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
• General Description: Oroxylin A is a naturally occurring flavonoid with a structure characterized by 5,7-dihydroxy-6-methoxy substitutions on its flavone backbone. It exhibits biological activity as an α-glucosidase inhibitor, and structural modifications, such as 8-aminomethylation, have been shown to enhance its inhibitory potency, suggesting potential therapeutic applications in metabolic disorders like type-II diabetes, as well as in cancer and viral infections.

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:

mosloflavone

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

oroxylin A 7-acetyl ester

Refernces

Synthesis and biological evaluation of novel 8-aminomethylated oroxylin A analogues as α-glucosidase inhibitors

10.1016/j.bmcl.2008.01.055

The research focuses on the synthesis and biological evaluation of novel 8-aminomethylated oroxylin A analogues as α-glucosidase inhibitors. The study was conducted by a team of researchers from the Indian Institute of Chemical Technology. They prepared a series of 8-aminomethylated derivatives (1a–1j) of oroxylin A through a Mannich reaction with various primary or secondary amines and para-formaldehyde. The synthesized compounds were tested for their α-glucosidase inhibition activity against both yeast and rat intestinal α-glucosidase. The results showed that some of these derivatives exhibited significantly better α-glucosidase inhibitory activity compared to the parent compound oroxylin A. The research highlights the potential of these novel analogues in treating diseases such as type-II diabetes mellitus, cancer, and viral infections. Key chemicals involved in the research include oroxylin A, primary and secondary amines (such as morpholinyl, N-methyl piperzinyl, benzylamino, etc.), para-formaldehyde, and 2-propanol. The study also references other related compounds like baicalein and chrysin, which were identified in previous research as having biological activities.