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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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The toxicity and metabolism of dihydroquercetin.
1958 Mar
Anti-inflammatory activity of taxifolin.
1971 Jun
Antinociceptive and anti-oedematogenic properties of astilbin, taxifolin and some related compounds.
2000 Mar
Inhibition of HEWL fibril formation by taxifolin: Mechanism of action.
2017
Patents

Sample Use Guides

In a preclinical study, rats with hepatitis were given 100 mg/kg dihydroquercetin s.c. for 4 days.
Route of Administration: Other
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
Created
by admin
on Sat Dec 16 11:35:51 GMT 2023
Edited
by admin
on Sat Dec 16 11:35:51 GMT 2023
Record UNII
EAS93SC1VS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAXIFOLIN, (±)-
Common Name English
DIHYDROQUERCETIN, (±)-
Common Name English
(±)-DIHYDROQUERCETIN
Common Name English
4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-2,3-DIHYDRO-3,5,7-TRIHYDROXY-, TRANS-(±)-
Systematic Name English
(±)-TAXIFOLIN
Common Name English
Code System Code Type Description
FDA UNII
EAS93SC1VS
Created by admin on Sat Dec 16 11:35:51 GMT 2023 , Edited by admin on Sat Dec 16 11:35:51 GMT 2023
PRIMARY
CAS
24198-97-8
Created by admin on Sat Dec 16 11:35:51 GMT 2023 , Edited by admin on Sat Dec 16 11:35:51 GMT 2023
PRIMARY
PUBCHEM
439533
Created by admin on Sat Dec 16 11:35:51 GMT 2023 , Edited by admin on Sat Dec 16 11:35:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID301017215
Created by admin on Sat Dec 16 11:35:51 GMT 2023 , Edited by admin on Sat Dec 16 11:35:51 GMT 2023
PRIMARY