E7881

Emodin

Name: Emodin
Brand: SIGMA

from Frangula bark, ≥90% (HPLC), casein Kinase 2 (CK2) inhibitor

Synonym(s):

1,3,8-Trihydroxy-6-methyl-9,10-anthracenedione, 1,3,8-Trihydroxy-6-methylanthraquinone, 6-Methyl-1,3,8-trihydroxyanthraquinone, Archin, Emodol, Frangula-emodin, Frangulic acid, Rheum emodin

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All Photos(3)

About This Item

Empirical Formula (Hill Notation):

C₁₅H₁₀O₅

CAS Number:

518-82-1

Molecular Weight:

270.24

NACRES:

NA.77

PubChem Substance ID:

24278164

UNSPSC Code:

12352200

EC Number:

208-258-8

MDL number:

MFCD00001207

Beilstein/REAXYS Number:

1888141

Product Name

Emodin, from Frangula bark, ≥90% (HPLC)

InChI

1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3

InChI key

RHMXXJGYXNZAPX-UHFFFAOYSA-N

SMILES string

Cc1cc(O)c2C(=O)c3c(O)cc(O)cc3C(=O)c2c1

biological source

Frangula bark

assay

≥90% (HPLC)

solubility

DMSO: soluble
aqueous base: soluble
ethanol: soluble

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... CSNK2A1(1457), CSNK2B(1460), ELA2(1991), NFKB1(4790), NKAP(79576), NKRF(55922)

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

Emodin has been used:

to investigate its regulatory mechanisms on lipopolysaccharide (LPS)-induced inflammatory injury in myocarditis
as a reference standard for the development and validation of high performance liquid chromatography (HPLC)-photodiode array (PDA) assay method
to inhibit Tau aggregation
for direct binding assay

Biochem/physiol Actions

Inhibitor of NF-κB activation and adhesion molecule expression. Casein Kinase 2 (CK2) inhibitor.

General description

Emodin is an anthraquinone derivative, extracted from rhubarb (Rheum palmatum). It has antibacterial, anti-neoplastic, anti-inflammatory and anti-angiogenesis properties. Emodin exhibits cytotoxic effects, apoptosis and stimulates the expression of hypoxia-inducible factor 1α, glutathione S-transferase P and N-acetyltransferase. It prevents the growth of prostate cancer cells. Emodin is used to treat constipation and hemorrhoid. It displays immunosuppressive and anti-diabetic effects.

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Antitumor activity of emodin against pancreatic cancer depends on its dual role: promotion of apoptosis and suppression of angiogenesis.

Sheng-Zhang Lin et al.

PloS one, 7(8), e42146-e42146 (2012-08-10)

Emodin has been showed to induce apoptosis of pancreatic cancer cells and inhibit tumor growth in our previous studies. This study was designed to investigate whether emodin could inhibit the angiogenesis of pancreatic cancer tissues and its mechanism. In accordance

Anticancer potential of emodin

Hsu SC and Chung JG

BioMedicine, 2(3), 108-116 (2012)

Casein kinase 2 (CK2)-mediated phosphorylation of Hsp90beta as a novel mechanism of rifampin-induced MDR1 expression

Kim SW, et al.

The Journal of Biological Chemistry, 290(27), 17029-17040 (2015)

Development and Validation of HPLC-PDA Assay method of Frangula emodin

Duca D and Farrugia C

Mediterranean Journal of Chemistry, 5(2), 374-386 (2016)

Identification and characterization of novel classes of macrophage migration inhibitory factor (MIF) inhibitors with distinct mechanisms of action.

Hajer Ouertatani-Sakouhi et al.

The Journal of biological chemistry, 285(34), 26581-26598 (2010-06-03)

Macrophage migration inhibitory factor (MIF), a proinflammatory cytokine, is considered an attractive therapeutic target in multiple inflammatory and autoimmune disorders. In addition to its known biologic activities, MIF can also function as a tautomerase. Several small molecules have been reported

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