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E7881

Sigma-Aldrich

Emodin

from Frangula bark, ≥90% (HPLC)

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
Beilstein/REAXYS Number:
1888141
EC Number:
208-258-8
MDL number:
MFCD00001207
UNSPSC Code:
12352200
PubChem Substance ID:
24278164
NACRES:
NA.77

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)

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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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Michael Podvinec et al.
Journal of medicinal chemistry, 53(4), 1483-1495 (2010-01-30)
Dengue fever is a viral disease that affects 50-100 million people annually and is one of the most important emerging infectious diseases in many areas of the world. Currently, neither specific drugs nor vaccines are available. Here, we report on
Emodin Attenuates Lipopolysaccharide-Induced Injury via Down-Regulation of miR-223 in H9c2 Cells
Yang Y, et al.
International Heart Journal, 18-048 (2019)
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)
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
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)
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