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Merck

R7269

Rhein

≥98% (HPLC), powder, cytotoxic agent

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

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About This Item

Empirical Formula (Hill Notation):
C15H8O6
CAS Number:
478-43-3
Molecular Weight:
284.22
NACRES:
NA.77
PubChem Substance ID:
24899390
UNSPSC Code:
12352200
EC Number:
207-521-4
MDL number:
MFCD00009618
Beilstein/REAXYS Number:
2222155

Key Documents

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Product Name

Rhein,

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

SMILES string

OC(=O)c1cc(O)c2C(=O)c3c(O)cccc3C(=O)c2c1

mp

≥300 °C (lit.)

storage temp.

2-8°C

Quality Level

100

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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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

R7269-BULK: + R7269-VAR: + R7269-50MG: + R7269-10MG:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN1893
MKCK6550
MKCC6525
MKBW5625V
MKBV1726V

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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
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.
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
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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