- Production
- Reactions
- Applications
- References
| Watchedfields = changed
| verifiedrevid = 476997017
| ImageFile =Gentisinsäure.svg
| ImageSize = 150
| ImageAlt = Skeletal formula of gentisic acid
| ImageFile1 = Gentisic acid 3D spacefill.png
| ImageSize1 = 150
| ImageAlt1 = Space-filling model of the gentisic acid molecule
| IUPACName =2,5-dihydroxybenzoic acid
| OtherNames =DHB
2,5-dihydroxybenzoic acid
5-Hydroxysalicylic acid
Gentianic acid
Carboxyhydroquinone
2,5-Dioxybenzoic Acid
Hydroquinonecarboxylic acid
| Reference =[1]
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3350
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = VP36V95O3T
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00628
| InChI = 1/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
| InChIKey = WXTMDXOMEHJXQO-UHFFFAOYAO
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1461
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WXTMDXOMEHJXQO-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =490-79-9
| PubChem =3469
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17189
| SMILES = O=C(O)c1cc(O)ccc1O
}}
|Section2={{Chembox Properties
| Formula = C7H6O4
| MolarMass = 154.12 g/mol
| Appearance = white to yellow powder
| Density =
| MeltingPtC = 200 to 205
| MeltingPt_notes = (Sublimes)
| BoilingPt =
| Solubility =
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}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 + O2maleylpyruvate
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
1. ^[https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=3469&loc=ec_rcs Gentisic acid - Compound Summary], PubChem.
2. ^{{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= }}
3. ^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}}
4. ^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}}.
5. ^{{cite book|last=Behrman|first=E.J.|title=Organic Reactions, Volume 35|date=1988|publisher=John Wiley & Sons Inc.|location=New York|isbn=978-0471832539|page=440|url=https://books.google.com/?id=sfjdPwAACAAJ&dq=0471832537}}
6. ^{{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}}
7. ^{{cite journal |vauthors=Strupat K, Karas M, Hillenkamp F |title=2,5-Dihidroxybenzoic acid: a new matrix for laser desorption-ionization mass spectrometry |journal=Int. J. Mass Spectrom. Ion Process. |volume=72 |issue=111 |pages=89–102 |year=1991 |doi=10.1016/0168-1176(91)85050-V |bibcode=1991IJMSI.111...89S}}
8. ^{{cite journal|last=Crumpton|first=J.|author2=Zhang, W. |author3=Santos, W. L. |title=Facile Analysis and Sequencing of Linear and Branched Peptide Boronic Acids by MALDI Mass Spectrometry|journal=Analytical Chemistry|year=2011|volume=83|issue=9|pages=3548–3554|doi=10.1021/ac2002565|pmid=21449540|pmc=3090651}}
{{Phenolic acid}}{{DEFAULTSORT:Gentisic Acid}}2. ^{{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= }}
3. ^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}}
4. ^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}}.
5. ^{{cite book|last=Behrman|first=E.J.|title=Organic Reactions, Volume 35|date=1988|publisher=John Wiley & Sons Inc.|location=New York|isbn=978-0471832539|page=440|url=https://books.google.com/?id=sfjdPwAACAAJ&dq=0471832537}}
6. ^{{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}}
7. ^{{cite journal |vauthors=Strupat K, Karas M, Hillenkamp F |title=2,5-Dihidroxybenzoic acid: a new matrix for laser desorption-ionization mass spectrometry |journal=Int. J. Mass Spectrom. Ion Process. |volume=72 |issue=111 |pages=89–102 |year=1991 |doi=10.1016/0168-1176(91)85050-V |bibcode=1991IJMSI.111...89S}}
8. ^{{cite journal|last=Crumpton|first=J.|author2=Zhang, W. |author3=Santos, W. L. |title=Facile Analysis and Sequencing of Linear and Branched Peptide Boronic Acids by MALDI Mass Spectrometry|journal=Analytical Chemistry|year=2011|volume=83|issue=9|pages=3548–3554|doi=10.1021/ac2002565|pmid=21449540|pmc=3090651}}
5 : Hydroquinones|Salicylic acids|Dihydroxybenzoic acids|Phenolic human metabolites|Human drug metabolites
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