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PURPUROGALLIN

Names

[ CAS No. ]:
569-77-7

[ Name ]:
PURPUROGALLIN

[Synonym ]:
2,3,4,6-Tetrahydroxy-benzocyclohepten-5-on
Purpurogalline
2,3,4,6-Tetrahydroxybenzocyclohepten-5-one
2,3,4,6-tetrahydroxy-5H-benzo[7]annulen-5-one
2,3,4,6-tetrahydroxy-5H-benzocyclohepten-5-one
2,3,4,5-tetrahydroxybenzo[7]annulen-6-one
EINECS 209-324-9
MFCD00004145

Biological Activity

[Description]:

Purpurogallin is a naturally phenol extracted from the plants of Quercus spp, has potent xanthine oxidase (XO) inhibitory activity with an IC50 of 0.2 µM. Purpurogallin has antioxidant and anti-inflammatory effects[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

[Target]

IC50: 0.2 µM (xanthine oxidase)[3]


[In Vitro]

Purpurogallin (50 or 100 µM; 7 or 25 hours; BV2 murine microglial cells) treatment attenuates the production of pro-inflammatory cytokines, including interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) by suppressing their mRNA and protein expression in LPS-stimulated BV2 microglial cells[1]. Purpurogallin (100 µM; 75-120 minutes; BV2 murine microglial cells) exhibits anti-inflammatory properties by suppressing the phosphatidylinositol 3-kinase/Akt and mitogen-activated protein kinase signaling pathways in LPS-stimulated BV2 microglial cells[1]. RT-PCR[1] Cell Line: BV2 murine microglial cells Concentration: 50 or 100 µM Incubation Time: 7 or 25 hours Result: Attenuated the production of pro-inflammatory cytokines, including interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) by suppressing their mRNA and protein expression. Western Blot Analysis[1] Cell Line: BV2 murine microglial cells Concentration: 100 µM Incubation Time: 75 minutes, 90 minutes, 120 minutes Result: Suppressed the phosphatidylinositol 3-kinase/Akt and mitogen-activated protein kinase signaling pathways.

[In Vivo]

Purpurogallin (100-400 μg/kg; intraperitoneal injection; for 48 or 72 hours; male Sprague-Dawley rats) exerts its neuroinflammation effect through the dual effect of inhibiting IL-6 and TNF-α mRNA expression and reducing HMGB1 protein and mRNA expression[2]. Animal Model: Fifty-four male Sprague-Dawley rats (250-350 g) with subarachnoid hemorrhage (SAH)[2] Dosage: 100 μg/kg, 200 μg/kg, 400 μg/kg Administration: Intraperitoneal injection; for 48 or 72 hours Result: Dose-dependently reduced HMGB1 protein expression. High dose reduced TNF-α and HMGB1 mRNA levels.

[References]

[1]. Park HY, et al. Purpurogallin exerts anti‑inflammatory effects in lipopolysaccharide‑stimulated BV2 microglial cells through the inactivation of the NF‑κB and MAPK signaling pathways. Int J Mol Med. 2013 Nov;32(5):1171-8.

[2]. Chang CZ, et al. Purpurogallin, a natural phenol, attenuates high-mobility group box 1 in subarachnoid hemorrhage induced vasospasm in a rat model. Int J Vasc Med. 2014;2014:254270.

[3]. Honda S, et al. Conversion to purpurogallin, a key step in the mechanism of the potent xanthine oxidase inhibitory activity of pyrogallol. Free Radic Biol Med. 2017 May;106:228-235.

Chemical & Physical Properties

[ Density]:
1.74g/cm3

[ Boiling Point ]:
357.9ºC at 760mmHg

[ Melting Point ]:
275ºC (dec.)(lit.)

[ Molecular Formula ]:
C11H8O5

[ Molecular Weight ]:
220.17800

[ Flash Point ]:
184.5ºC

[ Exact Mass ]:
220.03700

[ PSA ]:
97.99000

[ LogP ]:
1.02240

[ Index of Refraction ]:
1.79

MSDS

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
S26;S36

[ HS Code ]:
2914400090

Synthetic Route

Customs

[ HS Code ]: 2914400090

[ Summary ]:
2914400090 other ketone-alcohols and ketone-aldehydes。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%


Related Compounds