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569-77-7

569-77-7 structure
569-77-7 structure
  • Name: PURPUROGALLIN
  • Chemical Name: purpurogallin
  • CAS Number: 569-77-7
  • Molecular Formula: C11H8O5
  • Molecular Weight: 220.17800
  • Catalog: Research Areas Cancer
  • Create Date: 2018-02-15 08:00:00
  • Modify Date: 2024-01-09 16:39:32
  • 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].

Name purpurogallin
Synonyms 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
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
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.

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
Hazard Codes Xi
Risk Phrases 36/37/38
Safety Phrases S26;S36
HS Code 2914400090
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%