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)

pka

6.75±0.20(Predicted)

form 

Solid

color 

Very Dark Brown

Merck 

7946

Stability:

Air Sensitive

LogP

2.050 (est)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DE8380000

MSDS

• Language:English Provider:SigmaAldrich

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; K_i = 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.

References

[1] Y INAMORI. Biological activity of purpurogallin.[J]. Bioscience, Biotechnology, and Biochemistry, 1997, 61 5: 890-892. DOI: 10.1271/bbb.61.890
[2] AO XUAN ZHEN. Purpurogallin Protects Keratinocytes from Damage and Apoptosis Induced by Ultraviolet B Radiation and Particulate Matter 2.5.[J]. Biomolecules & Therapeutics, 2019, 27 4: 395-403. DOI: 10.4062/biomolther.2018.151
[3] JOHN F. BARNARD  John F H  David L Vander Jagt. Small molecule probes of glyoxalase I and glyoxalase II[J]. Biochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology, 1994, 1208 1: Pages 127-135. DOI: 10.1016/0167-4838(94)90169-4
[4] M ABOU-KARAM  W T S. Inhibition of oncogene product enzyme activity as an approach to cancer chemoprevention. Tyrosine-specific protein kinase inhibition by purpurogallin from Quercus sp. nutgall.[J]. Phytotherapy Research, 1999, 13 4: 337-340. DOI: 10.1002/(sici)1099-1573(199906)13:4<337::aid-ptr451>3.0.co;2-j
[5] MUKUL DAS  Hasan M  David R Bickers. Plant phenols as invitro inhibitors of glutathione S-transferase(s)[J]. Biochemical and biophysical research communications, 1984, 120 2: Pages 427-433. DOI: 10.1016/0006-291x(84)91271-3
[6] VESER J. Kinetics and inhibition studies of catechol O-methyltransferase from the yeast Candida tropicalis.[J]. Journal of Bacteriology, 1987, 169 8: 3696-3700. DOI: 10.1128/jb.169.8.3696-3700.1987

PURPUROGALLIN(569-77-7)Related Product Information

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