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E7881 Sigma-Aldrich

Emodin

from Frangula bark, ≥90% (HPLC)

Synonym: 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

  • CAS Number 518-82-1

  • Empirical Formula (Hill Notation) C15H10O5

  • Molecular Weight 270.24

  •  Beilstein/REAXYS Number 1888141

  •  EC Number 208-258-8

  •  MDL number MFCD00001207

  •  PubChem Substance ID 24278164

  •  NACRES NA.77

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Properties

Related Categories Anti-Proliferative Agents, Antitumor Agents, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cancer Research,
Quality Level   200
biological source   Frangula bark
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

Packaging

250 mg in poly bottle

50 mg in glass insert

Biochem/physiol Actions

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

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
CB7920600
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

The Role of Inflammation in Neurodegeneration

It is well established that the brain can sense and react to peripheral insults through the rapid induction of fever and other neuroendocrine changes in response to events such as infection and tissu...
Scott Hauser, Technology Transfer Specialist, Sigma® Life Science
Biofiles, Vol. 8, No. 19
Keywords: Adhesion, Central Nervous System, Diseases, Gene expression, Inflammation, Neurodegenerative Diseases, Reductions

Peer-Reviewed Papers
15

References

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