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529-53-3

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529-53-3 Usage

Description

Scutellarein is a flavone that has been isolated from S. baicalensis and has antioxidant, enzyme inhibitory, anti-inflammatory, and antiproliferative biological activities. It has antioxidant activity in a total reactive antioxidant potential (TRAP) assay when used at a concentration of 1 μg/ml. Scutellarein inhibits sucrose hydrolysis by rat intestinal α-glucosidase and ATPase activity of the severe acute respiratory syndrome (SARS) coronavirus helicase nsP13 (IC50s = 12 and 0.86 μM, respectively). It decreases nitric oxide (NO) release and mRNA expression of inducible NO synthase (iNOS) and TNF-α induced by LPS in RAW 264.7 macrophages when used at a concentration of 50 μM. In vivo, scutellarein (0.5 μg/g) decreases tumor weight and volume in an HT-1080 human fibrosarcoma mouse xenograft model.

Chemical Properties

Yellow solid

Uses

Scutellarein is a flavonoid that can be found in Scutellaria lateriflora. Scutellarein is a hydrolysis product of Scutellarein (S201900), its glucuronide conjugated analogue.

Definition

ChEBI: Flavone substituted with hydroxy groups at C-4', -5, -6 and -7.

Check Digit Verification of cas no

The CAS Registry Mumber 529-53-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 9 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 529-53:
(5*5)+(4*2)+(3*9)+(2*5)+(1*3)=73
73 % 10 = 3
So 529-53-3 is a valid CAS Registry Number.
InChI:InChI=1/C15H10O6/c16-8-3-1-7(2-4-8)11-5-9(17)13-12(21-11)6-10(18)14(19)15(13)20/h1-6,16,18-20H

529-53-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name scutellarein

1.2 Other means of identification

Product number -
Other names SCUTELLAREIN

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:529-53-3 SDS

529-53-3Synthetic route

5-hydroxy-4',6,7-trimethoxyflavone
19103-54-9

5-hydroxy-4',6,7-trimethoxyflavone

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With hydrogen bromide; acetic acid In water97%
scutellarein 7-O-β-D-glucuronopyranoside methyl ester
119262-68-9

scutellarein 7-O-β-D-glucuronopyranoside methyl ester

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With sulfuric acid In ethanol; water at 95℃; for 7h; Temperature; Time; Inert atmosphere;96%
With hydrogenchloride In ethanol at 90℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere;92.1%
5,6,7,4'-tetramethoxyflavone
1168-42-9

5,6,7,4'-tetramethoxyflavone

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With hydrogen bromide; acetic acid at 125℃; for 22h; Temperature; Inert atmosphere;94%
With hydrogen bromide; acetic acid at 120℃; for 24h; Inert atmosphere;90%
With hydrogen iodide
scutellarin
27740-01-8

scutellarin

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With sulfuric acid; water at 20℃; for 0.166667h; Concentration;93%
With sulfuric acid In ethanol; water at 120℃; for 48h; Inert atmosphere;85%
With sulfuric acid In water at 90℃; for 20h;45%
4,5,6,7-tetra-O-acetylflavone
1180-46-7

4,5,6,7-tetra-O-acetylflavone

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With methanol; sulfuric acid for 23h; Reagent/catalyst; Solvent; Temperature; Reflux;92.3%
6-hydroxy-5,7-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
6938-19-8

6-hydroxy-5,7-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With pyridine hydrochloride at 190 - 200℃; Cooling with ice; Inert atmosphere;86%
With pyridine hydrochloride at 180℃; for 6h; Inert atmosphere;2.6 g
5,6,7-trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
6563-66-2

5,6,7-trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With hydrogen bromide; acetic acid for 23h; Heating;82%
7-hydroxy-5,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
15044-65-2

7-hydroxy-5,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With hydrogen iodide
6-demethoxytangeretin
6601-66-7

6-demethoxytangeretin

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With hydrogen iodide; acetic anhydride
hispidulin
1447-88-7

hispidulin

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With pyridine hydrochloride for 3h;
plantaginin
26046-94-6

plantaginin

A

D-Glucose
2280-44-6

D-Glucose

B

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With hydrogenchloride for 2h;
With hydrogenchloride In methanol for 3h; Heating;
isoscutellarein
41440-05-5

isoscutellarein

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 100℃; for 4h;
hydrogenchloride
7647-01-0

hydrogenchloride

isoscutellarein
41440-05-5

isoscutellarein

scutellarein
529-53-3

scutellarein

pectolinarigenin

pectolinarigenin

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With hydrogen iodide
scutellarin

scutellarin

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With sulfuric acid
1-(4-methoxy-phenyl)-3-(2,3,4,6-tetramethoxy-phenyl)-propane-1,3-dione
859076-89-4

1-(4-methoxy-phenyl)-3-(2,3,4,6-tetramethoxy-phenyl)-propane-1,3-dione

hydrogen iodide
10034-85-2

hydrogen iodide

scutellarein
529-53-3

scutellarein

1-(4-methoxy-phenyl)-3-(2,3,4,6-tetramethoxy-phenyl)-propane-1,3-dione
859076-89-4

1-(4-methoxy-phenyl)-3-(2,3,4,6-tetramethoxy-phenyl)-propane-1,3-dione

hydrogen iodide
10034-85-2

hydrogen iodide

A

scutellarein
529-53-3

scutellarein

B

isoscutellarein
41440-05-5

isoscutellarein

Conditions
ConditionsYield
at 135℃;
scutellarein 6,7-di-O-β-D-glucuronide

scutellarein 6,7-di-O-β-D-glucuronide

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With 4b-glucuronidase at 37℃; for 2h; pH=5.2;
plantaginin
26046-94-6

plantaginin

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
Acid hydrolysis;
With water Acidic conditions;
2,4,6-trihydroxyacetophenone
480-66-0

2,4,6-trihydroxyacetophenone

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: K2CO3 / acetone / 0.17 h / 20 °C
1.2: 45 percent / acetone / 24 h / Heating
2.1: ZnCl2; AcOH / 2 h / 140 - 150 °C
3.1: 84 mg / aq. NaOH; aq. H2O2 / 3 h / cooling
4.1: 82 percent / aq. HBr; acetic acid / 23 h / Heating
View Scheme
5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one
480-44-4

5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ZnCl2; AcOH / 2 h / 140 - 150 °C
2: 84 mg / aq. NaOH; aq. H2O2 / 3 h / cooling
3: 82 percent / aq. HBr; acetic acid / 23 h / Heating
View Scheme
pectolinarigenin
101737-23-9

pectolinarigenin

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84 mg / aq. NaOH; aq. H2O2 / 3 h / cooling
2: 82 percent / aq. HBr; acetic acid / 23 h / Heating
View Scheme
4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: K2CO3 / acetone / 0.17 h / 20 °C
1.2: 45 percent / acetone / 24 h / Heating
2.1: ZnCl2; AcOH / 2 h / 140 - 150 °C
3.1: 84 mg / aq. NaOH; aq. H2O2 / 3 h / cooling
4.1: 82 percent / aq. HBr; acetic acid / 23 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / water / 5 h / 0 - 25 °C / pH 10 - 11
2: 12 h / 140 - 160 °C / 600.06 - 675.07 Torr
3: hydrogen bromide; L-valine / 32 h / 124 °C
View Scheme
1-(2,4-dihydroxy-3,6-dimethoxy)phenylethanone
7499-99-2

1-(2,4-dihydroxy-3,6-dimethoxy)phenylethanone

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium-<4-methoxy benzoate>
2: aqueous hydriodic acid
View Scheme
p-Methoxybenzoic anhydride
794-94-5

p-Methoxybenzoic anhydride

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium-<4-methoxy benzoate>
2: aqueous hydriodic acid
View Scheme
1-(6-hydroxy-2,3,4-trimethoxy-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione
724459-08-9

1-(6-hydroxy-2,3,4-trimethoxy-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; sodium acetate
2: acetic acid anhydride; aqueous hydriodic acid
View Scheme
5,6,7-trihydroxy-2-[4-({5-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-α-L-arabinofuranosyl}oxy)phenyl]-4H-1-benzopyran-4-one

5,6,7-trihydroxy-2-[4-({5-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-α-L-arabinofuranosyl}oxy)phenyl]-4H-1-benzopyran-4-one

A

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

B

scutellarein
529-53-3

scutellarein

Conditions
ConditionsYield
With hydrogenchloride; water for 0.666667h; Reflux;
scutellarein
529-53-3

scutellarein

benzyl bromide
100-39-0

benzyl bromide

7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5,6-dihydroxy-4H-chromen-4-one
62252-32-8

7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5,6-dihydroxy-4H-chromen-4-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;93%
With potassium carbonate In acetone for 6h; Solvent; Time; Temperature; Reflux;53.8%

529-53-3Relevant articles and documents

-

Gumenyuk

, (1975)

-

Synthesis and protective effect of scutellarein on focal cerebral ischemia/reperfusion in rats

Qian, Lihua,Shen, Minzhe,Tang, Hao,Tang, Yuping,Zhang, Li,Fu, Yifan,Shi, Qianping,Li, Nian-Guang

, p. 10667 - 10674,8 (2012)

Scutellarein, the main metabolite of scutellarin in vivo, has relatively better solubility, bioavailability and bio-activity than scutellarin. However, compared with scutellarin, it is very difficult to obtain scutellarein from Nature. Therefore, the present study focused on establishing an efficient route for the synthesis of scutellarein by hydrolyzing scutellarin. Neurological deficit score and cerebral infarction volume with the administration of scutellarein were then used to compare its neuroprotective effects on focal cerebral ischemia/reperfusion in rats induced by middle cerebral artery occlusion (MCAO) with those of scutellarin. The results showed that scutellarein had better protective effect on focal cerebral ischemia/reperfusion than scutellarin, which laid the foundation for further research and development of scutellarein as a promising candidate for ischemic cerebro-vascular disease.

Synthesis and Bioactivity Characterization of Scutellarein Sulfonated Derivative

Gu, Ting,Zhong, Yue,Lu, Yu-Ting,Sun, Ying,Dong, Ze-Xi,Wu, Wen-Yu,Shi, Zhi-Hao,Li, Nian-Guang,Xue, Xin,Fang, Fang,Li, He-Min,Tang, Yu-Ping

, (2017)

Scutellarin (1) has been widely used to treat acute cerebral infarction in clinic, but poor aqueous solubility decreases its bioavailability. Interestingly, scutellarin (1) could be metabolized into scutellarein (2) in vivo. In this study, a sulfonic group was introduced at position C-8 of scutellarein (2) to enhance the aqueous solubility of the obtained derivative (3). DPPH (1,1-diphenyl-2-picrylhydrazyl)-radical scavenging ability and antithrombic activity were also conducted to determine its bioactivity. The result showed that scutellarein derivate (3) could be a better agent for ischemic cerebrovascular disease treatment.

-

Bandyukova,Khalmatov

, (1967)

-

Organic synthesis method of scutellarein

-

, (2020/07/12)

The invention provides an organic synthesis method of scutellarein, wherein the organic synthesis method comprises the following steps: 1) by using p-methoxycinnamic acid as a raw material, synthesizing p-methoxycinnamoyl chloride under the catalytic action of an acyl chloride reagent and a catalyst; step 2) carrying out esterification reaction on p-methoxycinnamoyl chloride and 3,4,5-trimethoxyphenol under the action of Lewis acid, and then carrying out Fries rearrangement, so as to obtain 9-hydroxy-5,6,7,4'-tetramethoxychalcone; step 3) performing intramolecular cyclization on the 9-hydroxy-5,6,7,4'-tetramethoxychalcone under the action of an oxidizing agent to obtain 5,6,7,4'-tetramethoxyflavone; and step 4) demethylating the 5,6,7,4'-tetramethoxyflavone under the protection of N2 underthe action of a demethylating reagent to generate scutellarin. As the reaction operation is simple and safe, the post-treatment operation is easy, and the yield is high, the method has a wide industrial application prospect.

Synthesis and biological evaluation of scutellarein alkyl derivatives as preventing neurodegenerative agents with improved lipid soluble properties

Li, He-Min,Gu, Ting,Wu, Wen-Yu,Yu, Shao-Peng,Fan, Tian-Yuan,Zhong, Yue,Li, Nian-Guang

, p. 771 - 780 (2019/11/02)

Background: Exogenous antioxidants are considered as a promising therapeutic approach to treat neurodegenerative diseases since they could prevent and/or minimize the neuronal damage by oxidation. Objective: Three series of lipophilic compounds structurally based on scutellarein (2), which is one metabolite of scutellarin (1) in vivo, have been designed and synthesized. Methods: Their antioxidant activity was evaluated by detecting the 2-thiobarbituric acid reactive substance (TBARS) produced in the ferrous salt/ascorbate-induced autoxidation of lipids, which were present in microsomal membranes of rat hepatocytes. The lipophilicity of these compounds indicated as partition coefficient between n-octanol and buffer was investigated by ultraviolet (UV) spectrophotometer. Results: This study indicated that compound 5e which had a benzyl group substituted at the C4'-OH position showed a potent antioxidant activity and good lipophilicity. Conclusion: 5e could be an effective candidate for preventing or reducing the oxidative status associated with the neurodegenerative processes.

Scaffold hopping strategy for the design, synthesis and biological activity evaluation of novel hexacyclic scutellarein derivatives with a 1,3-oxazine ring fused at A-ring

Zhong, Yue,Lu, Yu-Ting,Sun, Ying,Li, Nian-Guang,Gu, Ting,Wu, Wen-Yu,Yu, Shao-Peng,Shi, Zhi-Hao

, p. 478 - 484 (2018/07/25)

Background: Discovery of novel agents with anticoagulant and antioxidant activity is very important to treat cerebrovascular disease. Lead compound LR3d discovered in our laboratory exhibited stronger anticoagulant ability and good antioxidant activity, compared with scutellarein (2), which is the major in vivo active metabolite of the natural product scutellarin (1). Objective: Design and synthesis novel scutellarein derivatives with improved anticoagulant and antioxidant activity. Methods: By utilizing a scaffold hopping strategy on LR3d, we describe the design and synthesis of a series of novel hexacyclic scutellarein derivatives 4 with a 1,3-oxazine ring fused at positions 7 and 8 in A ring. The thrombin inhibitory activities of all these new compounds were studied by the analysis of thrombin time (TT), activated partial thromboplastin time (APTT), prothrombin time (PT) and fibrinogen (FIB). The antioxidant abilities of these analogs were evaluated by using 3-(4,5)-dimethylthiahiazo (-z-y1)-3,5-di-phenytetrazoliumromide (MTT) method through 1,1- diphenyl-2-picrylhydrazyl radical 2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl (DPPH) assay. Results: Nine new hexacyclic scutellarein derivatives with a 1,3-oxazine ring fused at A-ring were synthesized, the results of the biological activity evaluation showed that compound 4e exhibited stronger anticoagulant and antioxidant ability compared to LR3d. Conclusion: 4e could be used for further development to treat ischemic cerebrovascular disease.

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