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34221-41-5

34221-41-5

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34221-41-5 Usage

Uses

Echinatin is used as an anticancer agent inhibiting DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.

Check Digit Verification of cas no

The CAS Registry Mumber 34221-41-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,4,2,2 and 1 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 34221-41:
(7*3)+(6*4)+(5*2)+(4*2)+(3*1)+(2*4)+(1*1)=75
75 % 10 = 5
So 34221-41-5 is a valid CAS Registry Number.
InChI:InChI=1/C16H14O4/c1-20-16-10-14(18)8-4-12(16)5-9-15(19)11-2-6-13(17)7-3-11/h2-10,17-18H,1H3/b9-5+

34221-41-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name (E)-3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

1.2 Other means of identification

Product number -
Other names 2-methoxy-4,4'-dihydroxychalcone

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:34221-41-5 SDS

34221-41-5Synthetic route

(E)-3-(2-methoxy-4-(methoxymethoxy)pheny l)-1-(4-(methoxymethoxy)phenyl)prop-2-en-1-one

(E)-3-(2-methoxy-4-(methoxymethoxy)pheny l)-1-(4-(methoxymethoxy)phenyl)prop-2-en-1-one

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
In ethanol Reflux;96%
1-(4-hydroxy-2-methoxy-phenyl)ethanone
493-33-4

1-(4-hydroxy-2-methoxy-phenyl)ethanone

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
With potassium hydroxide for 0.25h; Heating;
4-hydroxy-2-methoxybenzaldehyde
18278-34-7

4-hydroxy-2-methoxybenzaldehyde

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
With potassium hydroxide at 100℃; for 0.25h;20 mg
(E)-2-methoxy-4-(2-methylbut-2-enyloxy)benzaldehyde
1189552-07-5

(E)-2-methoxy-4-(2-methylbut-2-enyloxy)benzaldehyde

A

Licochalcone E

Licochalcone E

B

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydroxide / methanol / 12 h / 20 °C
2: hydrogenchloride / ethanol; water / 1 h / 40 °C
3: ethanol; water / 24 h / 180 °C
View Scheme
(E)-3-[2-methoxy-4-(2-methylbut-2-enyloxy)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
1308719-08-5

(E)-3-[2-methoxy-4-(2-methylbut-2-enyloxy)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one

A

Licochalcone E

Licochalcone E

B

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
In ethanol; water at 180℃; for 24h;
(E)-3-[2-methoxy-4-(2-methylbut-2-enyloxy)phenyl]-1-[4-(tetrahydropyranyloxy) phenyl]prop-2-en-1-one
1224514-27-5

(E)-3-[2-methoxy-4-(2-methylbut-2-enyloxy)phenyl]-1-[4-(tetrahydropyranyloxy) phenyl]prop-2-en-1-one

A

Licochalcone E

Licochalcone E

B

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / ethanol; water / 1 h / 40 °C
2: ethanol; water / 24 h / 180 °C
View Scheme
4-hydroxy-2-methoxybenzaldehyde
18278-34-7

4-hydroxy-2-methoxybenzaldehyde

A

Licochalcone E

Licochalcone E

B

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / acetone / 3 h / Reflux
2: potassium hydroxide / methanol / 12 h / 20 °C
3: hydrogenchloride / ethanol; water / 1 h / 40 °C
4: ethanol; water / 24 h / 180 °C
View Scheme
C26H30O6

C26H30O6

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
With hydrogenchloride; water In ethanol Time;
1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone
16162-69-9

1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone

2-methoxy-4-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde
163041-68-7

2-methoxy-4-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / ethanol / 20 °C
2: hydrogenchloride; water / ethanol
View Scheme
4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydride
2: sodium hydroxide / methanol; water / 20 °C
3: ethanol / Reflux
View Scheme
4-hydroxy-2-methoxybenzaldehyde
18278-34-7

4-hydroxy-2-methoxybenzaldehyde

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydride
2: sodium hydroxide / methanol; water / 20 °C
3: ethanol / Reflux
View Scheme
1-[4-(methoxymethoxy)phenyl]-1-ethanone
85699-00-9

1-[4-(methoxymethoxy)phenyl]-1-ethanone

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / methanol; water / 20 °C
2: ethanol / Reflux
View Scheme
2-methoxy-4-(methoxylmethoxy)benzaldehyde
114628-32-9

2-methoxy-4-(methoxylmethoxy)benzaldehyde

echinatin
34221-41-5

echinatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / methanol; water / 20 °C
2: ethanol / Reflux
View Scheme
echinatin
34221-41-5

echinatin

acetyl chloride
75-36-5

acetyl chloride

(E)-4-(3-(4-acetoxy-2-methoxyphenyl)acryloyl)phenyl acetate

(E)-4-(3-(4-acetoxy-2-methoxyphenyl)acryloyl)phenyl acetate

Conditions
ConditionsYield
Stage #1: echinatin With dmap In dichloromethane for 0.166667h; Cooling with ice;
Stage #2: acetyl chloride With triethylamine In dichloromethane at 20℃;		70%
echinatin
34221-41-5

echinatin

4,4'-dihydroxy-2-methoxydihydrochalcone

4,4'-dihydroxy-2-methoxydihydrochalcone

Conditions
ConditionsYield
With zinc In acetic acid for 0.333333h; Heating;5 mg
echinatin
34221-41-5

echinatin

4-(4''-acetoxy-2'',4-dimethoxy-2-(methoxymethoxy)-5'-methyl-1',2',3',4'-tetrahydro-[1,1':3',1''-terphenyl]-2'-carbonyl)phenyl acetate

4-(4''-acetoxy-2'',4-dimethoxy-2-(methoxymethoxy)-5'-methyl-1',2',3',4'-tetrahydro-[1,1':3',1''-terphenyl]-2'-carbonyl)phenyl acetate

4-(4''-acetoxy-2'',4-dimethoxy-2-(methoxymethoxy)-5'-methyl-1',2',3',4'-tetrahydro-[1,1':3',1''-terphenyl]-2'-carbonyl)phenyl acetate

4-(4''-acetoxy-2'',4-dimethoxy-2-(methoxymethoxy)-5'-methyl-1',2',3',4'-tetrahydro-[1,1':3',1''-terphenyl]-2'-carbonyl)phenyl acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dmap / dichloromethane / 0.17 h / Cooling with ice
1.2: 20 °C
2.1: toluene / 48 h / 130 °C / Sealed tube
View Scheme
echinatin
34221-41-5

echinatin

4-(4''-acetoxy-5-bromo-2'',4-dimethoxy-2-(methoxymethoxy)-5'-methyl-1',2',3',4'-tetrahydro-[1,1':3',1''-terphenyl]-2'-carbonyl)phenyl acetate

4-(4''-acetoxy-5-bromo-2'',4-dimethoxy-2-(methoxymethoxy)-5'-methyl-1',2',3',4'-tetrahydro-[1,1':3',1''-terphenyl]-2'-carbonyl)phenyl acetate

4-(4''-acetoxy-5-bromo-2'',4-dimethoxy-2-(methoxymethoxy)-5'-methyl-1',2',3',4'-tetrahydro-[1,1':3',1''-terphenyl]-2'-carbonyl)phenyl acetate

4-(4''-acetoxy-5-bromo-2'',4-dimethoxy-2-(methoxymethoxy)-5'-methyl-1',2',3',4'-tetrahydro-[1,1':3',1''-terphenyl]-2'-carbonyl)phenyl acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dmap / dichloromethane / 0.17 h / Cooling with ice
1.2: 20 °C
2.1: toluene / 48 h / 130 °C / Sealed tube
View Scheme

34221-41-5Relevant articles and documents

A new isoflavone and the corresponding isoflavanone of licorice root

Saitoh,Noguchi,Shibata

, p. 144 - 147,145.146 (1978)

-

Chalcones, inhibitors for topoisomerase i and cathepsin B and L, as potential anti-cancer agents

Kim, Seok-Ho,Lee, Eunyoung,Baek, Kyung Hye,Kwon, Han Byeol,Woo, Hyunjung,Lee, Eung-Seok,Kwon, Youngjoo,Na, Younghwa

, p. 3320 - 3324 (2013/06/27)

In order to diversify the pharmacological activity of chalcones and extend the scaffold of topoisomerase and cathepsins B and L inhibitors, we have designed and synthesized total 18 chalcone compounds and tested their biological activity. In the topoisome

Highly efficient synthesis of licochalcone E through water-accelerated [3,3]-sigmatropic rearrangement of allyl aryl ether

Jeon, Jae-Ho,Kim, Mi Ran,Kwon, Eun Mi,Lee, Na Ri,Jun, Jong-Gab

, p. 1059 - 1062 (2012/01/13)

-

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