Graphislactone A

Base Information

• Chemical Name: Graphislactone A
• CAS No.: 52179-44-9
• Molecular Formula: C16H14O6
• Molecular Weight: 302.28
• Mol file: 52179-44-9.mol

Synonyms:

Chemical Property of Graphislactone A

Chemical Property:

• PSA: 89.13000
• LogP: 2.68300

Purity/Quality:

99% ^*data from raw suppliers

Graphislactone A ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Graphislactone A is the major analogue of a family of phenolic benzopyranones isolated from a mycobiont of lichens of the genus Graphis, first reported by Japanese researchers at Kobe Pharmaceutical University in 1997. Graphislactone A protects against oxidative injury by dose-dependent free radical scavenging and antioxidant activity.

Technology Process of Graphislactone A

There total 13 articles about Graphislactone 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: 89.0%

4,7-bis-benzyloxy-3,9-dimethoxy-1-methyl-benzo[c]chromen-6-one (852810-91-4) → graphislactone A (52179-44-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/j.tetlet.2005.03.046

Reference yield: 39.0%

7-methoxy-5-(7-methoxy-5-methyl-benzo[1,3]dioxol-5-yl)-2,2-dimethyl-4H-benzo[1,3]dioxin-4-one (1170034-86-2) → graphislactone A (52179-44-9)

Guidance literature:

With boron trichloride; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/ejoc.200801278

Reference yield:

2-benzyloxy-3-methoxy-5-methyl-phenol (852810-83-4) → graphislactone A (52179-44-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / EDC; DMAP / CH₂Cl₂

2: 88 percent / nBu₃P; K₂CO₃; DMA / Pd(OAc)2

3: 89 percent / H₂ / Pd/C / ethyl acetate

With dmap; tributylphosphine; hydrogen; 2,4-dichlorophenoxyacetic acid dimethylamine; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium diacetate; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1016/j.tetlet.2005.03.046

upstream raw materials:

4,7-bis-benzyloxy-3,9-dimethoxy-1-methyl-benzo[c]chromen-6-one

2-benzyloxy-3-methoxy-5-methyl-phenol

2-benzyloxy-6-iodo-4-methoxy-benzaldehyde

2-benzyloxy-5-hydroxymethyl-3-methoxy-phenol

Refernces

• 1、 Abe, Hitoshi,Nishioka, Keisuke,Takeda, Shigemitsu,Arai, Masatsugu,Takeuchi, Yasuo,Harayama, Takashi. "Synthesis of graphislactones A-D through a palladium-mediated biaryl coupling reaction of phenyl benzoate derivatives". . p. 3197 - 3200. Retrieved 2007/10/03.