beta-Anhydroicaritin

Base Information

• Chemical Name: beta-Anhydroicaritin
• CAS No.: 38226-86-7
• Molecular Formula: C21H20 O6
• Molecular Weight: 368.386
• ChEMBL ID: CHEMBL497654
• DSSTox Substance ID: DTXSID801316333
• Metabolomics Workbench ID: 139245
• Nikkaji Number: J533.196J
• Wikidata: Q105212814
• Mol file: 38226-86-7.mol

Synonyms:38226-86-7;beta-Anhydroicaritin;CHEMBL497654;3,5-dihydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-4-one;SCHEMBL4220888;DTXSID801316333;HY-N1940;BDBM50272557;AKOS030573400;AC-34806;AS-75851;CS-0018251;E80752;3,7-dimethanesulfonyl-8-prenyl-4''-methoxy Chrysin;3,5-dihydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-9,10-dihydro-4h,8h-pyrano[2,3-f]chromen-4-one

Chemical Property of beta-Anhydroicaritin

Chemical Property:

• Vapor Pressure: 3.82E-14mmHg at 25°C
• Melting Point: 222-223 °C
• Boiling Point: 575.3±50.0 °C(Predicted)
• PKA: 6.56±0.60(Predicted)
• PSA: 89.13000
• Density: 1.349
• LogP: 3.98340
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 368.12598835
• Heavy Atom Count: 27
• Complexity: 618

Purity/Quality:

98%,99%, ^*data from raw suppliers

Anhydroicaritin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2=C(O1)C=C(C3=C2OC(=C(C3=O)O)C4=CC=C(C=C4)OC)O)C
• Uses: β-Anhydroicaritin is an Icartin (I163680) derivative displaying anti-inflammatory activity and inhibition of human phosphodiesterase-5.

Technology Process of beta-Anhydroicaritin

There total 18 articles about beta-Anhydroicaritin 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: 93.3%

formic acid (64-18-6) + icaritin (118525-40-9) → 3,5-dihydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-4-one (38226-86-7)

Guidance literature:

for 20h; Reflux;

DOI:10.1080/14786419.2020.1844686

Reference yield: 93.3%

formic acid (64-18-6) + 3,4'-di-O-methyl-8-(3-methyl-2-butenyl)kaempferol (55929-05-0) → 3,5-dihydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-4-one (38226-86-7)

Guidance literature:

for 20h; Reflux;

Reference yield: 87.0%

3,5-diacetoxy-2-(4-acetoxy-phenyl)-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-4-one (28610-35-7) + dimethyl sulfate (77-78-1) → 3,5-dihydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-4-one (38226-86-7)

Guidance literature:

3,5-diacetoxy-2-(4-acetoxy-phenyl)-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-4-one; dimethyl sulfate; With potassium carbonate; In acetone; at 60 ℃; for 2h;

In methanol; acetone; for 10h; Reflux;

upstream raw materials:

C₃₉H₅₀O₂₀

3,5-diacetoxy-2-(4-acetoxy-phenyl)-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-4-one

dimethyl sulfate

2-hydroxy-4,6-dimethoxyacetophenone

Downstream raw materials:

3,5,4'-trimethoxy-6'',6''-dimethyldihydropyrano<2'',3'':7,8>flavone

5-hydroxy-3-sulfamide-4'-methoxy-6'',6''-dimethyl-4'',5''-dihydropyrano[2'',3'':7,8]-flavone

3,5-dihydroxy-4'-methoxy-3'-sulfonic acid-6'',6''-dimethyl-4'',5''-dihydropyrano[2'',3'':7,8]-flavone

5-hydroxy-3-methanesulfonyl-4'-methoxy-6'',6''-dimethyl-4'',5''-dihydropyrano[2'',3'':7,8]-flavone

Refernces

• 1、 -. "5-substituted icaritin derivative and anti-tumor application thereof". Paragraph 0016-0018. . Retrieved 2020/11/26.
• 2、 -. "Flavone derivative and preparation method and medical application of flavone derivative". . . Retrieved 2019/09/05.