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    6,7-Dihydroxycoumarin
    Information
    CAS No. 305-01-1 Price $30 / 20mg
    Catalog No.CFN99115Purity>=98%
    Molecular Weight178.14Type of CompoundCoumarins
    FormulaC9H6O4Physical DescriptionPowder
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    6,7-Dihydroxycoumarin

    6,7-Dihydroxycoumarin
    Product Name 6,7-Dihydroxycoumarin
    CAS No.: 305-01-1
    Catalog No.: CFN99115
    Molecular Formula: C9H6O4
    Molecular Weight: 178.14 g/mol
    Purity: >=98%
    Type of Compound: Coumarins
    Physical Desc.: Powder
    Targets: HO-1 | NO | AP-1 | MCP-1 | TNF-伪 | PPAR | NF-kB | PI3K
    Source: The peels of Aesculus hippocastanum L.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Price: $30 / 20mg
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  • The Korea Journal of Herbology2016, 29-35
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  • Related Screening Libraries
    Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
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  • Biological Activity
    Description: 6,7-Dihydroxycoumarin(Esculetin) has various biological and pharmaceutical properties including anti-edema, anti-inflammatory, anti-tumour, hepatoprotective, anti-osteoarthritis and anti-rheumatoid arthritis effects. It inhibits lipoxygenases (LOs), p42/44 MAPK activation, PI3-kinase activation, as well as NF-kappaB and AP-1 activation, it exhibits competitive inhibition against the oxidation of 3-(3,4-dihydroxyphenyl)- alanine by mushroom, the IC50 value of is 43 microM.
    Targets: HO-1 | NO | AP-1 | MCP-1 | TNF-α | PPAR | NF-kB | PI3K
    In vitro:
    Int J Oncol. 2015 Jan;46(1):265-71.
    Esculetin (6,7-dihydroxycoumarin): a potential cancer chemopreventive agent through suppression of Sp1 in oral squamous cancer cells.[Pubmed: 25310400]
    Esculetin (6,7-Dihydroxycoumarin), a coumarin compound, is known to inhibit proliferation and induce apoptosis in several types of human cancer cells and is regarded as a promising chemotherapeutic agent.
    METHODS AND RESULTS:
    The purpose of the present study was to investigate the anti-proliferative effects of esculetin on two oral squamous cell carcinoma (OSCC) cell lines, HN22 and HSC4, through regulation of specificity protein 1 (Sp1). We examined the apoptotic effects of esculetin were measured by MTS assay, DAPI staining, Annexin V, PI staining, RT-PCR, western blot analysis and immunocytochemistry in HN22 and HSC4 cells. Taken together, the results of the present study indicate that esculetin had anti-proliferative effect on the growth of OSCC cells (HN22 and HSC4) in a dose- and time-dependent manner. The treatment of HN22 and HSC4 cells with esculetin led to a significant reduction in growth and induced apoptosis, followed by the regulation of Sp1 and Sp1 regulatory protein.
    CONCLUSIONS:
    This indicates that esculetin inhibited cell growth and induced apoptosis by suppressing Sp1 in HN22 and HSC4 cells, suggesting it to be a potent anticancer drug candidate for oral cancer.
    Food Funct. 2014 Sep;5(9):2371-7.
    Esculetin inhibits the inflammatory response by inducing heme oxygenase-1 in cocultured macrophages and adipocytes.[Pubmed: 25088305]

    METHODS AND RESULTS:
    In this study, we investigated the anti-inflammatory effects of esculetin (6,7-Dihydroxycoumarin,ECT) through up-regulation of heme oxygenase-1 (HO-1) in cocultured macrophages and adipocytes. RAW264.7 macrophages and differentiated 3T3-L1 adipocytes were cocultured in serum-free Dulbecco's modified Eagle's medium with or without ECT for 24 h. Nitric oxide (NO), tumor necrosis factor-α (TNF-α), and monocyte chemoattractant protein-1 (MCP-1) production was measured in the coculture supernatant. ECT decreased the secretion of NO, TNF-α, and MCP-1. The expression of adipogenic proteins, including peroxisome proliferator-activated receptors γ (PPARγ) and CCAAT/enhancer binding protein α (C/EBPα) in cocultured adipocytes and inducible nitric oxide synthase (iNOS) in cocultured macrophages, was inhibited by ECT. Additionally, HO-1 expression was induced in cocultured macrophages and adipocytes. Silencing of HO-1 expression increased the production of NO, TNF-α, and MCP-1 in cocultured cells, in spite of the presence of ECT.
    CONCLUSIONS:
    This study demonstrated that ECT exhibited anti-inflammatory properties by inhibiting the production of proinflammatory cytokines in the interaction between adipocytes and macrophages through HO-1 expression. ECT may have the potential to improve chronic inflammation in obesity.
    Eur. J. Pharmacol., 1999, 370(3):297-305
    Esculetin suppresses proteoglycan metabolism by inhibiting the production of matrix metalloproteinases in rabbit chondrocytes.[Pubmed: 10334506]
    The possible mechanism of the chondroprotective effect of 6,7-Dihydroxycoumarin (esculetin) was investigated using primary cultures of rabbit articular chondrocytes.
    METHODS AND RESULTS:
    Esculetin (EST) significantly suppressed the proteoglycan depletion and the release of pulse-labeled [35S]proteoglycan from the matrix layer of rabbit chondrocytes treated with recombinant human interleukin-1alpha. The matrix metalloproteinase inhibitor, 1,10-phenanthroline, also blocked the proteoglycan depletion and [35S]proteoglycan release. From these results, it is likely that recombinant human interleukin-1alpha-induced proteoglycan depletion is mediated by matrix metalloproteinases. Although esculetin did not directly inhibit collagenolytic activity in the culture media, it significantly suppressed the production of pro-matrix metalloproteinase-1/interstitial procollagenase and pro-matrix metalloproteinase-3/prostromelysin 1, accompanied by a decrease in the steady-state levels of their mRNAs.
    CONCLUSIONS:
    These results suggest that esculetin is a therapeutically effective candidate for inhibition of cartilage destruction in osteoarthritis and rheumatoid arthritis.
    6,7-Dihydroxycoumarin Description
    Source: The peels of Aesculus hippocastanum L.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 5.6136 mL 28.0678 mL 56.1356 mL 112.2712 mL 140.3391 mL
    5 mM 1.1227 mL 5.6136 mL 11.2271 mL 22.4542 mL 28.0678 mL
    10 mM 0.5614 mL 2.8068 mL 5.6136 mL 11.2271 mL 14.0339 mL
    50 mM 0.1123 mL 0.5614 mL 1.1227 mL 2.2454 mL 2.8068 mL
    100 mM 0.0561 mL 0.2807 mL 0.5614 mL 1.1227 mL 1.4034 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Kinase Assay:
    Biochem Pharmacol. 2003 Jun 1;65(11):1897-905.
    Esculetin inhibits Ras-mediated cell proliferation and attenuates vascular restenosis following angioplasty in rats.[Pubmed: 12781342]
    The proliferation of vascular smooth muscle cells (VSMCs) induced by injury to the intima of arteries is an important etiologic factor in vascular proliferative disorders such as atherosclerosis and restenosis. Esculetin, derived from the Chinese herb Artemisia scoparia, is well known as a lipoxygenase inhibitor.
    METHODS AND RESULTS:
    We have investigated the inhibitory effects of esculetin (6,7-Dihydroxycoumarin) on VSMC proliferation and intimal hyperplasia by balloon angioplasty in the rat. We determined, using [3H]thymidine incorporation and the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, that esculetin inhibited the proliferation of VSMCs via a lipoxygenase-independent pathway. Three predominant signaling pathways were identified to be inhibited by esculetin: (a) the activation of p42/44 mitogen-activated protein kinase (MAPK) and the downstream effectors of c-fos and c-jun immediate early genes by means of western and reverse transcription-polymerase chain reaction (RT-PCR) analyses; (b) the activation of nuclear factor-kappaB (NF-kappaB) and activator protein-1 (AP-1), using the electrophoretic mobility shift assay; and (c) the activation of phosphoinositide 3-kinase (PI 3-kinase) and cell cycle progression, by western blot analysis and flow cytometric detection. Furthermore, esculetin also profoundly inhibited Ras activation, a shared upstream event of the above signaling cascades. In vascular injury studies, intraperitoneal administration of esculetin significantly suppressed intimal hyperplasia induced by balloon angioplasty.
    CONCLUSIONS:
    We conclude that esculetin blocks cell proliferation via the inhibition of an upstream effector of Ras and downstream events including p42/44 MAPK activation, PI 3-kinase activation, immediate early gene expression, as well as NF-kappaB and AP-1 activation. It also inhibits intimal hyperplasia after balloon vascular injury in the rat, indicating the therapeutic potential for treating restenosis after arterial injury.
    Biosci Biotechnol Biochem. 2003 Mar;67(3):631-4.
    Mushroom tyrosinase inhibitory activity of esculetin isolated from seeds of Euphorbia lathyris L.[Pubmed: 12723615 ]
    A tyrosinase inhibitor was isolated from the seeds of Euphorbia lathyris L. by bioassay-guided fractionation and purification, using silica gel column chromatography. It was identified as esculetin (6,7-Dihydroxycoumarin)by comparing its physical properties and spectral data with those of an authentic sample. The IC50 value of esculetin(6,7-Dihydroxycoumarin) in the mushroom tyrosinase activity test was 43 microM. The kinetic study indicates that esculetin(6,7-Dihydroxycoumarin) exhibited competitive inhibition against the oxidation of 3-(3,4-dihydroxyphenyl)-alanine by mushroom tyrosinase. The structure-activity relationships among five esculetin(6,7-Dihydroxycoumarin) analogs suggest that hydroxyl groups at the C6 and C7 positions of the coumarin skeleton played an important role in the expression of tyrosinase inhibitory activity.
    Cell Research:
    Obesity (Silver Spring). 2006 Oct;14(10):1691-9.
    Esculetin induces apoptosis and inhibits adipogenesis in 3T3-L1 cells.[Pubmed: 17062797 ]
    Cell lines:3T3-L1 mouse embryo fibroblasts
    Concentrations: 0, 50, 100, 200, 400, 800 μM
    Incubation Time: 6, 12, 24, or 48 hours
    Method:
    Tests are performed in 96-well plates. For mature adipocytes, cells are seeded (5000 cells/well), grown to confluency, induced to differentiate, and grown to maturation. For preadipocytes, a seeding density of 2500 cells/well is used, and cells are cultured overnight before treatment. Cells are incubated with either DMSO or increasing concentrations of esculetin for 6, 12, 24, or 48 hours. For the post-confluent preadipocytes, a seeding density of 2500 cells/well is used, and cells are grown to confluency before treatment. Esculetin (100 or 200 μM) in 0.01% DMSO carrier is added with the induction medium for Days 0 to 2, 2 to 4, and 4 to 6 of adipogenesis. Medium is changed every 2 days. Before assay for cell viability, cells are washed with DMEM/10% FBS three times, and 100 μL of DMEM/10% FBS medium is added to each well before treatment with 20 μL MTS assay solution per well. Cells are incubated for 1 hour at 37 °C; then 25 μL of 10% sodium dodecyl sulfate is added to each well. The absorbance is measured at 490 nm in a plate reader to determine the formazan concentration, which is proportional to the number of live cells.
    Animal Research:
    Braz J Med Biol Res. 2015 Mar;48(3):245-53.
    Esculetin(6,7-Dihydroxycoumarin), a coumarin derivative, exerts in vitro and in vivo antiproliferative activity against hepatocellular carcinoma by initiating a mitochondrial-dependent apoptosis pathway.[Pubmed: 25517918 ]
    Animal Models: C57BL/6J mice implanted with Hepa1-6 cells
    Formulation: physiological saline
    Dosages:200, 400, or 700 mg/kg/day
    Administration: i.p.
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