2,4-Dihydroxybenzoic acid
Chemical structure of 2,4-dihydroxybenzoic acid
Names
Preferred IUPAC name
2,4-Dihydroxybenzoic acid
Other names
β-Resorcylic acid
β-Resorcinolic acid
p-Hydroxysalicylic acid
2,4-DHBA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.770 Edit this at Wikidata
UNII
  • InChI=1S/C7H6O4/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,8-9H,(H,10,11) checkY
    Key: UIAFKZKHHVMJGS-UHFFFAOYSA-N checkY
  • C1=CC(=C(C=C1O)O)C(=O)O
Properties
C7H6O4
Molar mass 154.12 g/mol
Melting point 229 °C (444 °F; 502 K)[2]
Acidity (pKa) 3.11, 8.55, 14.0[1]
Hazards
GHS labelling:[3]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P280, P302+P352, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2,4-Dihydroxybenzoic acid (Resochin,[4] sontochin,[4] SN-7619,[4] β-resorcylic acid) is a dihydroxybenzoic acid.

As a resorcylic acid, it is one of the three isomeric crystalline acids that are both carboxyl derivatives of resorcinol and dihydroxy derivatives of benzoic acid.[5] Synthesis from resorcinol is via the Kolbe-Schmitt reaction.[6]

It is a degradation product of cyanidin glycosides from tart cherries in cell cultures.[7] It is also a metabolite found in human plasma after cranberry juice consumption.[8]

Resochin is especially effective against avian malaria. Because the initial testing during the chemical development process used avian malaria its efficacy was recognised immediately.[4]


References

  1. ^ Haynes, p. 5.91
  2. ^ Haynes, p. 3.190
  3. ^ GHS: GESTIS 492493
  4. ^ a b c d Jensen, Markus; Mehlhorn, Heinz (2009-07-11). Ryan, Una; Walochnik, Julia (eds.). "Seventy-five years of Resochin in the fight against malaria". Parasitology Research. Springer. 105 (3): 609–627. doi:10.1007/s00436-009-1524-8. PMID 19593586. S2CID 8037461.
  5. ^ Resorcyclic acid on merriam-webster on-line dictionary
  6. ^ Becker, Heinz G. O., ed. (1993). Organikum: organisch-chemisches Grundpraktikum (in German) (19th (rev. and expanded) ed.). Leipzig: Johann Ambrosius Barth [de]. pp. 351–352. ISBN 978-3-335-00343-4.
  7. ^ Seeram, Navindra P.; Bourquin, Leslie D.; Nair, Muraleedharan G. (2001). "Degradation Products of Cyanidin Glycosides from Tart Cherries and Their Bioactivities". Journal of Agricultural and Food Chemistry. 49 (10): 4924–4929. doi:10.1021/jf0107508. PMID 11600045.
  8. ^ Zhang, Kai; Zuo, Yuegang (2004). "GC-MS Determination of Flavonoids and Phenolic and Benzoic Acids in Human Plasma after Consumption of Cranberry Juice". Journal of Agricultural and Food Chemistry. 52 (2): 222–227. doi:10.1021/jf035073r. PMID 14733499.

Cited sources

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