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1,7-Dihydroxy-2,3-dimethoxyxanthone

CAS# 78405-33-1

1,7-Dihydroxy-2,3-dimethoxyxanthone

2D Structure

Catalog No. BCN7523----Order now to get a substantial discount!

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Quality Control of 1,7-Dihydroxy-2,3-dimethoxyxanthone

3D structure

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1,7-Dihydroxy-2,3-dimethoxyxanthone

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Chemical Properties of 1,7-Dihydroxy-2,3-dimethoxyxanthone

Cas No. 78405-33-1 SDF Download SDF
PubChem ID 10039726 Appearance Powder
Formula C15H12O6 M.Wt 288.25
Type of Compound Xanthones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1,7-dihydroxy-2,3-dimethoxyxanthen-9-one
SMILES COC1=C(C(=C2C(=C1)OC3=C(C2=O)C=C(C=C3)O)O)OC
Standard InChIKey BLXIZCDWQXDWQF-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H12O6/c1-19-11-6-10-12(14(18)15(11)20-2)13(17)8-5-7(16)3-4-9(8)21-10/h3-6,16,18H,1-2H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 1,7-Dihydroxy-2,3-dimethoxyxanthone

The roots of Polygala tenuifolia.

Biological Activity of 1,7-Dihydroxy-2,3-dimethoxyxanthone

Description1. 1,7-Dihydroxy-2,3-dimethoxyxanthone shows significant inhibitory effects on LPS-induced NO production in BV2 microglia cells. 2. 1,7-Dihydroxy-2,3-dimethoxyxanthone antagonises in a non competitive but, reversible manner the contractions induced by chemical inflammatory mediators in the guinea pig trachea in vitro, thus, it may have medicinal use in the management of inflammation, asthma and allergy.
TargetsNO

1,7-Dihydroxy-2,3-dimethoxyxanthone Dilution Calculator

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1,7-Dihydroxy-2,3-dimethoxyxanthone Molarity Calculator

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Preparing Stock Solutions of 1,7-Dihydroxy-2,3-dimethoxyxanthone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.4692 mL 17.3461 mL 34.6921 mL 69.3842 mL 86.7303 mL
5 mM 0.6938 mL 3.4692 mL 6.9384 mL 13.8768 mL 17.3461 mL
10 mM 0.3469 mL 1.7346 mL 3.4692 mL 6.9384 mL 8.673 mL
50 mM 0.0694 mL 0.3469 mL 0.6938 mL 1.3877 mL 1.7346 mL
100 mM 0.0347 mL 0.1735 mL 0.3469 mL 0.6938 mL 0.8673 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 1,7-Dihydroxy-2,3-dimethoxyxanthone

Xanthones from Polygala alpestris (Rchb.).[Pubmed:18998397]

Z Naturforsch C. 2004 May-Jun;59(5-6):335-8.

Bioactivity-guided fractionation of Polygala alpestris L. (Rchb.) extracts led to the identification of two new xanthones, 1,3,7-trihydroxy-2,6-dimethoxyxanthone (1) and 2,3-methylenedioxy-4,7-dihydroxyxanthone (2). In addition five known compounds 3,4-dimethoxy-1,7-dihydroxyxanthone (3), 1,3-dihydroxy-7-methoxyxanthone (4), 1,7-Dihydroxy-2,3-dimethoxyxanthone (5), 3',6-O-disinapoyl sucrose (6) and 3',5'-dimethoxybiphenyl-4-olo (7) were isolated. The structures of the isolated compounds were established by means of high resolution mass spectrometry, mono- and bi-dimensional NMR spectroscopy. All isolated compounds were tested for cytotoxic activity against three tumor cell lines (LoVo, HL-60, K 562).

Role of gastric mucus secretion, oxinitrergic system and sulfhydryl groups on the gastroprotection elicited by Polygala cyparissias (Polygalaceae) in mice.[Pubmed:23600395]

J Pharm Pharmacol. 2013 May;65(5):767-76.

OBJECTIVES: This study has aimed to assess the mechanisms of action for the gastroprotective effect of the acetone extract (PCAE) and methanol fraction (PCMF) of Polygala cyparissias, as well as to evaluate the activity of 1,3,6,8-tetrahydroxy-2,7-dimethoxyxanthone (1), 1,7-Dihydroxy-2,3-dimethoxyxanthone (2) and astragalin (3). METHODS: Gastric secretion and mucus content were determined by pylorus ligation in mice. Nitric oxide (NO) and sulfhydryl group participation were observed by the pretreatment of mice with L-NAME or NEM. Acute ulcer was induced by ethanol/HCl and chronic ulcer by acetic acid. Anti-Helicobacter pylori activity was evaluated by the agar solid dilution assay. KEY FINDINGS: Neither PCAE nor PCMF had the ability to reduce H(+) concentration. However, both of them enhanced mucus secretion. PCAE demonstrated its gastroprotection in a NO-dependent manner, while PCMF exerted the activity depending on the sulfhydryl group. In chronic ulcer, the curative ratios for the PCAE and PCMF were 67.5 and 58.4%, respectively. No effect over H. pylori was detected. Compounds 1, 2 and 3 were able to reduce lesions in the order of 79.6, 73.8 and 67.6%, respectively. CONCLUSIONS: The data suggested that PCAE and PCMF displayed antiulcer activity due to different mechanisms and with the participation of phenolic compounds obtained from the plant.

In vitro effect of the extract and the 1,7-dihydroxy-2,3-dimethoxy xanthone from Polygala cyparissias on the contractions induced by inflammatory mediators and ovalbumin in normal and actively sensitised trachea from guinea pig.[Pubmed:10344473]

Inflamm Res. 1999 Apr;48(4):218-23.

OBJECTIVE: This study describes the in vitro action of the hydroalcoholic extract and the 1,7-dihydroxy-2,3-dimethoxy xanthone isolated from P. cyparissias on agonist and ovalbumin induced contractions in trachea, from normal and actively sensitised guinea pigs. RESULTS: The hydroalcoholic extract of P. cyparissias (0.125 to 1 mg/ml), incubated with the guinea-pig trachea for 20 min, had no effect on the resting tone of the preparations, but caused a concentration-dependent, reversible and non competitive inhibition of contractions induced by acetylcholine, histamine, compound 48/80, bradykinin, substance P, prostaglandin E2 and the stable analogue of thromboxane A2 mimetic U 46619. The calculated mean IC50 values for the hydroalcoholic extract were: 0.37, 0.51, 0.06, 0.32, 0.48, 0.3 and 0.17 mg/ml, respectively. Also, the extract of P. cyparissias (0.125 to 0.5 mg/ml) antagonised, in a graded manner (IC50 of 0.46 mg/ml) ovalbumin-induced contractions in guinea-pig trachea obtained from animals which had been actively sensitised to this antigen. Pre-incubation of the preparations with the purifed xanthone isolated from P. cyparssias (2.5 to 80 microg/ml; 10.0 to 310.0 microM) caused significant and concentration-dependent, reversible and noncompetitive inhibition of the contractile responses elicited by acetylcholine, histamine, bradykinin, substance P, U 46619 and prostaglandin E2. The calculated mean IC50 values for these effects were: 132.0, 73.0, 9.2, 32.0, 110.6 and 66.0 microM, respectively. At very high concentrations (I55.0-620.0 microM) the xanthone also antagonised contraction induced by KCl in guinea-pig trachea (IC50 of 190.0 microM). CONCLUSIONS: Taken together these and our previous in vivo results are consistent with the view that the active principles present in P. cyparissias, including the 1,7-dihydroxy-2,3-dimethoxy xanthone, antagonise, in a non competitive but, reversible manner the contractions induced by chemical inflammatory mediators in the guinea pig trachea in vitro. Thus, these results might explain at least in part, the medicinal use of this plant in the management of inflammation, asthma and allergy.

Chemical constituents of Polygala tenuifolia roots and their inhibitory activity on lipopolysaccharide-induced nitric oxide production in BV2 microglia.[Pubmed:21740104]

J Enzyme Inhib Med Chem. 2012 Feb;27(1):1-4.

A methanolic extract of the roots of Polygala tenuifolia (Polygalaceae) significantly attenuated nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated BV2 microglia cells. Five xanthones, 1-hydroxy-7-methoxyxanthone (1), 3,6-dihydroxy-1,2,7-trimethoxyxanthone (2), 1,3,6-trihydroxy-2,7-dimethoxyxanthone (3), 1,7-Dihydroxy-2,3-dimethoxyxanthone (4) and 1,7-dihydroxy-3-methoxyxanthone (5), and five phenylpropanoids, 4-hydroxy-3-methoxypropiophenone (6), methyl 4-hydroxy-3-methoxycinnamic acid (7), 3,4,5-trimethoxycinnamic acid (8), 4-methoxycinnamic acid (9) and beta-d-(3-O-sinapoyl) fructofuranosyl-alpha-d-(6-O-sinapoyl)glucopyranoside (10), were isolated from CHCl(3) fraction using bioactivity-guided fractionation. Among these compounds, compounds 1, 2, 4, 5 and 7 showed significant inhibitory effects on LPS-induced NO production in BV2 microglia cells at the concentration ranging from 10.0 to 100.0 muM.

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