681535

Withaferin A

from Withania somnifera, ≥94% (HPLC), solid, anti-inflammatory lactone, Calbiochem^®

• Synonym(s): Withaferin A, Withania somnifera
• Empirical Formula (Hill Notation): C₂₈H₃₈O₆
• CAS Number: 5119-48-2
• Molecular Weight: 470.60
• MDL number: MFCD10687098
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Product Name: Withaferin A, Withania somnifera, A cell-permeable steroidal lactone that displays antitumor, anti-inflammatory, radiosensitizing, and immunosuppressive properties.
• Quality Level: 100
• description: RTECS - KE7288500
• assay: ≥94% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: white
• solubility: DMSO: 10 mg/mL; ethanol: 5 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: O1[C@H](CC(=C(C1=O)CO)C)[C@H]([C@@H]2[C@@]3([C@H]([C@H]4[C@@H]([C@@]5([C@@]6(O[C@@H]6C4)[C@H](C=CC5=O)O)C)CC3)CC2)C)C
• InChI: 1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
• InChI key: DBRXOUCRJQVYJQ-CKNDUULBSA-N

Description

General description

A cell-permeable steroidal lactone that displays antitumor, anti-inflammatory, radiosensitizing, and immunosuppressive properties. Potently inhibits angiogenesis both in vitro (IC₅₀ = 12 nM against HUVEC proliferation) and in vivo (80% inhibition at 7 µg/kg/day in C57BL/6J mice, s.c.) and NF-κB activation (IC₅₀ = 500 nM in TNF-α-induced endothelial cells) by targeting the ubiquitin-mediated proteasome pathway. At higher concentrations (~5 µM) also affects AP-1 transcription and induces cell death.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
A steroidal lactone that displays antitumor, anti-inflammatory, radiosensitizing, and immunosuppressive properties.

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 12 nM against angiogenesis in vitro by inhibiting HUVEC proliferation

Packaging

Packaged under inert gas

Other Notes

Mohan, R., et al. 2004. Angiogenesis7, 115.
Jeyaprakasam, B., et al. 2003. Life Sci.74, 125.
Devi, P.U., et al. 1995. Cancer Lett.95, 189.
Kupchan, S.M., et al. 1969. J. Org. Chem.34, 3858.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Carcinogenic / Teratogenic (D)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: 438.8 °F
• flash_point_c: 226 °C