2,5-Dihydroxybenzoic acid

HCID 3469CAS 490-79-9
Substructure searchFind similar structures

Basic information

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

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
Nikkaji
J6.046A

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

Experimental & physicochemical properties

LogP1.74
Solubility5.0 mg/mL at 5 °C
Melting Point199.5 °C
Vapor Pressure0.0000021 [mmHg]
Physical Description · 2 items

Solid; [Merck Index] Light yellow crystals; [Aldrich MSDS]

Solid

Collision Cross Section · 2 items

122.67 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

125 Ų [M-H]-

Physicochemical properties

Melting point
204 · 204-208 °C(lit.)
Boiling point
237.46 °C · 237.46°C (rough estimate)
Density
1.3725 · 1.3725 (rough estimate)
refractive index
1.64 · 1.6400 (estimate)
storage temp.
30 °C · Store below +30°C.
solubility
It is soluble in alcohol and ether.

Safety & regulation

GHS classification

GHS Classification · 6 items

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]；H315 (94%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (94%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (92.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

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.；Reported as not meeting GHS hazard criteria per 1 of 67 reports by companies.；There are 10 notifications provided by 66 of 67 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

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%)；Skin Irrit. 2 (94%)；Eye Irrit. 2 (94%)；STOT SE 3 (92.5%)

Toxicology

Adverse EffectsNeurotoxin - Other CNS neurotoxin

Regulatory information

Regulatory Information · 2 items

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

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
LY3850000
hs_code
29182990
risk_code
22-36/37/38

Chemistry & industry

Pharmacology

Metabolism/Metabolites5-hydroxylation is a known human metabolite of salicylic acid.
Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 2 items

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:；• Personal Care
General Manufacturing InformationBenzoic acid, 2,5-dihydroxy-: ACTIVE
Applications · 5 items

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.

UsesMedicine, as sodium gentisate (analgesic).

Uses2,5-dihydroxybenzoic acid areused 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 areused as intermediates for the production of other organic chemicals, resins, polyesters, plasticizers, dyestuffs, preservatives, and rubber chemicals.

General DescriptionAspirin metabolite.

Upstream & downstream products

Upstream raw materials

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

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