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
• Article Data: 14

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

Description

5,7-Dihydroxychromone is a flavone decomposition product that exhibits diverse biological activities, including antimicrobial, antioxidant, and neuroprotective properties. It is found in A. hypogaea and has the ability to reduce radial growth of soil pathogenic fungi R. solani and S. rolfsii, while having no effect on soil pathogenic bacteria of the genus Bradyrhizobium.

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

• 108-73-6 3,5-dihydroxyphenol 
• 59887-89-7 7-hydroxy-4H-chromen-4-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 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 
• 2258-42-6 formyl acetic anhydride 

Downstream Products

• 95603-93-3 Acetic acid 7-acetoxy-8-benzyl-4-oxo-4H-chromen-5-yl ester 
• 95603-91-1 Acetic acid 7-acetoxy-6,8-dibenzyl-4-oxo-4H-chromen-5-yl ester 
• 1447463-66-2 methyl 2-((2-(3,4-difluorophenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl)oxy)acetate 
• 480-23-9 orobol 
• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 
• 1177261-89-0 hirtellanine B 
• 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 
• 121565-36-4 5,7-dihydroxy-8-(1-phenyl-2-propenyl)chromone 

Relevant articles and documents

Synthesis of 5,7 dihydroxychromone

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Natural and Synthetic Flavonoids as Potent Mycobacterium tuberculosis UGM Inhibitors

This study reports a novel class of inhibitors of uridine 5′-diphosphate (UDP) galactopyranose mutase (UGM) derived from a screening of natural products. This enzyme is an essential biocatalyst involved in the cell wall biosynthesis of Mycobacterium tuberculosis. Flavonoids are potent inhibitors of UGM. The synthesis of novel methylated flavonoids allowed a structure–activity relationship analysis to be performed and which functional groups and structural elements were required for UGM inhibition could be determined. The binding mode of one of the best inhibitors was found to be noncompetitive. Docking simulations indicated that this molecule was likely to bind UGM in its open conformation, in a cavity recently identified as a “druggable” pocket. Importantly, two of the best inhibitors of the M. tuberculosis UGM displayed moderate activity against whole M. tuberculosis cells. This study reports the first natural products that act as inhibitor of UGM. Given the importance of natural products in medicinal chemistry, these results create new opportunities for the discovery of new antitubercular agents.

Natural product Hirtellanine B and its derivatives in the preparation process for the preparation of medicine for treating tumor with the application of the

The present invention provides a preparation method of a natural product Hirtellanine B, wherein 2,4,6-trihydroxyacetophenone is adopted as a raw material, and steps of compound a preparation, compound b preparation, compound c preparation, compound d preparation, compound e preparation, compound f preparation, compound g preparation, and the like are performed to prepare the natural product Hirtellanine B. According to the present invention, biological activity screening is performed on Hirtellanine B and 14 Hirtellanine B derivatives, and results show that the natural product Hirtellanine B can inhibit proliferations of Jurkat cells, Raji cells and K562 cells, and the compounds provide a certain inhibition activity for tumor cells. The method has characteristics of easily available raw material, high reaction yield and reasonable operation, and is suitable for industrial production. The Hirtellanine B and the derivatives thereof can be used for preparing tumor treatment drugs, and have great clinical values. The natural product Hirtellanine B preparation method reaction formulas are as the follows.