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Purpurogallin carboxylic acid

CAS# 5146-12-3

Purpurogallin carboxylic acid

Catalog No. BCX1481----Order now to get a substantial discount!

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Chemical structure

Purpurogallin carboxylic acid

3D structure

Chemical Properties of Purpurogallin carboxylic acid

Cas No. 5146-12-3 SDF Download SDF
PubChem ID 269315.0 Appearance Powder
Formula C12H8O7 M.Wt 264.19
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2,3,4,5-tetrahydroxy-6-oxobenzo[7]annulene-8-carboxylic acid
SMILES C1=C2C=C(C(=C(C2=C(C(=O)C=C1C(=O)O)O)O)O)O
Standard InChIKey PJSKCCANFAFYHW-UHFFFAOYSA-N
Standard InChI InChI=1S/C12H8O7/c13-6-3-5(12(18)19)1-4-2-7(14)10(16)11(17)8(4)9(6)15/h1-3,14,16-17H,(H,13,15)(H,18,19)
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.

Purpurogallin carboxylic acid Dilution Calculator

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Purpurogallin carboxylic acid Molarity Calculator

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Preparing Stock Solutions of Purpurogallin carboxylic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.7852 mL 18.9258 mL 37.8515 mL 75.7031 mL 94.6289 mL
5 mM 0.757 mL 3.7852 mL 7.5703 mL 15.1406 mL 18.9258 mL
10 mM 0.3785 mL 1.8926 mL 3.7852 mL 7.5703 mL 9.4629 mL
50 mM 0.0757 mL 0.3785 mL 0.757 mL 1.5141 mL 1.8926 mL
100 mM 0.0379 mL 0.1893 mL 0.3785 mL 0.757 mL 0.9463 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 Purpurogallin carboxylic acid

Interactions of Fungi and Algae from the Greenland Ice Sheet.[Pubmed:35608637]

Microb Ecol. 2023 Jul;86(1):282-296.

Heavily pigmented glacier ice algae Ancylonema nordenskioldii and Ancylonema alaskanum (Zygnematophyceae, Streptophyta) reduce the bare ice albedo of the Greenland Ice Sheet, amplifying melt from the largest cryospheric contributor to eustatic sea-level rise. Little information is available about glacier ice algae interactions with other microbial communities within the surface ice environment, including fungi, which may be important for sustaining algal bloom development. To address this substantial knowledge gap and investigate the nature of algal-fungal interactions, an ex situ co-cultivation experiment with two species of fungi, recently isolated from the surface of the Greenland Ice Sheet (here proposed new species Penicillium anthracinoglaciei Perini, Frisvad and Zalar, Mycobank (MB 835602), and Articulospora sp.), and the mixed microbial community dominated by glacier ice algae was performed. The utilization of the dark pigment Purpurogallin carboxylic acid-6-O-beta-D-glucopyranoside (C(18)H(18)O(12)) by the two fungi was also evaluated in a separate experiment. P. anthracinoglaciei was capable of utilizing and converting the pigment to Purpurogallin carboxylic acid, possibly using the sugar moiety as a nutrient source. Furthermore, after 3 weeks of incubation in the presence of P. anthracinoglaciei, a significantly slower decline in the maximum quantum efficiency (F(v)/F(m), inverse proxy of algal stress) in glacier ice algae, compared to other treatments, was evident, suggesting a positive relationship between these species. Articulospora sp. did uptake the glycosylated purpurogallin, but did not seem to be involved in its conversion to aglycone derivative. At the end of the incubation experiments and, in conjunction with increased algal mortality, we detected a substantially increasing presence of the zoosporic fungi Chytridiomycota suggesting an important role for them as decomposers or parasites of glacier ice algae.

Virtual screening of National Cancer Institute database for claudin-4 inhibitors: Synthesis, biological evaluation, and molecular dynamics studies.[Pubmed:30474874]

J Cell Biochem. 2019 May;120(5):8588-8600.

Claudin-4 (CLDN4) is a vital member of tight-junction proteins that is often overexpressed in cancer and other malignancies. The three-dimensional structure of human CLDN4 was constructed based on homology modeling approach. A total of 265 242 molecules from the National Cancer Institute (NCI) database has been utilized as a dataset for this study. In the present work, structure-based virtual screening is performed with the NCI database using Glide. By molecular docking, 10 candidate molecules with high scoring functions, which binds to the active site of CLDN4 were identified. Subsequently, molecular dynamics simulations of membrane protein were used for optimization of the top-three lead compounds (NCI110039, NCI344682, and NCI661251) with CLDN4 in a dynamic system. The lead molecule from NCI database NCI11039 (Purpurogallin carboxylic acid) was synthesized and cytotoxic properties were evaluated with A549, MCF7 cell lines. Our docking and dynamics simulations predicted that ARG31, ASN142, ASP146, and ARG158 as critically important residues involved in the CLDN4 activity. Finally, three lead candidates from the NCI database were identified as potent CLDN4 inhibitors. Cytotoxicity assays had proved that Purpurogallin carboxylic acid had an inhibitory effect towards breast (MCF7) and lung (A549) cancer cell lines. Computational insights and in vitro (cytotoxicity) studies reported in this study are expected to be helpful for the development of novel anticancer agents.

Characterization of an UV- and VIS-absorbing, purpurogallin-derived secondary pigment new to algae and highly abundant in Mesotaenium berggrenii (Zygnematophyceae, Chlorophyta), an extremophyte living on glaciers.[Pubmed:22092588]

FEMS Microbiol Ecol. 2012 Mar;79(3):638-48.

Mesotaenium berggrenii is one of few autotrophs that thrive on bare glacier surfaces in alpine and polar regions. This extremophilic alga produces high amounts of a brownish vacuolar pigment, whose chemical constitution and ecological function is largely unknown until now. Field material was harvested to isolate and characterize this pigment. Its tannin nature was determined by photometric methods, and the structure determination was carried out by means of HPLC-MS and 1D- and 2D-NMR spectroscopy. The main constituent turned out to be Purpurogallin carboxylic acid-6-O-beta-d-glucopyranoside. This is the first report of such a phenolic compound in this group of algae. Because of its broad absorption capacities of harmful UV and excessive VIS radiation, this secondary metabolite seems to play an important role for the survival of this alga at exposed sites. Attributes and abundances of the purpurogallins found in M. berggrenii strongly suggest that they are of principal ecophysiological relevance like analogous protective pigments of other extremophilic microorganisms. To prove that M. berggrenii is a true psychrophile, photosynthesis measurements at ambient conditions were carried out. Sequencing of the 18S rRNA gene of this alpine species and of its arctic relative, the filamentous Ancylonema nordenskioldii, underlined their distinct taxonomic position within the Zygnematophyceae.

Benzotropolone inhibitors of estradiol methylation: kinetics and in silico modeling studies.[Pubmed:15755652]

Bioorg Med Chem. 2005 Apr 1;13(7):2501-7.

Natural and synthetic benzotropolone compounds were assessed in vitro for their ability to inhibit hydroxyestradiol methylation by catechol-O-methyltransferase (COMT). The compounds were also modeled in silico with a homology model of human COMT. Purpurogallin (1), Purpurogallin carboxylic acid (2), and theaflavin-3,3'-digallate (6) were the most potent inhibitors of 2-hydroxy and 4-hydroxyestradiol methylation (IC(50) 0.22-0.50microM). Compounds 1 and 6 decreased the V(max) and increased the K(m) of COMT, indicating a mixed-type inhibition. Compounds 1 and 2 bound to COMT by inserting the six-membered ring of the benzotropolone into the active site. Decreased acidity of the hydroxyl groups on this ring or increased bulkiness reduced potency. Compound 6 bound by inserting the galloyl ester into the active site, which allowed the compound to overcome increased bulkiness and resulted in restored potency. Further studies are needed to determine the impact in vivo of COMT inhibition by these compounds.

[Separation and identification of two benzotropolones from teapigment].[Pubmed:15524291]

Zhong Yao Cai. 2004 Jun;27(6):410-1.

OBJECTIVE: To study the chemical constituents of teapigment. METHOD: Some constituents were isolated by chromatographic methods and identified by chemical constituents and their structures were elucidated by spectral data. RESULT: From teapigment, two compounds have been isolated and identified as purpurogallin (I) and Purpurogallin carboxylic acid (II). CONCLUSION: These compounds were main pigments obtained from teapigment for the first time, and likely to be active compounds of teapigment.

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