Icaritin
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Icaritin ??
- ???
- 239℃
- ?? ?
- 582.0±50.0 °C(Predicted)
- ??
- 1.359
- ???
- 206.7℃
- ?? ??
- 2-8°C
- ???
- DMSO: ???5mg/mL, ??(??)
- ??? ??
- ??
- ?? ?? (pKa)
- 6.44±0.40(Predicted)
- ??
- ?? ????? ?? ?????
- ?? ??(λmax)
- 368nm(MeOH)(lit.)
- 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
- InChIKey
- TUUXBSASAQJECY-UHFFFAOYSA-N
- SMILES
- C1(C2=CC=C(OC)C=C2)OC2=C(C/C=C(/C)\C)C(O)=CC(O)=C2C(=O)C=1O
??
| WGK ?? | 3 | ||
|---|---|---|---|
| RTECS ?? | DJ3100870 | ||
| HS ?? | 29329990 | ||
| ???? ??? | 11 - Combustible Solids |
Icaritin C??? ??, ??, ??
??? ??
Yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from epimedium.??
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).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.Icaritin ?? ?? ? ???
???
?? ??
Icaritin ?? ??
???( 288)?? ??
| ??? | ?? | ??? | ?? | ?? ? | ?? |
|---|---|---|---|---|---|
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| Shanghai Zheyan Biotech Co., Ltd. | 18017610038 |
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Icaritin ?? ??:
??? ??? ?????? ????? ????
Baohuoside V
(+/-)-Naringenin
Quercetin
Epimedium Extract
Icariin
epimedoside A
4H-1-Benzopyran-4-one, 3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-8-(3-hydroxy-3-methylbutyl)-2-(4-methoxyphenyl)-
Genipin
Icariside I
13,14-Didehydromatridin-15-one
Catalpol
Cabazitaxel
Anhydroicaritin