2,3,5,4＇-Tetrahydroxy stilbene-2-Ο-β-D-glucoside Chemical Properties

Boiling point:

715.0±60.0 °C(Predicted)

Density 

1.593±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

H2O: soluble5mg/mL, clear (warmed)

form 

powder

pka

8.78±0.40(Predicted)

color 

white to brown

Water Solubility 

H2O: 5mg/mL, clear (warmed)

InChI

InChI=1/C20H22O9/c21-9-15-16(25)17(26)18(27)20(28-15)29-19-11(7-13(23)8-14(19)24)4-1-10-2-5-12(22)6-3-10/h1-8,15-18,20-27H,9H2/b4-1+/t15-,16-,17+,18-,20+/s3

InChIKey

JAYVHSBYKLLDJC-BGLDUWRXNA-N

SMILES

O([C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)C1C(=CC(O)=CC=1/C=C/C1C=CC(O)=CC=1)O |&1:1,2,3,5,7,r|

CAS DataBase Reference

82373-94-2

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26

WGK Germany 

3

HS Code 

29389090

2,3,5,4＇-Tetrahydroxy stilbene-2-Ο-β-D-glucoside Usage And Synthesis

Description

2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside is derived from the root of Polygonaceae species Polygonum multiflorum and is a stilbene compound. It has antioxidant, hypotensive, anti-aging, anti-inflammatory, hypolipidemic, cardioprotective and neuroprotective effects. It can also inhibit the formation of 5-HETE, HHT and thromboxane B2.

Uses

2,3,4'',5-Tetrahydroxystilbene 2-O-Glucoside is a scavenging agent, that attenuates free radicals and upregulate antioxidant?/detoxifying enzymes to protect against oxidative damage. It also protects UB/OC-2 cells from H2O2-induced autophagy and apoptosis in vitro.

Definition

ChEBI: (E)-2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside is a stilbenoid that is trans-stilbene which has been substituted by hydroxy groups at positions 2, 3, 5, and 4', and in which the hydroxy group at positon 2 has then been converted to the corresponding the beta-D-glucoside. It has a role as an antioxidant, a cyclooxygenase 2 inhibitor, an anti-inflammatory agent, a cardioprotective agent, a platelet aggregation inhibitor and an apoptosis inhibitor. It is a stilbenoid, a beta-D-glucoside and a member of resorcinols.

General Description

2,3,5,4′ -Tetrahydroxystilbene-2-O-beta-glucoside (THSG) is a Polygoni Multiflori based polyphenol.

Biochem/physiol Actions

2,3,5,4′-Tetrahydroxystilbene 2-O-β-D-glucoside induces the expression and enhances the activity of EPO. The compound stimulates mitochondrial biogenesis, and expression of hemoglobin in non-hematopoietic cells. 2,3,5,4′-Tetrahydroxystilbene 2-O-β-D-glucoside has demonstrated protective effects in cardiovascular disease and ischemia models.

Physiological effects

Stilbene glycosides have the functions of brain protection, free radical scavenging, blood lipid lowering, liver protection, anti-tumor, vasodilation, and inhibition of atherosclerosis.

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