Jump to content

Gentisic acid: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
CheMoBot (talk | contribs)
Bots
141,565 edits
Updating {{chembox}} (no changed fields - added verified revid) per Chem/Drugbox validation (report errors or bugs)
OAbot (talk | contribs)
Bots
441,761 edits
m Open access bot: pmc updated in citation with #oabot.
 
(31 intermediate revisions by 21 users not shown)
Line 1: Line 1:
{{chembox
{{chembox
|Watchedfields = changed
| verifiedrevid = 476997017
|verifiedrevid = 476997017
|ImageFile=Gentisinsäure.svg
|ImageFile =Gentisinsäure.svg
|ImageSize=
|ImageSize = 150
|IUPACName=2,5-dihydroxybenzoic acid
|ImageAlt = Skeletal formula of gentisic acid
⚫
|OtherNames=DHB<br>2,5-dihydroxybenzoic acid<br>5-Hydroxysalicylic acid<br>Gentianic acid<br>Carboxyhydroquinone<br>2,5-Dioxybenzoic Acid<br>Hydroquinonecarboxylic acid
|ImageFile1 = Gentisic acid 3D spacefill.png
⚫
|Reference=<ref>[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=3469&loc=ec_rcs Gentisic acid - Compound Summary], [[PubChem]].</ref>
|ImageSize1 = 150
⚫
|Section1= {{Chembox Identifiers
|ImageAlt1 = Space-filling model of the gentisic acid molecule
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|PIN =2,5-Dihydroxybenzoic acid
⚫
| ChemSpiderID = 3350
⚫
|OtherNames =DHB<br>5-Hydroxysalicylic acid<br>Gentianic acid<br>Carboxyhydroquinone<br>2,5-Dioxybenzoic Acid<br>Hydroquinonecarboxylic acid
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
|Reference =<ref>[https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=3469&loc=ec_rcs Gentisic acid - Compound Summary], [[PubChem]].</ref>
⚫
| UNII = VP36V95O3T
⚫
|Section1={{Chembox Identifiers
⚫
| KEGG_Ref = {{keggcite|correct|kegg}}
⚫
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫
| KEGG = C00628
⚫
|ChemSpiderID = 3350
⚫
| InChI = 1/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
⚫
|UNII_Ref = {{fdacite|correct|FDA}}
⚫
| InChIKey = WXTMDXOMEHJXQO-UHFFFAOYAO
⚫
|UNII = VP36V95O3T
⚫
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫
|KEGG_Ref = {{keggcite|correct|kegg}}
⚫
| ChEMBL = 1461
⚫
|KEGG = C00628
⚫
| 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)
|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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫
|ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫
| StdInChIKey = WXTMDXOMEHJXQO-UHFFFAOYSA-N
⚫
|ChEMBL = 1461
⚫
| CASNo_Ref = {{cascite|correct|CAS}}
⚫
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫
| CASNo=490-79-9
⚫
|StdInChI = 1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
| PubChem=3469
| ChEBI_Ref = {{ebicite|correct|EBI}}
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫
|StdInChIKey = WXTMDXOMEHJXQO-UHFFFAOYSA-N
⚫
| ChEBI = 17189
⚫
|CASNo_Ref = {{cascite|correct|CAS}}
⚫
| SMILES = O=C(O)c1cc(O)ccc1O
⚫
|CASNo =490-79-9
|PubChem =3469
|ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
|ChEBI = 17189
⚫
|SMILES = O=C(O)c1cc(O)ccc1O
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>7</sub>H<sub>6</sub>O<sub>4</sub>
|Formula = C<sub>7</sub>H<sub>6</sub>O<sub>4</sub>
| MolarMass = 154.12 g/mol
|MolarMass = 154.12 g/mol
| Appearance = white to yellow powder
|Appearance = white to yellow powder
|MeltingPtC = 204
| Density =
| MeltingPt_ref=<ref name=crc>Haynes, p. 3.190</ref>
| MeltingPt = 200 - 205 C (Sublimes)
| pKa = 2.97<ref>Haynes, p. 5.91</ref>
| BoilingPt =
| Solubility =
⚫
}}
|Section3= {{Chembox Hazards
| MainHazards=
| FlashPt=
| Autoignition=
}}
}}
}}
⚫
}}
'''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|coauthors=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=1972-08-31|first=G|last=Levy|author2=Tsuchiya, T|volume=287|issue=9|pages=430–2|pmid=5044917 }}</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>
It is also found in the African tree ''[[Alchornea cordifolia]]'' and in [[wine]].<ref>{{cite journal|doi=10.3390/molecules14020827 |doi-access=free |title=Comparison of Phenolic Acids and Flavan-3-ols During Wine Fermentation of Grapes with Different Harvest Times |date=2009 |last1=Tian |first1=Rong-Rong |last2=Pan |first2=Qiu-Hong |last3=Zhan |first3=Ji-Cheng |last4=Li |first4=Jing-Ming |last5=Wan |first5=Si-Bao |last6=Zhang |first6=Qing-Hua |last7=Huang |first7=Wei-Dong |journal=Molecules |volume=14 |issue=2 |pages=827–838 |pmc=6253884 }}</ref>


== Production ==
== Production ==
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>Hudnall, Phillip M. (2005) "Hydroquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a13_499}}.</ref>
: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>
This conversion is an example of a [[Kolbe–Schmitt reaction]].
This conversion is an example of a [[Kolbe–Schmitt reaction]].

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=978-0471832539|page=440|url=https://books.google.com/books?id=sfjdPwAACAAJ&q=0471832537}}</ref><ref>{{cite journal|author1=Schock, R. U. Jr. |author2=Tabern, D. L. |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}}<!--|access-date=15 May 2014--></ref>

==Reactions==
In the presence of the enzyme [[gentisate 1,2-dioxygenase]], gentisic acid reacts with [[oxygen]] to give [[maleylpyruvate]]:
:2,5-dihydroxybenzoate + O<sub>2</sub> <math>\rightleftharpoons</math> maleylpyruvate


== Applications ==
== Applications ==
As a [[hydroquinone]], gentisic acid is readily oxidised and is used as an [[antioxidant]] [[excipient]] in some [[pharmaceutical]] preparations.
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]], <ref>{{cite journal |author=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 Processes |volume=72 |issue=111 |pages=89–102 |year=1991 |doi=10.1016/0168-1176(91)85050-V |bibcode=1991IJMSI.111...89S}}</ref> and has been shown to conveniently detect peptides incorporating the boronic acid moiety by MALDI. <ref>{{cite journal|last=Crumpton|first=J.|coauthors=Zhang, W.; 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|url=http://pubs.acs.org/doi/abs/10.1021/ac2002565|pmid=21449540|pmc=3090651}}</ref>
In the laboratory, it is used as a sample matrix in [[matrix-assisted laser desorption/ionization]] (MALDI) [[mass spectrometry]],<ref>{{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}}</ref> and has been shown to conveniently detect peptides incorporating the boronic acid moiety by MALDI.<ref>{{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}}</ref>


== References ==
== References ==
{{reflist}}
{{reflist}}
==Cited sources==
*{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = [[CRC Handbook of Chemistry and Physics]] | edition = 97th | publisher = [[CRC Press]] | isbn = 9781498754293}}


{{Phenolic acid}}
{{Phenolic acid}}
Line 66: Line 73:
[[Category:Salicylic acids]]
[[Category:Salicylic acids]]
[[Category:Dihydroxybenzoic acids]]
[[Category:Dihydroxybenzoic acids]]
[[Category:Human metabolites]]
[[Category:Phenolic human metabolites]]
[[Category:Phenolic compounds found in wine]]
[[Category:Human drug metabolites]]
[[Category:Chemical compounds found in Euphorbiaceae]]

Latest revision as of 18:01, 4 January 2024

Gentisic acid[1]
Skeletal formula of gentisic acid
Space-filling model of the gentisic acid molecule
Names
Preferred IUPAC name
2,5-Dihydroxybenzoic acid
Other names
DHB
5-Hydroxysalicylic acid
Gentianic acid
Carboxyhydroquinone
2,5-Dioxybenzoic Acid
Hydroquinonecarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.017 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11) checkY
    Key: WXTMDXOMEHJXQO-UHFFFAOYSA-N checkY
  • InChI=1/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
    Key: WXTMDXOMEHJXQO-UHFFFAOYAO
  • O=C(O)c1cc(O)ccc1O
Properties
C7H6O4
Molar mass 154.12 g/mol
Appearance white to yellow powder
Melting point 204 °C (399 °F; 477 K)[3]
Acidity (pKa) 2.97[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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.[4]

It is also found in the African tree Alchornea cordifolia and in wine.[5]

Production

[edit]

Gentisic acid is produced by carboxylation of hydroquinone.[6]

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.[7][8]

Reactions

[edit]

In the presence of the enzyme gentisate 1,2-dioxygenase, gentisic acid reacts with oxygen to give maleylpyruvate:

2,5-dihydroxybenzoate + O2 maleylpyruvate

Applications

[edit]

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,[9] and has been shown to conveniently detect peptides incorporating the boronic acid moiety by MALDI.[10]

References

[edit]
  1. ^ Gentisic acid - Compound Summary, PubChem.
  2. ^ Haynes, p. 5.91
  3. ^ Haynes, p. 3.190
  4. ^ Levy, G; Tsuchiya, T (1972-08-31). "Salicylate accumulation kinetics in man". New England Journal of Medicine. 287 (9): 430–2. doi:10.1056/NEJM197208312870903. PMID 5044917.
  5. ^ Tian, Rong-Rong; Pan, Qiu-Hong; Zhan, Ji-Cheng; Li, Jing-Ming; Wan, Si-Bao; Zhang, Qing-Hua; Huang, Wei-Dong (2009). "Comparison of Phenolic Acids and Flavan-3-ols During Wine Fermentation of Grapes with Different Harvest Times". Molecules. 14 (2): 827–838. doi:10.3390/molecules14020827. PMC 6253884.
  6. ^ Hudnall, Phillip M. (2005) "Hydroquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. Wiley-VCH, Weinheim. doi:10.1002/14356007.a13_499.
  7. ^ Behrman, E.J. (1988). Organic Reactions, Volume 35. New York: John Wiley & Sons Inc. p. 440. ISBN 978-0471832539.
  8. ^ Schock, R. U. Jr.; Tabern, D. L. (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.
  9. ^ 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.
  10. ^ 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.

Cited sources

[edit]
Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=Gentisic_acid&oldid=1193607884"