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34221-41-5

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34221-41-5 Usage

Description

4,4'-DIHYDROXY-2-METHOXYCHALCONE is a chalcone derivative characterized by its chemical structure featuring two hydroxyl groups at the 4 and 4' positions, and a methoxy group at the 2 position. It is a naturally occurring compound found in various plants and has been recognized for its potential biological activities.

Uses

Used in Pharmaceutical Industry:
4,4'-DIHYDROXY-2-METHOXYCHALCONE is used as a bioactive compound for its potential therapeutic applications. It has been identified for its various pharmacological properties, which include anti-inflammatory, antioxidant, and antimicrobial activities. These properties make it a promising candidate for the development of new drugs targeting a range of health conditions.
Used in Anticancer Applications:
Similar to Echinatin, 4,4'-DIHYDROXY-2-METHOXYCHALCONE is used as an anticancer agent, inhibiting key enzymes such as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1. By targeting these enzymes, it can disrupt essential cellular processes in cancer cells, leading to their growth inhibition and eventual death. This makes it a valuable compound in the development of novel anticancer therapies.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic efficacy of 4,4'-DIHYDROXY-2-METHOXYCHALCONE, it can be incorporated into various drug delivery systems. These systems, which may include organic and metallic nanoparticles, can improve the compound's solubility, stability, and targeted delivery to cancer cells, thereby enhancing its overall effectiveness in cancer treatment.

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

Synthesis and topoisomerase II inhibitory and cytotoxic activity of oxiranylmethoxy- and thiiranylmethoxy-chalcone derivatives

Na, Younghwa,Nam, Jung-Min

scheme or table, p. 211 - 214 (2011/02/25)

In order to find potential anticancer drug candidate targeting topoisomerases enzyme, we have designed and synthesized oxiranylmethoxy- and thiiranylmethoxy-retrochalcone derivatives and evaluated their pharmacological activity including topoisomerases inhibitory and cytotoxic activity. Of the compounds prepared compound 25 showed comparable or better cytotoxic activity against cancer cell lines tested. Compound 25 inhibited MCF7 (IC50: 0.49 ± 0.21 μM) and HCT15 (IC50: 0.23 ± 0.02 μM) carcinoma cell growth more efficiently than references. In the topoisomerases inhibition test, all the compounds were inactive to topoisomerase I but moderate inhibitors to topoisomerase II enzyme. Especially, compound 25 inhibited topoisomerase II activity with comparable extent to etoposide at 100 μM concentrations. Correlation between cytotoxicity and topoisomerase II inhibitory activity implies that compound 25 can be a possible lead compound for anticancer drug impeding the topoisomerase II function.

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