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5,7-Dihydroxychromone

$448

  • Brand : BIOFRON

  • Catalogue Number : BD-P0760

  • Specification : 98.5%(HPLC&TLC)

  • CAS number : 31721-94-5

  • PUBCHEM ID : 5281343

  • Volume : 25mg

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Catalogue Number

BD-P0760

Analysis Method

HPLC,NMR,MS

Specification

98.5%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

Appearance

Yellow crystal

Botanical Source

Bauhinia Linn./various plant materials, e.g. Garcinia conrauana bark and peanut shells

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1=COC2=CC(=CC(=C2C1=O)O)O

Synonyms

4H-1-Benzopyran-4-one, 5,7-dihydroxy-/5,7-dihydroxy-4H-1-benzopyran-4-one/5,7-Dihydroxychromone/2H-1-Benzopyran-2-one, 5,7-dihydroxy-/5,7-Dihydroxy-4H-chromen-4-one/5,7-Dihydroxy-2H-chromen-2-one/5,7-dihydroxy-chromen-4-one/5,7-Dihydroxy-chromen-4-on/5,7-DIHYDROXYCOUMARIN

IUPAC Name

5,7-dihydroxychromen-4-one

Applications

5,7-Dihydroxychromone, the extract of Cudrania tricuspidata, activates Nrf2/ARE signal and exerts neuroprotective effects against 6-hydroxydopamine (6-OHDA)-induced oxidative stress and apoptosis. 5,7-Dihydroxychromone inhibits the expression of activated caspase-3 and caspase-9 and cleaved PARP in 6-OHDA-induced SH-SY5Y cells[1].

Density

1.6±0.1 g/cm3

Solubility

Methanol; DMF

Flash Point

170.8±21.4 °C

Boiling Point

399.4±42.0 °C at 760 mmHg

Melting Point

232-273℃

InChl

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

InChl Key

NYCXYKOXLNBYID-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2914400000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:31721-94-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

24234013

Abstract

A flavonoid decomposition product that is present in peanut (Arachis hypogaea) shells, 5,7-dihydroxychromone (DHC), was found to inhibit the radial growth of cultures of the soil pathogenic fungiRhizoctonia solani andSclerotium rolfsii with I50 (the concentrations of DHC required to inhibit growth 50%) values of 18 and 26µM, respectively. Radicle elongation of velvetleaf, corn, peanut, and wheat was inhibited by DHC with I50 values of 30, 50, 65 and 200µM, respectively. DHC had no effect on the growth ofBradyrhizobium sp. at 10µM in medium containing low (1.0 g/liter) mannitol as the carbon source, although the related flavones luteolin and chrysin each promoted bacterial growth at 10µM 48 hr after inoculation. When tested in high (10.0 g/liter) mannitol medium, DHC initially inhibited growth ofBradyrhizobium sp., but 120 hr after inoculation the growth of all treatments were similar. These results suggest a role for DHC released from peanut shells in suppressing pathogenic fungal infection and competing plant growth but not forBradyrhizobium growth promotion.

Title

Phytotoxic and Antimicrobial Activity of 5,7-dihydroxychromone From Peanut Shells

Author

S F Vaughn

Publish date

1995 Feb

PMID

24128514

Abstract

A novel multiwall carbon nanotube/poly(ethylene terephthalate) (MWCNT/PET) composite electrode was developed for the determination of 5,7-dihydroxychromone and luteolin in peanut hulls in combination with capillary electrophoresis (CE). The electrode was fabricated by packing a mixture of MWCNTs and melted PET in a piece of fused-silica capillary under heat. Because of the simple composition of the phenolic constituents in peanut hulls, they were used to demonstrate the performance of the fabricated electrode. The results indicated that 5,7-dihydroxychromone and luteolin were well separated within 12 min in a 40 cm long capillary at a separation voltage of 12 kV using a 50mM borate buffer (pH 9.2). The MWCNT-based electrode exhibited significantly lower detection potentials, enhanced signal-to-noise characteristics, and higher resistance to surface fouling compared to graphite/PET composite electrode. It showed long-term stability and reproducibility with a relative standard deviation of 2.6% for the peak current (n = 15). The relation between peak current and analyte concentration was linear over about three orders of magnitude. The proposed method has been applied to determine the two bioactive constituents in real samples.

Title

Determination of 5,7-dihydroxychromone and Luteolin in Peanut Hulls by Capillary Electrophoresis With a Multiwall Carbon Nanotube/Poly(ethylene Terephthalate) Composite Electrode

Author

Shijun Sheng 1 , Luyan Zhang, Gang Chen

Publish date

2014 Feb 15

PMID

25818191

Abstract

Aims: The aim of this study was to prove the neuroprotective effect of 5,7-Dihydroxychromone (DHC) through the Nrf2/ARE signaling pathway. To elucidate the mechanism, we investigated whether 6-hydroxydopamine (6-OHDA)-induced neurotoxicity in SH-SY5Y cells could be attenuated by DHC via activating the Nrf2/ARE signal and whether DHC could down-regulate 6-OHDA-induced excessive ROS generation
Main methods: To evaluate the neuroprotective effect of DHC against 6-OHDA-induced apoptosis, FACS analysis was performed using PI staining. The inhibitory effect of DHC against 6-OHDA-induced ROS generation was evaluated by DCFH-DA staining assay. Additionally, translocation of Nrf2 to the nucleus and increased Nrf2/ARE binding activity, which subsequently resulted in the up-regulation of the Nrf2-dependent antioxidant gene expressions including HO-1, NQO1, and GCLc, were evaluated by Western blotting and EMSA.
Key findings: Pre-treatment of DHC, one of the constituents of Cudrania tricuspidata, significantly protects 6-OHDA-induced neuronal cell death and ROS generation. Also, DHC inhibited the expression of activated caspase-3 and caspase-9 and cleaved PARP in 6-OHDA-induced SH-SY5Y cells. DHC induced the translocation of Nrf2 to the nucleus and increased Nrf2/ARE binding activity which results in the up-regulation of the expression of Nrf2-dependent antioxidant genes, including HO-1, NQO1, and GCLc. The addition of Nrf2 siRNA abolished the neuroprotective effect of DHC against 6-OHDA-induced neurotoxicity and the expression of Nrf2-mediated antioxidant genes.
Significance: Activation of Nrf2/ARE signal by DHC exerted neuroprotective effects against 6-OHDA-induced oxidative stress and apoptosis. This finding will give an insight that activating Nrf2/ARE signal could be a new potential therapeutic strategy for neurodegenerative disease.

KEYWORDS

5,7-Dihydroxychromone; 6-OHDA; Cudrania tricuspidata; Neuroprotection; Nrf2/ARE pathway; Oxidative stress.

Title

Neuroprotection Against 6-OHDA-induced Oxidative Stress and Apoptosis in SH-SY5Y Cells by 5,7-Dihydroxychromone: Activation of the Nrf2/ARE Pathway

Author

Dong-Woo Kim 1 , Kyoung-Tae Lee 2 , Jaeyoung Kwon 3 , Hak Ju Lee 2 , Dongho Lee 4 , Woongchon Mar 5

Publish date

2015 Jun 1