Sulochrin

Base Information

• Chemical Name: Sulochrin
• CAS No.: 519-57-3
• Molecular Formula: C17H16O7
• Molecular Weight: 332.31
• Hs Code.: 2918990090
• UNII: 8NA53C271Z
• DSSTox Substance ID: DTXSID80199860
• Nikkaji Number: J11.583E
• Wikidata: Q27098405
• Metabolomics Workbench ID: 50401
• ChEMBL ID: CHEMBL61133
• Mol file: 519-57-3.mol

Synonyms:methyl 2-(2,6-dihydroxy-4-methylbenzoyl)-5-hydroxy-3-methoxybenzoate;sulochrin

Chemical Property of Sulochrin

Chemical Property:

• Vapor Pressure: 6.96E-14mmHg at 25°C
• Melting Point: 242-248 °C (decomp)
• Boiling Point: 576.3°Cat760mmHg
• PKA: 6.55±0.25(Predicted)
• Flash Point: 212.6°C
• PSA: 113.29000
• Density: 1.378g/cm³
• LogP: 2.13800
• Storage Temp.: 2-8°C
• Solubility.: DMF: soluble
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 332.08960285
• Heavy Atom Count: 24
• Complexity: 454

Purity/Quality:

98%min ^*data from raw suppliers

Sulochrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=C(C(=C1)O)C(=O)C2=C(C=C(C=C2OC)O)C(=O)OC)O
• Uses: Sulochrin is a fungal metabolite isolated from a number of Aspergillus and Penicillium sp.. An anti-angiogenic agent, sulochrin inhibits VEGF leading to inhibition of capillary-like tube formation of human umbilical vein endothelial cells. Sulochrin also inhibits eosinophil activation and chemotaxis. Sulochrin is an inhibitor of the degranulation, activation and chemotaxis of eosinophils.

Technology Process of Sulochrin

There total 13 articles about Sulochrin 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: 81.0%

5-benzyloxy-2-(2,6-bis-benzyloxy-4-methyl-benzoyl)-3-methoxy-benzoic acid methyl ester (178749-82-1) → sulochrin (519-57-3)

Guidance literature:

With palladium dihydroxide; cyclohexene; In ethanol; Heating;

DOI:10.1016/S0960-894X(99)00305-4

Reference yield:

1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → sulochrin (519-57-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 33 percent / K₂CO₃ / acetonitrile / Heating

2: 96 percent / K₂CO₃ / acetonitrile / Heating

3: 96 percent / LiAlH₄ / tetrahydrofuran

4: 43 percent / NBS / CCl₄

5: 82 percent / DEAD, PPh₃ / tetrahydrofuran

6: 45 percent / n-BuLi / tetrahydrofuran / -78 °C

7: 54 percent / PDC / dimethylformamide

8: 81 percent / Bu₄(NH₄), KMnO₄, pyridine / dimethylformamide

9: K₂CO₃ / dimethylformamide

10: 81 percent / Pd(OH)2/C, cyclohexene / ethanol / Heating

With pyridine; palladium dihydroxide; potassium permanganate; N-Bromosuccinimide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; Bu₄(NH₄); potassium carbonate; triphenylphosphine; cyclohexene; diethylazodicarboxylate; In tetrahydrofuran; tetrachloromethane; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(99)00305-4

Reference yield:

(3-(benzyloxy)-5-methoxyphenyl)methanol (50637-28-0) → sulochrin (519-57-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 43 percent / NBS / CCl₄

2: 82 percent / DEAD, PPh₃ / tetrahydrofuran

3: 45 percent / n-BuLi / tetrahydrofuran / -78 °C

4: 54 percent / PDC / dimethylformamide

5: 81 percent / Bu₄(NH₄), KMnO₄, pyridine / dimethylformamide

6: K₂CO₃ / dimethylformamide

7: 81 percent / Pd(OH)2/C, cyclohexene / ethanol / Heating

With pyridine; palladium dihydroxide; potassium permanganate; N-Bromosuccinimide; dipyridinium dichromate; n-butyllithium; Bu₄(NH₄); potassium carbonate; triphenylphosphine; cyclohexene; diethylazodicarboxylate; In tetrahydrofuran; tetrachloromethane; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(99)00305-4

upstream raw materials:

5-benzyloxy-2-(2,6-bis-benzyloxy-4-methyl-benzoyl)-3-methoxy-benzoic acid methyl ester

1-carbomethoxy-3,5-dihydroxybenzene

(3-(benzyloxy)-5-methoxyphenyl)methanol

methyl 2,6-dihydroxy-4-methylbenzoate

Downstream raw materials:

methyl 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate

2,6-dihydroxy-4-methyl-benzoic acid

3-hydroxy-5-methoxy-benzoic acid methyl ester

sulochrin triacetate

Refernces