Pyrogallol

• CAT Number: R020327
• CAS Number: 87-66-1
• Molecular Formula: C6H6O3
• Molecular Weight: 126.111
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: benzene-1,2,3-triol
• InChI: InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H
• InChIKey: WQGWDDDVZFFDIG-UHFFFAOYSA-N
• SMILES: C1=CC(=C(C(=C1)O)O)O

Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a white solid although because of its sensitivity toward oxygen, samples are typically brownish. Pyrogallol can be used in hair dying, dying of suturing materials and for oxygen absorption in gas analysis. It also has antiseptic properties. Pyrogallol was also used as a developing agent in black-and-white developers, but its use is largely historical except for special purpose applications. (Hydroquinone is more commonly used today.)

Reference

1:Self-assembly of magnesium-seamed hexameric pyrogallol[4]arene nanocapsules. Zhang C, Patil RS, Li T, Barnes CL, Atwood JL.Chem Commun (Camb). 2017 Apr 13;53(31):4312-4314. doi: 10.1039/c7cc01208j. PMID: 28322394 2:Conversion to purpurogallin, a key step in the mechanism of the potent xanthine oxidase inhibitory activity of pyrogallol. Honda S, Fukuyama Y, Nishiwaki H, Masuda A, Masuda T.Free Radic Biol Med. 2017 May;106:228-235. doi: 10.1016/j.freeradbiomed.2017.02.037. Epub 2017 Feb 20. PMID: 28223196 3:A novel pyrogallol red-based assay to assess catalase activity: Optimization by response surface methodology. Abderrahim M, Arribas SM, Condezo-Hoyos L.Talanta. 2017 May 1;166:349-356. doi: 10.1016/j.talanta.2017.01.059. Epub 2017 Jan 27. PMID: 28213244 4:Controlled 2D Assembly of Nickel-Seamed Hexameric Pyrogallol[4]arene Nanocapsules. Zhang C, Patil RS, Liu C, Barnes CL, Atwood JL.J Am Chem Soc. 2017 Mar 1;139(8):2920-2923. doi: 10.1021/jacs.7b00037. Epub 2017 Feb 14. PMID: 28177625 5:Effects of Pyrogallol on Growth and Cytotoxicity of Wild-Type and katG Mutant Strains of Vibrio vulnificus. Lim JY, Kim CM, Rhee JH, Kim YR.PLoS One. 2016 Dec 9;11(12):e0167699. doi: 10.1371/journal.pone.0167699. eCollection 2016. PMID: 27936080 Free PMC Article6:Novel MWCNTs/graphene oxide/pyrogallol composite with enhanced sensitivity for biosensing applications. Mohamed MA, Yehia AM, Banks CE, Allam NK.Biosens Bioelectron. 2017 Mar 15;89(Pt 2):1034-1041. doi: 10.1016/j.bios.2016.10.025. Epub 2016 Oct 11. PMID: 27818046 7:Artificial Spores: Cytocompatible Coating of Living Cells with Plant-Derived Pyrogallol. Kim JY, Lee H, Park T, Park J, Kim MH, Cho H, Youn W, Kang SM, Choi IS.Chem Asian J. 2016 Nov 22;11(22):3183-3187. doi: 10.1002/asia.201601237. Epub 2016 Oct 26. PMID: 27706902 8:Pyrogallol abates VSMC migration via modulation of Caveolin-1, matrix metalloproteinase and intima hyperplasia in carotid ligation mouse. Ma YD, Thiyagarajan V, Tsai MJ, Lue SI, Chia YC, Shyue SK, Weng CF.Environ Toxicol Pharmacol. 2016 Dec;48:63-75. doi: 10.1016/j.etap.2016.10.005. Epub 2016 Oct 15. PMID: 27768988 9:Identification of Pyrogallol in the Ethyl Acetate-Soluble Part of Coffee as the Main Contributor to Its Xanthine Oxidase Inhibitory Activity. Honda S, Masuda T.J Agric Food Chem. 2016 Oct 10. [Epub ahead of print] PMID: 27680749 10:Effect of high-doses pyrogallol on oxidative damage, transcriptional responses and microcystins synthesis in Microcystis aeruginosa TY001 (Cyanobacteria). Wang J, Liu Q, Feng J, Lv JP, Xie SL.Ecotoxicol Environ Saf. 2016 Dec;134P1:273-279. doi: 10.1016/j.ecoenv.2016.09.010. Epub 2016 Sep 16. PMID: 27643987