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Pyrogallol

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Pyrogallol Basic information
Product Name:Pyrogallol
Synonyms:1,2,3-Trihydroxybenzen;1,2,3-trihydroxy-benzen;1,2,3-trihydroxybenzen(czech);1,2,3-trihydroxybenzene(pyrogallol);2,3-Dihydroxyphenol;Benzene, 1,2,3-trihydroxy-;benzene-1,2,3-triol;C.I. Oxidation Base 32
CAS:87-66-1
MF:C6H6O3
MW:126.11
EINECS:201-762-9
Product Categories:ACS Grade;Building Blocks;Chemical Synthesis;Essential Chemicals;Inorganic Salts;Organic Building Blocks;Oxygen Compounds;FINE Chemical & INTERMEDIATES;Aromatic Hydrocarbons (substituted) & Derivatives;Nutrition Research;Phytochemicals by Plant (Food/Spice/Herb);s wort);Pharmacopoeia;Pharmacopoeia A-Z;Food additive , Antioxidant anticorrosive;Polyols;Research Essentials;Solutions and Reagents;87-66-1
Mol File:87-66-1.mol
Pyrogallol Structure
Pyrogallol Chemical Properties
Melting point 43-47 °C(lit.)
Boiling point 309 °C
bulk density600kg/m3
density 1.112 g/mL at 25 °C(lit.)
vapor density 4.4 (vs air)
vapor pressure 10 mm Hg ( 167.7 °C)
refractive index n20/D 1.387
Fp >230 °F
storage temp. Store below +30°C.
solubility water: soluble
pkapK1:9.03(0);pK2:11.63(+1) (25°C)
form Very Fine Crystalline Powder
color White
PH4-5 (50g/l, H2O, 20℃)
Water Solubility 400 g/L (25 ºC)
Sensitive Light Sensitive
Merck 14,8000
BRN 907431
Stability:Stable, but decolourises in light. Combustible. Incompatible with strong oxidising agents, alkalies, metal oxides, ammonia, antipyrine, phenol, iodine, lime water, menthol, potassium permanganate, strong bases.
Major Applicationpharmaceutical (small molecule)
Cosmetics Ingredients FunctionsHAIR DYEING
InChI1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H
InChIKeyWQGWDDDVZFFDIG-UHFFFAOYSA-N
SMILESOc1cccc(O)c1O
LogP-0.47
CAS DataBase Reference87-66-1(CAS DataBase Reference)
NIST Chemistry Reference1,2,3-Benzenetriol(87-66-1)
EPA Substance Registry SystemPyrogallol (87-66-1)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-52/53-68-40-36/38
Safety Statements 22-24/25-61-36/37-26
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS UX2800000
8
TSCA TSCA listed
HS Code 2907 29 00
HazardClass 6.1
PackingGroup III
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Aquatic Chronic 3
Muta. 2
Hazardous Substances Data87-66-1(Hazardous Substances Data)
ToxicityLD50 orally in rabbits: 1.6 g/kg (Dollahite)
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
Pyrogallol Usage And Synthesis
DescriptionPyrogallol 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 PropertiesWhite or nearly white needle- or leaf-shaped crystals or crystalline powder.Pyrogallol is practically odorless.
Chemical Propertieswhite crystalline solid
Uses

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.

UsesComplexing agent; reducing agent; alkaline solution indicator for gaseous oxygen.
UsesPyrogallol 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 MethodsPyrogallol 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.
DefinitionChEBI: A benzenetriol carrying hydroxy groups at positions 1, 2 and 3.
General DescriptionOdorless white to gray solid. Sinks and mixes with water.
Air & Water ReactionsTurns gray on exposure to light or air. Water soluble.
Reactivity ProfilePyrogallol is a strong reducing agent. Reacts with alkalis, NH3, antipyrine, camphor, phenol, iron and lead salts, iodine, lime water, menthol and KMnO4.
HazardToxic by ingestion and skin absorption.
Health HazardThe 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.
Health HazardInhalation 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 HazardPyrogallol is probably combustible.
Contact allergensPyrogallol belongs to the phenols group. It is an old photograph developer and a low sensitizer in hair dyes.
Biochem/physiol ActionsPyrogallol also referred to as 1,2,3-trihydroxybenzene inhibits the response to nitric oxide (NO) in the rat anococcygeus muscle.
Safety ProfileHuman 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.
CarcinogenicityPyrogallol 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.
References[1] LUC MAGNANI  Jean C H  Emile M Gaydou. Spectrophotometric measurement of antioxidant properties of flavones and flavonols against superoxide anion[J]. Analytica Chimica Acta, 2000, 411 1: Pages 209-216. DOI: 10.1016/s0003-2670(00)00717-0
[2] LI* X. Improved Pyrogallol Autoxidation Method: A Reliable and Cheap Superoxide-Scavenging Assay Suitable for All Antioxidants[J]. Journal of Agricultural and Food Chemistry, 2012, 60 25: 6418-6424. DOI: 10.1021/jf204970r
[3] CHI-SEN CHANG  Guia H L  Chia Lin Chang. Reactive oxygen species scavenging activities in a chemiluminescence model and neuroprotection in rat pheochromocytoma cells by astaxanthin, beta-carotene, and canthaxanthin[J]. Kaohsiung Journal of Medical Sciences, 2013, 29 8: Pages 412-421. DOI: 10.1016/j.kjms.2012.12.002
[4] TINGTING WANG. Fisetin Protects DNA Against Oxidative Damage and Its Possible Mechanism.[J]. Advanced pharmaceutical bulletin, 2016, 6 2: 267-270. DOI: 10.15171/apb.2016.037
[5] AMY L SINDLER. Age and exercise training alter signaling through reactive oxygen species in the endothelium of skeletal muscle arterioles.[J]. Journal of applied physiology, 2013: 681-693. DOI: 10.1152/japplphysiol.00341.2012
[6] V MORENO-MANZANO. Selective involvement of superoxide anion, but not downstream compounds hydrogen peroxide and peroxynitrite, in tumor necrosis factor-alpha-induced apoptosis of rat mesangial cells.[J]. The Journal of Biological Chemistry, 2000, 275 17: 12684-12691. DOI: 10.1074/jbc.275.17.12684
[7] SINDHU MATHEW  Zainul A Z  T Emilia Abraham. Reactivity of phenolic compounds towards free radicals under in vitro conditions[J]. Journal of Food Science and Technology, 2015, 52 9: 5790-5798. DOI: 10.1007/s13197-014-1704-0
[8] REED J D. Nutritional toxicology of tannins and related polyphenols in forage legumes.[J]. Journal of animal science, 1995, 73 5: 1516-1528. DOI: 10.2527/1995.7351516x
Tag:Pyrogallol(87-66-1) Related Product Information
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