U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of CIANIDANOL

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

HIDE SMILES / InChI

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

Description
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

Targets

Primary TargetPharmacologyConditionPotency
93.3 µM [IC50]
36.7 µM [IC50]
13.1 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Cianidanol

Approved Use

Cianidanol was introduced in 1976 as an adjunct in the treatment of liver disorders

Launch Date

1975
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibition of in vitro low-density lipoprotein oxidation by oligomeric procyanidins present in chocolate and cocoas.
2001
Measurement of trans-resveratrol, (+)-catechin, and quercetin in rat and human blood and urine by gas chromatography with mass selective detection.
2001
Green tea: biochemical and biological basis for health benefits.
2001
Protective effect of phenolic compounds isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death.
2001
Catechins in tea: chemistry and analysis.
2001
Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid.
2001 Apr
Inhibitory effect of (+)-catechin on the growth of influenza A/PR/8 virus in MDCK cells.
2001 Apr
Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
2001 Apr
Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus.
2001 Apr
In vivo synergy between green tea extract and levofloxacin against enterohemorrhagic Escherichia coli O157 infection.
2001 Apr
Ester bond-containing tea polyphenols potently inhibit proteasome activity in vitro and in vivo.
2001 Apr 20
Evaluation of antioxidant activity of epigallocatechin gallate in biphasic model systems in vitro.
2001 Feb
Catechin intake and associated dietary and lifestyle factors in a representative sample of Dutch men and women.
2001 Feb
Apoptosis-inducing activity of high molecular weight fractions of tea extracts.
2001 Feb
Structural features of procyanidin interactions with salivary proteins.
2001 Feb
Polyphyenolics increase t-PA and u-PA gene transcription in cultured human endothelial cells.
2001 Feb
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
Degradation of green tea catechins in tea drinks.
2001 Jan
Thiolysis-HPLC characterization of apple procyanidins covering a large range of polymerization states.
2001 Jan
(+)-Catechin inhibits intestinal tumor formation and suppresses focal adhesion kinase activation in the min/+ mouse.
2001 Jan 1
Is the cancer protective effect correlated with growth inhibitions by green tea (-)-epigallocatechin gallate mediated through an antioxidant mechanism?
2001 Jan 26
Black tea extract, thearubigin fraction, counteracts the effect of tetanus toxin in mice.
2001 Jun
Black tea is a powerful chemopreventor of reactive oxygen and nitrogen species: comparison with its individual catechin constituents and green tea.
2001 Jun 1
Identification of procyanidins and anthocyanins in blueberries and cranberries (Vaccinium spp.) using high-performance liquid chromatography/mass spectrometry.
2001 Mar
Synthesis of a 3,4,5-trimethoxybenzoyl ester analogue of epigallocatechin-3-gallate (EGCG): a potential route to the natural product green tea catechin, EGCG.
2001 Mar 22
EGCG, a major component of green tea, inhibits tumour growth by inhibiting VEGF induction in human colon carcinoma cells.
2001 Mar 23
The effects of phenolic components of tea on the production of pro- and anti-inflammatory cytokines by human leukocytes in vitro.
2001 Mar 7
Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea.
2001 Mar 8
[Polyphenol constituents from Salacia species: quantitative analysis of mangiferin with alpha-glucosidase and aldose reductase inhibitory activities].
2001 May
The in vitro inhibitory effect of tannin derivatives on 3-hydroxy-3-methylglutaryl-coenzyme a reductase on vero cells.
2001 May
Patents

Sample Use Guides

In Vivo Use Guide
Take 1~3 packet daily
Route of Administration: Oral
In Vitro Use Guide
The in vitro effect of the drug was assessed using cianidanol at 10(-6), 10(-5) and 10(-4) M concentrations.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:05:38 GMT 2023
Edited
by admin
on Fri Dec 15 15:05:38 GMT 2023
Record UNII
8R1V1STN48
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIANIDANOL
INN   JAN   MART.   WHO-DD  
INN  
Official Name English
(+)-CATECHIN [USP-RS]
Common Name English
CATECHIN
MI   VANDF  
Common Name English
D-CATECHOL
Common Name English
(+)-CATECHOL
Systematic Name English
(+)-CATECHIN (CONSTITUENT OF MARITIME PINE) [DSC]
Common Name English
cianidanol [INN]
Common Name English
2H-1-BENZOPYRAN-3,5,7-TRIOL, 2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-, (2R,3S)-
Systematic Name English
(+)-CATECHIN
Common Name English
CATECHIN, D-
Common Name English
(+)-CATECHIN (CONSTITUENT OF GRAPE SEEDS OLIGOMERIC PROANTHOCYANIDINS) [DSC]
Common Name English
CIANIDANOL [MART.]
Common Name English
CIANIDOL
Common Name English
CATECHIN [VANDF]
Common Name English
(+)-CATECHIN (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT) [DSC]
Common Name English
CATECHIN [MI]
Common Name English
Cianidanol [WHO-DD]
Common Name English
NSC-2819
Code English
CATECHUIC ACID
Common Name English
CIANIDANOL [JAN]
Common Name English
CATERGEN
Common Name English
CATECHINIC ACID
Common Name English
Classification Tree Code System Code
LIVERTOX 414
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
DSLD 119 (Number of products:75)
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
Code System Code Type Description
CAS
154-23-4
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
WIKIPEDIA
CATECHIN
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
NCI_THESAURUS
C63654
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
DAILYMED
8R1V1STN48
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
CHEBI
15600
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
CHEBI
23053
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
RXCUI
1367177
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY RxNorm
SMS_ID
100000081900
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
RS_ITEM_NUM
1096790
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
FDA UNII
8R1V1STN48
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL311498
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
EVMPD
SUB06226MIG
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
MESH
D002392
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID3022322
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
PUBCHEM
9064
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-825-1
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
NSC
2819
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
DRUG BANK
DB14086
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
INN
4804
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
DRUG CENTRAL
629
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY
MERCK INDEX
m3172
Created by admin on Fri Dec 15 15:05:38 GMT 2023 , Edited by admin on Fri Dec 15 15:05:38 GMT 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
IN-VITRO
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.
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
TARGET -> INHIBITOR
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Secondary metabolite detected in developing cacao seeds.
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY