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118525-40-9

Basic Information
CAS No.: 118525-40-9
Name: Icaritin
Article Data: 24
Cas Database
Molecular Structure:
Molecular Structure of 118525-40-9 (Icaritin)
Formula: C21H20O6
Molecular Weight: 368.386
Synonyms: 4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)- (9CI);
EINECS: N/A
Density: 1.36 g/cm3
Melting Point: 239 °C
Boiling Point: 581.992 °C at 760 mmHg
Flash Point: 206.679 °C
Solubility: N/A
Appearance: N/A
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 100.13000
LogP: 4.09410
Synthetic route
489-32-7

icariin

118525-40-9

icaritin

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

5,7-dimethoxymethyl icaritin

118525-40-9

icaritin

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

C28H24O7

118525-40-9

icaritin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sulfuric acid In methanol
icariside-II

icariside-II

118525-40-9

icaritin

Conditions
ConditionsYield
With sulfuric acid
With potassium hydroxide
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    118525-40-9 Icaritin

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    Icaritin

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    Icaritin

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  • 118525-40-9

  • Casno:

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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