Oroxin A

Base Information

• Chemical Name: Oroxin A
• CAS No.: 57396-78-8
• Molecular Formula: C21H20O10
• Molecular Weight: 432.384
• DSSTox Substance ID: DTXSID70904521
• Nikkaji Number: J146.446I
• Wikidata: Q72497982
• Metabolomics Workbench ID: 141468
• ChEMBL ID: CHEMBL516858
• Mol file: 57396-78-8.mol

Synonyms:oroxin A

Chemical Property of Oroxin A

Chemical Property:

• Boiling Point: 784.0±60.0 °C(Predicted)
• PKA: 5.92±0.40(Predicted)
• Density: 1.642±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 432.10564683
• Heavy Atom Count: 31
• Complexity: 677

Purity/Quality:

OroxinA 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O

Technology Process of Oroxin A

There total 8 articles about Oroxin A 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%

Baicalin methyl ester (82475-03-4) → Oroxin A (57396-78-8,31567-75-6)

Guidance literature:

With sodium tetrahydroborate; at 25 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.03.085

Reference yield: 32.0%

methanol (67-56-1) + Baicalin methyl ester (82475-03-4) → 5,6-dihydroxy-7-methoxyflavone (29550-13-8) + Oroxin A (57396-78-8,31567-75-6)

Guidance literature:

With sodium tetrahydroborate; at 25 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.03.085

Reference yield:

4-oxo-2-phenyl-4H-1-benzopyran-5,6,7-triyl triacetate (67047-05-6) → Oroxin A (57396-78-8,31567-75-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / K₂CO₃, KI / acetone / 4 h / Heating

2: 60 percent / H₂ / Pd/C / acetone

3: 81 percent

4: 5percent aq. KOH / acetone / 0.25 h / Heating

With potassium hydroxide; hydrogen; potassium carbonate; potassium iodide; palladium on activated charcoal; In acetone;

upstream raw materials:

5,6-Diacetoxy-7-hydroxyflavon-7-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosid)

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

4-oxo-2-phenyl-4H-1-benzopyran-5,6,7-triyl triacetate

5,6-diacetoxy-7-hydroxyflavone

Downstream raw materials:

5,6-dihydroxy-7-methoxyflavone

5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one

Refernces

• 1、 Chen, Haijun,He, Guihua,Li, Cailong,Dong, Longrong,Xie, Xiaobo,Wu, Jianlei,Gao, Yu,Zhou, Jia. "Development of a concise synthetic approach to access oroxin A". . p. 45151 - 45154. Retrieved 2015/01/08.