2-[(3S)-2,6-dioxopiperidin-3-yl]-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase ID: 133283
• Molecular Formular: C13H10N2O4
• Molecular Mass: 258.2295
• Monoisotopic Mass: 258.06405681
• SMILES: c1ccc2c(c1)C(=O)N(C2=O)[C@H]1CCC(=O)NC1=O
• Canonical SMILES: O=C1CC[C@@H](C(=O)N1)N1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)/t9-/m0/s1
• InChIKey: UEJJHQNACJXSKW-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3S)-2,6-dioxopiperidin-3-yl]-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: (+)-thalidomide
• Synonyms: S(-)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione; (-)-Thalidomide; (S)-(-)-2-(2,6-Dioxo-3-piperidinyl)-1H-iso-indole-1,3(2H)-dione; (S)-Thalidomide; NSC 91730; (S)-(-)-Thalidomide

Database IDs

• CAS Number: 841-67-8
• MDL Number: MFCD00210219
• PubChem SID: 24899969; 162227560
• PubChem CID: 92142

CALCULATED PROPERTIES

• Acid pKa: 11.593279
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.01570701
• LogD (pH = 7.4): 0.015679834
• Log P: 0.015707357
• Molar Refractivity: 64.3248 cm^3
• Polarizability: 24.014824 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Butyl Acetate; DMSO: soluble; Ethanol; ethanol: insoluble; Ethyl Acetate; H2O: insoluble; Methanol; Sparingly soluble in Water
• Apperance: white solid; White Solid
• Melting Point: 269-271°C
• Optical Rotation: [α]23/D -62.6°, c = 2 in DMF(lit.)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: TI4925050
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 61-22
• Safety Statements: 53-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

Pharmacology Properties

• Gene Information: human ... LITAF(9516), TNF(7124)mouse ... Nos2(18126)rat ... Nos1(24598)

Product Information

• Purity: >98%

DETAILS

Sigma Aldrich - T150

Biochem/physiol Actions
(-)-Thalidomide selectively inhibits biosynthesis of tumor necrosis factor α (TNF-α); inhibitor of angiogenesis. (S)-Thalidomide is a teratogenic enatiomer.

Toronto Research Chemicals - T338860

Optically active isomer of Thalidomide, which inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative.

REFERENCES

• D’Amato, r.J., et al.: Proc. Natl. Acad. Sci. USA, 91, 4082 (1994)
• Makonkawkeyoon, S., et al.: Proc. Natl. Acad. Sci. USA, 90, 5974 (1994)
• Schumacher, H., et al.: J. Pharmacol. Exp. Therap., 160, 189 (1968)