Icariins

Superiority:

Icaritin Basic information
Product Name:    Icaritin
Synonyms:    ICARITIN;3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one;3,7-bis(2-hydroxyethyl)icaritin;Icaritin, >98%;3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one;Icaritin(Anhydroicaritin);Icaritin>;4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-
CAS:    118525-40-9
MF:    C21H20O6
MW:    368.38
EINECS:    
Product Categories:    plant extract;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
Mol File:    118525-40-9.mol
Icaritin Structure
Icaritin Chemical Properties
Melting point     239℃
Boiling point     582.0±50.0 °C(Predicted)
density     1.359
Fp     206.7℃
storage temp.     2-8°C
solubility     DMSO: soluble5mg/mL, clear (warmed)
form     powder
pka    6.44±0.40(Predicted)
color     light yellow to dark yellow
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
Safety Information
WGK Germany     3
RTECS     DJ3100870
HS Code     29329990
MSDS Information
Icaritin Usage And Synthesis
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.
Icaritin Preparation Products And Raw materials
Raw materials    Icaritin-->Icariin-->Icariside I-->baohuoside I-->KAEMPFEROLTETRAACETATE-->Dimethyl sulfate
Preparation Products    Desmethylanhydroicaritin