Icariin

Base Information

• Chemical Name: Icariin
• CAS No.: 489-32-7
• Molecular Formula: C33H40O15
• Molecular Weight: 676.672
• Hs Code.: 29389090
• European Community (EC) Number: 610-440-0
• UNII: VNM47R2QSQ
• DSSTox Substance ID: DTXSID00964133
• Nikkaji Number: J15.942E
• Wikipedia: Icariin
• Wikidata: Q5985057
• Metabolomics Workbench ID: 153110
• ChEMBL ID: CHEMBL553204
• Mol file: 489-32-7.mol

Synonyms:3-((6-deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one;icariin

Chemical Property of Icariin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 231-232 °C
• Refractive Index: 1.679
• Boiling Point: 948.5 °C at 760 mmHg
• PKA: 5.90±0.40(Predicted)
• Flash Point: 300.9 °C
• PSA: 238.20000
• Density: 1.55 g/cm³
• LogP: 0.06790
• Storage Temp.: room temp
• Solubility.: DMSO: soluble50mg/mL, clear, colorless to dark yellow
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 9
• Exact Mass: 676.23672056
• Heavy Atom Count: 48
• Complexity: 1170

Purity/Quality:

98% ^*data from raw suppliers

Icariin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O)O)O
• Recent ClinicalTrials: Icariin to Prevent Corticosteroid-related Memory Changes
• Origin and Sources: Icariin is a prenylated flavonol glycoside isolated from the Epimedium herb. Epimedium is a perennial herb with high medicinal value, and its active ingredient, icariin, is considered the main bioactive component.
• Chemical Structure and Properties: Icariin presents a chemical structure belonging to 8-prenyl flavonoid glycosides and appears as a pale yellow powder. It is soluble in ethyl acetate and ethanol but insoluble in chloroform, ether, and benzene.
• Pharmacological Activities: Icariin exhibits numerous pharmacological activities, including:; 1. Osteoprotective effect: Promotes bone formation and inhibits bone resorption, making it a promising candidate for bone tissue engineering.; 2. Neuroprotective effect: Shows potential in disorders of the nervous system such as Alzheimer's disease, Parkinson's disease, and depression.; 3. Cardiovascular protective effect: Protects cardiomyocytes and vein endothelium from harmful factors, reducing hypertrophy and apoptosis.; 4. Anti-cancer effect: Synergizes with other anti-tumor drugs and radiation therapy, inhibiting tumor growth and inducing apoptosis.; 5. Anti-inflammatory effect: Inhibits the production of pro-inflammatory cytokines and reduces inflammation.; 6. Immunoprotective effect: Regulates immunocytes and cytokines, contributing to immune modulation.; 7. Reproductive function: Enhances reproductive function and anti-aging effects.
• Mechanisms of Action: Icariin mediates its pharmacological effects through various mechanisms, including:; Activation of protein kinase B (Akt), peroxisome proliferator-activated receptor (PPAR), and silent mating type information regulation 2 homolog 1 (SIRT1).; Inhibition of nuclear factor-κB (NF-κB) and the production of pro-inflammatory cytokines.; Inhibition of phosphodiesterase-5 (PDE5) and the hypothalamic-pituitary-adrenal (HPA) axis.
• Therapeutic Potential: Icariin shows potential therapeutic benefits in various disorders, such as cerebral ischemia, Alzheimer's disease, Parkinson's disease, multiple sclerosis, and depression. It's extensive therapeutic capacities make it a promising agent for disease prevention and therapy, particularly in bone tissue engineering, cardiovascular diseases, and cancer treatment.

Technology Process of Icariin

There total 12 articles about Icariin 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: 94.0%

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)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 3h;

DOI:10.3762/bjoc.11.135

Reference yield: 32.8%

UDP-glucose (133-89-1) + icariside II (113558-15-9) → icariin (489-32-7)

Guidance literature:

With 7-O-glucosyltransferase from Epimedium pseudowushanense; In dimethyl sulfoxide; at 30 ℃; for 12h; pH=7.4; Reagent/catalyst; Temperature; pH-value; regiospecific reaction; Kinetics; Catalytic behavior; Green chemistry; Enzymatic reaction;

DOI:10.1039/c9ob01352k

Reference yield:

C39H48O19 → icariin (489-32-7)

Guidance literature:

With hydrogenchloride; In ethanol; water; at 50 ℃; for 0.333333h; Temperature;

upstream raw materials:

icaritin

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

kaempferol

UDP-glucose

Refernces

• 1、 Feng, Keping,Chen, Ridao,Xie, Kebo,Chen, Dawei,Liu, Jimei,Du, Wenyu,Yang, Lin,Dai, Jungui. "Ep7GT, a glycosyltransferase with sugar donor flexibility from: Epimedium pseudowushanense, catalyzes the 7- O -glycosylation of baohuoside". supporting information. p. 8106 - 8114. Retrieved 2019/09/19.