| Identification | Back Directory | [Name]
PURPUROGALLIN | [CAS]
569-77-7 | [Synonyms]
C09964
MLS0007
NSC 35676
NSC 646653
CHEBI:8647
AIDS138915
AIDS-138915
AKOS 209-004
KBio1_001351
KBio2_000828
KBio2_003396
KBio2_005964
KBio3_001663
SPBio_000424
KBioSS_000828
Oprea1_685478
PURPUROGALLIN
DivK1c_006407
PURPUROGALLINE
SPECTRUM210505
Spectrum_000348
NCGC00095229-01
NCGC00095229-02
Spectrum2_000582
Spectrum4_001547
PURPUROGALLIN(RG)
PURPUROGALLIN, TECH.
SDCCGMLS-0066536.P001
1,2,3,9-tetrahydroxy-8-benzo[7]annulenone
1,2,3,9-tetrahydroxybenzo[7]annulen-8-one
2,3,4,6-TETRAHYDROXY-BENZOCYCLOHEPTEN-5-ONE
BENZOCYCLOHEPTENE-5-ONE,2,3,4,6-TETRAHYDROXY-
2,3,4,6-tetrahydroxy-5H-benzo[7]annulen-5-one
2,3,4,6-tetrahydroxy-5h-benzocycloheptene-5-on
2,3,4,6-tetrahydroxy-5h-benzocycloheptene-5-one
2,3,4,6-Tetrahydroxy-5H-benzo[a]cyclohepten-5-one | [EINECS(EC#)]
209-324-9 | [Molecular Formula]
C11H8O5 | [MDL Number]
MFCD00004145 | [MOL File]
569-77-7.mol | [Molecular Weight]
220.18 |
| Chemical Properties | Back Directory | [Appearance]
BROWN FINE CRYSTALLINE POWDER | [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 | [Cosmetics Ingredients Functions]
HUMECTANT
SKIN CONDITIONING | [LogP]
2.050 (est) |
| Hazard Information | Back Directory | [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. | [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. | [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 |
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Energy Chemical
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Maya High Purity Chemicals
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