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
ε(extinction coefficient)
>2000 at 337nm
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
$22.3
Updated
2025/07/31
Sigma-Aldrich
Product number
85707
Product name
2,5-Dihydroxybenzoic acid
Purity
matrix substance for MALDI-MS, >99.0% (HPLC)
Packaging
250mg
Price
$296
Updated
2025/07/31
Sigma-Aldrich
Product number
PHR3329
Product name
2,5-Dihydroxybenzoic acid
Purity
certified reference material, pharmaceutical secondary standard
Packaging
50MG
Price
$817
Updated
2025/07/31
Sigma-Aldrich
Product number
85707
Product name
2,5-Dihydroxybenzoic acid
Purity
matrix substance for MALDI-MS, >99.0% (HPLC)
Packaging
1g
Price
$953
Updated
2025/07/31
Sigma-Aldrich
Product number
149357
Product name
2,5-Dihydroxybenzoic acid
Purity
98%
Packaging
10g
Price
$47.1
Updated
2025/07/31
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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

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.

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 .

Definition

ChEBI: 2,5-dihydroxybenzoic acid is a dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions. It has a role as a MALDI matrix material, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a human metabolite, a fungal metabolite and a mouse metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 2,5-dihydroxybenzoate.

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.]

References

[1] RAVI JOSHI. Antioxidant activity and free radical scavenging reactions of gentisic acid: in-vitro and pulse radiolysis studies.[J]. Free Radical Research, 2012, 46 1: 11-20. DOI: 10.3109/10715762.2011.633518
[2] KEIKO ASHIDATE . Gentisic acid, an aspirin metabolite, inhibits oxidation of low-density lipoprotein and the formation of cholesterol ester hydroperoxides in human plasma[J]. European journal of pharmacology, 2005, 513 3: Pages 173-179. DOI: 10.1016/j.ejphar.2005.03.012
[3] J. F. CUNHA. The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: the role of potassium channels and vasoactive intestinal peptide receptors.[J]. Brazilian Journal of Medical and Biological Research, 2001, 4 1: 381-388. DOI: 10.1590/s0100-879x2001000300013
[4] SIMEI SUN. Gentisic acid prevents the transition from pressure overload-induced cardiac hypertrophy to heart failure.[J]. Scientific Reports, 2019: 3018. DOI: 10.1038/s41598-019-39423-8
[5] STEVEN MINK. Gentisic acid sodium salt, a phenolic compound, is superior to norepinephrine in reversing cardiovascular collapse, hepatic mitochondrial dysfunction and lactic acidemia in Pseudomonas aeruginosa septic shock in dogs.[J]. Intensive Care Medicine Experimental, 2016, 4 1: 24. DOI: 10.1186/s40635-016-0095-0

2,5-Dihydroxybenzoic acid Preparation Products And Raw materials

Raw materials

Hydroquinone

Preparation Products

Flecainide
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2,5-Dihydroxybenzoic acid Suppliers

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View Lastest Price from 2,5-Dihydroxybenzoic acid manufacturers

Shandong Vital Biotechnology Co., Ltd.
Product
2,5-Dihydroxybenzoic acid 490-79-9
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
100tons
Release date
2025-11-20
HANGZHOU HAILAN CHEMICAL CO.,LTD.
Product
2,5-Dihydroxybenzoic acid 490-79-9
Price
US $0.00/kg
Min. Order
1kg
Purity
99%min
Supply Ability
2000KGS
Release date
2025-10-24
Ningbo Qingteng Plastic Cost.,Ltd.
Product
DHB 490-79-9
Price
US $10.00/box
Min. Order
1box
Purity
99.99%
Supply Ability
9999
Release date
2025-07-31

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