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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

Preparation Products

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2,5-Dihydroxybenzoic acid Suppliers

Shanghai Arbor Chemical Co., Ltd.
Tel
021-60451682 15021268886
Fax
+86-21-60451682
Email
sales@arborchemical.com
Country
China
ProdList
856
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55
Nanjing Tianyi Chemical Technology Co., Ltd
Tel
15150528611
Fax
151-5052-8611
Email
779881375@qq.com
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China
ProdList
71
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58
Hangzhou Xiao Bei Medical Technology Co., LTD
Tel
571-8526-3177 13962438025
Email
beixi.dong@heryipharma.com
Country
China
ProdList
165
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Nanjing chemical reagent co. LTD
Tel
025-025-58369808 17895012682
Fax
025-85312034
Email
1848231502@qq.com
Country
China
ProdList
3501
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Hubei Baoling Chemical Technology Co. , Ltd.
Tel
13129969326
Email
2797487194@qq.com
Country
China
ProdList
1007
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58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
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Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
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84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Beijing HwrkChemical Technology Co., Ltd
Tel
010-89508211 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
8418
Advantage
55
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View Lastest Price from 2,5-Dihydroxybenzoic acid manufacturers

Hebei Yanxi Chemical Co., Ltd.
Product
2,5-dihydroxybenzoic acid 490-79-9
Price
US $40.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10 tons
Release date
2023-09-18
Hebei Chuanghai Biotechnology Co,.LTD
Product
2, 5-Dihydroxybenzoic Acid 490-79-9
Price
US $10.70/KG
Min. Order
10KG
Purity
99%
Supply Ability
10000kg
Release date
2024-08-20
Hebei Fengjia New Material Co., Ltd
Product
2,5-DIHYDROXYBENZOIC ACID 490-79-9
Price
US $120.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
1000000
Release date
2024-08-09

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