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Pyrogallol

$52

  • Brand : BIOFRON

  • Catalogue Number : BD-P0284

  • Specification : 98.0%(HPLC)

  • CAS number : 87-66-1

  • PUBCHEM ID : 1057

  • Volume : 500mg

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Catalogue Number

BD-P0284

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

Appearance

White crystalline powder

Botanical Source

Structure Type

Simple Phenolic Compounds

Category

Standards;Natural Pytochemical;API

SMILES

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

Synonyms

1,2,3-trishydroxybenzene/trihydroxybenzene/1,2,3-Trihydroxybenzene/Pyrogallol/PYROGALL/benzene-1,2,3-triol/Fourrine 85/Benzol-1,2,3-triol/pyrogallic/1,2,3-Benzenetriolgallol/Piral/1,2,3-trihydroxy-benzene/Fourrine PG/Phloroglucinol Impurity 1

IUPAC Name

benzene-1,2,3-triol

Applications

Pyrogallol is a polyphenol compound, which has anti-fungal and anti-psoriatic properties. Pyrogallol is a reductant that is able to generate free radicals, in particular superoxide anions.

Density

1.453

Solubility

Methanol; Water

Flash Point

164.3±16.9 °C

Boiling Point

309 ºC

Melting Point

131-135 ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2907290000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:87-66-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29247864

Abstract

Pyrogallol is a simple phenolic compound that serves as an attractive chemical with broad applications in food, agricultural, dyeing, printing, cosmetic, photography, chemical and pharmaceutical industries owing to its antioxidant, antibacterial, antiseptic, anticancer, oxygen-absorbing and strong reducing properties. Currently, pyrogallol is commercially produced by thermal decarboxylation of gallic acid under high temperature and pressure. However, this process is limited by the inaccessible raw material, the strict reaction conditions and the relatively low product yield. Here, we report establishment of a novel and efficient biosynthetic pathway for the synthesis of pyrogallol. First, we identified and characterized an efficient 2,3-dihydroxybenzoic acid (2,3-DHBA) 1-monoxygenase from a series of oxygenases and hydroxylases based on the structural similarity in the substrates and products, which enabled non-natural production of pyrogallol from 2,3-DHBA. Then, over-expression of 2,3-DHBA synthase and 2,3-DHBA 1-monoxygenase achieved synthesis of pyrogallol in Escherichia coli, with a titer of 201.52mg/L at 24h. Further optimizations by enhancement of the carbon flux through the shikimate pathway, modular optimization of the pathway and alleviation of the pyrogallol autoxidation boosted pyrogallol titer to 1035.75mg/L in shake flask experiments. This work constructed an efficient microbial platform for gram per liter level production of pyrogallol, indicating the great potential for industrial biomanufacturing of pyrogallol.

Copyright © 2017 International Metabolic Engineering Society. Published by Elsevier Inc. All rights reserved.

KEYWORDS

Escherichia coli; Metabolic engineering; Phenolic compounds; Pyrogallol; Shikimate pathway

Title

Microbial synthesis of pyrogallol using genetically engineered Escherichia coli.

Author

Wang J1, Shen X1, Yuan Q2, Yan Y3.

Publish date

2018 Jan

PMID

31554359

Abstract

BACKGROUND:
Colon cancer is aggressive and it causes 0.5 million deaths per year. Practicing natural medicines for cancer treatment is safer than conventional drugs. World health organization emphasizes on the importance of practicing natural medicines and developing natural product based drugs for cancer treatment. Recently we reported an anti colon cancer activity associated with pyrogallol isolated from medicinal plant Acacia nilotica in HT-29 cells in vitro. To extend our observation in this study we evaluated in vivo colon tumor remission property of acetone extract of A. nilotica (ACE) and pyrogallol.

MATERIALS AND METHODS:
In vivo toxicity of ACE and pyrogallol was assessed and In vivo tumor remission activity of ACE and pyrogallol was determined in murine model.

RESULTS:
Mice were tolerated different doses of ACE and pyrogallol. Tumor size was considerably reduced in pyrogallol treated mice similar to doxorubicin. Tumor bearing mice treated with ACE and pyrogallol showed mild decline in body weight.

CONCLUSION:
Pyrogallol was found to be an effective anti colon cancer agent with less toxicity.

KEYWORDS

Acacia nilotica; Colon cancer; Helicobacter pylori; Pyrogallol; Toxicity

Title

In Vivo Anti Cancer Potential of Pyrogallol in Murine Model of Colon Cancer.

Author

Revathi S1, Hakkim FL2,3, Ramesh Kumar N4, Bakshi HA5,6, Sangilimuthu AY7, Tambuwala MM5, Changez M8, Nasef6, Krishnan M4, Kayalvizhi N1.

Publish date

2019 Sep 1

PMID

31426282

Abstract

Though Pyrogallol, one of the natural polyphenols, was known to have anti-inflammatory and antitumor effects in breast and colon cancers, the underlying antitumor mechanisms of Pyrogallol, still remain unclear so far. Here, the antitumor mechanisms of Pyrogallol were elucidated in Hep3B and Huh7 hepatocellular carcinoma cells (HCCs). Pyrogallol showed significant cytotoxicity and reduced the number of colonies in Hep3B and Huh7 cells. Interestingly, Pyrogallol induced S-phase arrest and attenuated the protein expression of CyclinD1, Cyclin E, Cyclin A, c-Myc, S-phase kinase-associated protein 2 (Skp2), p-AKT, PI3K, increased the protein expression of p27, and also reduced the fluorescent expression of Cyclin E in Hep3B and Huh7 cells. Furthermore, Pyrogallol disturbed the interaction between Skp2, p27, and c-Myc in Huh7 cells. Notably, Pyrogallol upregulated miRNA levels of miR-134, and conversely, miR-134 inhibition rescued the decreased expression levels of c-Myc, Cyclin E, and Cyclin D1 and increased the expression of p27 by Pyrogallol in Huh7 cells. Taken together, our findings provide insight that Pyrogallol exerts antitumor effects in HCCs via miR-134 activation-mediated S-phase arrest and inhibition of PI3K/AKT/Skp2/cMyc signaling as a potent anticancer candidate.

KEYWORDS

Pyrogallol; S-phase arrest; Skp2; c-Myc; miR-134

Title

Antitumor Effect of Pyrogallol via miR-134 Mediated S Phase Arrest and Inhibition of PI3K/AKT/Skp2/cMyc Signaling in Hepatocellular Carcinoma.

Author

Ahn H1, Im E1, Lee DY2, Lee HJ1, Jung JH1, Kim SH3.

Publish date

2019 Aug 16