Oroxylin A

Base Information

• Chemical Name: Oroxylin A
• CAS No.: 480-11-5
• Molecular Formula: C16H12O5
• Molecular Weight: 284.268
• European Community (EC) Number: 663-302-7
• UNII: 53K24Z586G
• DSSTox Substance ID: DTXSID70197375
• Nikkaji Number: J12.179G
• Wikipedia: Oroxylin_A
• Wikidata: Q3356627
• Metabolomics Workbench ID: 24179
• ChEMBL ID: CHEMBL183513
• Mol file: 480-11-5.mol

Synonyms:5,7-dihydroxy-6-methoxy-2-phenylchromen-4-one;oroxylin;oroxylin A

Chemical Property of Oroxylin A

Chemical Property:

• Vapor Pressure: 2.6E-12mmHg at 25°C
• Melting Point: 195-197oC
• Refractive Index: 1.6200 (estimate)
• Boiling Point: 540.9°Cat760mmHg
• PKA: 6.48±0.40(Predicted)
• Flash Point: 207.4°C
• PSA: 79.90000
• Density: 1.42g/cm³
• LogP: 2.87980
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 284.06847348
• Heavy Atom Count: 21
• Complexity: 426

Purity/Quality:

95%-98% ^*data from raw suppliers

Oroxylin?A 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC=CC=C3)O

Technology Process of Oroxylin A

There total 30 articles about Oroxylin 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: 88.0%

5,6,7-trimethoxyflavone (973-67-1) → oroxylin A (480-11-5)

Guidance literature:

With hydrogen bromide; acetic acid; for 2h; Heating;

DOI:10.1248/cpb.51.339

Reference yield: 73.0%

5-hydroxy-6-methoxyflavone-7-O-β-D-glucuronide methyl ester (82475-02-3) → oroxylin A (480-11-5)

Guidance literature:

With sulfuric acid; In water; at 100 ℃; for 3h;

DOI:10.1080/14786419.2019.1650359

Reference yield: 60.0%

5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one (491-67-8) + methyl iodide (74-88-4) → oroxylin A (480-11-5) + mosloflavone (740-33-0)

Guidance literature:

With potassium carbonate; In acetone; for 2h; Heating;

DOI:10.1271/bbb.68.369

upstream raw materials:

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

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

oroxyloside

5,6,7-trimethoxyflavone

Downstream raw materials:

C₂₅H₂₂O₇

oroxylin A 7-O-glucuronide

oroxylin A 7-acetyl ester

C₁₈H₁₅BrO₅

Refernces

• 1、 Siddikov,Yuldashev,Abdullaev. "Flavonoids from Scutellaria phyllostachya roots". . p. 324 - 325. Retrieved 2007.
• 2、 Grano, Ruel Valerio Robles De,Nisar, Madiha,Sung, Herman H.-Y.,Vashchenko, Elena V.,Vashchenko, Valerii V.,Williams, Ian D.. "Crystal structures of the flavonoid Oroxylin A and the regioisomers Negletein and Wogonin". . p. 490 - 499. Retrieved 2020/05/18.
• 3、 -. "Process for Preparing Oroxylin A". Paragraph 0033-0038. . Retrieved 2019/03/08.