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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

Beilstein:

1888141

EC Number:

208-258-8

MDL number:

MFCD00001207

UNSPSC Code:

12352200

PubChem Substance ID:

24278164

NACRES:

NA.77

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)

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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

GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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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

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)

Anticancer potential of emodin

Hsu SC and Chung JG

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

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)

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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