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7,8-Dihydroxy-4-methylcoumarin

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-D2026

  • Specification : 98%

  • CAS number : 2107-77-9

  • Formula : C10H8O4

  • Molecular Weight : 192.17

  • PUBCHEM ID : 5355836

  • Volume : 20mg

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Catalogue Number

BF-D2026

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

192.17

Appearance

Powder

Botanical Source

synthesis

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1=CC(=O)OC2=C1C=CC(=C2O)O

Synonyms

4-METHYLDAPHNETIN/7,8-dihydroxy-4-methyl-2H-1-benzopyran-2-one/7,8-Dihydroxy-4-methyl-2H-chromen-2-one/2H-1-Benzopyran-2-one, 7,8-dihydroxy-4-methyl-/7,8-dihydroxy-4-methyl-chromen-2-one/7,8-DIHYDROXY-4-METHYLCOUMARIN/4-methyl-7,8-dihydroxycoumarin/Coumarin,7,8-dihydroxy-4-methyl/7,8-dihydroxy-4-methyl-2H-2-chromenone/4-Methyldaphnetine

IUPAC Name

7,8-dihydroxy-4-methylchromen-2-one

Density

1.5±0.1 g/cm3

Solubility

Flash Point

176.0±22.2 °C

Boiling Point

421.5±45.0 °C at 760 mmHg

Melting Point

242-246 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932200000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:2107-77-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29849874

Abstract

We have previously demonstrated that human heat shock protein 90 (HSP90), an intracellular self protein, is the target of cellular and humoral autoimmune responses in patients with carotid atherosclerosis. In this study, we evaluated in vitro whether oxidative stress, a feature of atherosclerotic plaque, alters HSP90 expression in endothelial cells, thus inducing surface localization of this molecule and whether the antioxidant compound 7,8-dihydroxy-4-methylcoumarin (7,8-DHMC) is able to prevent oxidative stress-induced alterations of HSP90 localization. By the use of flow cytometry, immunofluorescence, enzyme-linked immunosorbent assay, and semiquantitative reverse-transcription polymerase chain reaction, we demonstrated that exposure of human umbilical vein endothelial cells (HUVEC) to the prooxidant compound H2O2 upregulated HSP90 surface expression and reduced its secretion without altering HSP90 gene expression and intracytoplasmic protein levels. Pretreatment of HUVEC with 7,8-DHMC prevented H2O2-induced alterations of HSP90 cellular distribution and secretion. Our results suggest that the strong oxidative conditions of atherosclerotic plaques promote the upregulation of HSP90 surface expression on endothelial cells, thus rendering the protein a possible target of autoimmune reactions. The antioxidant 7,8-DHMC, by preventing oxidative-stress-triggered HSP90 surface upregulation, may be useful to counteract possible autoreactive reactions to HSP90.

Title

Oxidative Stress Induces HSP90 Upregulation on the Surface of Primary Human Endothelial Cells: Role of the Antioxidant 7,8-Dihydroxy-4-methylcoumarin in Preventing HSP90 Exposure to the Immune System

Author

Elisabetta Profumo 1 , Brigitta Buttari 1 , Lavinia Tinaburri 2 , Daniela D'Arcangelo 3 , Maurizio Sorice 4 , Antonella Capozzi 4 , Tina Garofalo 4 , Antonio Facchiano 3 , Rita Businaro 5 , Prashant Kumar 6 , Brajendra K Singh 6 , Virinder S Parmar 6 7 8 , Luciano Saso 9 , Rachele Riganò 1

Publish date

. 2018 Apr 10

PMID

25752619

Abstract

7,8-Dihydroxy-4-methylcoumarin (Dhmc) is a precursor in the synthesis of derivatives of 4-methyl coumarin, which has excellent radical scavenging properties. In this study, we investigated whether Dhmc protects against oxidative stress and ischemic brain injury. We found that Dhmc protected against glutamate toxicity in hippocampal HT-22 cells in a concentration-dependent manner in vitro. Dhmc inhibited glutamate-induced glutathione depletion and generation of reactive oxygen species, suggesting that Dhmc has an antioxidant effect. In addition, Dhmc inhibited glutamate-induced depletion of hippocalcin, a protein that buffers intracellular calcium and prevents calcium-induced cell death. In our in vivo studies, Dhmc reduced infarct volume in neonatal rats when administered 4 h after cerebral hypoxia/ischemia injury and attenuated the hypoxia/ischemia injury-induced decrease of hippocalcin expression in neonatal rats. Taken together, these results suggest that Dhmc prevents glutamate-induced toxicity by scavenging free radicals and regulating hippocalcin expression. Dhmc may represent a promising agent in the treatment of acute and chronic neurological disorders induced by oxidative stress.

Title

7,8-Dihydroxy-4-methylcoumarin Provides Neuroprotection by Increasing Hippocalcin Expression

Author

Xiaomei Jin 1 , Yamin Wang, Xiaojing Li, Xianxing Tan, Zhigang Miao, Yuanyuan Chen, Ronald C Hamdy, Balvin H L Chua, Jiming Kong, Heqing Zhao, Xingshun Xu

Publish date

2015 Apr

PMID

24935826

Abstract

We report a combined some (infrared, Raman and NMR) spectroscopic and quantum chemistry study on 7,8-Dihydroxy-4-Methylcoumarin molecule (78D4MC). The Raman and IR spectra of 78D4MC molecule were recorded and analyzed in the region 3500-50 cm(-1) and 4000-400 cm(-1), respectively. Potential energy scans were performed at the MMFF level of theory. All possible conformers, which are results at the MMFF level theory, were re-computed at the B3LYP functional with cc-pVDZ basis set. The optimized geometrical parameters, harmonic vibrational wavenumbers and NMR chemical shifts of the most stable conformer were calculated at the B3LYP/6-311G(d,p), cc-pVTZ and cc-pVQZ level in the proximity of the isolated molecule. DFT calculations were combined with Pulay’s scaled quantum mechanics force field (SQMFF) methodology in order to fit the theoretical wavenumbers to the experimental ones.

KEYWORDS

7,8-Dihydroxy-4-Methylcoumarin; DFT; FT-IR spectra; FT-Raman spectra; NMR spectra.

Title

Infrared, Raman and NMR Spectra, Conformational Stability and Vibrational Assignment of 7,8-Dihydroxy-4-Methylcoumarin

Author

Yusuf Erdogdu 1 , Semran Saglam 2

Publish date

2014 Nov 11


Description :

4-Methyldaphnetin is a precursor in the synthesis of derivatives of 4-methyl coumarin. 4-Methyldaphnetin has potent, selective anti-proliferative and apoptosis-inducing effects on several cancer cell lines. 4-Methyldaphnetin possesses radical scavenging property and strongly inhibits membrane lipid peroxidation[1][2][3].