2,5-Dihydroxybenzoic acid

Base Information

• Chemical Name: 2,5-Dihydroxybenzoic acid
• CAS No.: 490-79-9
• Molecular Formula: C7H6O4
• Molecular Weight: 154.122
• Hs Code.: 29182990
• European Community (EC) Number: 207-718-5
• NSC Number: 49098,27224
• UNII: VP36V95O3T
• DSSTox Substance ID: DTXSID4060078
• Nikkaji Number: J6.046A
• Wikipedia: Gentisic_acid
• Wikidata: Q417831
• NCI Thesaurus Code: C76714
• RXCUI: 1368641
• Metabolomics Workbench ID: 37104
• ChEMBL ID: CHEMBL1461
• Mol file: 490-79-9.mol

Synonyms:2,5-dihydroxybenzoate;2,5-dihydroxybenzoic acid;2,5-dihydroxybenzoic acid, monosodium salt;gentisic acid;lithium 2,5-dihydroxybenzoate

Chemical Property of 2,5-Dihydroxybenzoic acid

Chemical Property:

• Appearance/Colour: white to light beige crystalline powder
• Vapor Pressure: 2.38E-07mmHg at 25°C
• Melting Point: 204-208 °C(lit.)
• Refractive Index: 1.6400 (estimate)
• Boiling Point: 406.9 °C at 760 mmHg
• PKA: 2.97(at 25℃)
• Flash Point: 214 °C
• PSA: 77.76000
• Density: 1.559 g/cm³
• LogP: 0.79600
• Storage Temp.: Store below +30°C.
• Solubility.: It is soluble in alcohol and ether.
• Water Solubility.: soluble
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 154.02660867
• Heavy Atom Count: 11
• Complexity: 157

Purity/Quality:

99% ^*data from raw suppliers

Gentisic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: C1=CC(=C(C=C1O)C(=O)O)O
• 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. 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.
• Uses: Medicine, as sodium gentisate (analgesic). 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.

Technology Process of 2,5-Dihydroxybenzoic acid

There total 88 articles about 2,5-Dihydroxybenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

2,5-bis-methoxymethoxy-benzoic acid methoxymethyl ester → 2,5-dihydroxybenzoic acid. (490-79-9)

Guidance literature:

With methanol; iodine; at 20 ℃; for 48h;

DOI:10.1016/j.tetlet.2004.02.039

Reference yield: 9.0%

benzoic acid (65-85-0,8013-63-6) → 2,3-Dihydroxybenzoic acid (303-38-8) + 2,5-dihydroxybenzoic acid. (490-79-9) + 3-Carboxyphenol (99-06-9) + 4-hydroxy-benzoic acid (99-96-7)

Guidance literature:

With oxygen; iron(II) sulfate; In water; at 40 ℃; for 3h; Further byproducts given;

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + hydroquinone (123-31-9,8027-02-9) → 2,5-dihydroxybenzoic acid. (490-79-9) + 2,5-dihydroxy-1,4-benzenedicarboxylic acid (610-92-4)

Guidance literature:

at 220 ℃;

DOI:10.1007/BF00899352 DOI:10.1021/jo01369a006

upstream raw materials:

2,5-Dihydroxybenzaldehyde

2,5-diacetoxytoluene

5-Aminosalicylic Acid

2-hydroxy-5-iodobenzoic acid

Downstream raw materials:

5-methoxysalicylic acid

Methyl 2,5-dihydroxybenzoate

ethyl 2,5-dihydroxybenzoate

2,3,6-trihydroxybenzoic acid

Refernces

• 1、 Vartak,Menon. "". . p. 1003,1004-1011. Retrieved 1971.
• 2、 Rahaman, Rubina,Munshi, Sandip,Banerjee, Sridhar,Chakraborty, Biswarup,Bhunia, Sarmistha,Paine, Tapan Kanti. "Dioxygen reactivity of iron(ii)-gentisate/1,4-dihydroxy-2-naphthoate complexes of N4 ligands: Oxidative coupling of 1,4-dihydroxy-2-naphthoate". . p. 16993 - 17004. Retrieved 2019.
• 3、 Gui, Lun,Long, Qizhang,Yao, Jian. "A chlorogenic acid esterase from a metagenomic library with unique substrate specificity and its application in caffeic and ferulic acid production from agricultural byproducts". . . Retrieved 2021/08/25.
• 4、 Nyúl, Eszter,Kuzma, Mónika,Mayer, Mátyás,Lakatos, Sándor,Almási, Attila,Perjési, Pál. "HPLC study on Fenton-reaction initiated oxidation of salicylic acid. Biological relevance of the reaction in intestinal biotransformation of salicylic acid". . p. 1040 - 1051. Retrieved 2018/10/24.