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Taxifolin

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Taxifolin Basic information

Product Name:
Taxifolin
Synonyms:
  • 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4h-1-benzopyran-4-on
  • 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4h-1-benzopyran-4-on(
  • 2,3-dihydro-3,3’,4’,5,7-pentahydroxy-flavon
  • 2theta-trans)-
  • 3,3’,4’,5,7-pentahydroxy-flavanon
  • dihydro-querceti
  • distylin
  • TAXIFOLIN(P)
CAS:
480-18-2
MF:
C15H12O7
MW:
304.25
EINECS:
207-543-4
Product Categories:
  • Inhibitors
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Flavanones
  • Aromatics
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • 480-18-2
Mol File:
480-18-2.mol
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Taxifolin Chemical Properties

Melting point:
230-233°C (dec.)
Boiling point:
365.09°C (rough estimate)
Density 
1.3326 (rough estimate)
refractive index 
1.4790 (estimate)
storage temp. 
-20°C
solubility 
DMSO (Slightly), Methanol (Slightly)
pka
7.39±0.60(Predicted)
form 
Solid
color 
White to Yellow
BRN 
5299277
InChI
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
InChIKey
CXQWRCVTCMQVQX-LSDHHAIUSA-N
SMILES
[C@H]1(C2=CC=C(O)C(O)=C2)OC2=CC(O)=CC(O)=C2C(=O)[C@@H]1O
LogP
0.950
CAS DataBase Reference
480-18-2(CAS DataBase Reference)
EPA Substance Registry System
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)- (480-18-2)
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Safety Information

Risk Statements 
22
Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
LK6920000
HazardClass 
IRRITANT
HS Code 
29329990

MSDS

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Taxifolin Usage And Synthesis

Structural chemistry

Taxifolin is a subclass of flavanonols, an isoflavanone in flavonoids family. The basic structure of two phenyl groups (ring A and ring B) which are joined together by a heterocyclic ring referred to as ring C . The structure contains 3-hydroxyl group at the C ring which is connected to the B ring at carbon-2. Taxifolin is a pentahydroxyflavone containing five hydroxyl groups at the 3-, 3'-, 4'-, 5- and 7-positions. It  has two stereocenters on the C-ring and 4 stereoisomers. It with the configuration of (2R, 3R) is one of them and it comprises 2 pairs of enantiomers.

Description

Taxifolin, a chemical substance extracted from pine plants such as larch and Douglas fir. It belongs to the bioflavonoid pseudo-vitamin P, and its scientific name is dihydroquercetin. Japanese scholar Fukui first isolated it from the leaves of conifers (Chamaecyparis obtusa), and its biological activity was subsequently discovered and confirmed.

Chemical Properties

Yellow Solid

Uses

An antioxidant flavenoid.

Uses

Reference Standard in the analysis of herbal medicinal products

Uses

(+)-Taxifolin is a flavanon compound which modulates chemopreventive genes.

Definition

ChEBI: A taxifolin that has (2R,3R)-configuration.

Application

Taxifolin is a flavonoid commonly found in onion, milk, French maritime pine bark and Douglas fir bark. It is also used in various commercial preparations like Legalon?, Pycnogenol?, and Venoruton?. This review focuses on taxifolin’s biological activities and related molecular mechanisms. It showed promising pharmacological activities in the management of inflammation, tumors, microbial infections, oxidative stress, cardiovascular, and liver disorders. The anti-cancer activity was more prominent than other activities evaluated using different in vitro and in vivo models. Further research on the pharmacokinetics, in-depth molecular mechanisms, and safety profile using well-designed randomized clinical studies are suggested to develop a drug for human use.

General Description

Taxifolin is a plant flavonoid, which may find applications in the treatment of coronary heart disease, angina pectoris, cerebral thrombosis, cerebral infarction and sequelae.

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