A benzoic acid with diverse biological activities
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Gentisic Acid

Item No. 27615

Technical Information
Formal Name
2,5-dihydroxy-benzoic acid
CAS Number
490-79-9
Synonyms
  • Carboxyhydroquinone
  • 5-Hydroxysalicylic Acid
  • NSC 27224
  • NSC 49098
  • NSC 78825
Molecular Formula
C7H6O4
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 2mg/mLDMSO: 3mg/mLEthanol: 10mg/mLPBS (pH 7.2): 2mg/mL
λmax
214, 237, 337 nm
SMILES
OC1=CC(C(O)=O)=C(O)C=C1
InChi Code
InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)
InChi Key
WXTMDXOMEHJXQO-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Gentisic acid is a benzoic acid that has been found in Gentiana and an active metabolite of aspirin (Item No. 70260) with diverse biological activities.1,2,3,4,5 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.1 Gentisic acid (1-10 μM) inhibits LDL oxidation and formation of cholesterol ester hydroperoxides in isolated human plasma.2 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 (Item No. 24115).3 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.4 It also prevents cardiovascular collapse and lactic acidemia in a canine model of P. aeruginosa-induced septic shock.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Joshi, R.P., Gangabhagirathi, R., Venu, S., et alAntioxidant activity and free radical scavenging reactions of gentisic acid: In-vitro and pulse radiolysis studies. Free Radic. Res. 46(1), 11-20 (2012).

    2. Ashidate, K., Kawamura, M., Mimura, D., et alGentisic acid, an aspirin metabolite, inhibits oxidation of low-density lipoprotein and the formation of cholesterol ester hydroperoxides in human plasma. Eur. J. Pharmacol. 513(3), 173-179 (2005).

    3. Cunha, J.F., Campestrini, F.D., Calixto, J.B., et alThe mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: The role of potassium channels and vasoactive intestinal peptide receptors. Braz. J. Med. Biol. Res. 34(4), 381-388 (2001).

    4. Sun, S., Kee, H.J., Ryu, Y.L., et alGentisic acid prevents the transition from pressure overload-induced cardiac hypertrophy to heart failure. Sci. Rep. 9(1), 3018 (2019).

    5. Mink, S., Roy Chowdhury, S.K., Gotes, J., et alGentisic 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. Intensive Care Med. Exp. 4(1), 24 (2016).