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489-32-7 Usage

Applications

Icariin inhibits the ROS-dependent JNK and p38 pathways.

Description

Icariin is one of the major flavonoids of the herb Epimedium, which has long been used in Tranditional Chinese Medicine to treat bone fracture and prevent osteoporosis. Research has shown that icariin should be an effective component for the bone-strengthening activity of the herb Epimedium, and one of the possible mechanisms for this activity is to stimulate the proliferation and enhance the osteogenic differentiation of marrow stromal cells. Icariin is reported to prevent and treat sexual dysfunction related diseases and improve the use of vasoconstriction. Icariin is used to prepare angiotensin converting enzyme inhibitor medicines, which can be used to treat hypertension-complicated coronary diseases.

References

[1] K. M. Chen, B. F. Ge, H. P. Ma, X. Y. Liu, M. H. Bai, Y, Wang (2005) Icariin, a flavonoid from the herb Epimedium enhances the osteogenic differentiation of rat primary bone marrow stromal cells, 60, 939-942 [2] Patent CN 1199647C “Application of icariin in preparation of medicine for preventing and treating sexual dysfunction” [3] Patent CN 104739851 A “New application of icariin, or icariin derivatives or icariin salt”

Chemical Properties

Light yellow to yellow solid

Uses

Different sources of media describe the Uses of 489-32-7 differently. You can refer to the following data:
1. hepatoprotective
2. Icariin has been used:in the preparation of topical treatment to determine its effects on the improvement of cutaneous wound healing in ratsto test its analgesic effects on lower back pain (LBP) in ratsas a potential treatment in osteoporosis condition in ratsto study its effects on palmitate (PA)-induced insulin resistance in skeletal muscle C2C12 myotubesas a neuroprotective agent to study its effects on amyloid-β (Aβ)-induced neuronal insulin resistance in human neuroblastoma SK-N-MC cells
3. Icariin has been used as a test material to investigate its, in vitro effect in promoting mouse hair follicle growth, which is assessed by vibrissae hair follicle (VHF) organ-culture model.

General Description

Icariin is a prenylated flavonol and the major bioactive compound found in Epimedium herb.

Biological Activity

icariin exhibits inhibitory effects on cgmp-specific phosphodiesterase pde5 and camp-specific phosphodiesterase pde4 activities. phosphodiesterase (pde) is a crucial regulator of camp/pka signaling. pdes are encoded by 21 genes which can be sdivided into 11 families according to the substrate specificities and subcellular localization. pdes are widely expressed in neurons. pde5 has been implicated in regulating some physiological processes such as smooth muscle relaxation and neuronal survival. pde4 has been associated with the darpp-32 signaling pathway and dopaminergic neurotransmission [1].

Biochem/physiol Actions

Icariin is a potent neuroprotective agent in neurodegenerative disorders and other disorders affecting the nervous system. It elicits anti-aging properties in unfertilized oocytes against age-related damage. Icariin exerts anti-inflammatory and antifibrotic properties aiding protection in chronic kidney disease (CKD)-associated renal fibrosis in mouse model. It also serves as an excellent antidiabetic and anti-atherosclerotic agent. Icariin is an excellent anti-cancer agent.

in vitro

icariin inhibited the activity of pde5 and pde4 in a dose- andconcentration-dependent manner. the ic50of icariin on pde5 was 0.43 μm and the ic50 on pde4 was 73.50 μm. icariin showed a selective inhibitory effect on cgmp-specific pde5 compared to camp-specific pde4 [2].icariincould also enhance the osteogenic differentiation of rat primary bone marrow stromal cells [3].

in vivo

in castrated rats, a 4-week oral administration of icariinat 1 mg/kg/day and 5 mg/kg/day improved the erectile function and increased nnos and inos expression [4].icariin also showed its effect on stimulating angiogenesis in human endothelial cells [5].

references

nishi a, kuroiwa m, miller d b, et al. distinct roles of pde4 and pde10a in the regulation of camp/pka signaling in the striatum[j]. the journal of neuroscience, 2008, 28(42): 10460-10471.xin z c, kim e k, lin c s, et al. effects of icariin on cgmp-specific pde5 and camp-specific pde4 activities[j]. asian journal of andrology, 2003, 5(1): 15-18.chen k m, ge b f, ma h p, et al. icariin, a flavonoid from the herb epimedium enhances the osteogenic differentiation of rat primary bone marrow stromal cells[j]. die pharmazie-an international journal of pharmaceutical sciences, 2005, 60(12): 939-942.liu w j, xin z c, xin h, et al. effects of icariin on erectile function and expression of nitric oxide synthase isoforms in castrated rats[j]. asian journal of andrology, 2005, 7(4): 381-388.chung b h, kim j d, kim c k, et al. icariin stimulates angiogenesis by activating the mek/erk-and pi3k/akt/enos-dependent signal pathways in human endothelial cells[j]. biochemical and biophysical research communications, 2008, 376(2): 404-408.

Check Digit Verification of cas no

The CAS Registry Mumber 489-32-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 9 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 489-32:
(5*4)+(4*8)+(3*9)+(2*3)+(1*2)=87
87 % 10 = 7
So 489-32-7 is a valid CAS Registry Number.
InChI:InChI=1/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1

489-32-7 Well-known Company Product Price

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  • TCI America

  • (I0862)  Icariin  >96.0%(HPLC)

  • 489-32-7

  • 200mg

  • 550.00CNY

  • Detail
  • TCI America

  • (I0862)  Icariin  >96.0%(HPLC)

  • 489-32-7

  • 1g

  • 1,590.00CNY

  • Detail

489-32-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name icariin

1.2 Other means of identification

Product number -
Other names ICARRIN

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:489-32-7 SDS

489-32-7Synthetic 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

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

icariin
489-32-7

icariin

Conditions
ConditionsYield
With ammonia In methanol at 20℃; for 3h;94%
UDP-glucose
133-89-1

UDP-glucose

icariside II
113558-15-9

icariside II

icariin
489-32-7

icariin

Conditions
ConditionsYield
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

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

icariin
489-32-7

icariin

Conditions
ConditionsYield
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

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

icariin
489-32-7

icariin

Conditions
ConditionsYield
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
118525-40-9

icaritin

icariin
489-32-7

icariin

Conditions
ConditionsYield
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

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

icariin
489-32-7

icariin

Conditions
ConditionsYield
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
16274-11-6

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

icariin
489-32-7

icariin

Conditions
ConditionsYield
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

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

icariin
489-32-7

icariin

Conditions
ConditionsYield
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
kaempferol
520-18-3

kaempferol

icariin
489-32-7

icariin

Conditions
ConditionsYield
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

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

icariin
489-32-7

icariin

Conditions
ConditionsYield
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

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

icariin
489-32-7

icariin

Conditions
ConditionsYield
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

C39H48O19

icariin
489-32-7

icariin

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 50℃; for 0.333333h; Temperature;6 mg
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
icariin
489-32-7

icariin

icariside II
113558-15-9

icariside II

Conditions
ConditionsYield
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%
icariin
489-32-7

icariin

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; water In methanol for 2h; Reflux;86%
With sulfuric acid; water In 1,4-dioxane for 24h; Reflux;23%
icariin
489-32-7

icariin

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 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
icariin
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

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
ConditionsYield
With pyridine; sulfur trioxide pyridine complex Inert atmosphere;22%
acetic anhydride
108-24-7

acetic anhydride

icariin
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

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

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

icariin
489-32-7

icariin

A

anthraglycoside B
23313-21-5

anthraglycoside B

B

icariside II
113558-15-9

icariside II

Conditions
ConditionsYield
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.
icariin
489-32-7

icariin

C27H30O11

C27H30O11

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

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

Conditions
ConditionsYield
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
icariin
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

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

Conditions
ConditionsYield
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
icariin
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)

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
ConditionsYield
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
icariin
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

(((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
ConditionsYield
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
icariin
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

(((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
ConditionsYield
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
icariin
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

(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
ConditionsYield
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
icariin
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

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
ConditionsYield
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
icariin
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

(((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
ConditionsYield
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
icariin
489-32-7

icariin

C55H69NO22

C55H69NO22

Conditions
ConditionsYield
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
icariin
489-32-7

icariin

C50H59BrO22

C50H59BrO22

Conditions
ConditionsYield
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
malonic acid
141-82-2

malonic acid

icariin
489-32-7

icariin

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

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

Conditions
ConditionsYield
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;

489-32-7Downstream Products

489-32-7Relevant articles and documents

Novel isopentenyl flavonoid compound and preparation method and application thereof

-

Paragraph 0037-0040, (2020/11/10)

The invention discloses a novel isopentenyl flavonoid compound which is prepared by the following steps: (1) taking herba epimedii, crushing or not crushing, extracting with a solvent for 1-3 times, extracting for 0.2-3 hours each time, combining extracting solutions obtained by two times, and concentrating the extracting solutions under reduced pressure to obtain extract, and (2) adding water into the extract to prepare a suspension, carrying out gradient elution separation on the suspension by using macroporous resin, carrying out gradient elution separation by using an ODS column, and finally purifying the isopentenyl flavonoid compound by using an efficient preparative liquid phase. The isopentenyl flavonoid compound can be converted into icariin under the conditions of heating, acid treatment, enzyme treatment, alkali treatment and the like. The method is simple and convenient to operate, and the prepared compound has high purity.

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 (2015/08/18)

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.

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