2-phenyl-2,3-dihydro-1,2-benzoselenazol-3-one

• ChemBase ID: 105101
• Molecular Formular: C13H9NOSe
• Molecular Mass: 274.17666
• Monoisotopic Mass: 274.98493491
• SMILES: O=c1n([se]c2c1cccc2)c1ccccc1
• Canonical SMILES: O=c1c2ccccc2[se]n1c1ccccc1
• InChI: InChI=1S/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H
• InChIKey: DYEFUKCXAQOFHX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-phenyl-2,3-dihydro-1,2-benzoselenazol-3-one
• IUPAC Traditional name: ebselen
• Synonyms: Ebselen; 2-Phenyl-1,2-benzisoselenazol-3(2H)-one; EBSELEN

Database IDs

• CAS Number: 60940-34-3
• MDL Number: MFCD00210937
• PubChem SID: 24278417; 162092086
• PubChem CID: 3194
• CHEMBL: 51085
• Chemspider ID: 3082
• Wikipedia Title: Ebselen

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.6548
• LogD (pH = 7.4): 2.6548
• Log P: 2.6548
• Molar Refractivity: 71.5419 cm^3
• Polarizability: 21.920458 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 180-181°C

Safety Information

• Storage Condition: 0°C
• RTECS: DE4140750
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 3283
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/25-33-50/53
• Safety Statements: 20/21-28-45-60-61
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H331-H373-H410
• GHS Precautionary statements: P261-P273-P301 + P310-P311-P501
• RID/ADR: UN 3283 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: >99%

DETAILS

MP Biomedicals - 02158809

Purity: >99%
Novel selenium-containing anti-flammatory agent. Inhibits 5-LO, CO, NADPH oxidase, and protein kinase C. Potent antioxidant. Possesses a unique glutathione peroxidase-like activity.
Also shown to be an inhibitor of free radical induced apoptosis and neuroprotective agent.

Sigma Aldrich - E3520

Biochem/physiol Actions
An organo-selenium compound possessing antioxidant properties. Inhibits mammalian lipoxygenases in the absence of thiol groups, and glutathione S-transferase and papain via the interaction with cysteine residues. Also inhibits indoleamine 2,3-dioxygenase by covalently modifying a cysteine residue, the effect being reversible with dithiothreitol.1 Inhibits oxidation of low density lipoproteins (LDL).

REFERENCES

• Cotgreave, I.A., et al., Biochem. Pharmacol. , 38 : 649 (1989).