(-)-MAACKIAIN

Base Information

• Chemical Name: (-)-MAACKIAIN
• CAS No.: 19908-48-6
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.268
• Mol file: 19908-48-6.mol

Synonyms:6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol,6a,12a-dihydro-, (?à)- (8CI);6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol,6a,12a-dihydro-, cis-(?à)-;(?à)-Maackiain;6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a,12a-dihydro-, cis-;dl-Maackiain;

Chemical Property of (-)-MAACKIAIN

Chemical Property:

• Vapor Pressure: 3.23E-08mmHg at 25°C
• Melting Point: 199-200 °C
• Refractive Index: 1.677
• Boiling Point: 436.2 °C at 760 mmHg
• PKA: 9.45±0.20(Predicted)
• Flash Point: 217.6 °C
• PSA: 57.15000
• Density: 1.48 g/cm³
• LogP: 2.73060
• Storage Temp.: 2-8°C

Purity/Quality:

≥98% ^*data from raw suppliers

Maackiain ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (±)-Maackiain can be used to improve collage synthesis of skin fibroblast to improve skin regeneration effects. It can also be used to inhibit expression of allergy-sensitive genes and fungicidal activity.

Technology Process of (-)-MAACKIAIN

There total 11 articles about (-)-MAACKIAIN 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: 92.0%

(+/-)-3-benzyloxy-8,9-methylenedioxyprerocarpan (76240-26-1) → (+/-)-3-hydroxy-8,9-methylenedioxyprerocarpan (2035-15-6,19908-48-6,23513-53-3,76496-57-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; acetone;

DOI:10.1016/S0040-4020(99)00490-1

Reference yield:

7-benzyloxy-2H-1-benzopyran (76240-25-0) → (+/-)-3-hydroxy-8,9-methylenedioxyprerocarpan (2035-15-6,19908-48-6,23513-53-3,76496-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / PdCl₂; LiCl / acetone / 2.5 h

2: 92 percent / H₂ / Pd/C / acetone; tetrahydrofuran

With hydrogen; lithium chloride; palladium dichloride; palladium on activated charcoal; In tetrahydrofuran; acetone; 1: Cyclization / 2: Hydrogenolysis;

DOI:10.1016/S0040-4020(99)00490-1

Reference yield:

2-(chloromercurio)-4,5-(methylenedioxy)phenol (61080-20-4) → (+/-)-3-hydroxy-8,9-methylenedioxyprerocarpan (2035-15-6,19908-48-6,23513-53-3,76496-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / PdCl₂; LiCl / acetone / 2.5 h

2: 92 percent / H₂ / Pd/C / acetone; tetrahydrofuran

With hydrogen; lithium chloride; palladium dichloride; palladium on activated charcoal; In tetrahydrofuran; acetone; 1: Cyclization / 2: Hydrogenolysis;

DOI:10.1016/S0040-4020(99)00490-1

upstream raw materials:

(+/-)-3-benzyloxy-8,9-methylenedioxyprerocarpan

2-(chloromercurio)-4,5-(methylenedioxy)phenol

7-benzyloxy-2H-1-benzopyran

1-(benzyloxy)-3-(prop-2-yn-1-yloxy)benzene

Downstream raw materials:

(+)-3[1-S-N(1-methyl)benzyl-carbamoyl]-6aS,11aS-maackiain

(-)-3[1-S-N(1-methyl)benzylcarbamoyl]-6aR,11aR-maackiain

rac-cabenegrin A-I