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| CAS No.: | 489-32-7 |
|---|---|
| Name: | Icariin |
| Molecular Structure: | |
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| Formula: | C33H40O15 |
| Molecular Weight: | 676.672 |
| 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; |
| EINECS: | 610-440-0 |
| Density: | 1.55 g/cm3 |
| Melting Point: | 231-232 °C |
| Boiling Point: | 948.5 °C at 760 mmHg |
| Flash Point: | 300.9 °C |
| Safety: | 24/25 |
| PSA: | 238.20000 |
| LogP: | 0.06790 |
icariin
| Conditions | Yield |
|---|---|
| With ammonia In methanol at 20℃; for 3h; | 94% |
| 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% |
icariin
| 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 |
icariin
| 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 |
icaritin
icariin
| 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 |
icariin
| 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 |
3,5,7-triacetoxy-2-(4-acetoxy-phenyl)-chromen-4-one
icariin
| 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 |
icariin
| 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 |
| 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 |
icariin
| 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 |
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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: C33H40O
Molecular 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 ,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.
