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
Show more names
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
- Formal charge
- 0
- Complexity
- 126
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.
- solubility
- DMSO (Soluble), Methanol (Slightly)
- pka
- 7.81 · 7.81±0.20(Predicted)
- form
- Liquid or Solid
- color
- Clear yellow-brown to brown
- PH
- 5 · 5-7 (50g/l, H2O, 20℃)
- Water Solubility
- SOLUBLE
- Sensitive
- Hygroscopic
- BRN
- 113913 · 113913
- Stability
- Stable. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, strong bases. Protect from moisture.
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- InChI
- 1S/C4H5NO3/c6-3-1-2-4(7)5(3)8/h8H,1-2H2
- InChIKey
- NQTADLQHYWFPDB-UHFFFAOYSA-N
- SMILES
- ON1C(=O)CCC1=O
- LogP
- -2.01 · -2.01
- CAS DataBase Reference
- 6066 · 6066-82-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 3791 M4T · MJE3791M4T
- NIST Chemistry Reference
- N-hydroxylsuccinimide(6066-82-6)
- EPA Substance Registry System
- 2 · 2,5-Pyrrolidinedione, 1-hydroxy- (6066-82-6)
- UNSPSC Code
- 12352115 · 12352115
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 315 · H315-H318
- Precautionary statements
- 264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P362+P364
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 22 · 22-24/25-26-36
- WGK Germany
- 3 · 3
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29251995 · 29251995
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Skin · Eye Dam. 1Skin Irrit. 2
- REACH Registrations
- Active
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
- Symbol(GHS)
- GHS05
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 22-24/25-26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H318
- REACH Registrations
- Active
- Hazard Classifications
- Eye Dam. 1Skin Irrit. 2
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P332+P313-P362+P364
Chemistry & industry
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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