ChemicalBook Product Catalog Chemical Reagents Organic reagents Aromatic acids 2,5-Dihydroxybenzoic acid

2,5-Dihydroxybenzoic acid

2,5-Dihydroxybenzoic acid Basic information
Product Name:2,5-Dihydroxybenzoic acid
Synonyms:Hydroguinonecarboxylicacid;Kyselina gentisinova;kyselina2,5-dihydroxybenzoova;kyselinagentisinova;Salicylic acid, 5-hydroxy-;2,5-Dihydroxybenzoic acid, 99% 5GR;MesalaMine IMpurity G;2,5-Dihydroxybenzoic acid, tech
CAS:490-79-9
MF:C7H6O4
MW:154.12
EINECS:207-718-5
Product Categories:Analytical Chemistry;Mass Spectrometry;Matrix Materials (MALDI-TOF-MS);Organic acids;Inhibitors;UltraPure MALDI Matrices;Armoracia rusticana (Horseradish);Building Blocks;C7;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Citrus aurantium (Seville orange);Humulus lupulus (Hops);Nutrition Research;Organic Building Blocks;Panax ginseng;Phytochemicals by Plant (Food/Spice/Herb);s wort);Vaccinium myrtillus (Bilberry)
Mol File:490-79-9.mol
2,5-Dihydroxybenzoic acid Structure
2,5-Dihydroxybenzoic acid Chemical Properties
Melting point 204-208 °C(lit.)
Boiling point 237.46°C (rough estimate)
density 1.3725 (rough estimate)
refractive index 1.6400 (estimate)
storage temp. Store below +30°C.
solubility It is soluble in alcohol and ether.
pka2.97(at 25℃)
form Crystalline Powder
color White to light beige
PH3.21(1 mM solution);2.56(10 mM solution);2.01(100 mM solution)
Water Solubility soluble
Merck 14,4398
BRN 2209119
InChIKeyWXTMDXOMEHJXQO-UHFFFAOYSA-N
LogP1.740
CAS DataBase Reference490-79-9(CAS DataBase Reference)
NIST Chemistry Reference2,5-Dihydroxybenzoic acid(490-79-9)
EPA Substance Registry SystemBenzoic acid, 2,5-dihydroxy- (490-79-9)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 26-36-37/39
WGK Germany 3
RTECS LY3850000
Hazard Note Harmful
TSCA Yes
HS Code 29182990
MSDS Information
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2,5-Dihydroxybenzoic acid English
SigmaAldrich English
ACROS English
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2,5-Dihydroxybenzoic acid Usage And Synthesis
DescriptionGentisic 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.
DescriptionGentisic 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.
Chemical Propertieswhite to light beige crystalline powder
UsesMedicine, as sodium gentisate (analgesic).
Uses2,5-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.
ApplicationAs 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 .
Production MethodsGentisic 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.

DefinitionChEBI: A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.
Synthesis Reference(s)Journal of the American Chemical Society, 72, p. 3292, 1950 DOI: 10.1021/ja01163a521
General DescriptionAspirin metabolite.
Safety ProfilePoison 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.
Purification MethodsCrystallise gentisic acid from hot water or *benzene/acetone. Dry it in a vacuum desiccator over silica gel. [Beilstein 10 H 384, 10 IV 1441.]
2,5-Dihydroxybenzoic acid Preparation Products And Raw materials
Raw materialsHydroquinone
Preparation ProductsFlecainide-->Methyl 2,5-dihydroxybenzoate-->3,6-DIHYDROXYXANTHONE-->GENTISIN-->Sodium gentisate-->2,5-Diamino-2,5-cyclohexadiene-1,4-dione
3,5-DIHYDROXYBENZOIC ACID METHYL ESTER,2,6-DIHYDROXYBENZOIC ACID METHYL ESTER 5-Methoxysalicylic acid 3,4-DIHYDROXYBENZOIC ACID MONOHYDRATE Ethyl 2-(Chlorosulfonyl)acetate 2'-Hydroxy-3-phenylpropiophenone Ascoric Acid 3-CHLORO-2,6-DIHYDROXYBENZOIC ACID 2,5-DIHYDROXYBENZOIC ACID SODIUM SALT HYDRATE 4-CHLORO-3,5-DIHYDROXYBENZOIC ACID 2-CHLORO-3,5-DIHYDROXYBENZOIC ACID 3-Hydroxybenzoic acid 4-METHOXY-2,3-DIHYDROXYBENZOIC ACID 4-BROMO-3,5-DIHYDROXYBENZOIC ACID MONOHYDRATE 3-METHOXY-4,5-DIHYDROXYBENZOIC ACID 6-FLUORO-2,3-DIHYDROXYBENZOIC ACID 3,5-DIHYDROXYBENZOIC ACID 9-DHB 3,4-DIHYDROXYBENZOIC ACID, [CARBOXYL-14C]
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