| Revision as of 12:10, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 463062596 of page Pyrogallol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 08:48, 30 July 2024 edit Beland (talk | contribs)Autopatrolled, Administrators236,639 editsm convert special characters found by Misplaced Pages:Typo Team/moss (via WP:JWB) |
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{{Short description|Benzene-1,2,3-triol}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 416731252 |
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| verifiedrevid = 464377558 |
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| Name = Pyrogallol |
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| Name = Pyrogallol |
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| ImageFile = pyrogallol.svg |
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| ImageFile = pyrogallol.svg |
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| ImageSize = 160px |
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| ImageSize = 160px |
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| ImageName = Skeletal formula |
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| ImageName = Skeletal formula |
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| ImageFile1 = Pyrogallol-3D-balls.png |
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| ImageFile1 = Pyrogallol-3D-balls.png |
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| ImageSize1 = 180px |
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| ImageSize1 = 180px |
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| ImageName1 = Ball-and-stick model |
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| ImageName1 = Ball-and-stick model |
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| ImageFile2 = Pyrogallol powder.jpg |
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| OtherNames = 1,2,3-Trihydroxybenzene<br />Pyrogallic acid |
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| PIN = Benzene-1,2,3-triol |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = 1,2,3-Trihydroxybenzene<br />Pyrogallic acid<br />1,2,3-Benzenetriol<ref name=crc>{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 9781498754293|page=3.38}}</ref> |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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⚫ |
|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13835557 |
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| ChemSpiderID = 13835557 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 307145 |
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| ChEMBL = 307145 |
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| EINECS = 201-762-9 |
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| KEGG = C01108 |
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| PubChem = 1057 |
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| RTECS = UX2800000 |
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| UNNumber = 2811 |
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| InChI = 1/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H |
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| InChI = 1/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H |
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| InChIKey = WQGWDDDVZFFDIG-UHFFFAOYAT |
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| InChIKey = WQGWDDDVZFFDIG-UHFFFAOYAT |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 87-66-1 |
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| CASNo = 87-66-1 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 16164 |
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| ChEBI = 16164 |
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| SMILES = Oc1cccc(O)c1O |
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| SMILES = Oc1cccc(O)c1O |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>6</sub>O<sub>3</sub> |
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| Formula = C<sub>6</sub>H<sub>6</sub>O<sub>3</sub> |
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| MolarMass = 126.11 g/mol |
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| MolarMass = 126.11 g/mol |
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| MeltingPtC = 125.5 |
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| MeltingPt = 131-134 °C |
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| MeltingPt_ref = <ref name=crc/> |
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| BoilingPt = 309 °C |
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| BoilingPtC = 307 |
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| Density = 1.45 g/cm<sup>3</sup> |
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| BoilingPt_ref = <ref name=crc/> |
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| Density = 1.453 g/cm<sup>3</sup> (4 °C)<ref name=crc/> |
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| RefractIndex = 1.561 (134 °C)<ref name=crc/> |
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}} |
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}} |
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| Section3 = {{Chembox Structure |
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| Structure_ref=<ref>{{cite journal|doi=10.1021/cg3003367 |title=Crystal Structures of Pyrogallol, Its Hydrate, and Stable Multiple ''Z'' {{prime}} Cocrystals with N-Heterocycles Containing Metastable Conformers of Pyrogallol |date=2012 |last1=Thakuria |first1=Ranjit |last2=Cherukuvada |first2=Suryanarayan |last3=Nangia |first3=Ashwini |journal=Crystal Growth & Design |volume=12 |issue=8 |pages=3944–3953 }}</ref> |
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| CrystalStruct = ] |
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| SpaceGroup = P2<sub>1</sub>/n |
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| PointGroup = |
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| LattConst_a = 12.1144(11) Å |
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| LattConst_b = 3.7765(3) Å |
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| LattConst_c = 13.1365(12) Å |
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| LattConst_alpha = |
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| LattConst_beta = 115.484(1) |
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| LattConst_gamma = |
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| LattConst_ref = |
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| LattConst_Comment = |
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| UnitCellVolume = |
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| UnitCellFormulas = 4 |
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}} |
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|Section7 = {{Chembox Hazards |
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| GHSPictograms = {{GHS07}}{{GHS08}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|302|312|332|341|412}} |
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| PPhrases = {{P-phrases|201|202|261|264|270|271|273|280|281|301+312|302+352|304+312|304+340|308+313|312|322|330|363|405|501}} |
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}} |
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}} |
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}} |
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'''Pyrogallol''' is an ] with the formula C<sub>6</sub>H<sub>3</sub>(OH)<sub>3</sub>. It is a water-soluble, white solid although samples are typically brownish because of its sensitivity toward oxygen.<ref name="Ullmann">{{Ullmann|last1=Fiege|first1=Helmut|last2=Heinz-Werner|first2=Voges|last3=Hamamoto|first3=Toshikazu|last4=Umemura|first4=Sumio|last5=Iwata|first5=Tadao|last6=Miki|first6=Hisaya|last7=Fujita|first7=Yasuhiro|last8=Buysch|first8=Hans-Josef|last9=Garbe|first9=Dorothea|last10=Paulus|first10=Wilfried|date=2014|page=1072|edition=7th|doi=10.1002/14356007.a19_313|title=Phenol Derivatives}}</ref> It is one of three ]s of ]s. |
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== Production and reactions== |
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It is produced in the manner first reported by ] in 1786: heating ] to induce decarboxylation.<ref name="Ullmann" /> |
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] |
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Gallic acid is also obtained from ]. Many alternative routes have been devised. One preparation involves treating ''para''-chlorophenoldisulfonic acid with ],<ref>{{Cite journal|last=Buzbee|first=Lloyd R.|date=1966-10-01|title=Rearranged Products from the Reaction of Benzenesulfonic Acids with Caustic|journal=The Journal of Organic Chemistry|volume=31|issue=10|pages=3289–3292|doi=10.1021/jo01348a042|issn=0022-3263}}</ref> a variant on the time-honored route to phenols from ]s.<ref>{{Cite journal|last1=Magro|first1=Angel A. Núñez|last2=Eastham|first2=Graham R.|last3=Cole-Hamilton|first3=David J.|date=2009-06-10|title=Preparation of Phenolic Compounds by Decarboxylation of Hydroxybenzoic Acids or Desulfonation of Hydroxybenzenesulfonic Acid, Catalysed by Electron Rich Palladium Complexes|journal=Dalton Transactions|language=en|issue=24|pages=4683–8|doi=10.1039/B900398C|pmid=19513476|issn=1477-9234}}</ref> |
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Polyhydroxybenzenes are relatively electron-rich. One manifestation is the easy C-acetylation of pyrogallol.<ref>{{cite journal |doi=10.15227/orgsyn.014.0040|first1=I. C.|last1=Badhwar |first2= K. |last2=Venkataraman|title=Gallacetophenone |journal=Organic Syntheses |year=1934 |volume=14 |page=40 }}</ref> |
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== Uses == |
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It was once used in ], dyeing of suturing materials. It also has ] properties. |
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In alkaline solution, pyrogallol undergoes deprotonation. Such solutions absorb ] from the air, turning brown. This conversion can be used to determine the amount of oxygen in a gas sample, notably by the use of the ]. Alkaline solutions of pyrogallol have been used for ] absorption in gas analysis. |
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=== Use in photography === |
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Pyrogallol was also used as a ] in the 19th and early 20th centuries in black-and-white developers. ] is more commonly used today. Its use is largely historical except for special purpose applications. It was still used by a few notable photographers including ]. In those days it had a reputation for erratic and unreliable behavior, due possibly to its propensity for oxidation. It experienced a revival starting in the 1980s due largely to the efforts of experimenters ] and ]. Hutchings spent over a decade working on pyrogallol formulas, eventually producing one he named PMK for its main ingredients: pyrogallol, ], and ] (the trade name of ] for sodium metaborate). This formulation resolved the consistency issues, and Hutchings found that an interaction between the greenish stain given to film by pyro developers and the color sensitivity of modern ] gave the effect of an extreme ]. From 1969 to 1977, Wimberley experimented with the Pyrogallol developing agent. He published his formula for WD2D in 1977 in Petersen's Photographic. PMK and other modern pyro formulations are now used by many black-and-white photographers. The Film Developing Cookbook has examples.<ref>{{Cite book|title=The Film Developing Cookbook|author1=Anchell, Stephen G. |author2=Troop, Bill |isbn=978-0240802770|year=1998}}</ref> |
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Another developer mainly based on pyrogallol was formulated by ]. The 510-pyro,<ref>{{Cite web|url=http://pyrostains.blogspot.com/|title=510-PYRO|website=510-PYRO}}</ref> is a concentrate that uses ] as ], and pyrogallol, ], and ] as combined developers in a single concentrated stock solution with long shelf life . This developer has both staining and tanning properties and negatives developed with it are immune to the ]. It can be used for small and large negative formats. |
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The Darkroom Cookbook (Alternative Process Photography) has examples.<ref>{{Cite book|title=The darkroom cookbook|last=Anchell|first=Stephen G.|isbn=9781138959187|edition=Fourth|publisher= Routledge|location=New York|oclc=938707611|year = 2016}}</ref> |
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==Safety== |
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Pyrogallol use, e.g. in hair dye formulations, is declining because of concerns about its toxicity.<ref>{{Cite web |url=http://msds.chem.ox.ac.uk/TR/1,2,3-trihydroxybenzene.html |title=Safety data for 1,2,3-trihydroxybenzene |access-date=2009-03-05 |archive-date=2009-02-28 |archive-url=https://web.archive.org/web/20090228081954/http://msds.chem.ox.ac.uk/TR/1,2,3-trihydroxybenzene.html |url-status=dead }}</ref> |
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Its {{LD50}} (oral, rat) is 300 mg/kg.<ref name="Ullmann" /> |
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Pure pyrogallol was found to be extremely ] when inserted ], but ] protect against its toxicity during everyday exposure.<ref>{{cite press release |title=Cancer Biologists Find DNA-Damaging Toxins in Common Plant-Based Foods |url=https://www.hopkinsmedicine.org/news/media/releases/cancer_biologists_find_dna_damaging_toxins_in_common_plant_based_foods |website=Johns Hopkins Medicine |access-date=11 February 2024}}</ref><ref>{{cite journal|journal=Food and Chemical Toxicology|volume=70|date=Aug 2014|pages=114–119|title=Salivary α-amylase, serum albumin, and myoglobin protect against DNA-damaging activities of ingested dietary agents in vitro|first1=M. Zulfiquer|last1=Hossain|first2=Kalpesh|last2=Patel|first3=Scott E.|last3=Kern|doi=10.1016/j.fct.2014.05.002|pmid=24842839 |pmc=4095877|postscript=,}} summarized in {{cite press release |title=Compounds in Saliva and Common Body Proteins May Fend Off DNA-Damaging Chemicals in Tea, Coffee and Liquid Smoke |url=https://www.hopkinsmedicine.org/news/media/releases/compounds_in_saliva_and_common_body_proteins_may_fend_off_dna_damaging_chemicals_in_tea_coffee_and_liquid_smoke |publisher=Johns Hopkins Medicine |access-date=11 February 2024|date=30 May 2014|first=Vanessa|last=Wasta|archive-url=https://web.archive.org/web/20240227200038/https://www.hopkinsmedicine.org/news/media/releases/compounds_in_saliva_and_common_body_proteins_may_fend_off_dna_damaging_chemicals_in_tea_coffee_and_liquid_smoke|archive-date=27 Feb 2024}}</ref> |
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==See also== |
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* ] |
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* ] (2,3,4-trihydroxyacetophenone) |
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* ] |
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* ] |
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==References== |
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{{reflist}} |
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{{Authority control}} |
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