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2306-27-6

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2306-27-6 Usage

Uses

Different sources of media describe the Uses of 2306-27-6 differently. You can refer to the following data:
1. Sinensetin, eupatorin, 3'-hydroxy-5,6,7,4'-tetramethoxyflavone and rosmarinic acid contents and antioxidative effect of Orthosiphon stamineus from Malaysia.
2. antiangiogenesis, antidiabetic
3. Sinensetin exhibits anti-fungal, anti-histamine activity; induce cell differentiation, inhibition of linoleic acid oxidation, inhibition of white blood cells in the human zona protein Interleukin -1-i nduced expression of tissue factor.

Definition

ChEBI: A pentamethoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 3' and 4' respectively.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Sinensetin is a citris flavonoid with anti-inflammatory and anti-proliferative activity. It has also been shown to enhance adipogenesis and lipolysis.

Check Digit Verification of cas no

The CAS Registry Mumber 2306-27-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,3,0 and 6 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2306-27:
(6*2)+(5*3)+(4*0)+(3*6)+(2*2)+(1*7)=56
56 % 10 = 6
So 2306-27-6 is a valid CAS Registry Number.
InChI:InChI=1/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(27-14)10-17(24-3)19(25-4)20(18)26-5/h6-10H,1-5H3

2306-27-6 Well-known Company Product Price

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  • Sigma-Aldrich

  • (89392)  Sinensetin  analytical standard

  • 2306-27-6

  • 89392-10MG

  • 5,654.61CNY

  • Detail

2306-27-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name sinensetin

1.2 Other means of identification

Product number -
Other names Pedalitin permethyl ether

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:2306-27-6 SDS

2306-27-6Synthetic route

3,4-dimethoxybenzoic acid chloride
3535-37-3

3,4-dimethoxybenzoic acid chloride

Eudesmic acid
118-41-2

Eudesmic acid

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Stage #1: 3,4-dimethoxybenzoic acid chloride; Eudesmic acid With triethylamine In dichloromethane at 0 - 20℃; for 2h;
Stage #2: With trimethylsilyl trifluoromethanesulfonate; triethylamine In dichloromethane at 95℃; for 2h;
81%
(E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one
114021-62-4

(E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With pyridine; iodine for 8h; Heating;71%
With selenium(IV) oxide; pentan-1-ol
3,4-dimethoxyphenylpropiolic acid
22511-06-4

3,4-dimethoxyphenylpropiolic acid

3,4,5-trimethoxyphenol
642-71-7

3,4,5-trimethoxyphenol

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With phosphorus pentaoxide; methanesulfonic acid for 4h; Ambient temperature;26%
jaceosidin
18085-97-7

jaceosidin

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
In methanol; dichloromethane for 16h;24%
3,6-dihydroxy-2,4-dimethoxyacetophenone
6962-57-8

3,6-dihydroxy-2,4-dimethoxyacetophenone

3,4-dimethoxybenzoic anhydride
24824-54-2

3,4-dimethoxybenzoic anhydride

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With sodium 3,4-dimethoxybenzoate at 180℃; unter vermindertem Druck; Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge und Behandeln des danach isolierten Reaktionsprodukts mit Dimethylsulfat, Kaliumcarbonat und Aceton;
3',4',5,6,7-pentahydroxyflavone
18003-33-3

3',4',5,6,7-pentahydroxyflavone

dimethyl sulfate
77-78-1

dimethyl sulfate

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With potassium carbonate; acetone
With potassium carbonate In acetone for 20h; Heating;70 mg
With potassium carbonate In acetone for 2h; Heating;0.200 g
4'-hydroxy-5,6,7,3'-tetramethoxyflavone
51145-80-3

4'-hydroxy-5,6,7,3'-tetramethoxyflavone

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
In diethyl ether
5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6-methoxy-chromen-4-one
22934-99-2

5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-6-methoxy-chromen-4-one

dimethyl sulfate
77-78-1

dimethyl sulfate

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With potassium carbonate In acetone
3',4',7-trihydroxy-5,6-dimethoxyflavone
88153-47-3

3',4',7-trihydroxy-5,6-dimethoxyflavone

dimethyl sulfate
77-78-1

dimethyl sulfate

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With potassium carbonate In acetone for 4h;
selenium(IV) oxide
7446-08-4

selenium(IV) oxide

pentan-1-ol
71-41-0

pentan-1-ol

(E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one
114021-62-4

(E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one

sinensetin
2306-27-6

sinensetin

2'-hydroxy-3,4,4',6'-tetramethoxychalcone

2'-hydroxy-3,4,4',6'-tetramethoxychalcone

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 65 percent / dimethyl dioxirane / acetone; CH2Cl2 / 1 h / 0 - 20 °C
2: 95 percent / K2CO3 / acetone / 6 h / Heating
3: 71 percent / I2; pyridine / 8 h / Heating
View Scheme
1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone
76650-20-9

1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
2: 65 percent / dimethyl dioxirane / acetone; CH2Cl2 / 1 h / 0 - 20 °C
3: 95 percent / K2CO3 / acetone / 6 h / Heating
4: 71 percent / I2; pyridine / 8 h / Heating
View Scheme
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / KOH / ethanol / 3 h / 20 °C
2: 90 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
3: 65 percent / dimethyl dioxirane / acetone; CH2Cl2 / 1 h / 0 - 20 °C
4: 95 percent / K2CO3 / acetone / 6 h / Heating
5: 71 percent / I2; pyridine / 8 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: ethanol; aq. NaOH solution
2: selenium dioxide; amyl alcohol
View Scheme
1-(2,4,6-trimethoxyphenyl)ethanone
832-58-6

1-(2,4,6-trimethoxyphenyl)ethanone

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / KOH / ethanol / 3 h / 20 °C
2: 90 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
3: 65 percent / dimethyl dioxirane / acetone; CH2Cl2 / 1 h / 0 - 20 °C
4: 95 percent / K2CO3 / acetone / 6 h / Heating
5: 71 percent / I2; pyridine / 8 h / Heating
View Scheme
1-(2,5-dihydroxy-4,6-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone

1-(2,5-dihydroxy-4,6-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / K2CO3 / acetone / 6 h / Heating
2: 71 percent / I2; pyridine / 8 h / Heating
View Scheme
6-hydroxy-2,3,4-trimethoxyacetophenone
22248-14-2

6-hydroxy-2,3,4-trimethoxyacetophenone

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 110 °C
2: pyridine; potassium hydroxide / 4 h / 60 °C
3: acetic acid; sulfuric acid / 16 h / Reflux
View Scheme
3,4-dimethoxybenzoic acid chloride
3535-37-3

3,4-dimethoxybenzoic acid chloride

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 110 °C
2: pyridine; potassium hydroxide / 4 h / 60 °C
3: acetic acid; sulfuric acid / 16 h / Reflux
View Scheme
2-Hydroxy-4,5,6,3',4'-pentamethoxydibenzoylmethane

2-Hydroxy-4,5,6,3',4'-pentamethoxydibenzoylmethane

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
With sulfuric acid; acetic acid for 16h; Reflux;
3,4,5-trimethoxyphenol
642-71-7

3,4,5-trimethoxyphenol

sinensetin
2306-27-6

sinensetin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium acetate / 2 h / 110 °C
2.1: boron trifluoride diethyl etherate; acetic acid / 4 h / 70 °C
3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
3.2: 2 h / 95 °C
View Scheme
sinensetin
2306-27-6

sinensetin

5-desmethylsinensetin
21763-80-4

5-desmethylsinensetin

Conditions
ConditionsYield
With hydrogenchloride; ethanol for 72h; Product distribution / selectivity; Heating / reflux;100%
With boron tribromide In dichloromethane at 0℃; for 0.5h;94%
With boron trichloride In tetrahydrofuran at -78℃;61%
With boron trichloride In dichloromethane
sinensetin
2306-27-6

sinensetin

3',4',5,6,7-pentahydroxyflavone
18003-33-3

3',4',5,6,7-pentahydroxyflavone

Conditions
ConditionsYield
With hydrogen iodide; acetic anhydride
sinensetin
2306-27-6

sinensetin

Veratric acid
93-07-2

Veratric acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 24h; Heating;3.4 mg
sinensetin
2306-27-6

sinensetin

1-(2,3,4,6-tetramethoxyphenyl)ethanone
7508-05-6

1-(2,3,4,6-tetramethoxyphenyl)ethanone

Conditions
ConditionsYield
(i) aq. KOH, EtOH, (ii) (methylation); Multistep reaction;
sinensetin
2306-27-6

sinensetin

5,8-dihydroxy-6,7-dimethoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone
683278-67-3

5,8-dihydroxy-6,7-dimethoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
2: 90 percent / dimethyl dioxirane / acetone; CH2Cl2 / 0.33 h / 0 - 20 °C
View Scheme
sinensetin
2306-27-6

sinensetin

nobiletin
478-01-3

nobiletin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
2: 90 percent / dimethyl dioxirane / acetone; CH2Cl2 / 0.33 h / 0 - 20 °C
3: 87 percent / K2CO3 / acetone; CH2Cl2 / 6 h / Heating
View Scheme
sinensetin
2306-27-6

sinensetin

3-hydroxy-5,6,7,8,3′,4′-hexamethoxyflavone
35154-55-3

3-hydroxy-5,6,7,8,3′,4′-hexamethoxyflavone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 94 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
2: 90 percent / dimethyl dioxirane / acetone; CH2Cl2 / 0.33 h / 0 - 20 °C
3: 87 percent / K2CO3 / acetone; CH2Cl2 / 6 h / Heating
4: 80 percent / dimethyl dioxirane / acetone; CH2Cl2 / 0.17 h / 0 - 20 °C
View Scheme
sinensetin
2306-27-6

sinensetin

3,3',4',5,6,7,8-heptamethoxyflavone
1178-24-1

3,3',4',5,6,7,8-heptamethoxyflavone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 94 percent / BBr3 / CH2Cl2 / 0.5 h / 0 °C
2: 90 percent / dimethyl dioxirane / acetone; CH2Cl2 / 0.33 h / 0 - 20 °C
3: 87 percent / K2CO3 / acetone; CH2Cl2 / 6 h / Heating
4: 80 percent / dimethyl dioxirane / acetone; CH2Cl2 / 0.17 h / 0 - 20 °C
5: 97 percent / K2CO3 / acetone / 1 h / Heating
View Scheme
5,6,7,4'-tetramethoxyflavone
1168-42-9

5,6,7,4'-tetramethoxyflavone

sinensetin
2306-27-6

sinensetin

tangeritin
481-53-8

tangeritin

3,5,6,7,3',4'-Hexamethoxyflavon
1251-84-9

3,5,6,7,3',4'-Hexamethoxyflavon

nobiletin
478-01-3

nobiletin

3,3',4',5,6,7,8-heptamethoxyflavone
1178-24-1

3,3',4',5,6,7,8-heptamethoxyflavone

A

gardenin B
2798-20-1

gardenin B

B

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

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

C

5-desmethylsinensetin
21763-80-4

5-desmethylsinensetin

D

artemetin
479-90-3

artemetin

E

5-hydroxy-6,7,8,3',4'-pentamethoxyflavone
2174-59-6

5-hydroxy-6,7,8,3',4'-pentamethoxyflavone

F

5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone
1176-88-1

5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone

Conditions
ConditionsYield
With hydrogenchloride; ethanol at 80℃; for 18 - 70h; Product distribution / selectivity; Heating / reflux;
With hydrogenchloride; ethanol; water at 80℃; for 18h; Conversion of starting material; Heating / reflux;
With ethanol; water for 24h; Product distribution / selectivity; Heating / reflux;

2306-27-6Relevant articles and documents

5,6-DIMETHOXY-7,3',4',-TRIHYDROXYFLAVONE FROM ANISOMELES OVATA

Rao, L. Jagan Mohan,Kumari, G. N. Krishna,Rao, N. S. Prakasa

, p. 1522 (1983)

5,6-Dimethoxy-7,3',4'-trihydroxyflavone was isolated from the aerial parts of Anisomeles ovata and characterized by both physical and chemical methods.Key Word Index - Anisomeles ovata; Labiatae; flavone; 5,6-dimethoxy-7,3',4'-trihydroxyflavone.

Synthesis and anti-proliferative activities of 5,6,7-trimethoxyflavones and their derivatives

Li, Wei,Liu, Kexiong,Su, Liang,Wang, Qiuan

supporting information, (2021/08/12)

A series of 5,6,7-trimethoxyflavones 1a-1g and their derivatives 2a-2g, 3a-3d, 4 and 5, including the natural products 5,6,7-trimethoxy-4’-hydroxyflavone (1a), 5,6,7,3’,4’ -pentamethoxyflavone (sinensetin, 1 b), 5,6,7-trimethoxy-3’,4’-methyl enedioxy flavone (1c), 5,6,7,3’-tetramethoxy-4,5’-methylenedioxyflavone (1e), 5,6,7, 3’,4’,5’-hextamethoxyflavone (1 g), 5-hydroxy-3,4,2’,3’,4’-pentamethoxy chal-cone (2 b), 5,4’-dihydroxy-6,7-dimethoxy flavone (cirsimaritin, 3a) and 5-hydroxy-6,7,3’, 4’-tetramethoxyflavone (5-demethylsinensetin, 3 b), 3,5,6,7,3’,4’-hexamethoxyflavone (3-methoxysinensetin, 4) and 5’-hydroxy-3,6,7,3’,4’-pentamethoxyflavone (5) were synthesized. Their anti-proliferative activity in?vitro was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2 and SUN-5) by the CTG assay. The results showed that most of the synthetic compounds exhibited moderate to high anti-proliferative activities. In particular, compound 3c possess IC50 (5.30 μM) values below 10 μM against Aspc-1 cells and are worthy of further investigation.

Use of flavone and flavanone derivatives in preparation of sedative and hypnotic drugs

-

Page/Page column 48; 49; 50; 51, (2017/07/01)

Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.

USE OF FLAVONE AND FLAVANONE DERIVATIVES IN PREPARATION OF SEDATIVE AND HYPNOTIC DRUGS

-

Paragraph 0223; 0235, (2015/07/22)

Disclosed is a use of flavones derivatives and flavanone derivatives in preparation of sedative and hypnotic drugs.

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