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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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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

Assay:

≥90% (HPLC)

Quality level:

200

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Properties

Product Name

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

biological source

Frangula bark

Quality Level

200

assay

≥90% (HPLC)

solubility

DMSO: soluble, aqueous base: soluble, ethanol: soluble

storage temp.

2-8°C

SMILES string

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

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

Gene Information

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

Description

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.

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.

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pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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)

Emodin and aloe-emodin suppress breast cancer cell proliferation through ERalpha inhibition

Huang PH, et al.

Evidence-Based Complementary and Alternative Medicine : ECAM, 2013 (2013)

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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