Icaritin supplier | CasNO.118525-40-9

Name
Icaritin
EINECS
CAS No. 118525-40-9
Article Data24
CAS DataBase
Density 1.36 g/cm³
Solubility
Melting Point 239 °C
Formula C₂₁H₂₀O₆
Boiling Point 581.992 °C at 760 mmHg
Molecular Weight 368.386
Flash Point 206.679 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)- (9CI);
PSA 100.13000
LogP 4.09410

Synthetic route

: 489-32-7
icariin

: 118525-40-9
icaritin

Conditions

Conditions	Yield
With water; sodium acetate; cellulase In ethanol; water; dimethyl sulfoxide at 37℃; pH=5.0;	100%
With cellulase
Multi-step reaction with 2 steps 1: β-glucanase; sodium acetate / aq. buffer / 5 h / 50 °C / Enzymatic reaction 2: sulfuric acid / ethanol; water / 5 h / 50 °C View Scheme

: 5-hydroxy-3,7-bis(methoxymethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-4H-chromen-4-one

: 118525-40-9
icaritin

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 2h; Reflux; Inert atmosphere;	96%

: 5,7-dimethoxymethyl icaritin

: 118525-40-9
icaritin

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 65℃; for 1h; Inert atmosphere;	95%

: C28H24O7

: 118525-40-9
icaritin

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 60℃;	87%
With sodium hydroxide In ethanol; water at 60℃;	87%

: 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

: 118525-40-9
icaritin

Conditions

Conditions	Yield
With cyclohexa-1,4-diene; palladium 10% on activated carbon In methanol at 20℃; for 2h;	86%
With cyclohexa-1,4-diene; palladium 10% on activated carbon In methanol at 20℃; for 2h;	84%

: 113558-15-9
icariside II

: 118525-40-9
icaritin

Conditions

Conditions	Yield
With sulfuric acid In ethanol; water at 50℃; for 5h;	82%
With sulfuric acid In ethanol; water at 50℃; for 5h;	82%
With sulfuric acid In ethanol; water at 50℃; for 5h;	82%

: C25H28O8

: 118525-40-9
icaritin

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; isopropyl alcohol for 6.16667h; Solvent; Reagent/catalyst; Inert atmosphere; Reflux;	70.6%

: 56725-99-6
3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin

: 118525-40-9
icaritin

Conditions

Conditions	Yield
With cellulase In dimethyl sulfoxide at 37℃; pH=5.7;	68%

: 118525-35-2
sagittatoside A

A: 2280-44-6
D-Glucose

B: 6014-42-2
L-rhamnose

C: 118525-40-9
icaritin

Conditions

Conditions	Yield
With sulfuric acid In methanol

...Expand

icariside-II: icariside-II

: 118525-40-9
icaritin

Conditions

Conditions	Yield
With sulfuric acid
With potassium hydroxide

icariside-I: icariside-I

A: 118525-40-9
icaritin

B: 521-45-9
IC-163

Conditions

Conditions	Yield
With potassium hydroxide

: 110623-72-8
4'-methoxy-5-hydroxy-8-3,3-dimethylallylflavone 3-O-β-D-glucopyranosyl(1<*>2)α-L-rhamnopyranoside-7-O-β-D-glucopyranoside

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: β-glucosidase 2: 1 N H2SO4 / methanol View Scheme

epimedium koreanum Nakai, leaves; 1-butanol-ether-hexane-methanol extract of: epimedium koreanum Nakai, leaves; 1-butanol-ether-hexane-methanol extract of

A: 118525-40-9
icaritin

B: 113558-15-9
icariside II

C: 56725-99-6
3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin

Conditions

Conditions	Yield
With hydrogenchloride; methanol; water at 80℃; for 8h; Product distribution / selectivity; Heating / reflux;
With sodium methylate In pyridine at 80℃; for 8h; Product distribution / selectivity; Heating / reflux;
With acetic acid; β-glucuronidase; naringinase; hesperidinase; β-galactosidase; cellulase; amyloglucosidase at 37℃; for 48h; pH=4.5; Product distribution / selectivity;
Stage #1: epimedium koreanum Nakai, leaves; 1-butanol-ether-hexane-methanol extract of With water at 121℃; for 0.5h; Stage #2: at 30℃; for 120h; Product distribution / selectivity;

...Expand

: 3-O-L-rhamnose-7-O-β-glucose-8-prenyl-4'-methoxychrysin

A: 118525-40-9
icaritin

B: 56725-99-6
3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin

Conditions

Conditions	Yield
With sulfuric acid; water In ethanol for 1.5h; Reflux;

: 100-09-4
4-methoxybenzoic acid

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: thionyl chloride / dichloromethane / 4 h / Reflux 2.1: potassium carbonate / acetone / 24.5 h / 65 °C 3.1: sodium carbonate; sodium hydrogencarbonate; Oxone / acetone; water; dichloromethane / 29 h / 0 °C / pH 9 3.2: 2 h / 20 °C 4.1: 5%-palladium/activated carbon; hydrogen / methanol; ethyl acetate / 24 h / 20 °C 5.1: potassium carbonate / acetone / 6 h / 20 °C 6.1: potassium carbonate / acetone / 12 h / 50 °C 7.1: N,N-diethylaniline / 0.5 h / 190 °C / Microwave irradiation 8.1: hydrogenchloride / methanol / 2 h / Reflux; Inert atmosphere View Scheme

Yield

Multi-step reaction with 8 steps
1.1: thionyl chloride / dichloromethane / 4 h / Reflux
2.1: potassium carbonate / acetone / 24.5 h / 65 °C
3.1: sodium carbonate; sodium hydrogencarbonate; Oxone / acetone; water; dichloromethane / 29 h / 0 °C / pH 9
3.2: 2 h / 20 °C
4.1: 5%-palladium/activated carbon; hydrogen / methanol; ethyl acetate / 24 h / 20 °C
5.1: potassium carbonate / acetone / 6 h / 20 °C
6.1: potassium carbonate / acetone / 12 h / 50 °C
7.1: N,N-diethylaniline / 0.5 h / 190 °C / Microwave irradiation
8.1: hydrogenchloride / methanol / 2 h / Reflux; Inert atmosphere
View Scheme

: 99-96-7
4-hydroxy-benzoic acid

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: sodium hydroxide / water / 4 h / 40 °C 2.1: thionyl chloride / dichloromethane / 4 h / Reflux 3.1: potassium carbonate / acetone / 24.5 h / 65 °C 4.1: sodium carbonate; sodium hydrogencarbonate; Oxone / acetone; water; dichloromethane / 29 h / 0 °C / pH 9 4.2: 2 h / 20 °C 5.1: 5%-palladium/activated carbon; hydrogen / methanol; ethyl acetate / 24 h / 20 °C 6.1: potassium carbonate / acetone / 6 h / 20 °C 7.1: potassium carbonate / acetone / 12 h / 50 °C 8.1: N,N-diethylaniline / 0.5 h / 190 °C / Microwave irradiation 9.1: hydrogenchloride / methanol / 2 h / Reflux; Inert atmosphere View Scheme

Yield

Multi-step reaction with 9 steps
1.1: sodium hydroxide / water / 4 h / 40 °C
2.1: thionyl chloride / dichloromethane / 4 h / Reflux
3.1: potassium carbonate / acetone / 24.5 h / 65 °C
4.1: sodium carbonate; sodium hydrogencarbonate; Oxone / acetone; water; dichloromethane / 29 h / 0 °C / pH 9
4.2: 2 h / 20 °C
5.1: 5%-palladium/activated carbon; hydrogen / methanol; ethyl acetate / 24 h / 20 °C
6.1: potassium carbonate / acetone / 6 h / 20 °C
7.1: potassium carbonate / acetone / 12 h / 50 °C
8.1: N,N-diethylaniline / 0.5 h / 190 °C / Microwave irradiation
9.1: hydrogenchloride / methanol / 2 h / Reflux; Inert atmosphere
View Scheme

: 100-07-2
4-methoxy-benzoyl chloride

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: potassium carbonate / acetone / 24.5 h / 65 °C 2.1: sodium carbonate; sodium hydrogencarbonate; Oxone / acetone; water; dichloromethane / 29 h / 0 °C / pH 9 2.2: 2 h / 20 °C 3.1: 5%-palladium/activated carbon; hydrogen / methanol; ethyl acetate / 24 h / 20 °C 4.1: potassium carbonate / acetone / 6 h / 20 °C 5.1: potassium carbonate / acetone / 12 h / 50 °C 6.1: N,N-diethylaniline / 0.5 h / 190 °C / Microwave irradiation 7.1: hydrogenchloride / methanol / 2 h / Reflux; Inert atmosphere View Scheme

Yield

Multi-step reaction with 7 steps
1.1: potassium carbonate / acetone / 24.5 h / 65 °C
2.1: sodium carbonate; sodium hydrogencarbonate; Oxone / acetone; water; dichloromethane / 29 h / 0 °C / pH 9
2.2: 2 h / 20 °C
3.1: 5%-palladium/activated carbon; hydrogen / methanol; ethyl acetate / 24 h / 20 °C
4.1: potassium carbonate / acetone / 6 h / 20 °C
5.1: potassium carbonate / acetone / 12 h / 50 °C
6.1: N,N-diethylaniline / 0.5 h / 190 °C / Microwave irradiation
7.1: hydrogenchloride / methanol / 2 h / Reflux; Inert atmosphere
View Scheme

: 5,7-bis(benzyloxy)-2-(4-methoxyphenyl)-4H-chromen-4-one

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: sodium carbonate; sodium hydrogencarbonate; Oxone / acetone; water; dichloromethane / 29 h / 0 °C / pH 9 1.2: 2 h / 20 °C 2.1: 5%-palladium/activated carbon; hydrogen / methanol; ethyl acetate / 24 h / 20 °C 3.1: potassium carbonate / acetone / 6 h / 20 °C 4.1: potassium carbonate / acetone / 12 h / 50 °C 5.1: N,N-diethylaniline / 0.5 h / 190 °C / Microwave irradiation 6.1: hydrogenchloride / methanol / 2 h / Reflux; Inert atmosphere View Scheme

Yield

Multi-step reaction with 6 steps
1.1: sodium carbonate; sodium hydrogencarbonate; Oxone / acetone; water; dichloromethane / 29 h / 0 °C / pH 9
1.2: 2 h / 20 °C
2.1: 5%-palladium/activated carbon; hydrogen / methanol; ethyl acetate / 24 h / 20 °C
3.1: potassium carbonate / acetone / 6 h / 20 °C
4.1: potassium carbonate / acetone / 12 h / 50 °C
5.1: N,N-diethylaniline / 0.5 h / 190 °C / Microwave irradiation
6.1: hydrogenchloride / methanol / 2 h / Reflux; Inert atmosphere
View Scheme

: 5,7-bis(benzyloxy)-3-hydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 5%-palladium/activated carbon; hydrogen / methanol; ethyl acetate / 24 h / 20 °C 2: potassium carbonate / acetone / 6 h / 20 °C 3: potassium carbonate / acetone / 12 h / 50 °C 4: N,N-diethylaniline / 0.5 h / 190 °C / Microwave irradiation 5: hydrogenchloride / methanol / 2 h / Reflux; Inert atmosphere View Scheme

: 491-54-3
4'-O-methylkaempferol

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 6 h / 20 °C 2: potassium carbonate / acetone / 12 h / 50 °C 3: N,N-diethylaniline / 0.5 h / 190 °C / Microwave irradiation 4: hydrogenchloride / methanol / 2 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere 2: caesium carbonate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 18 h / 10 - 20 °C / Inert atmosphere 3: europium(III) trifluoromethanesulfonate / dichloromethane / 2 h / -5 - 0 °C / Inert atmosphere 4: hydrogenchloride / 1,4-dioxane; isopropyl alcohol / 6.17 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere 2: caesium carbonate; tetrabutylammomium bromide / tetrahydrofuran / 40 h / 30 °C / Inert atmosphere 3: europium(III) trifluoromethanesulfonate / dichloromethane / 2 h / -5 - 0 °C / Inert atmosphere 4: hydrogenchloride / 1,4-dioxane; isopropyl alcohol / 6.17 h / Inert atmosphere; Reflux View Scheme

: 5-hydroxy-3,7-bis(methoxymethoxy)-2-(4-methoxyphenyl)-4H-chromen-4-one

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 12 h / 50 °C 2: N,N-diethylaniline / 0.5 h / 190 °C / Microwave irradiation 3: hydrogenchloride / methanol / 2 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: caesium carbonate; tetrabutylammomium bromide / tetrahydrofuran / 40 h / 30 °C / Inert atmosphere 2: europium(III) trifluoromethanesulfonate / dichloromethane / 2 h / -5 - 0 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane; isopropyl alcohol / 6.17 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 3 steps 1: caesium carbonate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 18 h / 10 - 20 °C / Inert atmosphere 2: europium(III) trifluoromethanesulfonate / dichloromethane / 2 h / -5 - 0 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane; isopropyl alcohol / 6.17 h / Inert atmosphere; Reflux View Scheme

: 5-(3-methylbut-2-enyloxy)-3,7-bis(methoxymethoxy)-2-(4-methoxyphenyl)-4H-chromen-4-one

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-diethylaniline / 0.5 h / 190 °C / Microwave irradiation 2: hydrogenchloride / methanol / 2 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: europium(III) trifluoromethanesulfonate / dichloromethane / 2 h / -5 - 0 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane; isopropyl alcohol / 6.17 h / Inert atmosphere; Reflux View Scheme

: 7-(benzyloxy)-5-hydroxy-3-(methoxymethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4Hchromen-4-one

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / methanol; water / 2.5 h / Reflux; Inert atmosphere 2: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride; water / methanol / 2.5 h / Inert atmosphere; Reflux 2: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme

: 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C 2: 18-crown-6 ether; potassium carbonate / acetone / 19.33 h / 20 °C 3: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / chlorobenzene / 24 h / 85 °C / Inert atmosphere 4: hydrogenchloride / methanol; water / 2.5 h / Reflux; Inert atmosphere 5: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C 2: potassium carbonate; 18-crown-6 ether / acetone / 19 h / 20 °C 3: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sodium hydrogencarbonate / chlorobenzene / 24 h / 85 °C / Inert atmosphere 4: hydrogenchloride; water / methanol / 2.5 h / Inert atmosphere; Reflux 5: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C
2: 18-crown-6 ether; potassium carbonate / acetone / 19.33 h / 20 °C
3: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / chlorobenzene / 24 h / 85 °C / Inert atmosphere
4: hydrogenchloride / methanol; water / 2.5 h / Reflux; Inert atmosphere
5: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C
View Scheme

Multi-step reaction with 5 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C
2: potassium carbonate; 18-crown-6 ether / acetone / 19 h / 20 °C
3: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sodium hydrogencarbonate / chlorobenzene / 24 h / 85 °C / Inert atmosphere
4: hydrogenchloride; water / methanol / 2.5 h / Inert atmosphere; Reflux
5: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C
View Scheme

: 16274-11-6
3,5,7-triacetoxy-2-(4-acetoxy-phenyl)-chromen-4-one

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: potassium iodide; potassium carbonate / acetone 2: dimethyl sulfate; potassium carbonate / acetone 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C 4: 18-crown-6 ether; potassium carbonate / acetone / 19.33 h / 20 °C 5: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / chlorobenzene / 24 h / 85 °C / Inert atmosphere 6: hydrogenchloride / methanol; water / 2.5 h / Reflux; Inert atmosphere 7: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 24 h / Reflux 2.1: potassium carbonate / tetrahydrofuran / 2 h / Reflux 2.2: 24 h / Reflux 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C 4.1: potassium carbonate; 18-crown-6 ether / acetone / 19 h / 20 °C 5.1: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sodium hydrogencarbonate / chlorobenzene / 24 h / 85 °C / Inert atmosphere 6.1: hydrogenchloride; water / methanol / 2.5 h / Inert atmosphere; Reflux 7.1: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: potassium iodide; potassium carbonate / acetone
2: dimethyl sulfate; potassium carbonate / acetone
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C
4: 18-crown-6 ether; potassium carbonate / acetone / 19.33 h / 20 °C
5: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / chlorobenzene / 24 h / 85 °C / Inert atmosphere
6: hydrogenchloride / methanol; water / 2.5 h / Reflux; Inert atmosphere
7: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C
View Scheme

Multi-step reaction with 7 steps
1.1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 24 h / Reflux
2.1: potassium carbonate / tetrahydrofuran / 2 h / Reflux
2.2: 24 h / Reflux
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C
4.1: potassium carbonate; 18-crown-6 ether / acetone / 19 h / 20 °C
5.1: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sodium hydrogencarbonate / chlorobenzene / 24 h / 85 °C / Inert atmosphere
6.1: hydrogenchloride; water / methanol / 2.5 h / Inert atmosphere; Reflux
7.1: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C
View Scheme

: 7-(benzyloxy)-5-hydroxy-3-(methoxymethoxy)-2-(4-methoxyphenyl)-4H-chromen-4-one

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 18-crown-6 ether; potassium carbonate / acetone / 19.33 h / 20 °C 2: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / chlorobenzene / 24 h / 85 °C / Inert atmosphere 3: hydrogenchloride / methanol; water / 2.5 h / Reflux; Inert atmosphere 4: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate; 18-crown-6 ether / acetone / 19 h / 20 °C 2: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sodium hydrogencarbonate / chlorobenzene / 24 h / 85 °C / Inert atmosphere 3: hydrogenchloride; water / methanol / 2.5 h / Inert atmosphere; Reflux 4: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1: 18-crown-6 ether; potassium carbonate / acetone / 19.33 h / 20 °C
2: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / chlorobenzene / 24 h / 85 °C / Inert atmosphere
3: hydrogenchloride / methanol; water / 2.5 h / Reflux; Inert atmosphere
4: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C
View Scheme

Multi-step reaction with 4 steps
1: potassium carbonate; 18-crown-6 ether / acetone / 19 h / 20 °C
2: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sodium hydrogencarbonate / chlorobenzene / 24 h / 85 °C / Inert atmosphere
3: hydrogenchloride; water / methanol / 2.5 h / Inert atmosphere; Reflux
4: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C
View Scheme

: 520-18-3
kaempferol

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: pyridine 2: potassium iodide; potassium carbonate / acetone 3: dimethyl sulfate; potassium carbonate / acetone 4: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C 5: 18-crown-6 ether; potassium carbonate / acetone / 19.33 h / 20 °C 6: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / chlorobenzene / 24 h / 85 °C / Inert atmosphere 7: hydrogenchloride / methanol; water / 2.5 h / Reflux; Inert atmosphere 8: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: pyridine / 20 °C 2.1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 24 h / Reflux 3.1: potassium carbonate / tetrahydrofuran / 2 h / Reflux 3.2: 24 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C 5.1: potassium carbonate; 18-crown-6 ether / acetone / 19 h / 20 °C 6.1: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sodium hydrogencarbonate / chlorobenzene / 24 h / 85 °C / Inert atmosphere 7.1: hydrogenchloride; water / methanol / 2.5 h / Inert atmosphere; Reflux 8.1: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: pyridine
2: potassium iodide; potassium carbonate / acetone
3: dimethyl sulfate; potassium carbonate / acetone
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C
5: 18-crown-6 ether; potassium carbonate / acetone / 19.33 h / 20 °C
6: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / chlorobenzene / 24 h / 85 °C / Inert atmosphere
7: hydrogenchloride / methanol; water / 2.5 h / Reflux; Inert atmosphere
8: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C
View Scheme

Multi-step reaction with 8 steps
1.1: pyridine / 20 °C
2.1: potassium iodide; potassium carbonate / N,N-dimethyl-formamide / 24 h / Reflux
3.1: potassium carbonate / tetrahydrofuran / 2 h / Reflux
3.2: 24 h / Reflux
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C
5.1: potassium carbonate; 18-crown-6 ether / acetone / 19 h / 20 °C
6.1: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sodium hydrogencarbonate / chlorobenzene / 24 h / 85 °C / Inert atmosphere
7.1: hydrogenchloride; water / methanol / 2.5 h / Inert atmosphere; Reflux
8.1: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C
View Scheme

: 2-(4-acetoxyphenyl)-7-(benzyloxy)-4-oxo-4H-chromene-3,5-diyl diacetate

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: dimethyl sulfate; potassium carbonate / acetone 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C 3: 18-crown-6 ether; potassium carbonate / acetone / 19.33 h / 20 °C 4: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / chlorobenzene / 24 h / 85 °C / Inert atmosphere 5: hydrogenchloride / methanol; water / 2.5 h / Reflux; Inert atmosphere 6: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: potassium carbonate / tetrahydrofuran / 2 h / Reflux 1.2: 24 h / Reflux 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C 3.1: potassium carbonate; 18-crown-6 ether / acetone / 19 h / 20 °C 4.1: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sodium hydrogencarbonate / chlorobenzene / 24 h / 85 °C / Inert atmosphere 5.1: hydrogenchloride; water / methanol / 2.5 h / Inert atmosphere; Reflux 6.1: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: dimethyl sulfate; potassium carbonate / acetone
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C
3: 18-crown-6 ether; potassium carbonate / acetone / 19.33 h / 20 °C
4: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / chlorobenzene / 24 h / 85 °C / Inert atmosphere
5: hydrogenchloride / methanol; water / 2.5 h / Reflux; Inert atmosphere
6: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C
View Scheme

Multi-step reaction with 6 steps
1.1: potassium carbonate / tetrahydrofuran / 2 h / Reflux
1.2: 24 h / Reflux
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 0 - 20 °C
3.1: potassium carbonate; 18-crown-6 ether / acetone / 19 h / 20 °C
4.1: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sodium hydrogencarbonate / chlorobenzene / 24 h / 85 °C / Inert atmosphere
5.1: hydrogenchloride; water / methanol / 2.5 h / Inert atmosphere; Reflux
6.1: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C
View Scheme

: 7-(benzyloxy)-3-(methoxymethoxy)-2-(4-methoxyphenyl)-5-((3-methylbut-2-en-1-yl)oxy)-4Hchromen-4-one

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / chlorobenzene / 24 h / 85 °C / Inert atmosphere 2: hydrogenchloride / methanol; water / 2.5 h / Reflux; Inert atmosphere 3: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sodium hydrogencarbonate / chlorobenzene / 24 h / 85 °C / Inert atmosphere 2: hydrogenchloride; water / methanol / 2.5 h / Inert atmosphere; Reflux 3: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C View Scheme

: icariin

: 118525-40-9
icaritin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate; hydrogenchloride / ethanol; water / 5 h / 50 °C / pH 5 / Enzymatic reaction 2: sulfuric acid / ethanol; water / 5 h / 50 °C View Scheme

: 64-18-6
formic acid

: 118525-40-9
icaritin

: 38226-86-7
3,5-dihydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-4-one

Conditions

Conditions	Yield
for 20h; Reflux;	93.3%

: 118525-40-9
icaritin

: 38226-86-7
3,5-dihydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-4-one

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 90℃; for 6h;	92%
With sulfuric acid; acetic acid at 90℃; for 6h;	92%
With polyphosphoric acid; air In N,N-dimethyl-formamide at 130℃; for 2h;	81%

: 118525-40-9
icaritin

: 105-36-2
ethyl bromoacetate

: 2,2'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-di-yl)bis(oxy)]diacetic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone for 6h; Reflux;	90%

: 110-52-1
1,4-dibromo-butane

: 118525-40-9
icaritin

: 3,7-bis(4-bromobutoxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	87%

: C15H24N2O17P2

: 118525-40-9
icaritin

: 113558-15-9
icariside II

Conditions

Conditions	Yield
With recombinant rhamnosyl transferase from Epimedium pseudowushanense; UDP-rhamnose synthase from Epimedium pseudowushanense; nicotinamide adenine dinucleotide; NADPH In dimethyl sulfoxide at 30℃; for 12h; pH=7.4; Enzymatic reaction; regioselective reaction;	87%

: 13734-41-3, 22838-58-0, 54895-12-4
N-Boc-(S/R)-valine

: 118525-40-9
icaritin

: C31H38N2O8*2ClH

Conditions

Conditions	Yield
Stage #1: N-Boc-(S/R)-valine; icaritin With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; Stage #2: With hydrogenchloride In dichloromethane; water at 20℃; for 0.333333h;	81%

: 2969-81-5
4-bromoethylbutanoate

: 118525-40-9
icaritin

: 4,4'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dibutyric acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone for 6h; Reflux;	80%

: 3744-87-4, 7764-95-6, 15761-38-3
N-t-butyloxycarbonyl-DL-alanine

: 118525-40-9
icaritin

: C27H30N2O8*2ClH

Conditions

Conditions	Yield
Stage #1: N-t-butyloxycarbonyl-DL-alanine; icaritin With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; Stage #2: With hydrogenchloride In dichloromethane; water at 20℃; for 0.333333h;	80%

: 118525-40-9
icaritin

: 623-48-3
ethyl iodoacetae

: 2,2'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-di-yl)bis(oxy)]diacetic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	79%

: 629-03-8
1 ,6-dibromohexane

: 118525-40-9
icaritin

: 3,7-bis[(6-bromohexyl)oxy]-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	78%

: 4549-32-0
1,8-dibromooctane

: 118525-40-9
icaritin

: 3,7-bis[(8-bromooctyl)oxy]-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	75%

: 118525-40-9
icaritin

: 540-51-2
2-bromoethanol

: 1067198-74-6
5-hydroxy-3,7-bis(2-hydroxyethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone for 6h; Reflux;	73%
With potassium carbonate In acetone Reflux;	61%
With potassium carbonate In acetone Reflux;	61%

: 109-01-3
1-methyl-piperazine

: 32315-10-9
bis(trichloromethyl) carbonate

: 118525-40-9
icaritin

: 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-(chromen-3-yl)-4-methylpiperazin-1-carboxylic acid ester

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; icaritin With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3.5h; Inert atmosphere; Stage #2: 1-methyl-piperazine With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	69%

...Expand

: 118525-40-9
icaritin

: 623-48-3
ethyl iodoacetae

: 2-[(3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-7-yl)oxy]acetic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	65%

: 118525-40-9
icaritin

: 762-04-9
phosphonic acid diethyl ester

: C25H29O9P

Conditions

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; tetrachloromethane at -10 - 20℃;	64%

: 37746-78-4
4-bromo-trans-crotonic acid ethyl ester

: 118525-40-9
icaritin

: 4,4'-[(5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3,7-diyl)bis(oxy)]dicrotonic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone for 6h; Reflux;	60%

: 24424-99-5
di-tert-butyl dicarbonate

: 118525-40-9
icaritin

: C26H28O8

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	59.8%

: 118525-40-9
icaritin

: 627-18-9
1-bromo-3-propanol

: 5-hydroxy-3,7-bis(3-hydroxypropoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone for 6h; Reflux;	55%
With potassium carbonate In acetone at 56℃; for 8h;	850 mg

: 118525-40-9
icaritin

: 6482-24-2
2-Bromoethyl methyl ether

: 5,7-dihydroxy-3-(2-methoxyethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux; Inert atmosphere;	55%

: 118525-40-9
icaritin

: 106-93-4
ethylene dibromide

: 3,7-bis(2-bromoethoxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	54%

: 118525-40-9
icaritin

: 105-36-2
ethyl bromoacetate

A: 2-[(5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)oxy]acetic acid ethyl ester

B: 2-[(3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-7-yl)oxy]acetic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone for 6h; Reflux;	A 41% B 12%

...Expand

: 118525-40-9
icaritin

: 535-11-5, 41978-69-2
Ethyl 2-bromopropionate

A: 2-[(5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)oxy]propionic acid ethyl ester

B: 2-[(3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-7-yl)oxy]propionic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone for 6h; Reflux;	A 40% B 10%

...Expand

Icaritin Specification

The 4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-, with the CAS registry number 118525-40-9, is also known as 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-chromen-4-one. It belongs to the product categories of Aromatics; Heterocycles; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals. This chemical's molecular formula is C₂₁H₂₀O₆ and molecular weight is 368.38. What's more, both its IUPAC name and systematic name are the same which is called 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one. It is a metabolite of Icariin. Icaritin and Desmethylicaritin, two metabolites of Icariin, dramatically inhibit the growth of most malignant cells. They also have significant antiangiogenesis properties, inhibiting or eliminating entirely the development of new malignant cells.

Physical properties about 4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)- are: (1)ACD/LogP: 5.244; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.20; (4)ACD/LogD (pH 7.4): 4.19; (5)ACD/BCF (pH 5.5): 5129.69; (6)ACD/BCF (pH 7.4): 500.96; (7)ACD/KOC (pH 5.5): 15286.30; (8)ACD/KOC (pH 7.4): 1492.84; (9)#H bond acceptors: 6; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 96.22 Å²; (13)Index of Refraction: 1.656; (14)Molar Refractivity: 99.583 cm³; (15)Molar Volume: 270.868 cm³; (16)Polarizability: 39.478×10^-24cm³; (17)Surface Tension: 62.147 dyne/cm; (18)Density: 1.36 g/cm³; (19)Flash Point: 206.679 °C; (20)Enthalpy of Vaporization: 90.242 kJ/mol; (21)Boiling Point: 581.992 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C1c3c(O/C(=C1/O)c2ccc(OC)cc2)c(c(O)cc3O)C\C=C(/C)C
(2) InChI: InChI=1S/C21H20O6/c1-11(2)4-9-14-15(22)10-16(23)17-18(24)19(25)20(27-21(14)17)12-5-7-13(26-3)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3
(3) InChIKey: TUUXBSASAQJECY-UHFFFAOYSA-N

Product Name

Icaritin

Synthetic route

Icaritin Specification

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