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Merck

681535

Withaferin A

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

Synonym(s):

Withaferin A, Withania somnifera

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About This Item

Empirical Formula (Hill Notation):
C28H38O6
CAS Number:
5119-48-2
Molecular Weight:
470.60
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD10687098

Key Documents

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Product Name

Withaferin A, Withania somnifera, A cell-permeable steroidal lactone that displays antitumor, anti-inflammatory, radiosensitizing, and immunosuppressive properties.

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

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

Quality Level

100

Related Categories

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

Disclaimer

Toxicity: Carcinogenic / Teratogenic (D)

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.

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.

Packaging

Packaged under inert gas

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

438.8 °F

flash_point_c

226 °C

Certificates of Analysis (COA)

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Global Trade Item Number

SKUGTIN
681535-5MGCN04055977260120
681535-1MGCN04055977260113

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