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Purpurogallin

Cat No.:V12110 Purity: ≥98%
Purpurogallin is a natural phenol found in Quercus genus.
Purpurogallin
Purpurogallin Chemical Structure CAS No.: 569-77-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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1mg
5mg
10mg
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Product Description
Purpurogallin is a natural phenol found in Quercus genus. It has strong xanthine oxidase (Xanthine Oxidase) inhibitory activity, and its IC50 is 0.2 µM. Purpurogallin has antioxidant and anti~inflammatory properties.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
When applied to BV2 murine microglia activated by lipopolysaccharide (LPS), gallicin (50 or 100 µM; 7 or 25 hours) reduces the production of proinflammatory cytokines, such as interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) mRNA and protein expression [1]. In LPS-stimulated BV2 microglia, purpurogallin (100 µM; 75-120 min; BV2 murine microglia) has anti-inflammatory activities by inhibiting the phosphatidylinositol 3-kinase/Akt and mitogen-activated protein kinase signaling pathways[1].
ln Vivo
Gallicin (100–400 μg/kg; intraperitoneal injection; 48–72 hours; male Sprague-Dawley rats) inhibits the expression of TNF-α and IL-6 mRNA while also decreasing the expression of HMGB1 protein and mRNA. impact of neuroinflammation[2].
Cell Assay
RT-PCR[1]
Cell Types: BV2 mouse microglia
Tested Concentrations: 50 or 100 µM
Incubation Duration: 7 or 25 hrs (hours)
Experimental Results: Attenuated production of pro-inflammatory cytokines, including interleukin 1β (IL-1β) and tumors Necrosis factor-alpha (TNF-alpha) inhibits its mRNA and protein expression.

Western Blot Analysis[1]
Cell Types: BV2 Mouse Microglia
Tested Concentrations: 100 µM
Incubation Duration: 75 min, 90 min, 120 min
Experimental Results: Inhibition of phosphatidylinositol 3-kinase/Akt and mitogen-activated protein kinase signal path.
Animal Protocol
Animal/Disease Models: 54 male subarachnoid hemorrhage (SAH) rats (250-350 g) [2]
Doses: 100 μg/kg, 200 μg/kg, 400 μg/kg
Route of Administration: intraperitoneal (ip) injection; 48 or Results at 72 hrs (hrs (hours)): dose-dependent reduction of HMGB1 protein expression. High doses diminished TNF-α and HMGB1 mRNA levels.
References

[1]. 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]. 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]. 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.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H8O5
Molecular Weight
220.17822
Exact Mass
220.037
CAS #
569-77-7
Appearance
Light brown to brown solid powder
Density
1.74g/cm3
Boiling Point
357.9ºC at 760mmHg
Melting Point
275ºC (dec.)(lit.)
Flash Point
184.5ºC
Index of Refraction
1.79
LogP
1.022
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~454.17 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (9.45 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (9.45 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.5417 mL 22.7087 mL 45.4174 mL
5 mM 0.9083 mL 4.5417 mL 9.0835 mL
10 mM 0.4542 mL 2.2709 mL 4.5417 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Comparison of lumen cross-sectional capacities of the basilar artery (bottom panel). Top panel represents micrographs of the BAs obtained from the healthy controls (A), the SAH only rats (B), the vehicle-treated SAH rats (C), SAH rats received 100 ug/kg/day purpurogallin treatment (D), SAH rats received 200 ug/kg/day (E), and 400 ug/kg/day purpurogallin treatment (F). Standard bar = 200 μm. * P < 0.01: compared with the SAH and sham operated group. # P > 0.05: comparison between the SAH group and the controls. ##, ### P > 0.05, * P < 0.01: purpurogallin + SAH groups compared with the SAH group. Data are means ± SEM (n = 9/group).[2]. 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.
  • Bar graph depicting purpurogallin on the time-course change of proinflammatory cytokines after the induction of SAH. Data are depicted for IL-1β, IL-6, IL-8, and TNF-α at 48 hr after first SAH and 72 hr after second SAH. Data in the figure are presented as means ± SD (n = 9). ∗, ∗∗ P < 0.01, and #, ##, ### P > 0.05 when compared with the SAH group.[2]. 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.
  • High-mobility group protein B1 (HMGB1) expression on 24 hr after first SAH and 72 hr after second SAH, respectively (Western blot). (A) SAH; (B) SAH + vehicle; (C) 100 ug/kg/day purpurogallin + SAH; (D) 200 ug/kg/day purpurogallin + SAH; and (E) 400 ug/kg/day purpurogallin in SAH rats. Purpurogallin tended to decrease HMGB1 expression in 48 hr after the induction of SAH. By the end of second SAH, purpurogallin dose-dependently attenuated HMGB1 protein expression. ∗, ∗∗ P < 0.01, experimental animals compared with the SAH group. #, ##, ### P > 0.05, compared with the animals subject to SAH.[2]. 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.
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