Taxifolin Property

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)

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)

Safety

Risk Statements 

22

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

LK6920000

HazardClass 

IRRITANT

HS Code 

29329990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

Taxifolin Chemical Properties,Usage,Production

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.