5,7-Dihydroxychromone

Base Information

• Chemical Name: 5,7-Dihydroxychromone
• CAS No.: 31721-94-5
• Molecular Formula: C9H6 O4
• Molecular Weight: 178.144
• Hs Code.: 2914400090
• ChEMBL ID: CHEMBL3604316
• DSSTox Substance ID: DTXSID30185617
• Metabolomics Workbench ID: 45806
• Nikkaji Number: J88.738B
• Wikidata: Q27105540
• Mol file: 31721-94-5.mol

Synonyms:5,7-dihydroxychromone

Chemical Property of 5,7-Dihydroxychromone

Chemical Property:

• Vapor Pressure: 5.94E-07mmHg at 25°C
• Melting Point: 232-273℃
• Boiling Point: 399.4oC at 760 mmHg
• PKA: 6.57±0.20(Predicted)
• Flash Point: 170.8oC
• PSA: 70.67000
• Density: 1.563g/cm3
• LogP: 1.20420
• Storage Temp.: 2-8°C
• Solubility.: insoluble in H2O; ≥5.41 mg/mL in EtOH with gentle warming; ≥7.05 mg/mL in DMSO
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 178.02660867
• Heavy Atom Count: 13
• Complexity: 248

Purity/Quality:

≥98% ^*data from raw suppliers

5,7-Dihydroxychromone phyproof? Reference Substance ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=COC2=CC(=CC(=C2C1=O)O)O
• Description: 5,7-Dihydroxychromone is a flavone decomposition product that has been found in A. hypogaea and has diverse biological activities, including antimicrobial, antioxidant, and neuroprotective properties. It reduces radial growth of the soil pathogenic fungi R. solani and S. rolfsii (IC50s = 18 and 26 μM, respectively) but has no effect on soil pathogenic bacteria of the genus Bradyrhizobium. 5,7-Dihydroxychromone (0.4, 2, and 10 μM) reduces increases in apoptosis and the levels of reactive oxygen species (ROS) induced by 6-OHDA in SH-SY5Y neuroblastoma cells. It also increases the levels of HO-1, NQO1, and GCLc in SH-SY5Y cells when used at concentrations ranging from 0.08 to 10 μM.

Technology Process of 5,7-Dihydroxychromone

There total 13 articles about 5,7-Dihydroxychromone 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: 90.3%

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) + methanesulfonyl chloride (124-63-0) → 5,7-dihydroxy-chromen-4-one (31721-94-5)

Guidance literature:

With boron trifluoride diethyl etherate; In N,N-dimethyl-formamide; at 20 - 90 ℃; for 3.83h;

Reference yield: 90.3%

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5,7-dihydroxy-chromen-4-one (31721-94-5)

Guidance literature:

With boron trifluoride diethyl etherate; methanesulfonyl chloride; at 20 - 90 ℃; for 3.83333h;

DOI:10.1016/j.tetlet.2010.03.092

Reference yield: 80.0%

7-hydroxy-4H-chromen-4-one (59887-89-7) → 5,7-dihydroxy-chromen-4-one (31721-94-5)

Guidance literature:

With Ru(CF₃CO₂)2(p-cymene)(H₂O); bis-[(trifluoroacetoxy)iodo]benzene; In trifluoroacetic acid; trifluoroacetic anhydride; at 80 ℃; for 16h;

DOI:10.1021/acs.orglett.5b01138

upstream raw materials:

2,4,6-trihydroxyacetophenone

formyl acetic anhydride

5,7-dihydroxy-4-oxo-4H-chromene-2-carboxylic acid

oxalic acid 2-ethoxycarbonyl-7-ethoxyoxalyloxy-4-oxo-4H-chromen-5-yl ester ethyl ester

Downstream raw materials:

orobol

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

hirtellanine B

methyl 2-((2-(3,4-difluorophenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl)oxy)acetate