Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H14O6 |
| Molecular Weight | 290.2681 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]1CC2=C(O[C@@H]1C3=CC(O)=C(O)C=C3)C=C(O)C=C2O
InChI
InChIKey=PFTAWBLQPZVEMU-DZGCQCFKSA-N
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1
| Molecular Formula | C15H14O6 |
| Molecular Weight | 290.2681 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/3896964
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/3896964
Cianidanol is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. One of the polyphenols present in green tea, (+)-catechin (Cianidanol), has been studied for its effects on animal models of hepatitis, as well as in human clinical studies. Pure (+)-catechin (also known as (+)- cyanidanol-3 – trade name Catergen) has been used to treat hepatitis since 1976. This compound has been shown to be an efficient immune stimulator, promoting activation of macrophages, cytotoxic-T-lymphocytes, and natural killer cells in mice. Several clinical studies demonstrate the effectiveness of (+)-catechin in the treatment of viral hepatitis. Pure (+)-catechin has been found to cause hemolysis in some patients, possibly by the promotion of antibody formation against (+)-catechin, which might cross-react with red blood cells. However, there are no reports in the literature of green tea, green tea extracts, or green tea polyphenols causing this side-effect.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL230 |
93.3 µM [IC50] | ||
Target ID: CHEMBL221 |
36.7 µM [IC50] | ||
Target ID: GO:0042554 |
13.1 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Cianidanol Approved UseCianidanol was introduced in 1976 as an adjunct in the treatment of liver disorders Launch Date1.89215998E11 |
|||
| Preventing | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Estimation of procyanidin chain length. | 2001 |
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| Biological actions of oligomeric procyanidins: proliferation of epithelial cells and hair follicle growth. | 2001 |
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| Inhibition of in vitro low-density lipoprotein oxidation by oligomeric procyanidins present in chocolate and cocoas. | 2001 |
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| Characterization of antioxidant effect of procyanidins. | 2001 |
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| Mechanism of antioxidant effect of catechins. | 2001 |
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| Measurement of trans-resveratrol, (+)-catechin, and quercetin in rat and human blood and urine by gas chromatography with mass selective detection. | 2001 |
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| Inhibition of carcinogenesis by dietary polyphenolic compounds. | 2001 |
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| Green tea: biochemical and biological basis for health benefits. | 2001 |
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| Epigallocatechin gallate protects U937 cells against nitric oxide-induced cell cycle arrest and apoptosis. | 2001 |
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| Protective effect of phenolic compounds isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death. | 2001 |
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| Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid. | 2001 Apr |
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| Phenolics and physico-chemical characteristics of persimmon during post-harvest storage. | 2001 Apr |
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| Inhibitory effect of (+)-catechin on the growth of influenza A/PR/8 virus in MDCK cells. | 2001 Apr |
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| Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production. | 2001 Apr |
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| Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus. | 2001 Apr |
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| Growth inhibitory effect of green tea extract and (-)-epigallocatechin in Ehrlich ascites tumor cells involves a cellular thiol-dependent activation of mitogenic-activated protein kinases. | 2001 Apr 16 |
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| Separation of apple procyanidins into different degrees of polymerization by high-speed counter-current chromatography. | 2001 Apr 27 |
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| Separation of phenolic compounds by high-performance liquid chromatography with absorbance and fluorimetric detection. | 2001 Apr 6 |
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| Effects of de-alcoholated red wine and its phenolic fractions on platelet aggregation. | 2001 Feb |
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| Evaluation of antioxidant activity of epigallocatechin gallate in biphasic model systems in vitro. | 2001 Feb |
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| Catechin intake and associated dietary and lifestyle factors in a representative sample of Dutch men and women. | 2001 Feb |
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| Studies in polyphenol chemistry and bioactivity. 3.(1,2) stereocontrolled synthesis of epicatechin-4alpha,8-epicatechin, an unnatural isomer of the B-type procyanidins. | 2001 Feb 23 |
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| Pharmacokinetics and system linearity of tea catechins in rat. | 2001 Jan |
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| Inhibitory effect of epigallocatechin-gallate on brain tumor cell lines in vitro. | 2001 Jan |
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| Modulation of the biosynthesis of some phenolic compounds in Olea europaea L. fruits: their influence on olive oil quality. | 2001 Jan |
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| Influence of metal ions on flavonoid protection against asbestos-induced cell injury. | 2001 Jan 1 |
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| Green tea catechins enhance tumor development in the colon without effects in the lung or thyroid after pretreatment with 1,2-Dimethylhydrazine or 2,2'-dihydroxy-di-n-propylnitrosamine in male F344 rats. | 2001 Jul 10 |
|
| Black tea extract, thearubigin fraction, counteracts the effect of tetanus toxin in mice. | 2001 Jun |
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| Atmospheric carbon dioxide, irrigation, and fertilization effects on phenolic and nitrogen concentrations in loblolly pine (Pinus taeda) needles. | 2001 Jun |
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| Formation and identification of 4'-O-methyl-(-)-epigallocatechin in humans. | 2001 Jun |
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| Nutrition and metabolism. | 2001 Jun |
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| Green tea polyphenol epigallocatechin inhibits DNA replication and consequently induces leukemia cell apoptosis. | 2001 Jun |
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| Green tea polyphenolic antioxidants and skin photoprotection (Review). | 2001 Jun |
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| Black tea is a powerful chemopreventor of reactive oxygen and nitrogen species: comparison with its individual catechin constituents and green tea. | 2001 Jun 1 |
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| Green tea polyphenols: novel irreversible inhibitors of dopa decarboxylase. | 2001 Jun 1 |
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| The role of inducible-nitric oxide in cocaine-induced kindling. | 2001 Mar |
|
| Antioxidant effects of water extracts from barley (Hordeum vulgare L.) prepared under different roasting temperatures. | 2001 Mar |
|
| Identification of procyanidins and anthocyanins in blueberries and cranberries (Vaccinium spp.) using high-performance liquid chromatography/mass spectrometry. | 2001 Mar |
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| Color and stability of pigments derived from the acetaldehyde-mediated condensation between malvidin 3-O-glucoside and (+)-catechin. | 2001 Mar |
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| Combination effect of lignin F and natural products. | 2001 Mar-Apr |
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| Furanocoumarins from the aerial parts of Dorstenia contrajerva. | 2001 May |
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| Fast determination of procyanidins and other phenolic compounds in food samples by micellar electrokinetic chromatography using acidic buffers. | 2001 May |
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| Water-soluble antioxidants inhibit macrophage recognition of oxidized erythrocytes. | 2001 May |
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| A tea catechin suppresses the expression of the high-affinity IgE receptor Fc epsilon RI in human basophilic KU812 cells. | 2001 May |
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| Chemiluminescence of hemoglobin and identification of related compounds with the hemoglobin chemiluminescence in plasma. | 2001 May |
|
| [Polyphenol constituents from Salacia species: quantitative analysis of mangiferin with alpha-glucosidase and aldose reductase inhibitory activities]. | 2001 May |
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| The in vitro inhibitory effect of tannin derivatives on 3-hydroxy-3-methylglutaryl-coenzyme a reductase on vero cells. | 2001 May |
|
| Green tea polyphenol (-)-epigallocatechin-3-gallate treatment to mouse skin prevents UVB-induced infiltration of leukocytes, depletion of antigen-presenting cells, and oxidative stress. | 2001 May |
|
| Anti-interferon gamma action of epigallocatechin-3-gallate mediated by specific inhibition of STAT1 activation. | 2001 May |
|
| Unusually large numbers of electrons for the oxidation of polyphenolic antioxidants. | 2001 May 3 |
Patents
| Substance Class |
Chemical
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by
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on
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Fri Dec 16 16:09:39 UTC 2022
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on
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| Record UNII |
8R1V1STN48
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| Record Status |
Validated (UNII)
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LIVERTOX |
414
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DSLD |
119 (Number of products:75)
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154-23-4
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CATECHIN
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C63654
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8R1V1STN48
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15600
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23053
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1367177
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1096790
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8R1V1STN48
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CHEMBL311498
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SUB06226MIG
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D002392
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DTXSID3022322
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9064
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205-825-1
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2819
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DB14086
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4804
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629
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M3172
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PRIMARY | Merck Index |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> CONSTITUENT ALWAYS PRESENT |
The compound was screened for it's antioxidant capacity in the DPPH assay, and displayed a high antioxidant activity, with an IC50 value of 49.0 uM.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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TARGET -> INHIBITOR | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
IN-VITRO
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Secondary metabolite detected in developing cacao seeds.
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
