Gentisic acid: Difference between revisions
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'''Gentisic acid''' is a [[dihydroxybenzoic acid]]. It is a derivative of [[benzoic acid]] and a minor (1%) product of the metabolic break down of [[aspirin]], excreted by the kidneys.<ref>{{cite journal|doi=10.1056/NEJM197208312870903|title=Salicylate accumulation kinetics in man|journal=New England Journal of Medicine|date=1972-09-31|first=G|last=Levy|author2=Tsuchiya, T|volume=287|issue=9|pages=430–2|pmid=5044917 |url= }}</ref> |
'''Gentisic acid''' is a [[dihydroxybenzoic acid]]. It is a derivative of [[benzoic acid]] and a minor (1%) product of the metabolic break down of [[aspirin]], excreted by the kidneys.<ref>{{cite journal|doi=10.1056/NEJM197208312870903|title=Salicylate accumulation kinetics in man|journal=New England Journal of Medicine|date=1972-09-31|first=G|last=Levy|author2=Tsuchiya, T|volume=287|issue=9|pages=430–2|pmid=5044917 |url= }}</ref> |
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It is also found in the African tree ''[[Alchornea cordifolia]]'' and in [[wine]].<ref>Comparison of Phenolic Acids and Flavan-3-ols During Wine Fermentation of Grapes with Different Harvest Times. Rong-Rong Tian, Qiu-Hong Pan, Ji-Cheng Zhan, Jing-Ming Li, Si-Bao Wan, Qing-Hua Zhang and Wei-Dong Huang, Molecules, 2009, 14, pages 827-838, {{doi|10.3390/molecules14020827}}</ref> |
It is also found in the African tree ''[[Alchornea cordifolia]]'' and in [[wine]].<ref>Comparison of Phenolic Acids and Flavan-3-ols During Wine Fermentation of Grapes with Different Harvest Times. Rong-Rong Tian, Qiu-Hong Pan, Ji-Cheng Zhan, Jing-Ming Li, Si-Bao Wan, Qing-Hua Zhang and Wei-Dong Huang, Molecules, 2009, 14, pages 827-838, {{doi|10.3390/molecules14020827}}</ref> |
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== Production == |
== Production == |
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It arises naturally by the action of [[oxygen|O<sub>2</sub>]] on [[2,5-dihydroxybenzoate]]. The reaction is catalyzed by [[gentisate 1,2-dioxygenase]]: |
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Gentisic acid is produced by carboxylation of [[hydroquinone]].<ref name=Ullmann>Phillip M. Hudnall "Hydroquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. 2005 Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a13_499}}.</ref> |
Gentisic acid is produced by carboxylation of [[hydroquinone]].<ref name=Ullmann>Phillip M. Hudnall "Hydroquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. 2005 Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a13_499}}.</ref> |
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:C<sub>6</sub>H<sub>4</sub>(OH)<sub>2</sub> + CO<sub>2</sub> → C<sub>6</sub>H<sub>3</sub>(CO<sub>2</sub>H)(OH)<sub>2</sub> |
:C<sub>6</sub>H<sub>4</sub>(OH)<sub>2</sub> + CO<sub>2</sub> → C<sub>6</sub>H<sub>3</sub>(CO<sub>2</sub>H)(OH)<sub>2</sub> |
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Alternatively the compound can be synthesized from [[salicylic acid]] via [[Elbs persulfate oxidation]].<ref>{{cite book|last=Behrman|first=E.J.|title=Organic Reactions, Volume 35|date=1988|publisher=John Wiley & Sons Inc.|location=New York|isbn=0471832537|page=440|url=https://books.google.com/books?id=sfjdPwAACAAJ&dq=0471832537&hl=en&sa=X&ei=sD50U5jiBM6QyAS1rYGYBA&ved=0CDYQ6AEwAA}}</ref><ref>{{cite journal|author1=R. U. Schock Jr. |author2=D. L. Tabern|title=The Persulfate Oxidation of Salicylic Acid. 2,3,5-Trihydroxybenzoic Acid|journal=The Journal of Organic Chemistry|date=1951|volume=16|issue=11|pages=1772–1775|doi=10.1021/jo50005a018}}<!--|accessdate=15 May 2014--></ref> |
Alternatively the compound can be synthesized from [[salicylic acid]] via [[Elbs persulfate oxidation]].<ref>{{cite book|last=Behrman|first=E.J.|title=Organic Reactions, Volume 35|date=1988|publisher=John Wiley & Sons Inc.|location=New York|isbn=0471832537|page=440|url=https://books.google.com/books?id=sfjdPwAACAAJ&dq=0471832537&hl=en&sa=X&ei=sD50U5jiBM6QyAS1rYGYBA&ved=0CDYQ6AEwAA}}</ref><ref>{{cite journal|author1=R. U. Schock Jr. |author2=D. L. Tabern|title=The Persulfate Oxidation of Salicylic Acid. 2,3,5-Trihydroxybenzoic Acid|journal=The Journal of Organic Chemistry|date=1951|volume=16|issue=11|pages=1772–1775|doi=10.1021/jo50005a018}}<!--|accessdate=15 May 2014--></ref> |
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==Reactions== |
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In the presence of the enzyme [[gentisate 1,2-dioxygenase]], gentisic acid reacts with [[oxygen]] to give [[maleylpyruvate]]: |
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== Applications == |
== Applications == |
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Revision as of 23:45, 12 December 2018
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| Names | |
|---|---|
| IUPAC name
2,5-dihydroxybenzoic acid
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| Other names
DHB
2,5-dihydroxybenzoic acid 5-Hydroxysalicylic acid Gentianic acid Carboxyhydroquinone 2,5-Dioxybenzoic Acid Hydroquinonecarboxylic acid | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.017 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C7H6O4 | |
| Molar mass | 154.12 g/mol |
| Appearance | white to yellow powder |
| Melting point | 200 to 205 °C (392 to 401 °F; 473 to 478 K) (Sublimes) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Gentisic acid is a dihydroxybenzoic acid. It is a derivative of benzoic acid and a minor (1%) product of the metabolic break down of aspirin, excreted by the kidneys.[2]
It is also found in the African tree Alchornea cordifolia and in wine.[3]
Production
Gentisic acid is produced by carboxylation of hydroquinone.[4]
- C6H4(OH)2 + CO2 → C6H3(CO2H)(OH)2
This conversion is an example of a Kolbe–Schmitt reaction.
Alternatively the compound can be synthesized from salicylic acid via Elbs persulfate oxidation.[5][6]
Reactions
In the presence of the enzyme gentisate 1,2-dioxygenase, gentisic acid reacts with oxygen to give maleylpyruvate:
- 2,5-dihydroxybenzoate + O2 maleylpyruvate
Applications
As a hydroquinone, gentisic acid is readily oxidised and is used as an antioxidant excipient in some pharmaceutical preparations.
In the laboratory, it is used as a sample matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry,[7] and has been shown to conveniently detect peptides incorporating the boronic acid moiety by MALDI.[8]
References
- ^ Gentisic acid - Compound Summary, PubChem.
- ^ Levy, G; Tsuchiya, T (1972-09-31). "Salicylate accumulation kinetics in man". New England Journal of Medicine. 287 (9): 430–2. doi:10.1056/NEJM197208312870903. PMID 5044917.
{{cite journal}}: Check date values in:|date=(help) - ^ Comparison of Phenolic Acids and Flavan-3-ols During Wine Fermentation of Grapes with Different Harvest Times. Rong-Rong Tian, Qiu-Hong Pan, Ji-Cheng Zhan, Jing-Ming Li, Si-Bao Wan, Qing-Hua Zhang and Wei-Dong Huang, Molecules, 2009, 14, pages 827-838, doi:10.3390/molecules14020827
- ^ Phillip M. Hudnall "Hydroquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. 2005 Wiley-VCH, Weinheim. doi:10.1002/14356007.a13_499.
- ^ Behrman, E.J. (1988). Organic Reactions, Volume 35. New York: John Wiley & Sons Inc. p. 440. ISBN 0471832537.
- ^ R. U. Schock Jr.; D. L. Tabern (1951). "The Persulfate Oxidation of Salicylic Acid. 2,3,5-Trihydroxybenzoic Acid". The Journal of Organic Chemistry. 16 (11): 1772–1775. doi:10.1021/jo50005a018.
- ^ Strupat K, Karas M, Hillenkamp F (1991). "2,5-Dihidroxybenzoic acid: a new matrix for laser desorption-ionization mass spectrometry". Int. J. Mass Spectrom. Ion Process. 72 (111): 89–102. Bibcode:1991IJMSI.111...89S. doi:10.1016/0168-1176(91)85050-V.
- ^ Crumpton, J.; Zhang, W.; Santos, W. L. (2011). "Facile Analysis and Sequencing of Linear and Branched Peptide Boronic Acids by MALDI Mass Spectrometry". Analytical Chemistry. 83 (9): 3548–3554. doi:10.1021/ac2002565. PMC 3090651. PMID 21449540.