All Photos(1)
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:
Molecular Weight:
284.22
Beilstein:
2222155
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
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
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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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 2
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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M Yaron et al.
Osteoarthritis and cartilage, 7(3), 272-280 (1999-05-18)
The etiology of osteoarthritis (OA) is still a matter of debate. Several factors are known to be involved in the destruction of the articular cartilage. Interleukin-1 (IL-1) plays an important role in the pathogenesis of osteoarthritis (OA) either directly or
J P Pelletier et al.
Clinical and experimental rheumatology, 21(2), 171-177 (2003-05-16)
The primary objective of this study was to evaluate the ex vivo therapeutic efficacy of diacerein and its active metabolite, rhein, on osteoarthritic (OA) cartilage chondrocyte DNA fragmentation and death in the experimental canine model of OA. The study also
Hyunjoon Kim et al.
Developmental cell, 56(8), 1118-1130 (2021-03-25)
Adenosine N6-methylation (m6A) is one of the most pervasive mRNA modifications, and yet the physiological significance of m6A removal (demethylation) remains elusive. Here, we report that the m6A demethylase FTO functions as a conserved regulator of motile ciliogenesis. Mechanistically, FTO
Alexandrina Ferreira Mendes et al.
Pharmacology & toxicology, 91(1), 22-28 (2002-08-24)
Diacerhein and rhein are anthraquinone compounds that ameliorate the course of osteoarthritis. Recent reports also suggest that these compounds may have antiinflammatory properties, but the cellular mechanisms by which they exert antiosteoarthritic and possibly antiinflammatory effects are still incompletely understood.
Carla Zannella et al.
Pharmaceuticals (Basel, Switzerland), 14(11) (2021-11-28)
The rapid spread of SARS-CoV-2 and the resulting pandemic has led to a spasmodic search for approaches able to limit the diffusion of the disease. The epigenetic machinery has aroused considerable interest in the last decades, and much evidence has
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