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Name	Icariin	EINECS	610-440-0
CAS No.	489-32-7	Density	1.55 g/cm³
PSA	238.20000	LogP	0.06790
Solubility	N/A	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	N/A	Appearance	N/A
Safety	24/25	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
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;	Article Data	3

Icariin 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

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.

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