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2,5-Dihydroxybenzoic acid

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2,5-Dihydroxybenzoic acid Basic information

Product Name:
2,5-Dihydroxybenzoic acid
Synonyms:
  • Hydroguinonecarboxylicacid
  • Kyselina 2,5-dihydroxybenzoova
  • Kyselina gentisinova
  • kyselina2,5-dihydroxybenzoova
  • kyselinagentisinova
  • Salicylic acid, 5-hydroxy-
  • 2,5-Dihydroxybenzoic acid, 99% 5GR
  • MesalaMine IMpurity G
CAS:
490-79-9
MF:
C7H6O4
MW:
154.12
EINECS:
207-718-5
Product Categories:
  • Analytical Chemistry
  • Mass Spectrometry
  • Organic acids
  • Matrix Materials (MALDI-TOF-MS)
  • UltraPure MALDI Matrices
  • Inhibitors
  • Armoracia rusticana (Horseradish)
  • Building Blocks
  • C7
  • Carbonyl Compounds
  • Carboxylic Acids
  • Chemical Synthesis
  • Citrus aurantium (Seville orange)
  • Humulus lupulus (Hops)
  • Hypericum perforatum (St John&#8242
  • Nutrition Research
  • Organic Building Blocks
  • Panax ginseng
  • Phytochemicals by Plant (Food/Spice/Herb)
  • s wort)
  • Vaccinium myrtillus (Bilberry)
Mol File:
490-79-9.mol
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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.
pka
2.97(at 25℃)
form 
Crystalline Powder
color 
White to light beige
Water Solubility 
soluble
Merck 
14,4398
BRN 
2209119
InChIKey
WXTMDXOMEHJXQO-UHFFFAOYSA-N
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)
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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

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2,5-Dihydroxybenzoic acid Usage And Synthesis

Description

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.

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. 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 (Item No. 24115). 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 Properties

white to light beige crystalline powder

Uses

Medicine, as sodium gentisate (analgesic).

Uses

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.

Definition

ChEBI: A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.

Production Methods

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.

Application

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 .

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 3292, 1950 DOI: 10.1021/ja01163a521

General Description

Aspirin metabolite.

Safety Profile

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.

Purification Methods

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.]

2,5-Dihydroxybenzoic acid Preparation Products And Raw materials

Raw materials

Preparation Products

2,5-Dihydroxybenzoic acidSupplier

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