Available from stock

Pyrogallol

SKU: Y0964

Category: Building Blocks, Intermediates, Reagents

Synonyms: 2-Hydroxyresorcinol, 1,2,3-Trihydroxybenzene, 2,3-Dihydroxyphenol, Pyrogallic acid; 87-66-1
CAS-Number: C₆H₆O₃
Molecular Formula: 126.11
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥99% (GC)
Appearance: White to off-white powder
Identity: 1H-NMR

Properties

Solvents: ethanol (20 mg/ml), water (20 mg/ml), DMSO (50 mg/ml).
Melting Point: 131 - 135 °C
Boiling Point: 309 °C (lit.)

Shipping: AMBIENT
Short Term Storage: RT
Long Term Storage: RT
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at RT.

Hazard statements: H302 + H312 + H332 - H341 - H412
Precautionary statements: P273 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P308 + P313
GHS Symbol: GHS07+GHS08
Signal word: Warning
Transportation: Not dangerous goods

Description: The Polyphenol pyrogallol is a powerful naturally occuring reducing agent. Due to its oxygen radical generating property, pyrogallol is commonly used as a photographic developing agent, in hair dying industry, as an antiseptic and to calculate the amount of oxygen in the air. Pyrogallol is a potent superoxide anion (O2•-) generator. Pyrogallol causes oxidative damage and induces mutagenesis, carcinogenesis and hepatotoxicity. It impairs immune responses, inhibits phagocytosis and suppresses the proliferation due to its strong free radical generating potential. As a superoxide generator it is commonly used to investigate the role of free radicals in the biological system. It is a potent inducer of Nrf2-mediated gene expression. Pyrogallol possesses anti-bacterial, anti-fungal, anti-psoriatic anti-cancer, anti-inflammatory and neuroprotective properties. Pyrogallol induces apoptosis in lung cancer cells via the overproduction of O2•- and affects mitogen activated protein kinases (MAPKs). Pyrogallol exerts antitumor effects via S-phase arrest and inhibition of PI3K/AKT/Skp2/cMyc signaling. Pyrogallol is a neuroprotective compound shown to work as dual modulators for the treatment of AD by inhibiting aggregation or promoting dissociation of Aβ and tau. Pyrogallol is an anti-biofilm agent. It reduces biofilm formation in S. aureus and S. epidermidis in a mechanism involving induction of bacterial oxidative stress. Pyrogallol can be used as an organic building block or intermediate for synthesis of different types of sensors (for colorimettic detection) or other biological active compounds (e.g. antivirals). It is also used as a metal-complexing agent.
Smiles: OC1=C(O)C=CC=C1O
InChi Key: WQGWDDDVZFFDIG-UHFFFAOYSA-N
References: (1) E. Nicolis, et al., Int. Immunopharmacol. 8, 1672 (2008) , (2) N. Ni, et al., Bioorg. Med. Chem. Lett. 18, 1567 (2008) , (3) Y.H. Han, et al., Toxicol. In Vitro 22, 1605 (2008) , (4) Y.H. Han, et al., Chem. Biol. Interact. 177, 107 (2009) , (5) G. Upadhyay, et al., Chem. Biol. Interact. 183, 333 (2010) (Review) , (6) M.S. Baliga & J.J. Dsouza, Eur. J. Cancer Prev. 20, 225 (2011) (Review) , (7) W.H. Park, Int. J. Oncol. 49, 785 (2016) , (8) M. Abderrahim, et al., Talant 166, 349 (2017) , (9) K. Inoue, et al., Luminescence 33, 277 (2018) , (10) H. Ahn, et al., Int. J. Mol. Sci. 20, 3985 (2019) , (11) A. Anantram & M. Degani, Fut. Med. Chem. 11, 2287 (2019) (Review) , (12) H. Su, et al., Nat. Commun. 12, 3623 (2021) , (13) V. Dangi, et al., Methods 220, 79 (2023) , (14) S. Kim, et al., Biomed. Pharmacother. 168, 115770 (2023) , (15) K.H.C. Roese, et al., J. Appl. Microbiol. (Epub ahead of print) (2023)
InChi: InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H

The Polyphenol pyrogallol is a powerful naturally occuring reducing agent. Due to its oxygen radical generating property, pyrogallol is commonly used as a photographic developing agent, in hair dying industry, as an antiseptic and to calculate the amount of oxygen in the air. Pyrogallol is a potent superoxide anion (O2•-) generator. Pyrogallol causes oxidative damage and induces mutagenesis, carcinogenesis and hepatotoxicity. It impairs immune responses, inhibits phagocytosis and suppresses the proliferation due to its strong free radical generating potential. As a superoxide generator it is commonly used to investigate the role of free radicals in the biological system. It is a potent inducer of Nrf2-mediated gene expression. Pyrogallol possesses anti-bacterial, anti-fungal, anti-psoriatic anti-cancer, anti-inflammatory and neuroprotective properties. Pyrogallol induces apoptosis in lung cancer cells via the overproduction of O2•- and affects mitogen activated protein kinases (MAPKs). Pyrogallol exerts antitumor effects via S-phase arrest and inhibition of PI3K/AKT/Skp2/cMyc signaling. Pyrogallol is a neuroprotective compound shown to work as dual modulators for the treatment of AD by inhibiting aggregation or promoting dissociation of Aβ and tau. Pyrogallol is an anti-biofilm agent. It reduces biofilm formation in S. aureus and S. epidermidis in a mechanism involving induction of bacterial oxidative stress. Pyrogallol can be used as an organic building block or intermediate for synthesis of different types of sensors (for colorimettic detection) or other biological active compounds (e.g. antivirals). It is also used as a metal-complexing agent.

SKU: Y0964 Category: Building Blocks, Intermediates, Reagents

Additional information

Additional information

Synonyms	2-Hydroxyresorcinol, 1,2,3-Trihydroxybenzene, 2,3-Dihydroxyphenol, Pyrogallic acid
Purity	≥99% (GC)
Appearance	White to off-white powder
CAS-Number	87-66-1
Molecular Formula	C6H6O3
Molecular Weight	126.11
Identity	1H-NMR
Solvents	ethanol (20 mg/ml), water (20 mg/ml), DMSO (50 mg/ml).
Melting Point	131 – 135 °C
Boiling Point	309 °C (lit.)
Smiles	OC1=C(O)C=CC=C1O
InChi Key	WQGWDDDVZFFDIG-UHFFFAOYSA-N
Shipping	AMBIENT
Short Term Storage	RT
Long Term Storage	RT
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at RT.
Hazard statements	H302 + H312 + H332 – H341 – H412
Precautionary statements	P273 – P280 – P301 + P312 – P302 + P352 + P312 – P304 + P340 + P312 – P308 + P313
GHS Symbol	GHS07+GHS08
Signal word	Warning
Transportation	Not dangerous goods
References	(1) E. Nicolis, et al., Int. Immunopharmacol. 8, 1672 (2008), (2) N. Ni, et al., Bioorg. Med. Chem. Lett. 18, 1567 (2008), (3) Y.H. Han, et al., Toxicol. In Vitro 22, 1605 (2008), (4) Y.H. Han, et al., Chem. Biol. Interact. 177, 107 (2009), (5) G. Upadhyay, et al., Chem. Biol. Interact. 183, 333 (2010) (Review), (6) M.S. Baliga & J.J. Dsouza, Eur. J. Cancer Prev. 20, 225 (2011) (Review), (7) W.H. Park, Int. J. Oncol. 49, 785 (2016), (8) M. Abderrahim, et al., Talant 166, 349 (2017), (9) K. Inoue, et al., Luminescence 33, 277 (2018), (10) H. Ahn, et al., Int. J. Mol. Sci. 20, 3985 (2019), (11) A. Anantram & M. Degani, Fut. Med. Chem. 11, 2287 (2019) (Review), (12) H. Su, et al., Nat. Commun. 12, 3623 (2021), (13) V. Dangi, et al., Methods 220, 79 (2023), (14) S. Kim, et al., Biomed. Pharmacother. 168, 115770 (2023), (15) K.H.C. Roese, et al., J. Appl. Microbiol. (Epub ahead of print) (2023)
InChi	InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H
Quantity	100 g, 500 g, Bulk