2,5-Dihydroxybenzoic acid
Basic information
- CAS
490-79-9- Standard SMILES
O=C(O)c1cc(O)ccc1O- InChIKey
WXTMDXOMEHJXQO-UHFFFAOYSA-N- Molecular formula
- C7H6O4
- Average molar mass
- 154.12 g/mol
- Monoisotopic mass
- 154.02660867
Overview
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 mouse metabolite, a fungal metabolite and a human metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 2,5-dihydroxybenzoate.
Names & identifiers
- Preferred name
- 2,5-Dihydroxybenzoic acid
- IUPAC
- 2,5-dihydroxybenzoic acid
- English name
- 2,5-Dihydroxybenzoic acid
- Molecular formula
- C7H6O4
- Molecular weight
- 154.12
Names & synonyms
2,5-DIHYDROXYBENZOIC ACIDgentisic acid490-79-9Benzoic acid, 2,5-dihydroxy-5-Hydroxysalicylic acidHydroquinonecarboxylic acidGensigenGensigon2,5-Dhba2,5-Dioxybenzoic acidSalicylic acid, 5-hydroxy-Kyselina gentisinova
Show more names
DHBGentisateGentisicPhloretate2,5-dihydroxybenzoic2,5-Dihydroxybenzoes?ureKyselina 2,5-dihydroxybenzoova
Acido gentisicoAcide gentisiqueAcidum gentisicumVP36V95O3TNSC-27224DTXSID4060078CHEBI:17189RefChem:639843
Database identifiers
- CAS
490-79-9- PubChem CID
- 3469
- DTXSID
DTXSID4060078- ChEMBL
CHEMBL1461- ChEBI
CHEBI:17189- UNII
- VP36V95O3T
- EC Number
- 207-718-5
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 157
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Other Aromatic Compounds
DrugsPharmaceuticals -> Metabolite of Acetylsalicylic acid
LogP
1.74
1.12
Solubility5.0 mg/mL at 5 °C
Melting Point199.5 °C
Vapor Pressure0.0000021 [mmHg]
Physical Description
Solid; [Merck Index] Light yellow crystals; [Aldrich MSDS]
Solid
Collision Cross Section
122.67 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
125 Ų [M-H]-
Physicochemical properties
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.5% (1 of 67) of reports.
Warning
H302 (94%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 67 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzoic acid, 2,5-dihydroxy-
Benzoic acid, 2,5-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses convulsions in intravenous lethal-dose studies of mice; [RTECS] A skin and strong eye irritant; Harmful by ingestion and skin absorption; Evidence of reproductive toxicity in experimental animals; [Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (94%)
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
Chemistry & industry
Pharmacology
Metabolism/Metabolites5-hydroxylation is a known human metabolite of salicylic acid.
Cellular LocationsCytoplasm
Uses & manufacturing
Uses
Excreted in urine of dogs following ingestion of salicylates; Used therapeutically (analgesic and anti-inflammatory); [Merck Index] An oxidative product of saligenin; [ChemIDplus] Used as an analgesic medicine; [Hawley]
Synthetic Polymer MALDI Matrix Compounds
Household ProductsInformation on 1 consumer products that contain Gentisic acid in the following categories is provided:
General Manufacturing InformationBenzoic acid, 2,5-dihydroxy-: ACTIVE
Applications
DescriptionGentisic 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.
DescriptionGentisic 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.
Related reactions
73 records
Compound notes
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