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118525-40-9

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118525-40-9 Usage

Chemical Properties

Yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from epimedium.

Uses

Icaritin is a hydrolytic product of Icariin, a traditional Chinese herbal medicine extracted from the Epimedium genus. Icaritin and Desmethylicaritin, is 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. Icaritin has been used in trials studying the treatment of Solid Tumors, Metastatic Breast Cancer, and Hepatocellular Carcinoma (HCC).

Biochem/physiol Actions

Icaritin is a component of Epimedium flavonoid isolated from Herba Epimedii, which enhances osteoblastic differentiation of mesenchymal stem cells (MSCs) while it inhibits adipogenic differentiation of MSCs by inhibiting PPAR-g pathway. Icaritin has no effect on MSCs proliferation. Also, icaritin potently inhibits chronic myeloid leukemia (CML) and breast cancer cells proliferation most likely by modulation of MAPK/ERK/JNK and JAK2/STAT3 /AKT signaling. As other flavonoids, icaritin may exert estrogen-like activities.

Synthesis

The novel total synthesis of icaritin, naturally occurring with important bioactive 8-prenylflavonoid, was performed via a reaction sequence of 8 steps including Baker-Venkataraman reaction, chemoselective benzyl or methoxymethyl protection, dimethyldioxirane (DMDO) oxidation, O-prenylation, Claisen rearrangement and deprotection, starting from 2,4,6-trihydroxyacetophenone and 4-hydroxybenzoic acid in overall yields of 23%. The key step was Claisen rearrangement under microwave irradiation.Total Synthesis of Icaritin via Microwave-assistance Claisen Rearrangement

Mode of action

Icaritin is a flavonoid first isolated from the Chinese herb H. epimedii that demonstrates anticancer activity against a variety of tumor cell lines. Icaritin was shown in vitro to sustain extracellular signal–regulated kinase (ERK) activity through stimulating estrogen receptors. Prolonged ERK activation arrested the cell cycle in the G2 stage and subsequently triggered apoptosis. It has been shown to inhibit fatty acid synthase, reducing IGF-1-induced activation of STAT3 in several melanoma cell lines.

Check Digit Verification of cas no

The CAS Registry Mumber 118525-40-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,8,5,2 and 5 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 118525-40:
(8*1)+(7*1)+(6*8)+(5*5)+(4*2)+(3*5)+(2*4)+(1*0)=119
119 % 10 = 9
So 118525-40-9 is a valid CAS Registry Number.
InChI:InChI=1/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

118525-40-9 Well-known Company Product Price

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  • CAS number
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  • TCI America

  • (I0974)  Icaritin  >96.0%(HPLC)

  • 118525-40-9

  • 10mg

  • 840.00CNY

  • Detail
  • TCI America

  • (I0974)  Icaritin  >96.0%(HPLC)

  • 118525-40-9

  • 50mg

  • 2,990.00CNY

  • Detail
  • Sigma

  • (SML0551)  Icaritin  ≥98% (HPLC)

  • 118525-40-9

  • SML0551-5MG

  • 1,020.24CNY

  • Detail
  • Sigma

  • (SML0551)  Icaritin  ≥98% (HPLC)

  • 118525-40-9

  • SML0551-25MG

  • 4,120.74CNY

  • Detail

118525-40-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one

1.2 Other means of identification

Product number -
Other names 3,7-dihydroxy-8-prenyl-4'-methoxychrysin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:118525-40-9 SDS

118525-40-9Synthetic route

icariin
489-32-7

icariin

icaritin
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

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

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
With hydrogenchloride In methanol for 2h; Reflux; Inert atmosphere;96%
5,7-dimethoxymethyl icaritin

5,7-dimethoxymethyl icaritin

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 65℃; for 1h; Inert atmosphere;95%
C28H24O7

C28H24O7

icaritin
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

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

icaritin
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%
icariside II
113558-15-9

icariside II

icaritin
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

C25H28O8

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

3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
With cellulase In dimethyl sulfoxide at 37℃; pH=5.7;68%
sagittatoside A
118525-35-2

sagittatoside A

A

D-Glucose
2280-44-6

D-Glucose

B

L-rhamnose
6014-42-2

L-rhamnose

C

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
With sulfuric acid In methanol
icariside-II

icariside-II

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
With sulfuric acid
With potassium hydroxide
icariside-I

icariside-I

A

icaritin
118525-40-9

icaritin

B

IC-163
521-45-9

IC-163

Conditions
ConditionsYield
With potassium hydroxide
4'-methoxy-5-hydroxy-8-3,3-dimethylallylflavone 3-O-β-D-glucopyranosyl(1<*>2)α-L-rhamnopyranoside-7-O-β-D-glucopyranoside
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

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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

icaritin
118525-40-9

icaritin

B

icariside II
113558-15-9

icariside II

C

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

3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin

Conditions
ConditionsYield
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;
3-O-L-rhamnose-7-O-β-glucose-8-prenyl-4'-methoxychrysin

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

A

icaritin
118525-40-9

icaritin

B

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

3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin

Conditions
ConditionsYield
With sulfuric acid; water In ethanol for 1.5h; Reflux;
4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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
4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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
4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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

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

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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

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

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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
4'-O-methylkaempferol
491-54-3

4'-O-methylkaempferol

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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

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

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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

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

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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

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

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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

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

icaritin
118525-40-9

icaritin

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

3,5,7-triacetoxy-2-(4-acetoxy-phenyl)-chromen-4-one

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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

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

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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
kaempferol
520-18-3

kaempferol

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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

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

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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

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

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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

icariin

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
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
formic acid
64-18-6

formic acid

icaritin
118525-40-9

icaritin

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

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

Conditions
ConditionsYield
for 20h; Reflux;93.3%
icaritin
118525-40-9

icaritin

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

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

Conditions
ConditionsYield
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%
icaritin
118525-40-9

icaritin

ethyl bromoacetate
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

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
ConditionsYield
With potassium carbonate In acetone for 6h; Reflux;90%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

icaritin
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

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

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Reflux;87%
C15H24N2O17P2

C15H24N2O17P2

icaritin
118525-40-9

icaritin

icariside II
113558-15-9

icariside II

Conditions
ConditionsYield
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%
icaritin
118525-40-9

icaritin

C31H38N2O8*2ClH

C31H38N2O8*2ClH

Conditions
ConditionsYield
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%
4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

icaritin
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

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
ConditionsYield
With potassium carbonate In acetone for 6h; Reflux;80%
N-t-butyloxycarbonyl-DL-alanine
3744-87-4, 7764-95-6, 15761-38-3

N-t-butyloxycarbonyl-DL-alanine

icaritin
118525-40-9

icaritin

C27H30N2O8*2ClH

C27H30N2O8*2ClH

Conditions
ConditionsYield
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%
icaritin
118525-40-9

icaritin

ethyl iodoacetae
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

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
ConditionsYield
With potassium carbonate In acetone for 12h; Reflux;79%
1 ,6-dibromohexane
629-03-8

1 ,6-dibromohexane

icaritin
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

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

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Reflux;78%
1,8-dibromooctane
4549-32-0

1,8-dibromooctane

icaritin
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

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

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Reflux;75%
icaritin
118525-40-9

icaritin

2-bromoethanol
540-51-2

2-bromoethanol

5-hydroxy-3,7-bis(2-hydroxyethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
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
ConditionsYield
With potassium carbonate In acetone for 6h; Reflux;73%
With potassium carbonate In acetone Reflux;61%
With potassium carbonate In acetone Reflux;61%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

icaritin
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

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
ConditionsYield
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%
icaritin
118525-40-9

icaritin

ethyl iodoacetae
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

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
ConditionsYield
With potassium carbonate In acetone for 12h; Reflux;65%
icaritin
118525-40-9

icaritin

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

C25H29O9P

C25H29O9P

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; tetrachloromethane at -10 - 20℃;64%
4-bromo-trans-crotonic acid ethyl ester
37746-78-4

4-bromo-trans-crotonic acid ethyl ester

icaritin
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

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
ConditionsYield
With potassium carbonate In acetone for 6h; Reflux;60%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

icaritin
118525-40-9

icaritin

C26H28O8

C26H28O8

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;59.8%
icaritin
118525-40-9

icaritin

1-bromo-3-propanol
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

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

Conditions
ConditionsYield
With potassium carbonate In acetone for 6h; Reflux;55%
With potassium carbonate In acetone at 56℃; for 8h;850 mg
icaritin
118525-40-9

icaritin

2-Bromoethyl methyl ether
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

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

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux; Inert atmosphere;55%
icaritin
118525-40-9

icaritin

ethylene dibromide
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

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

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Reflux;54%
icaritin
118525-40-9

icaritin

ethyl bromoacetate
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

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

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
ConditionsYield
With potassium carbonate In acetone for 6h; Reflux;A 41%
B 12%
icaritin
118525-40-9

icaritin

Ethyl 2-bromopropionate
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

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

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

118525-40-9Relevant articles and documents

Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen - Cope rearrangement

Mei, Qinggang,Wang, Chun,Zhao, Zhigang,Yuan, Weicheng,Zhang, Guolin

, p. 1220 - 1225 (2015)

The hemisynthesis of the naturally occurring bioactive flavonoid glycoside icariin (1) has been accomplished in eleven steps with 7% overall yield from kaempferol. The 4?-OH methylation of kaempferol, the 8-prenylation of 3-O-methoxymethyl-4?-O-methyl-5- O-prenyl-7-O-benzylkaempferol (8) via para-Claisen-Cope rearrangement catalyzed by Eu(fod)3 in the presence of NaHCO3 , and the glycosylation of icaritin (3) are the key steps.

Magnesium dicarboxylates promote the prenylation of phenolics that is extended to the total synthesis of icaritin

Fu, Xuewen,Lu, Xiaoxia,Wang, Chun,Wen, Yongju,Xiong, Wei,Zhang, Guolin,Zhang, Jichao

, p. 1117 - 1124 (2022/02/16)

The prenylation of phenolic substrates promoted by magnesium dicarboxylates was developed. An investigation of the scope demonstrated that substrates with electron-donating group(s) gave better yields than those with electron-withdrawing group(s). Althoug

Convenient and efficient total synthesis method for icaritin and derivatives of icaritin

-

Paragraph 0063; 0084-0088, (2020/02/06)

The invention belongs to the field of natural medicine synthesis and particularly relates to a convenient and efficient total synthesis method for icaritin and derivatives of icaritin. The specific technical scheme is as follows: 2'-hydroxyacetophenone and benzaldehyde are used as raw materials, firstly, isopentene groups are introduced in aromatic rings of raw materials under the catalysis of anorganic polyacid metal ion complex, a flavonol framework is constructed under mild and green conditions, and an isopentenyl flavone compound comprising the icaritin and derivatives of icaritin is further synthesized. The method effectively overcomes the limitation of poor substrate solubility and poor regioselectivity when flavone is constructed firstly and then isopentene groups are introduced, the problems of frequent introduction and removal of protecting groups in a conventional isopentenylation method are solved, and the synthesis route is greatly simplified; and meanwhile, the problems of complex products and more byproducts in an isopentene group rearrangement method are solved. The total synthesis method provided by the invention is mild in condition, convenient to operate, high intotal yield and suitable for mass production of the isopentenyl flavone compound.

Preparation and medical application methods of icaritin derivative

-

, (2019/10/23)

The invention relates to preparation and medical application methods of an icaritin derivative. The preparation method comprises taking trihydroxyacetophenone, chloromethyl methyl ether and the like as initial raw materials to connect isopentene groups to an 8th carbon through vicinal rearrangement, then performing serial reaction of formation of a flavone framework, and lastly, performing dehydration to introduce propylene groups to synthesize the icaritin derivative. The preparation method of the icaritin derivative is low in the cost of the synthetic routes, simple in operation, high in recovery rate and applicable to industrial production. Pharmacological effect experiments prove that the icaritin derivative has the pharmacological effect of activating organism endogenous stem cells and achieves the rehabilitation function of repair traumatic pathological changes of blood vessels, nerves, endothelial cells and matrixes and can be applied to preparing drugs for repairing traumatic pathological changes of tissues, thereby having a good prospect in fields such as drugs for rehabilitation of pathological changes of erectile dysfunction.

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