Pyrogallol | CAS#87-66-1

MedKoo Cat#: 328062 | Name: Pyrogallol

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pyrogallol is an organic compound that 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.

Chemical Structure

Pyrogallol

CAS#87-66-1

Theoretical Analysis

MedKoo Cat#: 328062

Name: Pyrogallol

CAS#: 87-66-1

Chemical Formula: C6H6O3

Exact Mass: 126.0317

Molecular Weight: 126.11

Elemental Analysis: C, 57.14; H, 4.80; O, 38.06

Price and Availability

Size	Price	Availability	Quantity
500g	USD 550.00	2 Weeks
1kg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Pyrogallol; 2,3-Dihydroxyphenol; Benzene-1,2,3-triol; C.I. 76515; Fouramine Brown AP; NSC 5035.

IUPAC/Chemical Name

1,2,3-Trihydroxybenzene

InChi Key

WQGWDDDVZFFDIG-UHFFFAOYSA-N

InChi Code

InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H

SMILES Code

OC1=C(O)C(O)=CC=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Pyrogallol is a superoxide anion generator and ROS inducer.

In vitro activity:

Pyrogallol inhibited human pulmonary A549 cell growth by inducing cell cycle arrest and apoptosis. Pyrogallol significantly inhibited A549 cell growth for 72 h, inducing G1 phase arrest at 24 or 48 h and apoptosis characterized by sub-G1 cells, annexin V staining, and mitochondrial membrane potential loss. It also depleted intracellular GSH and increased ROS levels, impacting cell viability. Reference: J Biochem Mol Toxicol. 2009 Jan-Feb;23(1):36-42. https://pubmed.ncbi.nlm.nih.gov/19202562/

In vivo activity:

In this study, pyrogallol demonstrated promising anti-colon cancer properties, leading to a significant reduction in tumor size comparable to the conventional drug doxorubicin. However, there were mild declines in body weight in mice treated with pyrogallol and the acetone extract of A. nilotica. Reference: Asian Pac J Cancer Prev. 2019 Sep 1;20(9):2645-2651. https://pubmed.ncbi.nlm.nih.gov/31554359/

	Solvent	mg/mL	mM
Solubility
	DMSO	25.0	198.24

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 126.11 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Su H, Yao S, Zhao W, Zhang Y, Liu J, Shao Q, Wang Q, Li M, Xie H, Shang W, Ke C, Feng L, Jiang X, Shen J, Xiao G, Jiang H, Zhang L, Ye Y, Xu Y. Identification of pyrogallol as a warhead in design of covalent inhibitors for the SARS-CoV-2 3CL protease. Nat Commun. 2021 Jun 15;12(1):3623. doi: 10.1038/s41467-021-23751-3. PMID: 34131140; PMCID: PMC8206078. 2. Han YH, Kim SH, Kim SZ, Park WH. Pyrogallol inhibits the growth of human pulmonary adenocarcinoma A549 cells by arresting cell cycle and triggering apoptosis. J Biochem Mol Toxicol. 2009 Jan-Feb;23(1):36-42. doi: 10.1002/jbt.20263. PMID: 19202562. 3. Revathi S, Hakkim FL, Ramesh Kumar N, Bakshi HA, Sangilimuthu AY, Tambuwala MM, Changez M, Nasef MM, Krishnan M, Kayalvizhi N. In Vivo Anti Cancer Potential of Pyrogallol in Murine Model of Colon Cancer. Asian Pac J Cancer Prev. 2019 Sep 1;20(9):2645-2651. doi: 10.31557/APJCP.2019.20.9.2645. PMID: 31554359; PMCID: PMC6976835. 4. Ma YD, Thiyagarajan V, Tsai MJ, Lue SI, Chia YC, Shyue SK, Weng CF. Pyrogallol abates VSMC migration via modulation of Caveolin-1, matrix metalloproteinase and intima hyperplasia in carotid ligation mouse. Environ Toxicol Pharmacol. 2016 Dec;48:63-75. doi: 10.1016/j.etap.2016.10.005. Epub 2016 Oct 15. PMID: 27768988.

In vitro protocol:

In vivo protocol:

1. Revathi S, Hakkim FL, Ramesh Kumar N, Bakshi HA, Sangilimuthu AY, Tambuwala MM, Changez M, Nasef MM, Krishnan M, Kayalvizhi N. In Vivo Anti Cancer Potential of Pyrogallol in Murine Model of Colon Cancer. Asian Pac J Cancer Prev. 2019 Sep 1;20(9):2645-2651. doi: 10.31557/APJCP.2019.20.9.2645. PMID: 31554359; PMCID: PMC6976835. 2. Ma YD, Thiyagarajan V, Tsai MJ, Lue SI, Chia YC, Shyue SK, Weng CF. Pyrogallol abates VSMC migration via modulation of Caveolin-1, matrix metalloproteinase and intima hyperplasia in carotid ligation mouse. Environ Toxicol Pharmacol. 2016 Dec;48:63-75. doi: 10.1016/j.etap.2016.10.005. Epub 2016 Oct 15. PMID: 27768988.

1: Kim JY, Lee H, Park T, Park J, Kim MH, Cho H, Youn W, Kang SM, Choi IS. Artificial Spores: Cytocompatible Coating of Living Cells with Plant-Derived Pyrogallol. Chem Asian J. 2016 Oct 5. doi: 10.1002/asia.201601237. [Epub ahead of print] PubMed PMID: 27706902. 2: Ma YD, Thiyagarajan V, Tsai MJ, Lue SI, Chia YC, Shyue SK, Weng CF. Pyrogallol abates VSMC migration via modulation of Caveolin-1, matrix metalloproteinase and intima hyperplasia in carotid ligation mouse. Environ Toxicol Pharmacol. 2016 Oct 15;48:63-75. doi: 10.1016/j.etap.2016.10.005. [Epub ahead of print] PubMed PMID: 27768988. 3: Honda S, Masuda T. Identification of Pyrogallol in the Ethyl Acetate-Soluble Part of Coffee as the Main Contributor to Its Xanthine Oxidase Inhibitory Activity. J Agric Food Chem. 2016 Oct 10. [Epub ahead of print] PubMed PMID: 27680749. 4: Wang J, Liu Q, Feng J, Lv JP, Xie SL. Effect of high-doses pyrogallol on oxidative damage, transcriptional responses and microcystins synthesis in Microcystis aeruginosa TY001 (Cyanobacteria). Ecotoxicol Environ Saf. 2016 Dec;134P1:273-279. doi: 10.1016/j.ecoenv.2016.09.010. PubMed PMID: 27643987. 5: Lima VN, Oliveira-Tintino CD, Santos ES, Morais LP, Tintino SR, Freitas TS, Geraldo YS, Pereira RL, Cruz RP, Menezes IR, Coutinho HD. Antimicrobial and enhancement of the antibiotic activity by phenolic compounds: Gallic acid, caffeic acid and pyrogallol. Microb Pathog. 2016 Oct;99:56-61. doi: 10.1016/j.micpath.2016.08.004. PubMed PMID: 27497894. 6: Nemec MJ, Kim H, Marciante AB, Barnes RC, Talcott ST, Mertens-Talcott SU. Pyrogallol, an absorbable microbial gallotannins-metabolite and mango polyphenols (Mangifera Indica L.) suppress breast cancer ductal carcinoma in situ proliferation in vitro. Food Funct. 2016 Sep 14;7(9):3825-33. doi: 10.1039/c6fo00636a. PubMed PMID: 27491891. 7: Patil RS, Zhang C, Atwood JL. Process Development for Separation of Conformers from Derivatives of Resorcin[4]arenes and Pyrogallol[4]arenes. Chemistry. 2016 Oct 17;22(43):15202-15207. doi: 10.1002/chem.201603090. PubMed PMID: 27463858. 8: Park WH. Pyrogallol induces the death of human pulmonary fibroblast cells through ROS increase and GSH depletion. Int J Oncol. 2016 Aug;49(2):785-92. doi: 10.3892/ijo.2016.3543. PubMed PMID: 27278810. 9: Shah SN, Li H, Lin JM. Enhancement of periodate-hydrogen peroxide chemiluminescence by nitrogen doped carbon dots and its application for the determination of pyrogallol and gallic acid. Talanta. 2016 Jun 1;153:23-30. doi: 10.1016/j.talanta.2016.02.056. PubMed PMID: 27130085. 10: Zhang QA, Wang X, Song Y, Fan XH, García Martín JF. Optimization of Pyrogallol Autoxidation Conditions and Its Application in Evaluation of Superoxide Anion Radical Scavenging Capacity for Four Antioxidants. J AOAC Int. 2016 Mar-Apr;99(2):504-11. doi: 10.5740/jaoacint.15-0223. PubMed PMID: 26997318. 11: Yariv-Shoushan S, Cohen Y. Encapsulated or Not Encapsulated? Ammonium Salts Can Be Encapsulated in Hexameric Capsules of Pyrogallol[4]arene. Org Lett. 2016 Mar 4;18(5):936-9. doi: 10.1021/acs.orglett.5b03655. PubMed PMID: 26886435. 12: Ramos II, Gregório BJ, Barreiros L, Magalhães LM, Tóth IV, Reis S, Lima JL, Segundo MA. Programmable flow system for automation of oxygen radical absorbance capacity assay using pyrogallol red for estimation of antioxidant reactivity. Talanta. 2016 Apr 1;150:599-606. doi: 10.1016/j.talanta.2015.12.061. PubMed PMID: 26838448. 13: Avram L, Goldbourt A, Cohen Y. Hexameric Capsules Studied by Magic Angle Spinning Solid-State NMR Spectroscopy: Identifying Solvent Molecules in Pyrogallol[4]arene Capsules. Angew Chem Int Ed Engl. 2016 Jan 18;55(3):904-7. doi: 10.1002/anie.201506683. PubMed PMID: 26634640. 14: Baruah K, Duy Phong HP, Norouzitallab P, Defoirdt T, Bossier P. The gnotobiotic brine shrimp (Artemia franciscana) model system reveals that the phenolic compound pyrogallol protects against infection through its prooxidant activity. Free Radic Biol Med. 2015 Dec;89:593-601. doi: 10.1016/j.freeradbiomed.2015.10.397. PubMed PMID: 26459033. 15: Attia AK, Salem WM, Mona AM. Voltammetric Assay of Metformin Hydrochloride Using Pyrogallol Modified Carbon Paste Electrode. Acta Chim Slov. 2015;62(3):588-94. PubMed PMID: 26454593. 16: Yalamati P, Bhongir AV, Karra M, Beedu SR. Comparative Analysis of Urinary Total Proteins by Bicinchoninic Acid and Pyrogallol Red Molybdate Methods. J Clin Diagn Res. 2015 Aug;9(8):BC01-4. doi: 10.7860/JCDR/2015/13543.6313. PubMed PMID: 26435938; PubMed Central PMCID: PMC4576529. 17: Hugo E, Reyes J, Montupil E, Bridi R, Lissi E, Denicola A, Rubio MA, López-Alarcón C. Kinetics of the Reaction of Pyrogallol Red, a Polyphenolic Dye, with Nitrous Acid: Role of NO and NO2. Molecules. 2015 Jun 8;20(6):10582-93. doi: 10.3390/molecules200610582. PubMed PMID: 26060920. 18: Patil RS, Kumari H, Barnes CL, Atwood JL. Anion- and Spacer-Directed Host-Guest Complexes of Bipyridine with Pyrogallol[4]arene. Chemistry. 2015 Jul 13;21(29):10431-5. doi: 10.1002/chem.201406574. PubMed PMID: 26046450. 19: Mendes V, Vilaça R, de Freitas V, Ferreira PM, Mateus N, Costa V. Effect of myricetin, pyrogallol, and phloroglucinol on yeast resistance to oxidative stress. Oxid Med Cell Longev. 2015;2015:782504. doi: 10.1155/2015/782504. PubMed PMID: 26000072; PubMed Central PMCID: PMC4427115. 20: Kirita M, Tanaka Y, Tagashira M, Kanda T, Maeda-Yamamoto M. Cloning and characterization of a novel O-methyltransferase from Flammulina velutipes that catalyzes methylation of pyrocatechol and pyrogallol structures in polyphenols. Biosci Biotechnol Biochem. 2015;79(7):1111-8. doi: 10.1080/09168451.2015.1015955. PubMed PMID: 25754602.