Icaritin

Base Information

• Chemical Name: Icaritin
• CAS No.: 118525-40-9
• Molecular Formula: C21H20O6
• Molecular Weight: 368.386
• Hs Code.: 29329990
• UNII: UFE666UELY
• DSSTox Substance ID: DTXSID00152154
• Nikkaji Number: J769.834H
• Wikidata: Q27291061
• Metabolomics Workbench ID: 153618
• ChEMBL ID: CHEMBL498485
• Mol file: 118525-40-9.mol

Synonyms:icaritin

Chemical Property of Icaritin

Chemical Property:

• Vapor Pressure: 3.82E-14mmHg at 25°C
• Melting Point: 239 °C
• Refractive Index: 1.656
• Boiling Point: 581.992 °C at 760 mmHg
• PKA: 6.44±0.40(Predicted)
• Flash Point: 206.679 °C
• PSA: 100.13000
• Density: 1.36 g/cm³
• LogP: 4.09410
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble5mg/mL, clear (warmed)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 368.12598835
• Heavy Atom Count: 27
• Complexity: 612

Purity/Quality:

98% ^*data from raw suppliers

Icaritin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C(=C(O2)C3=CC=C(C=C3)OC)O)C
• Recent ClinicalTrials: The Phase III Study of Icaritin Versus Sorafenib in PD-L1 Positive Advanced Hepatocellular Carcinoma Subjects
• 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).

Technology Process of Icaritin

There total 44 articles about Icaritin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

icariin (489-32-7) → icaritin (118525-40-9)

Guidance literature:

With water; sodium acetate; cellulase; In ethanol; water; dimethyl sulfoxide; at 37 ℃; pH=5.0;

DOI:10.1021/np800049y

Reference yield: 96.0%

5-hydroxy-3,7-bis(methoxymethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-4H-chromen-4-one → icaritin (118525-40-9)

Guidance literature:

With hydrogenchloride; In methanol; for 2h; Reflux; Inert atmosphere;

DOI:10.2174/157017861109140903103927

Reference yield: 95.0%

5,7-dimethoxymethyl icaritin → icaritin (118525-40-9)

Guidance literature:

With hydrogenchloride; In methanol; water; at 65 ℃; for 1h; Inert atmosphere;

upstream raw materials:

sagittatoside A

icariin

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

4-methoxybenzoic acid

Downstream raw materials:

8-prenylkaempferol

3,7-dimethanesulfonyl-8-prenyl-4'-methoxychrysin

icariin

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

Refernces

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

10.3762/bjoc.11.135

The study presents an efficient semi-synthetic approach to produce the bioactive flavonoid glycoside icariin from kaempferol through an eleven-step process with a 7% overall yield. The key steps involve the selective methylation of kaempferol's 4′-OH group, a para-Claisen–Cope rearrangement catalyzed by Eu(fod)3 in the presence of NaHCO3 to achieve 8-prenylation, and the glycosylation of icaritin. The researchers optimized the selective methylation and rearrangement processes to improve yields and selectivity, ultimately synthesizing icariin and its related compound icariside I with 7% and 16% overall yields, respectively. The synthesized compounds were fully characterized using various spectroscopic techniques, confirming their structures and bioactivity.