3,4-Dihydroxybenzoic acid

Base Information

• Chemical Name: 3,4-Dihydroxybenzoic acid
• CAS No.: 99-50-3
• Molecular Formula: C7H6O4
• Molecular Weight: 154.122
• Hs Code.: 29182990
• European Community (EC) Number: 202-760-0
• NSC Number: 16631
• UNII: 36R5QJ8L4B
• DSSTox Substance ID: DTXSID4021212
• Nikkaji Number: J11.618A
• Wikipedia: Protocatechuic acid
• Wikidata: Q418599
• Pharos Ligand ID: WGB329FV2GX1
• Metabolomics Workbench ID: 37892
• ChEMBL ID: CHEMBL37537
• Mol file: 99-50-3.mol

Synonyms:3,4-dihydroxybenzoic acid;protocatechuic acid;protocatechuic acid, carboxy-14C-labeled;protocatechuic acid, monosodium salt

Chemical Property of 3,4-Dihydroxybenzoic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.75E-07mmHg at 25°C
• Melting Point: 197-200 °C (dec.)(lit.)
• Refractive Index: 1.6400 (estimate)
• Boiling Point: 410.7 °C at 760 mmHg
• PKA: 4.48(at 25℃)
• Flash Point: 216.3 °C
• PSA: 77.76000
• Density: 1.559 g/cm³
• LogP: 0.79600
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: 20g/l
• Water Solubility.: Soluble in hot alcohol and ether. Slightly soluble in water.
• XLogP3: 1.1
• 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

Protocatechuic Acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: C1=CC(=C(C=C1C(=O)O)O)O
• Description: Protocatechuic acid (3,4-dihydroxybenzoic acid, PCA) is a simple phenolic acid. It is found in a large variety of edible plants and possesses various pharmacological activities.Protocatechuic acid has an antibacterial effect, and has different degrees of antibacterial effect on Pseudomonas aeruginosa, Escherichia coli, Typhoid bacillus, Shigella, Alcaligenes, Bacillus subtilis and Staphylococcus aureus in vitro. It also has expectorant and anti-asthmatic effects. It is clinically used to treat chronic bronchitis.
• Physical properties: Protocatechuic acid has a density of 1.54g/cm3 and a melting point of about 200°C. It is soluble in ethanol, ether, acetone, ethyl acetate, soluble in hot water, slightly soluble in cold water, and insoluble in benzene and chloroform. Decomposes in boiling water and emits carbon dioxide. Its aqueous solution is green when it meets ferric chloride, and red when it meets sodium bicarbonate. It is a white to brown crystalline powder that will change color in the air.
• Uses: 3,4-Dihydroxybenzoic Acid is a metabolite of polyphenols such as Phloretin (P339000) and Quercetin (Q509500). A phenolic acid antioxidant and chemopreventive agent 3,4-Dihydroxybenzoic acid is a metabolite of polyphenols such as phloretin and quercetin. It is also a phenolic acid antioxidant present in fruits, vegetables and nuts. Further, it is found to be an efficacious chemopreventive agent in several carcinogenesis models. In addition to this, it acts as an anti-inflammatory agent.

Technology Process of 3,4-Dihydroxybenzoic acid

There total 303 articles about 3,4-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:

cyanidin-3-O-glucoside (47705-70-4,142506-26-1) → 3,4-Dihydroxybenzoic acid (99-50-3) + cyanidin (13306-05-3) + acide 2,4,6-trihydroxybenzoique (83-30-7)

Guidance literature:

at 95 ℃; for 24h;

DOI:10.1021/jf9036722

Reference yield:

3-Carboxyphenol (99-06-9) → 3,4-Dihydroxybenzoic acid (99-50-3) + 2,3-Dihydroxybenzoic acid (303-38-8) + 2,5-dihydroxybenzoic acid. (490-79-9)

Guidance literature:

With dinitrogen monoxide; In water; pH=6.2; Further Variations:; Reagents; pH-values; dose; G-values; Product distribution; γ-Irradiation;

DOI:10.1139/v01-058

Reference yield:

benzoic acid (65-85-0,8013-63-6) → 3,4-Dihydroxybenzoic acid (99-50-3) + 2,3-Dihydroxybenzoic acid (303-38-8) + 2,5-dihydroxybenzoic acid. (490-79-9) + 3-Carboxyphenol (99-06-9) + salicylic acid (69-72-7,25496-36-0,8052-31-1) + 4-hydroxy-benzoic acid (99-96-7)

Guidance literature:

With diethylenetriaminopentaacetic acid; dihydrogen peroxide; iron(II); In water; Product distribution;

DOI:10.1021/j100038a029

upstream raw materials:

piperonal

oxalyl dichloride

1,2-dimethoxybenzene

4-allylguaiacol

Downstream raw materials:

bis(3,4-dihydroxyphenyl)methanone

3,4-dihydroxybenzoic acid methyl ester

Ethyl protocatechuate

3-nitro-4-hydroxybenzoic acid

Refernces

• 1、 Bains, Jasleen,Boulanger, Martin J.,Wulff, Jeremy E.. "Investigating terephthalate biodegradation: Structural characterization of a putative decarboxylating cis-dihydrodiol dehydrogenase". . p. 284 - 293,10. Retrieved 2012.
• 2、 Piattelli et al.. "". . p. 997. Retrieved 1963.
• 3、 Di Nardo, Giovanna,Gazzola, Silvia,Gilardi, Gianfranco,Pollegioni, Loredano,Rosini, Elena,Valetti, Francesca,Vignali, Elisa. "Multi-Enzymatic Cascade Reactions for the Synthesis of cis,cis-Muconic Acid". . p. 114 - 123. Retrieved 2021/10/07.
• 4、 Cheng, Lu,Wang, Huihui,Cai, Hengrui,Zhang, Jie,Gong, Xu,Han, Wei. "Iron-catalyzed arene C-H hydroxylation". . p. 77 - 81. Retrieved 2021/10/05.