scutellarin Methylester Chemical Properties

Boiling point:

804.0±65.0 °C(Predicted)

Density 

1.697±0.06 g/cm3(Predicted)

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

powder

pka

5.92±0.40(Predicted)

color 

Yellow

InChIKey

LNIVUWPCHRNJLG-BPZKQFRZNA-N

SMILES

O(C1=C(O)C(O)=C2C(=C1)OC(C1=CC=C(O)C=C1)=CC2=O)[C@@H]1O[C@H](C(OC)=O)[C@@H](O)[C@H](O)[C@H]1O |&1:21,23,28,30,32,r|

scutellarin Methylester Usage And Synthesis

Effect

The improvement effect of scutellarin methylester on ischemic brain tissue showed that scutellarin methylester can effectively improve the local cerebral blood flow of ischemia-reperfusion in rats, and significantly reduce the degree of ischemic damage to brain tissue. The mechanism may be In order to inhibit cerebral vasospasm caused by protein kinase activation, increase local cerebral blood flow, improve cerebral microcirculation, and reduce inflammatory cell adhesion and infiltration, thereby reducing brain damage.

Mechanism of action

Scutellarin methylester mainly inhibits the formation of thrombus in vitro through three steps, reducing platelet count, inhibiting platelet aggregation function, inhibiting coagulation function in vivo, and promoting fibrinolytic activity, of which the latter two have stronger effects.    

Uses

Scutellarin methyl ester is a constituent of Breviscapine which is a crude extract of several flavonoids of Erigeron breviscapus[1][2].

Definition

ChEBI: Scutellarin methyl ester is a glucosiduronic acid and a member of flavonoids.

Synthesis

GENERAL STEPS: Two 100 ml bottles of methanol were taken and cooled to 0°C under nitrogen protection and acetyl chloride (2.8 ml, 30 mmol) was added slowly. After keeping the reaction at 0°C for 30 min, a DMF solution (15 mL) of (2S,3S,4S,5R,6S)-6-((5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-benzopyran-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid (Compound 1, 4.62 g, 10 mmol) was added and stirred for 15 min. Slowly return to room temperature and gradually a white solid precipitated. The reaction mixture was heated to 40°C to continue the reaction for 4 hours, followed by cooling to -10°C for 1 hour. The reaction mixture was filtered and the filter cake was washed with water and dried under vacuum. A yellow solid (2S,3S,4S,5R,6S)-6-((5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-benzopyran-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid methyl ester was obtained (target product, 3.65 g) in 77% yield.

References

[1] Zhao M, et al. Structural identification of related substances in Breviscapine by UPLC-QTOF-MS. Zhongguo Zhong Yao Za Zhi. 2018 Jul;43(14):2872-2877. DOI:10.19540/j.cnki.cjcmm.2018.0089
[2] Gao J, et al. Therapeutic Effects of Breviscapine in Cardiovascular Diseases: A Review. Front Pharmacol. 2017 May 23;8:289. DOI:10.3389/fphar.2017.00289

scutellarin Methylester(119262-68-9)Related Product Information

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