87-66-1 Usage
Description
Pyrogallol is a natural oxidant that can generate superoxide (O2-) in alkaline solutions through autoxidation to a semiquinone radical. Importantly, the semiquinone radical can react with O2- in an acidic environment to produce a quinone and H2O2. Pyrogallol autoxidation is used in superoxide dismutase activity assays. It can also be used in assays to assess antioxidant capacity. Pyrogallol is used in some biological systems as an O2- scavenger. In other biological systems, it is used as an O2- generator. Pyrogallol effectively scavenges DPPH radical and ABTS+ in vitro. Pyrogallol is a product of tannin degradation to gallic acid by ruminant microbes and has hepatotoxic and nephrotoxic effects in vivo.
Chemical Properties
Different sources of media describe the Chemical Properties of 87-66-1 differently. You can refer to the following data:
1. White or nearly white needle- or
leaf-shaped crystals or crystalline powder.Pyrogallol is practically odorless.
2. white crystalline solid
Uses
Different sources of media describe the Uses of 87-66-1 differently. You can refer to the following data:
1. Pyrogallol possesses importance as a spectrophotometric reagent in the determination of niobium and tantalum. The absorptions of niobium and tantalum complexes are usually measured at 340 and 335 nm, respectively. The niobium complex is formed in slightly acidic medium, and the tantalum complex in strongly acidic medium (4 N HC1). The absorption spectra are pH-dependen.
2. Complexing agent; reducing agent; alkaline solution indicator for gaseous oxygen.
3. Pyrogallol is used in the manufacture of various dyes; in dyeing furs, hairs, and feathers; for staining leather; in engraving;as a developer in photography; and as an analytical reagent..
Production Methods
Pyrogallol is prepared by heating dried gallic acid at about
200°C with the loss of carbon dioxide or by the
chlorination of cyclohexanol to tetrachlorocyclohexanone,
followed by hydrolysis.
Definition
ChEBI: A benzenetriol carrying hydroxy groups at positions 1, 2 and 3.
General Description
Odorless white to gray solid. Sinks and mixes with water.
Air & Water Reactions
Turns gray on exposure to light or air. Water soluble.
Reactivity Profile
Pyrogallol is a strong reducing agent. Reacts with alkalis, NH3, antipyrine, camphor, phenol, iron and lead salts, iodine, lime water, menthol and KMnO4.
Hazard
Toxic by ingestion and skin absorption.
Health Hazard
Different sources of media describe the Health Hazard of 87-66-1 differently. You can refer to the following data:
1. The toxic symptoms are similar to those of phenol. It can enter the body by absorption through skin and ingestion. The poisoning effects are nausea, vomiting, gastritis, hemolysis, methemoglobinemia, kidney and liver damage, convulsions, and congestion of lungs. High doses can cause death. Ingestion of 2–3 g of solid can be fatal to humans. The LD50 values varied widely in species. The oral LD50 value in mice is about 300 mg/kg.
2. Inhalation of dust causes irritation of nose and throat. Ingestion may cause severe gastrointestinal irritation, convulsions, circulatory collapse, and death. Contact with eyes causes irritation. Skin contact can cause local discoloration, irritation, eczema, and death; repeated contact can cause sensitization.
Fire Hazard
Pyrogallol is probably combustible.
Contact allergens
Pyrogallol belongs to the phenols group. It is an old
photograph developer and a low sensitizer in hair dyes.
Biochem/physiol Actions
Pyrogallol also referred to as 1,2,3-trihydroxybenzene inhibits the response to nitric oxide (NO) in the rat anococcygeus muscle.
Safety Profile
Human poison by ingestion and subcutaneous routes. An experimental poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported.
1 198 PPRSOO PYROSULFURYL CHLORIDE
Readdy absorbed through the skin. Human systemic effects by ingestion: convulsions, dyspnea, gastrointestinal effects. A severe skin and eye irritant. Incompatible with alkalies, NH3, antipyrine, phenol, iron and lead salts, iodine, KMn04. When heated to decomposition it emits acrid smoke and irritating fumes. Used as a topical antibacterial agent, as an intermediate, hair dye component, and analytical reagent.
Carcinogenicity
Pyrogallol was not carcinogenic
in mouse and rabbit chronic dermal studies. Mice were
treated twice weekly with pyrogallol in acetone (50%) on
the shaved flank for life. There was no increase in dermal or
systemic tumors. A similar study in rabbits also
revealed no skin tumors, although positive controls showed
an increase in tumors in both mice and rabbits.
Pyrogallol was considered to be cocarcinogenic when
administered dermally three times a week together with
the skin carcinogen benzo[a]pyrene for 440 days;
pyrogallol administered alone caused no increase in skin
tumors.
Check Digit Verification of cas no
The CAS Registry Mumber 87-66-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 87-66:
(4*8)+(3*7)+(2*6)+(1*6)=71
71 % 10 = 1
So 87-66-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H
87-66-1Relevant articles and documents
Study on in Vitro Preparation and Taste Properties of N-Ethyl-2-Pyrrolidinone-Substituted Flavan-3-Ols
Han, Zisheng,Ho, Chi-Tang,Jiang, Zongde,Lai, Guoping,Qin, Chunyin,Wan, Xiaochun,Wen, Mingchun,Zhai, Xiaoting,Zhang, Hui,Zhang, Liang
, (2022/04/07)
N-ethyl-2-pyrrolidinone-substituted flavan-3-ols (EPSFs) were prepared by an in vitro model reaction, and the taste thresholds of EPSFs and their dose-over-threshold factors in large-leaf yellow tea (LYT) were investigated. The effects of initial reactant
Method for promoting iron-catalyzed oxidation of aromatic compound carbon - hydrogen bond to synthesize phenol by ligand
-
Paragraph 0106-0107; 0129, (2021/09/21)
The method comprises the following steps: iron is used as - a catalyst metal; a sulfur-containing amino acid or cystine-derived dipeptide is a ligand; and under the common action of hydrogen peroxide as an oxidizing agent, an aromatic compound is synthesized to prepare a phenol. Under the action of an acid as an accelerant and hydrogen peroxide as an oxidizing agent, the aryl carbon - hydrogen bond is directly hydroxylated to form a phenolic compound, and the method for preparing the phenol by the catalytic oxidation reaction has a plurality of advantages. The reaction raw materials, the oxidant and the promoter are wide in source, low in price, environment-friendly and good in stability. The aromatic compound carbon - hydrogen bonds directly participate in the reaction to react in one step to form phenol. The reaction condition is mild, the functional group compatibility and the application range are wide. The reaction selectivity is good; under the optimized reaction conditions, the target product separation yield can reach 85%.
RETRACTED ARTICLE: Selective photocatalytic conversion of guaiacol using g-C3N4 metal free nanosheets photocatalyst to add-value products
Rojas,Espinoza-Villalobos,Salazar,Escalona,Contreras,Melin,Laguna-Bercero,Sánchez-Arenillas,Vergara,Caceres-Jensen,Rodriguez-Becerra,Barrientos
, (2021/09/06)
Valorization of lignin into high valuable chemical is a critical challenge. Its availability is a key factor for the development of viable lignocellulosic processes to replace fossil derived compounds. In this work, new insights on the high photocatalytic conversion of guaiacol (82%) as a lignin model compound was achieved, also, high selectivity to p-benzoquinone (59%), catechol (27%), and pyrogallol (6%) was obtained using metal-free pyrolyzed g-C3N4 under visible light irradiation. To highlight the new insights, experimental parameters were modified to control the reaction mechanism to increase selectivity and photo-conversion. g-C3N4 photocatalyst was synthesized through urea calcination at 550 °C and the photocatalytic performance was assessed in terms of pyrolysis time, where higher time resulted in better photocatalytic activity. This effect was attributed to smaller structures and therefore better quantum confinement of the charges. The oxidation was promoted by [rad]OH radicals, which were detected through EPR operando mode and the addition of radical scavengers. A reaction pathway was proposed, in which the ·OH attacks guaiacol through a methoxy group. The photocatalytic reaction can be tuned using external oxidant agents such as O2 and/or H2O2 to promote certain radical formation, enhancing conversion rates and promoting selectivity for a specific product, where yield shifting from p-benzoquinone to pyrogallol was experimentally observed.
