Gentisic acid is a dihydroxy benzoic 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.
Gentisic acid is a benzoic acid that has been found in Gentiana and an active metabolite of aspirin with diverse biological activities. It decreases radiation-induced production of thiobarbituric acid reactive substances (TBARS), hydrogen peroxide, and protein carbonyls, increases superoxide dismutase activity, and prevents hemolysis in isolated human erythrocytes when used at concentrations ranging from 5 to 100 μM. Gentisic acid (1-10 μM) inhibits LDL oxidation and formation of cholesterol ester hydroperoxides in isolated human plasma. It induces relaxation of isolated guinea pig trachea (EC50 = 20 μM), an effect that is reduced by the large-conductance calcium-activated potassium channel blocker charybdotoxin . Gentisic acid (10 and 100 mg/kg) reduces cardiac hypertrophy and fibrosis and pulmonary remodeling, suppresses the renin-angiotensin-aldosterone system, and inhibits cardiac dysfunction in a mouse model of transverse aortic constriction-induced cardiac hypertrophy. It also prevents cardiovascular collapse and lactic acidemia in a canine model of P. aeruginosa-induced septic shock.
White to light beige crystalline powder. 2,5-Dihydroxybenzoic Acid [490-79-9]
(gentisic acid, 2,5-DHBA), C7H6O4, Mr 154.1,
mp 205 C, is soluble in water and alcohols but
insoluble in benzene and chloroform. The acid is
stable in boiling water and gives a deep blue color
with iron(III) chloride. Here, the acid decomposes to form p-benzoquinone [106-51-4] and
carbon dioxide. 2–5-Dihydroxybenzoic acid is used as an
antirheumatic drug and, more recently, as a color
developer for thermal paper.
2,5-dihydroxybenzoic acid areused as intermediates for pharmaceuticals (especially for antipyetic anlgesic, antirheumatism) and other organic synthesis. They are used as matrix for ionization of peptides, proteins and carbohydrates. In industrial field, they areused as intermediates for the production of other organic chemicals, resins, polyesters, plasticizers, dyestuffs, preservatives, and rubber chemicals.
Medicine, as sodium gentisate (analgesic).
As a hydroquinone , gentisic acid is readily oxidized 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 .
Gentisic acid is produced by carboxylation of hydroquinone.
C6H4(OH)2 + CO2 → C6H3(CO2H)(OH)2
This conversion is an example of a Kolbe–Schmitt reaction.
ChEBI: 2,5-dihydroxybenzoic acid is a dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions. It has a role as a MALDI matrix material, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a human metabolite, a fungal metabolite and a mouse metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 2,5-dihydroxybenzoate.
Poison bp intravenous
route. Moderately toxic by ingestion and
intraperitoneal routes. Experimental
teratogenic and reproductive effects.
Mutation data reported. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Crystallise gentisic acid from hot water or *benzene/acetone. Dry it in a vacuum desiccator over silica gel. [Beilstein 10 H 384, 10 IV 1441.]
[1] RAVI JOSHI. Antioxidant activity and free radical scavenging reactions of gentisic acid: in-vitro and pulse radiolysis studies.[J]. Free Radical Research, 2012, 46 1: 11-20. DOI:
10.3109/10715762.2011.633518[2] KEIKO ASHIDATE . Gentisic acid, an aspirin metabolite, inhibits oxidation of low-density lipoprotein and the formation of cholesterol ester hydroperoxides in human plasma[J]. European journal of pharmacology, 2005, 513 3: Pages 173-179. DOI:
10.1016/j.ejphar.2005.03.012[3] J. F. CUNHA. The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: the role of potassium channels and vasoactive intestinal peptide receptors.[J]. Brazilian Journal of Medical and Biological Research, 2001, 4 1: 381-388. DOI:
10.1590/s0100-879x2001000300013[4] SIMEI SUN. Gentisic acid prevents the transition from pressure overload-induced cardiac hypertrophy to heart failure.[J]. Scientific Reports, 2019: 3018. DOI:
10.1038/s41598-019-39423-8[5] STEVEN MINK. Gentisic acid sodium salt, a phenolic compound, is superior to norepinephrine in reversing cardiovascular collapse, hepatic mitochondrial dysfunction and lactic acidemia in Pseudomonas aeruginosa septic shock in dogs.[J]. Intensive Care Medicine Experimental, 2016, 4 1: 24. DOI:
10.1186/s40635-016-0095-0
