R7269

Sigma-Aldrich

Rhein

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

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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Packaging

10, 50 mg in glass insert

Biochem/physiol Actions

Constituent that is enriched in rhubarb with anti-inflammatory, anti-osteoarthritic, and anti-cancer activity. It reduces IL-1β production and secretion, caspase-3 activity, inducible nitric oxide synthase activity, and phosphorylation of c-Jun and c-Jun NH2-terminal kinase (JNK).

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Certificate of Analysis

Certificate of Origin

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...
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....
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...
Baoen Chen et al.
Journal of the American Chemical Society, 134(43), 17963-17971 (2012-10-11)
The direct nucleic acid repair dioxygenase FTO is an enzyme that demethylates N(6)-methyladenosine (m(6)A) residues in mRNA in vitro and inside cells. FTO is the first RNA demethylase discovered that also serves a major regulatory function in mammals. Together with...
Tom Coenye et al.
Antimicrobial agents and chemotherapy, 51(4), 1541-1544 (2007-01-16)
We report that certain anthraquinones (AQs) reduce Streptococcus mutans biofilm formation on hydroxyapatite at concentrations below the MIC. Although AQs are known to generate reactive oxygen species, the latter do not underlie the observed effect. Our results suggest that AQs...

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