Cianidanol

Cianidanol Basic information
Product Name:Cianidanol
Synonyms:(+)-CATECHIN;CATECHIN, (+)-;(+)-3,3’4′,5,7-FLAVANEPENTOL;3,3′,4′,5,7-PENTAHYDROXYFLAVANE;[2R,3S]-2-[3,4-DIHYDROXYPHENYL]-3,4-DIHYDRO-1[2H]-BENZOPYRAN-3,4,7-TRIOL;2-(3,4-dihydroxyphenyl)-3,4-dihydro-(2r-trans)-2h-1-benzopyran-7-triol;5,7-triol,2-(3,4-dihydroxyphenyl)-3,4-dihydro-,(2R-trans)-2H-1-Benzopyran-3;catechin(flavan)
CAS:154-23-4
MF:C15H14O6
MW:290.27
EINECS:205-825-1
Product Categories:Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Pharmaceutical Intermediates;Biochemistry;Flavonoids;Natural Plant Extract;Aromatics;Chiral Reagents;Elisa Kit-plant ELISA Kit
Mol File:154-23-4.mol
Cianidanol Structure
Cianidanol Chemical Properties
Melting point 175-177 °C (anhydrous)(lit.)
Boiling point 352.36°C (rough estimate)
alpha D18 +16 to +18.4°
density 1.2451 (rough estimate)
refractive index 1.4359 (estimate)
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated, Heated)
pka9.54±0.10(Predicted)
form neat
color Light Orange to Light Brown
Merck 14,1902
InChIKeyPFTAWBLQPZVEMU-DZGCQCFKSA-N
LogP0.510
CAS DataBase Reference154-23-4
EPA Substance Registry System2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3S)- (154-23-4)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS DJ3450000
8-10-23
HS Code 29329990
ToxicityLD50 oral in rat: > 10gm/kg
MSDS Information
ProviderLanguage
CianidanolEnglish
Cianidanol Usage And Synthesis
Chemical PropertiesTan Solid
UsesLabelled (+)-Catechin (C217500). (+)-Catechin is a flavonoid found primarily in higher woody plants as (+)-Catechin along with (-)-Epicatechin (cis form). Antidiarrheal.
Uses(+)-Catechin is a flavonoid found primarily in higher woody plants as (+)-Catechin along with (-)-Epicatechin (cis form). Antidiarrheal.
Usesprocollagen production inhibitoe, hepatoprotectant
UsesCianidanol, also known as (+)-catechin; (+)-3,3′4′,5,7-flavanepentol; 3,3′,4′, 5,7-pentahydroxyflavane, [R,3S]-2-[3,4-dihydroxyphenyl]-3,4-dihydro-1[2H]- benzopyran-3,4,7-triol, or 2-(3,4-dihydroxyphenyl)-3,4-dihydro-(2r-trans)-2h- 1-benzopyran-7-triol, is a flavonoid associated with a variety of blood disorders. An association of cianidanol and immune hemolytic anemia and thrombocytopenia has been suggested in numerous case reports. In several reports, the presence of flavonoid-dependent antibodies against red blood cells is evident with cianidanol combining with erythrocyte membranes and inducing development of autoantibodies and antibodies.Several patients had platelet antibodies with increased serum-bindable IgG values without the presence of cianidanol and several with high platelet-associated IgG levels.Antibodies against cianidanol were not detectable in certain cases.The hemolytic anemia caused acute renal failure in some patients and can be life threatening, leading to fatalities. Upon cessation of treatment with cianidanol, hematology appears to return to normal over time.
These side effects do not appear to be specific to cianidanol as the formation of IgE and IgG antibodies to troxerutin (Venoruton) and silymarin (Kegalon) was also evident with patients presenting with fever, skin eruptions, and intravascular hemolysis often demonstrating high IgG titers.Furthermore, cianidanol-induced hemolysis might also occur after sensitization by other flavonoids including rutin.
DefinitionChEBI: The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.
Brand nameAusoliver;Cirramina;Transepar.
World Health Organization (WHO)Cianidanol, which is extracted from the tropical plant Uncaria gambir, was introduced in 1976 as an adjunct in the treatment of liver disorders. Following a cluster of cases of haemolytic anaemia reported in 1985 from Naples, Italy, four of which were fatal, the company suspended sales worldwide. Although subsequently reintroduced in Switzerland and France for the treatment of acute and chronic hepatitis-B, it was later definitively withdrawn in Switzerland on detailed reassessment and the manufacturer has now withdrawn the product worldwide.
General Description(+)-Catechin is an important beneficial compound, belonging to the flavonoid class, which is present abundantly in red wine.
Cianidanol Preparation Products And Raw materials
Preparation ProductsCACAO PIGMENT–>Procyanidin B1

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