- Product Name:
- 2,5-Dihydroxybenzoic acid
- Kyselina 2,5-dihydroxybenzoova
- Kyselina gentisinova
- Salicylic acid, 5-hydroxy-
- 2,5-Dihydroxybenzoic acid, 99% 5GR
- MesalaMine IMpurity G
- Product Categories:
- Analytical Chemistry
- Mass Spectrometry
- Organic acids
- Matrix Materials (MALDI-TOF-MS)
- UltraPure MALDI Matrices
- Armoracia rusticana (Horseradish)
- Building Blocks
- Carbonyl Compounds
- Carboxylic Acids
- Chemical Synthesis
- Citrus aurantium (Seville orange)
- Humulus lupulus (Hops)
- Hypericum perforatum (St John′
- Nutrition Research
- Organic Building Blocks
- Panax ginseng
- Phytochemicals by Plant (Food/Spice/Herb)
- s wort)
- Vaccinium myrtillus (Bilberry)
- Mol File:
2,5-Dihydroxybenzoic acid Chemical Properties
- Melting point:
- 204-208 °C(lit.)
- Boiling point:
- 237.46°C (rough estimate)
- 1.3725 (rough estimate)
- refractive index
- 1.6400 (estimate)
- storage temp.
- Store below +30°C.
- It is soluble in alcohol and ether.
- 2.97(at 25℃)
- Crystalline Powder
- White to light beige
- Water Solubility
- CAS DataBase Reference
- 490-79-9(CAS DataBase Reference)
- NIST Chemistry Reference
- 2,5-Dihydroxybenzoic acid(490-79-9)
- EPA Substance Registry System
- Benzoic acid, 2,5-dihydroxy- (490-79-9)
2,5-Dihydroxybenzoic acid Usage And Synthesis
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 (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
white to light beige crystalline powder
Medicine, as sodium gentisate (analgesic).
2,5-dihydroxybenzoic acid are?used 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 are?used as intermediates for the production of other organic chemicals, resins, polyesters, plasticizers, dyestuffs, preservatives, and rubber chemicals.
ChEBI: A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.
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.
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 .
Journal of the American Chemical Society, 72, p. 3292, 1950 DOI: 10.1021/ja01163a521
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.]
- 021-60451683- ;021-50171870
- 010-82848833- ;010-82848833-
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- 2,5-Dihydroxybenzoic acid