Icariin supplier | CasNO.489-32-7

Name
Icariin
EINECS 610-440-0
CAS No. 489-32-7
Article Data3
CAS DataBase
Density 1.55 g/cm³
Solubility
Melting Point 231-232 °C
Formula C₃₃H₄₀O₁₅
Boiling Point 948.5 °C at 760 mmHg
Molecular Weight 676.672
Flash Point 300.9 °C
Transport Information
Appearance
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4H-1-Benzopyran-4-one,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-7-(b-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-(9CI);Icariin (8CI);Icariine;Icariln;Ieariline;Epimedium Extract powder;
PSA 238.20000
LogP 0.06790

Synthetic route

: 3-O-(2′′′′,3′′′′,4′′′′-tri-O-acetyl-α-L-rhamnopyranosyl)-7-O-(2′′′,3′′′,4′′′,6′′′-tetra-O-acetyl-β-D-glucopyranosyl)icaritin

: 489-32-7
icariin

Conditions

Conditions	Yield
With ammonia In methanol at 20℃; for 3h;	94%

: 133-89-1
UDP-glucose

: 113558-15-9
icariside II

: 489-32-7
icariin

Conditions

Conditions	Yield
With 7-O-glucosyltransferase from Epimedium pseudowushanense In dimethyl sulfoxide at 30℃; for 12h; pH=7.4; Kinetics; Catalytic behavior; Reagent/catalyst; Temperature; pH-value; Green chemistry; Enzymatic reaction; regiospecific reaction;	32.8%

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

: 489-32-7
icariin

Conditions

Conditions	Yield
Multi-step reaction with 5 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 3: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere 4: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere 5: ammonia / methanol / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 5 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
3: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere
4: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere
5: ammonia / methanol / 3 h / 20 °C
View Scheme

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

: 489-32-7
icariin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: palladium 10% on activated carbon; cyclohexa-1,4-diene / methanol / 2 h / 20 °C 2: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere 3: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere 4: ammonia / methanol / 3 h / 20 °C View Scheme

: 118525-40-9
icaritin

: 489-32-7
icariin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere 2: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere 3: ammonia / methanol / 3 h / 20 °C View Scheme

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

: 489-32-7
icariin

Conditions

Conditions	Yield
Multi-step reaction with 8 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 6: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere 7: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere 8: ammonia / methanol / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 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
6: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere
7: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere
8: ammonia / methanol / 3 h / 20 °C
View Scheme

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

: 489-32-7
icariin

Conditions

Conditions	Yield
Multi-step reaction with 10 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 8: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere 9: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere 10: ammonia / methanol / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 10 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
8: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere
9: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere
10: ammonia / methanol / 3 h / 20 °C
View Scheme

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

: 489-32-7
icariin

Conditions

Conditions	Yield
Multi-step reaction with 7 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 5: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere 6: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere 7: ammonia / methanol / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 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
5: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere
6: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere
7: ammonia / methanol / 3 h / 20 °C
View Scheme

: 520-18-3
kaempferol

: 489-32-7
icariin

Conditions

Conditions	Yield
Multi-step reaction with 11 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 9: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere 10: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere 11: ammonia / methanol / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 11 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
9: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere
10: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere
11: ammonia / methanol / 3 h / 20 °C
View Scheme

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

: 489-32-7
icariin

Conditions

Conditions	Yield
Multi-step reaction with 9 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 7: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere 8: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere 9: ammonia / methanol / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 9 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
7: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere
8: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere
9: ammonia / methanol / 3 h / 20 °C
View Scheme

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

: 489-32-7
icariin

Conditions

Conditions	Yield
Multi-step reaction with 6 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 4: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere 5: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere 6: ammonia / methanol / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 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
4: silver carbonate / chloroform; N,N-dimethyl-formamide / 30 h / 20 °C / Molecular sieve; Darkness; Inert atmosphere
5: silver(l) oxide / dichloromethane / 32 h / Molecular sieve; Inert atmosphere
6: ammonia / methanol / 3 h / 20 °C
View Scheme

: C39H48O19

: 489-32-7
icariin

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water at 50℃; for 0.333333h; Temperature;	6 mg

: 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

: 489-32-7
icariin

: 113558-15-9
icariside II

Conditions

Conditions	Yield
With Cunninghamella blakesleana In methanol for 120h; Microbiological reaction; regioselective reaction;	95.1%
With cellulase In dimethyl sulfoxide at 37℃; pH=5.7; Enzymatic reaction;	84%
With β-glucanase; sodium acetate In aq. buffer at 50℃; for 5h; Enzymatic reaction;	79%

: 489-32-7
icariin

: 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; water In methanol for 2h; Reflux;	86%
With sulfuric acid; water In 1,4-dioxane for 24h; Reflux;	23%

: 489-32-7
icariin

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

Conditions

Conditions	Yield
With sulfuric acid In ethanol; water at 50℃; for 24h;	60%
With rhamnosidase In aq. phosphate buffer at 60℃; for 24h; pH=6.8; Enzymatic reaction;	1.3 g
With sulfuric acid In ethanol; water at 50℃; for 24h;	450 mg

: 489-32-7
icariin

: sodium ((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxytetrahydro-6-methyl-2H-pyran-2-yl)oxy)-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-2-yl)methyl sulfate

Conditions

Conditions	Yield
With pyridine; sulfur trioxide pyridine complex Inert atmosphere;	22%

: 108-24-7
acetic anhydride

: 489-32-7
icariin

: 3-O-(2′′′′,3′′′′,4′′′′-tri-O-acetyl-α-L-rhamnopyranosyl)-7-O-(2′′′,3′′′,4′′′,6′′′-tetra-O-acetyl-β-D-glucopyranosyl)icaritin

Conditions

Conditions	Yield
Stage #1: icariin With triethylamine In N,N-dimethyl-formamide for 0.166667h; Cooling with ice; Stage #2: acetic anhydride In N,N-dimethyl-formamide for 6h; Cooling with ice;	15%

: 518-82-1
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

: 489-32-7
icariin

A: 23313-21-5
anthraglycoside B

B: 113558-15-9
icariside II

Conditions

Conditions	Yield
With glycosyltransferase from Carthamus tinctorius (L.) (Honghua) recombinant; UDP; Cleland's reagent In aq. buffer at 30℃; for 12h; pH=7.4; Enzymatic reaction; regiospecific reaction;	A 26 %Chromat. B 24 %Chromat.

...Expand

: 489-32-7
icariin

: C27H30O11

Conditions

Conditions	Yield
With cell suspension cultures of Glycyrrhiza uralensis In N,N-dimethyl-formamide for 168h; Microbiological reaction; regioselective reaction;

: 489-32-7
icariin

: (((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromene-3-yl)oxy)methyl)phosphonic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: β-glucanase; sodium acetate / aq. buffer / 5 h / 50 °C / Enzymatic reaction 2: sulfuric acid / ethanol; water / 5 h / 50 °C 3: caesium carbonate / acetone / Inert atmosphere; Reflux 4: 2,6-dimethylpyridine; trimethylsilyl bromide / dichloromethane / 20 °C / Inert atmosphere View Scheme

: 489-32-7
icariin

: (((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromen-3-yl)oxy)methyl)phosphonate disodium

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: β-glucanase; sodium acetate / aq. buffer / 5 h / 50 °C / Enzymatic reaction 2: sulfuric acid / ethanol; water / 5 h / 50 °C 3: caesium carbonate / acetone / Inert atmosphere; Reflux 4: 2,6-dimethylpyridine; trimethylsilyl bromide / dichloromethane / 20 °C / Inert atmosphere 5: sodium methylate / methanol / 0.5 h / 20 °C / Cooling with ice View Scheme

: 489-32-7
icariin

: 6(((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4Η-chromene-3,7-diyl)bis(oxy))bis(methyl))bis(phosphonic acid diethyl ester)

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: β-glucanase; sodium acetate / aq. buffer / 5 h / 50 °C / Enzymatic reaction 2: sulfuric acid / ethanol; water / 5 h / 50 °C 3: caesium carbonate / acetone / Inert atmosphere; Reflux View Scheme

: 489-32-7
icariin

: (((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)oxo-4Η-chromene-3,7-diyl)bis(oxy))bis(methylene))bisphosphonate sodium

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: β-glucanase; sodium acetate / aq. buffer / 5 h / 50 °C / Enzymatic reaction 2: sulfuric acid / ethanol; water / 5 h / 50 °C 3: caesium carbonate / acetone / Inert atmosphere; Reflux 4: 2,6-dimethylpyridine; trimethylsilyl bromide / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere 5: sodium hydroxide / methanol / 0.5 h View Scheme

: 489-32-7
icariin

: (((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromene-3,7-diyl)bis(oxy))bis(methylene))bisphosphonic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: β-glucanase; sodium acetate / aq. buffer / 5 h / 50 °C / Enzymatic reaction 2: sulfuric acid / ethanol; water / 5 h / 50 °C 3: caesium carbonate / acetone / Inert atmosphere; Reflux 4: 2,6-dimethylpyridine; trimethylsilyl bromide / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere View Scheme

: 489-32-7
icariin

: (2S)-2-((((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en1-yl)-4-oxo-4H-chromen-3-yl)oxy)(ethoxy)phosphoryl)amino)-3-methylbutanoate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: β-glucanase; sodium acetate / aq. buffer / 5 h / 50 °C / Enzymatic reaction 2: sulfuric acid / ethanol; water / 5 h / 50 °C 3: triethylamine; dmap / dichloromethane / 49 h / 0 - 20 °C View Scheme

: 489-32-7
icariin

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: β-glucanase; sodium acetate / aq. buffer / 5 h / 50 °C / Enzymatic reaction 2: sulfuric acid / ethanol; water / 5 h / 50 °C 3: triethylamine; dmap / dichloromethane / 49 h / 0 - 20 °C View Scheme

: 489-32-7
icariin

: (((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromen-3-yl)oxy)methyl)phosphonate diethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: β-glucanase; sodium acetate / aq. buffer / 5 h / 50 °C / Enzymatic reaction 2: sulfuric acid / ethanol; water / 5 h / 50 °C 3: caesium carbonate / acetone / Inert atmosphere; Reflux View Scheme

: 489-32-7
icariin

: C55H69NO22

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / N,N-dimethyl-formamide / 0.17 h / Cooling with ice 1.2: 6 h / Cooling with ice 2.1: potassium carbonate; potassium iodide / acetone / 0.17 h 2.2: 20 °C 3.1: potassium carbonate; potassium iodide / acetone / 0.17 h / 20 °C 3.2: 0.5 h / 20 °C View Scheme

: 489-32-7
icariin

: C50H59BrO22

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / N,N-dimethyl-formamide / 0.17 h / Cooling with ice 1.2: 6 h / Cooling with ice 2.1: potassium carbonate; potassium iodide / acetone / 0.17 h 2.2: 20 °C View Scheme

: 141-82-2
malonic acid

: 489-32-7
icariin

: 8-prenylkaempferol-4'-methylether-3-O-rhamnoside-7-O-(6-O-malonyl)-β-D-glucopyranoside

Conditions

Conditions	Yield
With DL-dithiothreitol; MatB from Arabidopsis thaliana; NbMaT1; ATP; magnesium chloride; Coenzyme A In aq. phosphate buffer at 30℃; for 12h; pH=7.5; Enzymatic reaction;

Icariin Chemical Properties

Molecular Structure of Icariin (CAS NO.489-32-7):

IUPAC Name:5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
Molecular Formula: C₃₃H₄₀OMolecular Weight: 676.6617 g/mol
H bond acceptors: 15
H bond donors: 8
Freely Rotating Bonds: 17
Polar Surface Area: 146.29Å²
Index of Refraction: 1.679
Molar Refractivity: 164.3 cm³
Molar Volume: 435 cm³
Surface Tension: 86.9 dyne/cm
Density: 1.55 g/cm³
Flash Point: 300.9 °C
Enthalpy of Vaporization: 144.62 kJ/mol
Boiling Point: 948.5 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Melting Point: 231-232 °C
Solubility: ethyl acetate, ethanol
Insolubility: chloroform,ether,benzene
Categories: Flavones; Functional Products; Natural Plant Extract; The group of Epimedii; plant extract

Icariin Specification

Icariin ,with CAS number of 489-32-7, can be called as 4H-1-Benzopyran-4-one,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-7-(b-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)- ; Ieariline . Icariin (CAS NO.489-32-7) is an important pharmaceutical intermediate.

Product Name

Icariin

Synthetic route

Icariin Chemical Properties

Icariin Specification

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