Methylophiopogonanone A

Base Information

• Chemical Name: Methylophiopogonanone A
• CAS No.: 74805-92-8
• Molecular Formula: C₁₉H₁₈O₆
• Molecular Weight: 342.348
• DSSTox Substance ID: DTXSID60703469
• Mol file: 74805-92-8.mol

Synonyms:methylophiopogonanone A

Chemical Property of Methylophiopogonanone A

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 580.117ºC at 760 mmHg
• PKA: 8.24±0.40(Predicted)
• Flash Point: 212.909ºC
• PSA: 85.22000
• Density: 1.411g/cm3
• LogP: 2.87730
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 342.11033829
• Heavy Atom Count: 25
• Complexity: 510

Purity/Quality:

99% ^*data from raw suppliers

Methylophiopogonanone A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=C2C(=C1O)C(=O)C(CO2)CC3=CC4=C(C=C3)OCO4)C)O
• Isomeric SMILES: CC1=C(C(=C2C(=C1O)C(=O)[C@@H](CO2)CC3=CC4=C(C=C3)OCO4)C)O
• Description: Methylophiopogonanone A is a homoisoflavonoid that has been found in O. japonicus roots and has diverse biological activities. It increases the uptake of rosuvastatin (Item Nos. 12029 | 18813) and atorvastatin in HEK293T cells expressing human organic anion transporting polypeptide 1B1 (OATP1B1; EC50s = 11.33 and 6 μM, respectively). Methylophiopogonanone A scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) and ABTS radicals in cell-free assays. In vivo, methylophiopogonanone A (10 mg/kg) decreases body weight gain and reduces serum and hepatic lipid levels in a rat model of high-fat diet-induced hyperlipidemia. It also reduces infarct size and myocardial apoptosis in mouse model of ischemia-reperfusion injury induced by transient occlusion of the left anterior descending coronary artery.

Technology Process of Methylophiopogonanone A

There total 6 articles about Methylophiopogonanone 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: 60.0%

dehydromethylophiopogonanone A → methylophiopogonanone A (74805-92-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In acetone; at 20 ℃; Inert atmosphere;

DOI:10.3987/COM-20-14231

Reference yield:

methylophiopogonone A (74805-90-6) → methylophiopogonanone A (74805-92-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

Reference yield:

1,3,5-trimethoxy-2,4-dimethyl benzene (1521-61-5) → methylophiopogonanone A (74805-92-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: boron trifluoride diethyl etherate / 1.5 h / 0 - 90 °C / Inert atmosphere

2.1: sodium hydride / mineral oil / 2.83 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C

3.1: aluminum (III) chloride / benzene / 3 h / 90 °C / Inert atmosphere

3.2: 2 h / 0 °C

4.1: palladium 10% on activated carbon; hydrogen / methanol; acetone / 20 °C / Inert atmosphere

5.1: hydrogenchloride / ethanol / 1 h / 90 °C

6.1: palladium 10% on activated carbon; hydrogen / acetone / 20 °C / Inert atmosphere

With hydrogenchloride; aluminum (III) chloride; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; sodium hydride; In methanol; ethanol; acetone; mineral oil; benzene;

DOI:10.3987/COM-20-14231

upstream raw materials:

methylophiopogonone A

1,3,5-trimethoxy-2,4-dimethyl benzene

1-(2-hydroxy-4,6-dimethoxy-3,5-dimethylphenyl)ethanone

leptorumol

Refernces

• 1、 Tada, Akihiro,Kasai, Ryoji,Saitoh, Tamotsu,Shoji, Junzo. "Studies on the Constituents of Ophiopogonis Tuber. V. Isolation of a Novel Class of Homoisoflavonoids and Determination of Their Structures (1)". . p. 1477 - 1484. Retrieved 2007/10/02.