Product Name

  • Name

    4,4'-DIHYDROXY-2-METHOXYCHALCONE

  • EINECS
  • CAS No. 34221-41-5
  • Article Data8
  • CAS DataBase
  • Density 1.282 g/cm3
  • Solubility
  • Melting Point 210°C (dec.)
  • Formula C16H14O4
  • Boiling Point 509.8 °C at 760 mmHg
  • Molecular Weight 270.285
  • Flash Point 193.3 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 34221-41-5 (4,4'-DIHYDROXY-2-METHOXYCHALCONE)
  • Hazard Symbols
  • Synonyms 2-Propen-1-one,3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-, (E)-;Chalcone, 4,4'-dihydroxy-2-methoxy-,(E)- (8CI);Echinatin;Retrochalcone;
  • PSA 66.76000
  • LogP 3.00250

Synthetic 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

2-Propen-1-one,3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-,(2E)- Specification

The CAS registry number of 2-Propen-1-one, 3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-,(2E)- is 34221-41-5. The IUPAC name is (2E)-3-(4-Hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one. In addition, the molecular formula is C16H14O4 and the molecular weight is 270.28. It belongs to the class of Chalcones.

Physical properties about 2-Propen-1-one, 3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-,(2E)- are: (1)ACD/LogP: 3.24; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.23; (4)ACD/LogD (pH 7.4): 3.09; (5)ACD/BCF (pH 5.5): 168.46; (6)ACD/BCF (pH 7.4): 121.83; (7)ACD/KOC (pH 5.5): 1363.75; (8)ACD/KOC (pH 7.4): 986.3; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 44.76 Å2; (13)Index of Refraction: 1.657; (14)Molar Refractivity: 77.55 cm3; (15)Molar Volume: 210.6 cm3; (16)Polarizability: 30.74 ×10-24cm3; (17)Surface Tension: 56.5 dyne/cm; (18)Density: 1.282 g/cm3; (19)Flash Point: 193.3 °C; (20)Enthalpy of Vaporization: 80.99 kJ/mol; (21)Boiling Point: 509.8 °C at 760 mmHg; (22)Vapour Pressure: 5.16E-11 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(c1ccc(O)cc1)\C=C\c2ccc(O)cc2OC
(2) 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+
(3) InChIKey: QJKMIJNRNRLQSS-WEVVVXLNBR

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