Icariside I

Base Information

• Chemical Name: Icariside I
• CAS No.: 56725-99-6
• Molecular Formula: C27H30O11
• Molecular Weight: 530.529
• DSSTox Substance ID: DTXSID30205283
• Nikkaji Number: J656.587E
• Wikidata: Q72482213
• Metabolomics Workbench ID: 142725
• ChEMBL ID: CHEMBL558499
• Mol file: 56725-99-6.mol

Synonyms:icariside I

Chemical Property of Icariside I

Chemical Property:

• Vapor Pressure: 4.24E-27mmHg at 25°C
• Melting Point: 252-253℃
• Refractive Index: 1.664
• Boiling Point: 801.329 °C at 760 mmHg
• PKA: 6.04±0.40(Predicted)
• Flash Point: 267.751 °C
• PSA: 179.28000
• Density: 1.475 g/cm³
• LogP: 1.56720
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 530.17881177
• Heavy Atom Count: 38
• Complexity: 892

Purity/Quality:

99%, ^*data from raw suppliers

IcarisideI(NewProduct) 98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)OC)O)OC4C(C(C(C(O4)CO)O)O)O)C
• Isomeric SMILES: CC(=CCC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)OC)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C

Technology Process of Icariside I

There total 16 articles about Icariside I 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: 80.0%

icariin → 3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one (56725-99-6)

Guidance literature:

With sulfuric acid; In ethanol; water; at 50 ℃; for 5h; pH=5; Enzymatic reaction;

Reference yield: 60.0%

icariin (489-32-7) → 3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin (56725-99-6)

Guidance literature:

With sulfuric acid; In ethanol; water; at 50 ℃; for 24h;

DOI:10.1371/journal.pone.0222803

Reference yield:

epimedium koreanum Nakai, leaves; 1-butanol-ether-hexane-methanol extract of → icaritin (118525-40-9) + icariside II (113558-15-9) + 3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin (56725-99-6)

Guidance literature:

With hydrogenchloride; methanol; water; at 80 ℃; for 8h; Product distribution / selectivity; Heating / reflux;

upstream raw materials:

icaritin

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

kaempferol

icariin

Downstream raw materials:

icaritin

2,3,4,5,6-pentahydroxy-hexanal

Refernces

• 1、 Chau, Yasmin,Li, Fu-Shuang,Levsh, Olesya,Weng, Jing-Ke. "Exploration of icariin analog structure space reveals key features driving potent inhibition of human phosphodiesterase-5". . . Retrieved 2019/09/30.
• 2、 -. "Herba Epimedii glycoside compound and use thereof". Paragraph 0195; 0196; 0197; 0198; 0199. . Retrieved 2017/08/24.