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1,3,6-Trihydroxy-5-methoxyxanthone

CAS# 41357-84-0

1,3,6-Trihydroxy-5-methoxyxanthone

Catalog No. BCN3454----Order now to get a substantial discount!

Product Name & Size Price Stock
1,3,6-Trihydroxy-5-methoxyxanthone:5mg Please Inquire In Stock
1,3,6-Trihydroxy-5-methoxyxanthone:10mg Please Inquire In Stock
1,3,6-Trihydroxy-5-methoxyxanthone:20mg Please Inquire In Stock
1,3,6-Trihydroxy-5-methoxyxanthone:50mg Please Inquire In Stock

Quality Control of 1,3,6-Trihydroxy-5-methoxyxanthone

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Chemical structure

1,3,6-Trihydroxy-5-methoxyxanthone

3D structure

Chemical Properties of 1,3,6-Trihydroxy-5-methoxyxanthone

Cas No. 41357-84-0 SDF Download SDF
PubChem ID 5493675 Appearance Yellow powder
Formula C14H10O6 M.Wt 274.2
Type of Compound Xanthones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1,3,6-trihydroxy-5-methoxyxanthen-9-one
SMILES COC1=C(C=CC2=C1OC3=CC(=CC(=C3C2=O)O)O)O
Standard InChIKey OIDDYVZHNYQRKQ-UHFFFAOYSA-N
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 1,3,6-Trihydroxy-5-methoxyxanthone

The herbs of Canscora decussata

Biological Activity of 1,3,6-Trihydroxy-5-methoxyxanthone

DescriptionStandard reference
In vitro

Natural products inhibiting Candida albicans secreted aspartic proteases from Tovomita krukovii.[Pubmed: 11842327]

Planta Med. 2002 Jan;68(1):49-54.


METHODS AND RESULTS:
Assay-guided fractionation of the ethanol extract of Tovomita krukovii resulted in the identification of four new xanthones (1 - 4) and ten known compounds (5 - 14). The structures of compounds 1 - 14 were determined by spectral data to be 3,5-dihydroxy-4-methoxyxanthone (1), 1,3,5,7-tetrahydroxy-8-isoprenylxanthone (2), 1,3,5-trihydroxy-8-isoprenylxanthone (3), 1,5,7-trihydroxy-8-isoprenylxanthone (4), 1,3,7-trihydroxy-2-isoprenylxanthone (5), 1,5-dihydroxyxanthone (6), 1,6-dihydroxy-5-methoxyxanthone (7), 1,3,5-trihydroxyxanthone (8), 1,3,6-Trihydroxy-5-methoxyxanthone (9), 1,6-dihydroxy-3,5-dimethoxyxanthone (10), 1,3,7-trihydroxyxanthone (11), 3-geranyl-2,4,6-trihydroxybenzophenone (12), betulinic acid (13), and 3,4-dihydroxybenzoic acid (14).
CONCLUSIONS:
Compounds 2, 3, 12 and 13 showed inhibitory effects against Candida albicans secreted aspartic proteases (SAP) with IC50 values of 15 microg/ml, 25 microg/ml, 40 microg/ml, and 6.5 microg/ml, respectively, while the other compounds were inactive. In addition, compound 12 showed activity against C. albicans, C. neoformans, S. aureus and methicillin resistant S. aureus (MRS).

Protocol of 1,3,6-Trihydroxy-5-methoxyxanthone

Structure Identification
J Asian Nat Prod Res. 2015;17(4):377-83.

Synthesis and antitumor activity evaluation of a novel series of xanthone derivatives.[Pubmed: 25628155]


METHODS AND RESULTS:
A natural xanthone, 1,3,6-Trihydroxy-5-methoxyxanthone, was totally synthesized for the first time by six steps in 31% overall yield. The xanthone skeleton was formed by a one-step synthesis in 80% yield, and five of its novel derivatives were also obtained by this approach. This synthetic strategy and all the derivatives could be further used for the preparation of other natural xanthones. All the xanthones were characterized by NMR and ESI-MS, and the cytotoxicity of these xanthones was evaluated against HepG2 and HT-29 cells, and the preliminary structure-activity relationship was evaluated from the results.
CONCLUSIONS:
It was proved that the presence of 3-OH group in the molecule is crucial for its biological activity, while the presence of substituents at C-5 and C-6 may also be beneficial.

Nat Prod Res. 2015;29(13):1217-21.

A new flavonoid from Cudrania cochinchinensis.[Pubmed: 25571958 ]


METHODS AND RESULTS:
Chemical investigation of the ethanol extract of the roots of Cudrania cochinchinensis led to the isolation of a new flavonoid, (6S,12S,13R)-1-methoxy cyanomaclurin (1), together with seven known compounds, 1,3,5-trihydroxy-4-(3'-hydroxy-3'-methylbutyl)xanthone (2), 1,3,6-trihydroxy-4-prenylxanthone (3), 1,3,6,7-tetrahydroxyxanthone (4), 1,3,5,6-tetrahydroxyxanthone (5), 1,3,6-Trihydroxy-5-methoxyxanthone (6), resveratrol (7) and oxyresveratrol (8).
CONCLUSIONS:
The structure of compound 1 was elucidated on the basis of 1D and 2D NMR spectra and the HR-ESI-MS data. The absolute stereochemistry was deduced via Rh2(OCOCF3)4-induced CD and NOESY spectra.

1,3,6-Trihydroxy-5-methoxyxanthone Dilution Calculator

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1,3,6-Trihydroxy-5-methoxyxanthone Molarity Calculator

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Preparing Stock Solutions of 1,3,6-Trihydroxy-5-methoxyxanthone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.647 mL 18.2349 mL 36.4697 mL 72.9395 mL 91.1743 mL
5 mM 0.7294 mL 3.647 mL 7.2939 mL 14.5879 mL 18.2349 mL
10 mM 0.3647 mL 1.8235 mL 3.647 mL 7.2939 mL 9.1174 mL
50 mM 0.0729 mL 0.3647 mL 0.7294 mL 1.4588 mL 1.8235 mL
100 mM 0.0365 mL 0.1823 mL 0.3647 mL 0.7294 mL 0.9117 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 1,3,6-Trihydroxy-5-methoxyxanthone

Synthesis and antitumor activity evaluation of a novel series of xanthone derivatives.[Pubmed:25628155]

J Asian Nat Prod Res. 2015;17(4):377-83.

A natural xanthone, 1,3,6-Trihydroxy-5-methoxyxanthone, was totally synthesized for the first time by six steps in 31% overall yield. The xanthone skeleton was formed by a one-step synthesis in 80% yield, and five of its novel derivatives were also obtained by this approach. This synthetic strategy and all the derivatives could be further used for the preparation of other natural xanthones. All the xanthones were characterized by NMR and ESI-MS, and the cytotoxicity of these xanthones was evaluated against HepG2 and HT-29 cells, and the preliminary structure-activity relationship was evaluated from the results. It was proved that the presence of 3-OH group in the molecule is crucial for its biological activity, while the presence of substituents at C-5 and C-6 may also be beneficial.

Natural products inhibiting Candida albicans secreted aspartic proteases from Tovomita krukovii.[Pubmed:11842327]

Planta Med. 2002 Jan;68(1):49-54.

Assay-guided fractionation of the ethanol extract of Tovomita krukovii resulted in the identification of four new xanthones (1 - 4) and ten known compounds (5 - 14). The structures of compounds 1 - 14 were determined by spectral data to be 3,5-dihydroxy-4-methoxyxanthone (1), 1,3,5,7-tetrahydroxy-8-isoprenylxanthone (2), 1,3,5-trihydroxy-8-isoprenylxanthone (3), 1,5,7-trihydroxy-8-isoprenylxanthone (4), 1,3,7-trihydroxy-2-isoprenylxanthone (5), 1,5-dihydroxyxanthone (6), 1,6-dihydroxy-5-methoxyxanthone (7), 1,3,5-trihydroxyxanthone (8), 1,3,6-Trihydroxy-5-methoxyxanthone (9), 1,6-dihydroxy-3,5-dimethoxyxanthone (10), 1,3,7-trihydroxyxanthone (11), 3-geranyl-2,4,6-trihydroxybenzophenone (12), betulinic acid (13), and 3,4-dihydroxybenzoic acid (14). Compounds 2, 3, 12 and 13 showed inhibitory effects against Candida albicans secreted aspartic proteases (SAP) with IC50 values of 15 microg/ml, 25 microg/ml, 40 microg/ml, and 6.5 microg/ml, respectively, while the other compounds were inactive. In addition, compound 12 showed activity against C. albicans, C. neoformans, S. aureus and methicillin resistant S. aureus (MRS).

A new flavonoid from Cudrania cochinchinensis.[Pubmed:25571958]

Nat Prod Res. 2015;29(13):1217-21.

Chemical investigation of the ethanol extract of the roots of Cudrania cochinchinensis led to the isolation of a new flavonoid, (6S,12S,13R)-1-methoxy cyanomaclurin (1), together with seven known compounds, 1,3,5-trihydroxy-4-(3'-hydroxy-3'-methylbutyl)xanthone (2), 1,3,6-trihydroxy-4-prenylxanthone (3), 1,3,6,7-tetrahydroxyxanthone (4), 1,3,5,6-tetrahydroxyxanthone (5), 1,3,6-Trihydroxy-5-methoxyxanthone (6), resveratrol (7) and oxyresveratrol (8). The structure of compound 1 was elucidated on the basis of 1D and 2D NMR spectra and the HR-ESI-MS data. The absolute stereochemistry was deduced via Rh2(OCOCF3)4-induced CD and NOESY spectra.

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