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Details

Stereochemistry RACEMIC
Molecular Formula C15H12O7
Molecular Weight 304.2516
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAXIFOLIN, (±)-

SMILES

O[C@@H]1[C@H](OC2=C(C1=O)C(O)=CC(O)=C2)C3=CC(O)=C(O)C=C3

InChI

InChIKey=CXQWRCVTCMQVQX-LSDHHAIUSA-N
InChI=1S/C15H12O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,14-19,21H/t14-,15+/m0/s1

HIDE SMILES / InChI

Molecular Formula C15H12O7
Molecular Weight 304.2516
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Dihydroquercetin (also known as taxifolin) is a flavonoid found in grapes, citrus fruits, onions, green tea, olive oil, and several herbs (such as milk thistle). Besides its antitumor, hepatoprotective, and anti-inflammatory activities, it is a potent antioxidant, which may contribute to its cardiovascular and neuroprotective properties. The drug was tested in vitro against cancer cells and in vivo, in preclinical models of liver diseases and cardiovascular diseases. The possible mechanism of actions involves the induction of phase II detoxifying enzymes and the suppression of cytochrome P450-dependent monooxygenases, apoptosis and disruption of cancer cell cycle progression.

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Funbound

ValueDoseCo-administeredAnalytePopulation
4.6%
unknown, unknown
DIHYDROQUERCETIN, ( )-(2R,3R)- plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
In a preclinical study, rats with hepatitis were given 100 mg/kg dihydroquercetin s.c. for 4 days.
Route of Administration: Other
In Vitro Use Guide
in a MTT cytotoxicity assay, HCT116 cells (1*10(4) cells per well) were plated onto 96-well plates, incubated at 37C for 24 h, and the cells were treated with various concentrations of dihydroquercetin (3.9-250 uM). After 24 h, 10 ml of CCK-8 solution was added to the wells, and incubation continued for another 3 h.
Substance Class Chemical
Record UNII
EAS93SC1VS
Record Status Validated (UNII)
Record Version