R7269

Rhein

• Synonym(s): 4,5-Dihydroxyanthraquinone-2-carboxylic acid, 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid, Cassic acid, Chrysazin 3-carboxylic acid, Monorhein, Rheic acid, Rhubarb yellow
• Empirical Formula (Hill Notation): C₁₅H₈O₆
• CAS Number: 478-43-3
• Molecular Weight: 284.22
• Beilstein: 2222155
• EC Number: 207-521-4
• MDL number: MFCD00009618
• PubChem Substance ID: 24899390
• NACRES: NA.77

Properties

• Quality Level: 100
• mp: ≥300 °C (lit.)
• storage temp.: 2-8°C
• SMILES string: OC(=O)c1cc(O)c2C(=O)c3c(O)cccc3C(=O)c2c1
• InChI: 1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)
• InChI key: FCDLCPWAQCPTKC-UHFFFAOYSA-N

Description

Application

Rhein has been used:

• as a potassium simplex optimization medium with amino acids (KSOMaa) to induce degeneration in embryos to study its effect on the intracellular and extracellular micro-RNA (miRNA) signature
• as a fat mass and obesity-associated protein (FTO) inhibitor to study its role in motile ciliogenesis in an m6A-dependent manner in Xenopus embryos
• as an FTO inhibitor to infer its antiviral action in relation with the SARS-associated coronavirus 2 (SARS-CoV-2) infection

Biochem/physiol Actions

Rhein, a cytotoxic agent, exhibits tumor suppression by activating apoptosis. It is a selective inhibitor of demethylase fat mass and obesity-associated protein (FTO). Rhein is known to participate in various biological processes including obesity and adipogenesis.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315 - H319 - H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves