroxypyrrolidine-2,5-dione
English name
N-Hydroxysuccinimide
Molecular formula
C4H5NO3
Molecular weight
115.09

Names & synonyms

N-Hydroxysuccinimide6066-82-61-hydroxypyrrolidine-2,5-dione1-Hydroxysuccinimide1-Hydroxy-2,5-pyrrolidinedioneHydroxysuccinimide2,5-Pyrrolidinedione, 1-hydroxy-Succinimide, N-hydroxy-MJE3791M4TNSC-74335DTXSID7064102RefChem:830145
Show more names
1-HYDROXY-PYRROLIDINE-2,5-DIONEHONSUN-HYDROXYSUCCINIMDEN-HYDROXYSUCCINAMIDENHS N-HYDROXYSUCCINIMIDE,
DTXCID7042855228-001-3HOSuN-hydroxy succinimideMFCD00005516N-hydroxysuccinimide (HOSu)NHSN-hydroxysuccinimid

Database identifiers

CAS
6066-82-6
PubChem CID
80170
DTXSID
DTXSID7064102
ChEMBL
CHEMBL403753
UNII
MJE3791M4T
EC Number
228-001-3
Nikkaji
J26.034G

Properties

Computed structural properties

XLogP
-1.4
Topological polar surface area
57.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
8

Physicochemical properties

Melting point
95 · 95-98 °C(lit.)
Boiling point
215.33 °C · 215.33°C (rough estimate)
Density
1.4769 · 1.4769 (rough estimate)
vapor pressure
0 Pa · 0Pa at 25℃
refractive index
1.408 · 1.4080 (estimate)
storage temp.
2 °C · Store at +2°C to +8°C.

Safety & regulation

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
hs_code
29251995
risk_code
36/37/38
Signal word
Danger

Chemistry & industry

Applications · 4 items

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).

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京一化生物科技有限公司13429882898; 13429882898

Related reactions

3,866 records

Linked notes

Loading…