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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
Molecular Weight:
154.12
MDL Number:
MFCD00002460
MOL File:
490-79-9.mol
MSDS File:
SDS
Last updated:2024-01-23 14:06:52

2,5-Dihydroxybenzoic acid 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
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)
EWG's Food Scores 1
FDA UNII VP36V95O3T
NIST Chemistry Reference 2,5-Dihydroxybenzoic acid(490-79-9)
EPA Substance Registry System Benzoic acid, 2,5-dihydroxy- (490-79-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P501
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
NFPA 704
1
2 0

2,5-Dihydroxybenzoic acid price More Price(57)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 85707 2,5-Dihydroxybenzoic acid matrix substance for MALDI-MS, >99.0% (HPLC) 490-79-9 10mg $21.2 2024-03-01 Buy
Sigma-Aldrich 85707 2,5-Dihydroxybenzoic acid matrix substance for MALDI-MS, >99.0% (HPLC) 490-79-9 250mg $281 2024-03-01 Buy
Sigma-Aldrich PHR3329 2,5-Dihydroxybenzoic acid certified reference material, pharmaceutical secondary standard 490-79-9 50MG $760 2024-03-01 Buy
Sigma-Aldrich 85707 2,5-Dihydroxybenzoic acid matrix substance for MALDI-MS, >99.0% (HPLC) 490-79-9 1g $906 2024-03-01 Buy
Sigma-Aldrich 149357 2,5-Dihydroxybenzoic acid 98% 490-79-9 10g $45.7 2024-03-01 Buy
Product number Packaging Price Buy
85707 10mg $21.2 Buy
85707 250mg $281 Buy
PHR3329 50MG $760 Buy
85707 1g $906 Buy
149357 10g $45.7 Buy

2,5-Dihydroxybenzoic acid Chemical Properties,Uses,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

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.

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 .

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.

Definition

ChEBI: 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 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

Global( 545)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Mojin Biotechnology Co., Ltd
+86-13288715578 +86-13231137666 sales@hbmojin.com China 12409 58
Hebei Yanxi Chemical Co., Ltd.
+8617531190177 peter@yan-xi.com China 5960 58
Anhui Ruihan Technology Co., Ltd
+8617756083858 daisy@anhuiruihan.com China 994 58
Sigma Audley
+86-18336680971 +86-18126314766 nova@sh-teruiop.com China 501 58
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Shanghai Daken Advanced Materials Co.,Ltd
+86-371-66670886 info@dakenam.com China 14770 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21703 55
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714 fandachem@gmail.com China 9359 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038 zheyansh@163.com CHINA 3620 58
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29919 58

View Lastest Price from 2,5-Dihydroxybenzoic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2,5-Dihydroxybenzoic acid pictures 2024-01-23 2,5-Dihydroxybenzoic acid
490-79-9
US $45.00-35.00 / kg 1kg 99.8% 200tons/year Sigma Audley
2,5-dihydroxybenzoic acid pictures 2023-09-18 2,5-dihydroxybenzoic acid
490-79-9
US $40.00-40.00 / kg 1kg 0.99 10 tons Hebei Yanxi Chemical Co., Ltd.
2,5-Dihydroxybenzoic acid pictures 2023-09-12 2,5-Dihydroxybenzoic acid
490-79-9
US $30.00 / kg 1kg 99% 20 tons Anhui Ruihan Technology Co., Ltd
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 Gentisic acid, 2-Carboxyhydroquinone, 2-Carboxybenzene-1,4-diol 2,5-Dihydroxybenzoic Acid, 97+% 2,5-Dihydroxyb Gentisic Acid 〔2,5-Dihydroxybenzoic Acid〕 2,5-DIHYDROXYBENZOIC ACID HYDROQUINONECARBOXYLIC ACID DIHYDROXYBENZOIC(2,5-) ACID Gentiana scabra P.E Hydrochinon acid GENTISIC ACID FREE ACID 2,5-dihdyroxybenzoic acid 2,5-Dihydroxybenzoic acid,DHB, Gentisic acid, Hydroquinonecarboxylic acid 5-Dihydroxybenzoic acid 2,5-Dihydroxybenzoic acid, 99% 50GR 2,5-dihydroxy-benzoicaci 2,5-Dioxybenzoic acid 5-Hydroxysalicylic acid 5-hydroxy-salicylicaci 5-hydroxysalicylicacid acido2,5-diidrossibenzoico Benzoic acid, 2,5-dihydroxy- Benzoicacid,2,5-dihydroxy- Gensigen Gensigon 2,5-Dihydroxybenzoic Acid [Matrix for MALDI-TOF/MS] DHB, Gentisic acid, Hydroquinonecarboxylic acid 3,6-Dihydroxybenzoic acid Carboxyhydroquinone RARECHEM AL BE 0043 Mesalazine (Mesalamine) EP Impurity G 2,5-Dihydroxybenzoic acid(2,5-DHBA、DHB) Mesalazine Impurity 7(Mesalazine EP Impurity G) DHB, 2,5-Dihydroxybenzoic acid Mesalazine Impurity G Mesalamine EP Impurity G 2,5-DihydroxybenzoicAcid[MatrixforMALDI-TOF/MS]> 2,5-Dihydroxybenzoic Acid > Dihydroxybenzoic MS 2,5-DIHYDROXYBENZOIC ACID FOR SYNTHESIS GENTISIC ACID CAS 490-79-9 Mesalamine Impurity-G(2,5-dihydrobenzoic acid) 5-Dihydroxybenzoic 2,5-Dihydroxybenzoes?ure Mesalazine EP Impurity GQ: What is Mesalazine EP Impurity G Q: What is the CAS Number of Mesalazine EP Impurity G Q: What is the storage condition of Mesalazine EP Impurity G Q: What are the applications of Mesalazine EP Impurity G Kyselina 2,5-dihydroxybenzoova 2,5-Dhba GENTISIC ACID DHB Gentisic Gentisate