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| | PURPUROGALLIN Basic information |
| Product Name: | PURPUROGALLIN | | Synonyms: | 2,3,4,6-tetrahydroxy-5h-benzocycloheptene-5-on;2,3,4,6-tetrahydroxy-5h-benzocycloheptene-5-one;2,3,4,6-TETRAHYDROXY-BENZOCYCLOHEPTEN-5-ONE;AKOS 209-004;PURPUROGALLIN;PURPUROGALLIN(RG);PURPUROGALLINE;BENZOCYCLOHEPTENE-5-ONE,2,3,4,6-TETRAHYDROXY- | | CAS: | 569-77-7 | | MF: | C11H8O5 | | MW: | 220.18 | | EINECS: | 209-324-9 | | Product Categories: | Tropolones;Tropolones & Azulenes | | Mol File: | 569-77-7.mol |  |
| | PURPUROGALLIN Chemical Properties |
| Melting point | 275 °C (dec.)(lit.) | | Boiling point | 321.11°C (rough estimate) | | density | 1.3824 (rough estimate) | | refractive index | 1.5140 (estimate) | | storage temp. | −20°C | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | Solid | | pka | 6.75±0.20(Predicted) | | color | Very Dark Brown | | Merck | 7946 | | Stability: | Air Sensitive | | LogP | 2.050 (est) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | RTECS | DE8380000 |
| | PURPUROGALLIN Usage And Synthesis |
| Description | Purpurogallin is a phenol that has been found in D. divisa and a derivative of pyrogallol that has diverse biological activities, including antimicrobial, antioxidant, and enzyme inhibitory properties. It is active against the Gram-positive bacteria S. aureus, methicillin-resistant S. aureus (MRSA), S. epidermidis, and B. subtilis (MICs = 11-110 μg/ml), the Gram-negative bacteria S. marcescens, P. vulgaris, K. pneumoniae, E. coli, S. typhi, and E. cloacae (MIC = 110 μg/ml for all), as well as P. falciparum strain FCB1 clone NC-1 (IC50 = 55 μM). Purpurogallin (2, 5, and 10 μM) scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in a cell-free assay and reduces hydrogen peroxide- and radiation-induced production of reactive oxygen species (ROS) in HaCaT keratinocytes. It inhibits the activity of EGFR, glutathione-S-transferase (GST), prolyl endopeptidase, and glyoxalase I (IC50s = 27.5, 8, 16, and 50 μM, respectively), as well as catechol O-methyltransferase (COMT; Ki = 0.074 μM), in cell-free assays. | | Chemical Properties | BROWN FINE CRYSTALLINE POWDER | | Uses | xanthine oxidase inhibitor, antioxidant | | Definition | ChEBI: A cyclic ketone that is 5H-benzocycloheptene bearing an oxo group at position 5 and hydroxy groups at positions 2, 3, 4 and 6. | | Enzyme inhibitor | This aglycone (FW = 220.18 g/mol) of a number of glycosides (e.g., dryophantin) from several nutgalls. Purpurogallin is a scavenger of polymorphonuclear leukocyte-derived oxyradicals and acts as a cardioprotector. Target(s): catechol O-methyltransferase; cystathionine b-synthase; glutathione-disulfide reductase; glutathione S-transferase; HIV-1 integrase; lactoylglutathione lyase, or glyoxalase I; 3-phosphoglycerate kinase; prolyl endopeptidase; protein-tyrosine kinase; and xanthine oxidase. |
| | PURPUROGALLIN Preparation Products And Raw materials |
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