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Merck
CN

W4016

Wedelolactone

≥98% (HPLC), powder

Synonym(s):

1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c][1]benzopyran-6-one, 7-Methoxy-5,11,12-trihydroxycoumestan

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About This Item

Empirical Formula (Hill Notation):
C16H10O7
CAS Number:
524-12-9
Molecular Weight:
314.25
MDL number:
MFCD07778564
UNSPSC Code:
12352200
PubChem Substance ID:
24724667
NACRES:
NA.77

Key Documents

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Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to brown

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

COc1cc(O)c-2c(OC(=O)c3c-2oc4cc(O)c(O)cc34)c1

InChI

1S/C16H10O7/c1-21-6-2-10(19)14-12(3-6)23-16(20)13-7-4-8(17)9(18)5-11(7)22-15(13)14/h2-5,17-19H,1H3

InChI key

XQDCKJKKMFWXGB-UHFFFAOYSA-N

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Biochem/physiol Actions

Wedelolactone inhibits NF-κB-mediated gene transcription in cells by blocking the phosphorylation and degradation of IκBα. Irreversible inhibitor of IKKα and β kinase activity (IC50 < 10 μM). Wedelolactone has no effects on p38 MAP kinase or Akt.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000213803
0000213803
0000143301
0000142193
0000052182

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Sivalokanathan Sarveswaran et al.
International journal of oncology, 41(6), 2191-2199 (2012-10-19)
Emerging studies indicate that metabolism of arachidonic acid through the 5-lipoxygenase (5-Lox) pathway plays a critical role in the survival of prostate cancer cells raising the possibility that 5-Lox can be targeted for an effective therapy of prostate cancer. Wedelolactone
Wei Zhang et al.
Toxicology letters, 209(2), 107-112 (2011-12-31)
The endothelin B2 (ET(B2)) receptors are induced in vascular smooth muscle cells (VSMCs) in cardiovascular diseases. We tested if in vitro short-term exposure to the pro-inflammatory cytokine tumor necrosis factor-α (TNF-α) could up-regulate ET(B2) receptors in rat mesenteric arteries, and
Qi-Mei Liu et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50(11), 4016-4022 (2012-08-21)
Eclipta prostrata L., (Asteraceae), is used in China for both food and medicine purposes. This research is concerned with the isolation and purification of phytochemical constituents from the aerial parts of E. prostrata, using gradient solvent fractionation, macroporous resin, silica
Petr Benes et al.
Cancer letters, 303(1), 29-38 (2011-02-15)
The naturally occurring coumestan wedelolactone has been previously shown to reduce growth of various cancer cells. So far, the growth-suppressing effect of wedelolactone has been attributed to the inhibition of the NFκB transcription factor and/or androgen receptors. We found that
Zhimin Chen et al.
The Journal of biological chemistry, 288(20), 14417-14427 (2013-04-13)
Signal transducers and activators of transcription 1 (STAT1) transduces signals from cytokines and growth factors, particularly IFN-γ, and regulates expression of genes involved in cell survival/death, proliferation, and migration. STAT1 is activated through phosphorylation on its tyrosine 701 by JAKs
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