| Revision as of 17:10, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 444193474 of page 2,6-Dihydroxypyridine for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 23:24, 27 September 2022 edit Allforrous (talk | contribs)Extended confirmed users27,565 edits →References: Commonscatinline template. |
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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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| verifiedrevid = 443313866 |
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| verifiedrevid = 477212102 |
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|ImageFile=2,6-Dihydroxypyridine.png |
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| ImageFile = 2,6-Dihydroxypyridine.png |
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|ImageSize=120px |
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| ImageSize = 120px |
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|IUPACName=6-Hydroxy-1''H''-pyridin-2-one |
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| PIN = 6-Hydroxypyridin-2(1''H'')-one |
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|OtherNames=2(1H)-Pyridinone, 6-hydroxy- 2(1H)-Pyridone |
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| OtherNames =2 (1''H'')-Pyridinone<br/> |
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6-hydroxy- (7CI,8CI) |
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6-Hydroxy-2(1''H'')-pyridone<br/> |
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1-Deazauracil |
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6-hydroxy- (7CI,8CI)<br/> |
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2-Hydroxy-6-pyridinone |
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1-Deazauracil<br/> |
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2-Hydroxy-6-pyridinone<br/> |
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6-Hydroxy-2-pyridone |
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6-Hydroxy-2-pyridone |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 62580 |
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| ChemSpiderID = 62580 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WLFXSECCHULRRO-UHFFFAOYSA-N |
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| StdInChIKey = WLFXSECCHULRRO-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 626-06-2 --> |
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| CASNo = 626-06-2 |
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| CASOther=<br>10357-84-3 (]) |
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| CASNo1_Ref = {{cascite|changed|??}} |
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| PubChem=69371 |
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| CASNo1 = 10357-84-3 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| CASNo1_Comment = (]) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 54009B6TXP |
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| PubChem = 69371 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 17681 |
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| ChEBI = 17681 |
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| SMILES=C1=CC(=O)NC(=C1)O |
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| SMILES = C1=CC(=O)NC(=C1)O |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=5|H=5|N=1|O=2 |
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| C=5|H=5|N=1|O=2 |
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| Appearance= colorless crystalline |
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| Appearance= colorless crystalline |
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| Density=1.379 ± 0.06 g/cm<sup>3</sup> |
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| Density=1.379 ± 0.06 g/cm<sup>3</sup> |
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| MeltingPt=190-191 <sup>o</sup>C (463.15-464.15 K) |
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| MeltingPtC=190-191 |
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| BoilingPt=387.2 ± 42.0 <sup>o</sup>C (660.35 ± 313.15 K) |
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| BoilingPtC=387.2 ± 42.0 |
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| Solubility=Soluble (41g/L) |
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| Solubility=Soluble (41g/L) |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| R Phrases=R36/37/38 |
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| S Phrases=S26/36 |
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| HPhrases = {{HPhrases|}} |
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| PPhrases = {{PPhrases|}} |
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| GHS_ref = <!-- No GHS data 12-2021. <ref>GHS: </ref> --> |
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'''2,6-Dihydroxypyridine''' is an ] with the molecular formula C<sub>5</sub>H<sub>3</sub>N(OH)<sub>2</sub>. It is a colorless solid. 2,6-Dihyroxypyridine is an intermediate in the degradation of ]. |
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== Preparation == |
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2,6-Dihydroxypyridine is an intermediate in the degradation of nicotine by the aerobic bacterium ''Arthrobacter nicotinovorans''. The following reaction shows the formation of the intermediate from L-nicotine of tobacco.<ref name="schulz2008">{{cite journal |title= Structure of 2,6-Dihydroxypyridine 3-hydroxylase from a Nicotine-degrading Pathway |journal= J. Mol. Biol. |year= 2008 |pages= 94–104 |doi= 10.1016/j.jmb.2008.03.032 |author1=Schulz, G. |author2=Treiber, N. |volume= 379 |pmid= 18440023 |issue= 1 }}</ref> |
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:] |
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The figure represents the pathway for the degradation of L-nicotine by ''A. nicotinovorans'' to 2,6-dihydroxypyridine |
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Another reaction of 2,6-dihydroxypyridine highlights its function as a substrate for ]. One example is the enzyme monooxygenase, which oxidizes the substrate by transferring one oxygen atom of O<small>2</small> to the substrate. The other oxygen atom is reduced to water. The product of the oxidase reaction was determined to be 2,3,6-tri-hydroxypyridine because of the results of the stoichiometry as well as the results of the ultraviolet spectrum. This reaction can be shown by the following equation: |
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:] |
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Arthrobacter oxydans, when grown on ]s, were most active in the oxidation of 2,6-dihydroxypyridine.<ref>{{cite journal |title= The Bacterial Oxidation of Nicotine VI. The Metabolism of 2,6-dihydroxypseudooxynicotine |journal= J. Biol. Chem. |year= 1965 |volume= 240 |issue= 9 |pages= 3669–3674 |pmid= 5835946 |author= Gherna, R |doi= 10.1016/S0021-9258(18)97197-8 |display-authors=etal|doi-access= free }}</ref> |
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== Structure and properties == |
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2,6-Dihydroxypyridine in principle can exist in five ]s: |
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:] |
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The distribution of these tautomers is solvent-dependent. Studies show that tautomer II is most common in ethanol, water, and DMSO.<ref>{{cite journal |title= A New Type of Calixarene: Octahydroxypyridinearenes |journal= Chemistry: A European Journal |year= 2001 |volume= 7 |issue= 2 |pages= 465–474 |doi= 10.1002/1521-3765(20010119)7:2<465::AID-CHEM465>3.0.CO;2-A |author= Gerkensmeier, T |pmid= 11271533 |display-authors=etal}}</ref> |
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== Other Applications == |
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2,6-Dihydroxypyridine has been investigated in an oxidation method of dyeing hair. The process utilizes 2,6-dihydroxypyridine as a coupling agent, and 2,4,5,6-tetraaminopyrimidine as a primary intermediate. This oxidation method intensifies the color of the dyed hair for several days.<ref>Wenke, G.; Wong, Y. Yellow Hair Color Dyeing Composition Having Improved Wear Properties. PCT Int. Appl. 2002. WO 2002024155 A1 20020328</ref> |
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== Main Reactions == |
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2,6-dihydroxypyridine is a key intermediate in the degradation of nicotine by certain bacteria. The enzyme 2,6-dihydroxypyridine-3-hydroxylase, which is produced in ''Escherichia coli'', is responsible for catalyzing the sixth step of nicotine degradation in the bacterium ''Arthrobacter nicotinovoran''. 2,6-dihydroxypyridine is hydroxylated by hydroperoxy-FAD. This reaction yields 2,3,6-tri-hydroxypyridine. This is shown in the following reaction:: |
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2,6-dihydroxypyridine hydroxylase is a dimeric flavoprotein, with one bound FAD molecule attached. The reaction is NADH-dependent and the enzyme only accepts 2,6-dihydroxypyridine as a substrate. Furthermore, the enzyme is inhibited by 2,6-dimethoxypyridine and 2,3-dihydroxypyridine.<ref name="schulz2008"/> |
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==References== |
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{{Reflist}} |
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==External links== |
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*{{Commonscatinline}} |
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{{DEFAULTSORT:Dihydroxypyridine, 2, 6-}} |
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] |