2,5-Dihydroxybenzoic acid

ChemicalBook > CAS DataBase List > 2,5-Dihydroxybenzoic acid

2,5-Dihydroxybenzoic acid

Product Name: 2,5-Dihydroxybenzoic acid
CAS No.: 490-79-9
Chemical Name: 2,5-Dihydroxybenzoic acid
Synonyms: GENTISIC ACID;DHB;Gentisate;2,5-Dhba;Gentisic;Phloretate;Kyselina 2,5-dihydroxybenzoova;Gensigen;Gensigon;2,5-Dihydroxyb
CBNumber: CB5853669
Molecular Formula: C7H6O4
Formula Weight: 154.12
MOL File: 490-79-9.mol

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2,5-Dihydroxybenzoic acid Property

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
PH: 3.21(1 mM solution);2.56(10 mM solution);2.01(100 mM solution)
Water Solubility: soluble
Merck: 14,4398
BRN: 2209119
InChIKey: WXTMDXOMEHJXQO-UHFFFAOYSA-N
LogP: 1.740
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

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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 85707
Product name: 2,5-Dihydroxybenzoic acid
Purity: matrix substance for MALDI-MS, >99.0% (HPLC)
Packaging: 10mg
Price: $21.2
Updated: 2024/03/01

Sigma-Aldrich

Product number: 85707
Product name: 2,5-Dihydroxybenzoic acid
Purity: matrix substance for MALDI-MS, >99.0% (HPLC)
Packaging: 250mg
Price: $281
Updated: 2024/03/01

Sigma-Aldrich

Product number: PHR3329
Product name: 2,5-Dihydroxybenzoic acid
Purity: certified reference material, pharmaceutical secondary standard
Packaging: 50MG
Price: $760
Updated: 2024/03/01

Sigma-Aldrich

Product number: 85707
Product name: 2,5-Dihydroxybenzoic acid
Purity: matrix substance for MALDI-MS, >99.0% (HPLC)
Packaging: 1g
Price: $906
Updated: 2024/03/01

Sigma-Aldrich

Product number: 149357
Product name: 2,5-Dihydroxybenzoic acid
Purity: 98%
Packaging: 10g
Price: $45.7
Updated: 2024/03/01

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2,5-Dihydroxybenzoic acid Chemical Properties,Usage,Production

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 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 Properties

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.

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.

Uses

Medicine, as sodium gentisate (analgesic).

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

Hydroquinone

Preparation Products

Flecainide

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View Lastest Price from 2,5-Dihydroxybenzoic acid manufacturers

Ouhuang Engineering Materials (Hubei) Co., Ltd

Product: Gentisic acid 490-79-9
Price: US $30.00/kg
Min. Order: 1kg
Purity: 99.7%
Supply Ability: 200000kg
Release date: 2024-04-25

Sigma Audley

Product: 2,5-Dihydroxybenzoic acid 490-79-9
Price: US $45.00-35.00/kg
Min. Order: 1kg
Purity: 99.8%
Supply Ability: 200tons/year
Release date: 2024-01-23

Hebei Yanxi Chemical Co., Ltd.

Product: 2,5-dihydroxybenzoic acid 490-79-9
Price: US $40.00-40.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 10 tons
Release date: 2023-09-18

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