Surf Wiki
Save to docs
general/hydroquinones

From Surf Wiki (app.surf) — the open knowledge base

Gentisic acid

|DHB |5-Hydroxysalicylic acid |Gentianic acid |Carboxyhydroquinone |2,5-Dioxybenzoic Acid |Hydroquinonecarboxylic acid |2,3-Dihydroxybenzoic acid |2,4-Dihydroxybenzoic acid |2,6-Dihydroxybenzoic acid |3,4-Dihydroxybenzoic acid |3,5-Dihydroxybenzoic acid 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.

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

Production

Gentisic acid is produced by carboxylation of hydroquinone. :

This conversion is an example of a Kolbe–Schmitt reaction.

Alternatively the compound can be synthesized from salicylic acid via Elbs persulfate oxidation.

Reactions

In the presence of the enzyme gentisate 1,2-dioxygenase and oxygen, gentisic acid undergoes a ring-opening reaction to give 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, and has been shown to conveniently detect peptides incorporating the boronic acid moiety by MALDI.

For detection of gentisic acid, the whole-cell biosensor has been developed by using maleylpyruvic acid-inducible gene expression system and gentisate 1,2-dioxygenase gene from chemolithoautotrophic bacterium Cupriavidus necator.

References

References

  1. "Gentisic acid - Compound Summary". [[PubChem]].
  2. (2016). "CRC Handbook of Chemistry and Physics". [[CRC Press]].
  3. (2016). "CRC Handbook of Chemistry and Physics". [[CRC Press]].
  4. Levy, G. (1972). "Salicylate accumulation kinetics in man". New England Journal of Medicine.
  5. (2009). "Comparison of Phenolic Acids and Flavan-3-ols During Wine Fermentation of Grapes with Different Harvest Times". Molecules.
  6. Hudnall, Phillip M.. "Hydroquinone".
  7. Behrman, E.J.. (1988). "Organic Reactions, Volume 35". John Wiley & Sons Inc..
  8. (1951). "The Persulfate Oxidation of Salicylic Acid. 2,3,5-Trihydroxybenzoic Acid". The Journal of Organic Chemistry.
  9. (1991). "2,5-Dihidroxybenzoic acid: a new matrix for laser desorption-ionization mass spectrometry". Int. J. Mass Spectrom. Ion Process..
  10. Crumpton, J.. (2011). "Facile Analysis and Sequencing of Linear and Branched Peptide Boronic Acids by MALDI Mass Spectrometry". Analytical Chemistry.
  11. Kutraite, I. (2024). "Maleylpyruvic Acid-Inducible Gene Expression System and Its Application for the Development of Gentisic Acid Biosensors". Analytical Chemistry.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

hydroquinones salicylic-acids dihydroxybenzoic-acids phenolic-human-metabolites human-drug-metabolites
Want to explore this topic further?

Ask Mako anything about Gentisic acid — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report