31721-94-5

Basic information

• Product Name: 5,7-dihydroxychromone
• Synonyms: 5,7-Dihydroxy-4H-chroMen-4-one;4H-1-Benzopyran-4-one, 5,7-dihydroxy-;5,7-Dihydroxy-4H-1-benzopyran-4-one;5,7-Dihydroxy-γ-chromene-4-one;5,7-Dihydroxy-4-chromone;5,7-Dihydroxychromen-4-one;7-Dihydroxychromone
• CAS NO: 31721-94-5
• Molecular Formula: C₉H₆O₄
• Molecular Weight: 178.14
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 31721-94-5.mol

Chemical Properties

• Melting Point: 232-273℃
• Boiling Point: 399℃
• Flash Point: 171℃
• Appearance: /
• Density: 1.563
• Vapor Pressure: 5.94E-07mmHg at 25°C
• Refractive Index: 1.689
• Storage Temp.: 2-8°C
• Solubility: insoluble in H2O; ≥5.41 mg/mL in EtOH with gentle warming; ≥7.05 mg/mL in DMSO
• PKA: 6.57±0.20(Predicted)
• CAS DataBase Reference: 5,7-dihydroxychromone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-dihydroxychromone(31721-94-5)
• EPA Substance Registry System: 5,7-dihydroxychromone(31721-94-5)

Safety Data

• Hazardous Substances Data: 31721-94-5(Hazardous Substances Data)

Usage

Uses

Used in Antimicrobial Applications:
5,7-Dihydroxychromone is used as an antimicrobial agent for its ability to reduce the radial growth of soil pathogenic fungi R. solani and S. rolfsii, with IC50s of 18 and 26 μM, respectively.
Used in Antioxidant Applications:
5,7-Dihydroxychromone is used as an antioxidant agent for its ability to reduce increases in apoptosis and the levels of reactive oxygen species (ROS) induced by 6-OHDA in SH-SY5Y neuroblastoma cells.
Used in Neuroprotective Applications:
5,7-Dihydroxychromone is used as a neuroprotective agent for its ability to increase the levels of HO-1, NQO1, and GCLc in SH-SY5Y cells when used at concentrations ranging from 0.08 to 10 μM.

in vitro

5,7-dihydroxychromone (dhc) (0.4–10 μm) was found to protect against neuronal cell death and the ros generation in a dose-dependent manner in 6-ohda-induced sh-sy5y cells. dhc (0.08–10 μm) also dose-dependently increased the induction of nuclear nrf2, which has a binding affinity to are and activates are-driven phase ii antioxidant enzymes; nqo1, ho-1, and gclc[1]. daphniphyllum macropodum fruit extract (dme) administration in vivo and its major component 5,7-dihydroxychromone (1, 5, and 10 μg/ml) treatment in vitro dose dependently increased the mrna expressions of pparγ and lxrα in 3t3-l1 cells, 5,7-dihydroxychromone (1 μg/ml ) also potently increased adipocyte differentiation, suggesting that it functions as a pparγ agonist and has anti-diabetic properties[2]. 5,7-dihydroxychromone also demonstrated significant activity against hiv replication in h9 lymphocyte cells[3].

references

[1]. kim d w, lee k, kwon j, et al. neuroprotection against 6-ohda-induced oxidative stress and apoptosis in sh-sy5y cells by 5, 7-dihydroxychromone: activation of the nrf2/are pathway[j]. life sciences, 2015, 130: 25-30.[2]. koo h j, kwak j h, kang s c. anti-diabetic properties of daphniphyllum macropodum fruit and its active compound[j]. bioscience, biotechnology, and biochemistry, 2014, 78(8): 1392-1401.[3]. wu p l, lin f w, wu t s, et al. cytotoxic and anti-hiv principles from the rhizomes of begonia nantoensis[j]. chemical and pharmaceutical bulletin, 2004, 52(3): 345-349.

InChI:InChI=1/C9H6O4/c10-5-3-7(12)9-6(11)1-2-13-8(9)4-5/h1-4,10,12H

Upstream product

• 480-66-0 2,4,6-trihydroxyacetophenone 
• 2258-42-6 formyl acetic anhydride 
• 108-73-6 3,5-dihydroxyphenol 
• 59887-89-7 7-hydroxy-4H-chromen-4-one 
• 124-63-0 methanesulfonyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 546115-69-9 oxalic acid 2-ethoxycarbonyl-7-ethoxyoxalyloxy-4-oxo-4H-chromen-5-yl ester ethyl ester 
• 35811-69-9 5,7-dihydroxy-4-oxo-4H-chromene-2-carboxylic acid 

Downstream Products

• 480-23-9 orobol 
• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 
• 1177261-89-0 hirtellanine B 
• 1447463-66-2 methyl 2-((2-(3,4-difluorophenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl)oxy)acetate 
• 1229578-70-4 C₂₉H₂₄O₈ 
• 1229578-69-1 C₄₅H₄₂O₁₀ 
• 1229578-61-3 C₂₁H₁₈O₇ 
• 903516-83-6 5,7-bis(benzyloxy)-4H-chromen-4-one 
• 491-80-5 5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 1393533-64-6 C₃₀H₂₄O₅ 
• 95603-91-1 Acetic acid 7-acetoxy-6,8-dibenzyl-4-oxo-4H-chromen-5-yl ester 
• 95603-93-3 Acetic acid 7-acetoxy-8-benzyl-4-oxo-4H-chromen-5-yl ester 
• 121565-36-4 5,7-dihydroxy-8-(1-phenyl-2-propenyl)chromone 

Relevant articles and documents

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An efficient protocol for Ru(II)-catalyzed direct C-H oxygenation of a broad range of flavone and chromone substrates was developed. This convenient and powerful synthetic tool allows for the rapid installation of the hydroxyl group into the flavone, chromone, and other related scaffolds and opens the way for analog synthesis of highly potent Aurora kinase inhibitors. The molecular docking simulations indicate that the formation of bidentate H-bonding patterns in the hinge regions between the 5-hydroxyflavonoids and Ala213 was the significant binding force, which is consistent with experimental and computational findings.

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