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Pyrogallol information


Pyrogallol
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Benzene-1,2,3-triol
Other names
1,2,3-Trihydroxybenzene
Pyrogallic acid
1,2,3-Benzenetriol[1]
Identifiers
CAS Number
  • 87-66-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16164 checkY
ChEMBL
  • ChEMBL307145 checkY
ChemSpider
  • 13835557 checkY
ECHA InfoCard 100.001.603 Edit this at Wikidata
EC Number
  • 201-762-9
KEGG
  • C01108
PubChem CID
  • 1057
RTECS number
  • UX2800000
UNII
  • 01Y4A2QXY0 checkY
UN number 2811
CompTox Dashboard (EPA)
  • DTXSID6025983 Edit this at Wikidata
InChI
  • InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H checkY
    Key: WQGWDDDVZFFDIG-UHFFFAOYSA-N checkY
  • InChI=1/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H
    Key: WQGWDDDVZFFDIG-UHFFFAOYAT
SMILES
  • Oc1cccc(O)c1O
Properties
Chemical formula
C6H6O3
Molar mass 126.11 g/mol
Density 1.453 g/cm3 (4 °C)[1]
Melting point 125.5 °C (257.9 °F; 398.6 K)[1]
Boiling point 307 °C (585 °F; 580 K)[1]
Refractive index (nD)
1.561 (134 °C)[1]
Structure[2]
Crystal structure
Monoclinic
Space group
P21/n
Lattice constant
a = 12.1144(11) Å, b = 3.7765(3) Å, c = 13.1365(12) Å
α = 90°, β = 115.484(1)°, γ = 90°
Formula units (Z)
4
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation markGHS08: Health hazard
Signal word
Warning
Hazard statements
H302, H312, H332, H341, H412
Precautionary statements
P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a water-soluble, white solid although samples are typically brownish because of its sensitivity toward oxygen.[3] It is one of three isomers of benzenetriols.

  1. ^ a b c d e Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.38. ISBN 9781498754293.
  2. ^ Thakuria, Ranjit; Cherukuvada, Suryanarayan; Nangia, Ashwini (2012). "Crystal Structures of Pyrogallol, Its Hydrate, and Stable Multiple Z ′ Cocrystals with N-Heterocycles Containing Metastable Conformers of Pyrogallol". Crystal Growth & Design. 12 (8): 3944–3953. doi:10.1021/cg3003367.
  3. ^ Fiege, Helmut; Heinz-Werner, Voges; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 1072. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.

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Pyrogallol

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Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a water-soluble, white solid although samples are typically brownish because of its...

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Pyrogallol hydroxytransferase

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In enzymology, a pyrogallol hydroxytransferase (EC 1.97.1.2) is an enzyme that catalyzes the chemical reaction 1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene...

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Hydrolysable tannin

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A hydrolysable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids...

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Syringol

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and 6) positions. It is the symmetrically dimethylated derivative of pyrogallol. It is a colorless solid, although typical samples are brown owing to...

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Trihydroxybenzenes

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solubility in water. The enzyme pyrogallol hydroxytransferase uses benzene-1,2,3,5-tetrol and benzene-1,2,3-triol (pyrogallol), whereas its two products are...

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Calixarene

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resorcinarenes and pyrogallolarenes are produced from resorcinol and pyrogallol, respectively. The aldehyde most often used is formaldehyde, while larger...

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Glutaric acid

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of carbon atoms (i.e. 5) is useful in decreasing polymer elasticity. Pyrogallol can be produced from glutaric diester. Glutaric acid may cause irritation...

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Phloroglucinol

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benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are...

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History of photography

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emulsions after Samman introduced the idea of adding dithionite to the pyrogallol developer.[citation needed] Berkeley discovered that with his own addition...

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cyclohexane derivative hexahydrogallic acid. Heating gallic acid gives pyrogallol (1,2,3-trihydroxybenzene). This conversion is catalyzed by gallate decarboxylase...

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current legislation restricts the use of certain substances, such as pyrogallol, formaldehyde, or paraformaldehyde, and bans the use of others, such as...

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Sumac

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name of R. coriaria. The leaves of certain sumacs yield tannin (mostly pyrogallol-type), a substance used in vegetable tanning. Notable sources include...

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C6H6O3

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Hydroxymethylfurfural Hydroxyquinol Isomaltol Levoglucosenone Maltol Phloroglucinol Pyrogallol Triacetic acid lactone This set index page lists chemical structure articles...

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Chestnut

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traction and abrasion, and have warm color. Chestnut tannin is one of the pyrogallol class of tannins (also known as hydrolysable tannin). As it tends to give...

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Pyrogallolarenes

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is a macrocycle, or a cyclic oligomer, based on the condensation of pyrogallol (1,2,3-trihydroxybenzene) and an aldehyde. Pyrogallolarenes are a type...

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Gallate decarboxylase

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reaction 3,4,5-trihydroxybenzoate ⇌ {\displaystyle \rightleftharpoons } pyrogallol + CO2 This enzyme belongs to the family of lyases, specifically the carboxy-lyases...

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Orsat gas analyser

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absorbents are: Potassium hydroxide (caustic potash) for carbon dioxide Pyrogallol (pyrogallic acid) for oxygen Copper(I) chloride (ammoniacal Cuprous chloride)...

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Herbert Bowyer Berkeley

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the British Journal of Photography Almanac included his new formula of pyrogallol, sulfite and citric acid in their publication. In Berkeley's new formula...

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Terminalia elliptica

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acid can be extracted from it. The bark and especially the fruit yield pyrogallol and catechol to dye and tan leather. Water stored in the stem is often...

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Polyphenol

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polyphenols contain repeating phenolic moieties of pyrocatechol, resorcinol, pyrogallol, and phloroglucinol connected by esters (hydrolyzable tannins) or more...

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Henna

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amaranth (red dye #2 banned in the US in 1976), silver nitrate, carmine, pyrogallol, disperse orange dye, and chromium. These have been found to cause allergic...

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Catechol

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1993 Recommendations for the Nomenclature of Organic Chemistry. Enol Pyrogallol Thiotimoline "Front Matter". Nomenclature of Organic Chemistry: IUPAC...

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Leo Baekeland

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had experimented with phenols and formaldehydes in 1872, particularly Pyrogallol and benzaldehyde. He created a "black guck" which he considered useless...

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Purpurogallin

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nutgalls and oak barks. Purpurogallin can be prepared by oxidation of pyrogallol with sodium periodate. Purpurogallin is bioactive It can inhibit 2-hydroxy...

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Caffeic acid

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instant coffee. The developing chemistry is similar to that of catechol or pyrogallol. It is also used as a matrix in MALDI mass spectrometry analyses. Isomers...

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