4-Aminobenzoic acid

Base Information

• Chemical Name: 4-Aminobenzoic acid
• CAS No.: 150-13-0
• Deprecated CAS: 8014-65-1
• Molecular Formula: C7H7NO2
• Molecular Weight: 137.138
• Hs Code.: 3922.49
• European Community (EC) Number: 205-753-0
• NSC Number: 7627
• UNII: TL2TJE8QTX
• DSSTox Substance ID: DTXSID6024466
• Nikkaji Number: J5.852A
• Wikipedia: 4-aminobenzoic acid
• Wikidata: Q284959
• NCI Thesaurus Code: C61634
• RXCUI: 74
• Metabolomics Workbench ID: 37770
• ChEMBL ID: CHEMBL542
• Mol file: 150-13-0.mol

Synonyms:Benzoic acid,4-amino-;para-aminobenzoate;Benzoic acid, 4-amino-;Anti-Chromotrichia factor;Acidum paraminobenzoicum;para-Aminobenzoic acid;Trichochromogenic factor;P.A.B.A. ( Para Aminobenzoic Acid );

Chemical Property of 4-Aminobenzoic acid

Chemical Property:

• Appearance/Colour: White to off white crystalline powder
• Vapor Pressure: 3.45E-05mmHg at 25°C
• Melting Point: 186-189 °C
• Refractive Index: 1.5323 (estimate)
• Boiling Point: 339.9 °C at 760 mmHg
• PKA: 2.50, 4.87(at 25℃)
• Flash Point: 159.4 °C
• PSA: 63.32000
• Density: 1.315 g/cm³
• LogP: 1.54820
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Solubility.: 95% ethanol: soluble5%, clear to slightly hazy, colorless to yel
• Water Solubility.: 4.7 g/L (20 ºC)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 137.047678466
• Heavy Atom Count: 10
• Complexity: 128

Purity/Quality:

p-Aminobenzoic acid, Free Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Sunscreens
• Canonical SMILES: C1=CC(=CC=C1C(=O)O)N
• Chemical Properties: 4-Aminobenzoic acid, also known as p-aminobenzoic acid, is an organic compound that appears as a white crystalline powder. It is easily soluble in hot water, ether, ethyl acetate, ethanol, and glacial acetic acid but difficult to dissolve in water, benzene, and insoluble in petroleum ether.
• Industrial Applications: Used as pharmaceutical and dye intermediates, as well as analytical reagents and sunscreen agents. An essential nutrient for many human pathogens but dispensable for humans. It‘s derivatives exhibit various biological activities.
• Biological Functions: Synthesized and utilized as a substrate for the synthesis of folic acid in many bacterial species, yeasts, and plants.; Plays a crucial role in folate metabolism and as a coenzyme Q precursor.; Important for microbial virulence but not essential or biosynthesized in mammals.
• Pharmacological Activities: Exhibits antibacterial, antiviral, and antioxidant activities.; Used in sunscreens to protect against UVB irradiation and as cytoprotective agents and direct anticoagulants.; Shows potential in dermatologic disorders treatment such as scleroderma, dermatomyositis, and Peyronie’s disease.; Promotes resistance against plant bacterial and viral pathogens and has plant growth modulator properties.
• Metabolic Pathways: Biosynthesized in organisms from chorismate by a reaction catalyzed by 4-amino-4-deoxychorismate synthase. Metabolized in the liver through N-acetylation or conjugation with glycine to produce 4-aminohippuric acid, which is then excreted in the urine.
• Chemical Synthesis: Synthesized from aniline through acylation reaction with acetyl chloride and subsequent reaction with an iodine-containing sodium hydroxide solution. Various methods include esterification reaction, reduction reaction, and acidification reaction.

Technology Process of 4-Aminobenzoic acid

There total 173 articles about 4-Aminobenzoic 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: 94.0%

4-Aminobenzonitrile (873-74-5) → 4-aminobenzamide (2835-68-9) + 4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1)

Guidance literature:

With water; at 140 ℃; for 6h; Sealed tube;

DOI:10.1007/s10562-016-1816-4

Reference yield:

4'-Carboxy-N-(4-dimethylamino-benzyliden)anilin (140140-19-8) → 4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) + 4-dimethylamino-benzaldehyde (100-10-7)

Guidance literature:

With borate buffer; water; In methanol; at 25 ℃; Rate constant; Kinetics; Mechanism; ΔG(activ.), ΔH(activ.), ΔS(activ.);

Reference yield:

Procaine (59-46-1,91484-72-9) → 4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) + 2-(Diethylamino)ethanol (100-37-8)

Guidance literature:

With Tris-HCl buffer; human liver carboxylesterase pI 4.5; at 37 ℃; pH=7.4; Enzyme kinetics;

DOI:10.1248/bpb.20.869

upstream raw materials:

2-(4-aminophenyl)-6-methyl-1,3-benzothiazole

4-Bromobenzoic acid

4-acetylamino-3-iodo-benzoic acid

4-(2-carboxyethylcarboxamido)benzoic acid

Downstream raw materials:

4-((cyanomethyl)amino)benzoic acid

4-amino-benzoic acid-(4-benzoyl-1-methyl-[4]piperidyl ester)

4,4'-(carbonylbis(azanediyl))dibenzoic acid

4-(pyridin-2-yl)benzoic acid

Refernces

• 1、 Bullock,Forbes. "". . p. 232,237. Retrieved 1933.
• 2、 Greenfield,Rosenzweig. "-". . p. 991. Retrieved 1940.
• 3、 Prei?, Sebastian,P?pcke, Ayla,Burkhardt, Lukas,Gro?mann, Luca,Lochbrunner, Stefan,Bauer, Matthias,Opatz, Till,Heinze, Katja. "Gold(II) Porphyrins in Photoinduced Electron Transfer Reactions". . p. 5940 - 5949. Retrieved 2019.
• 4、 Rondestvedt Jr.. "-". . p. 3118. Retrieved 1977.
• 5、 Patro, Birija S.,Adhikari, Soumyakanti,Mukherjee, Tulsi,Chattopadhyay, Subrata. "Possible role of hydroxyl radicals in the oxidative degradation of folic acid". . p. 67 - 71. Retrieved 2005.
• 6、 Manyar, Haresh,Moody, Thomas S.,Rahman, Md Taifur,Smyth, Megan,Wharry, Scott. "FAST Hydrogenations as a Continuous Platform for Green Aromatic Nitroreductions". . p. 581 - 586. Retrieved 2020.
• 7、 Altendorf,Bacher,Lingens. "Biosynthesis of p-aminobenzoic acid. II. Demonstration of an intermediate in a mutant of Aerobacter aerogenes". . p. 1602 - 1604. Retrieved 1969.
• 8、 Coleman, Tom,Wong, Siew Hoon,Podgorski, Matthew N.,Bruning, John B.,De Voss, James J.,Bell, Stephen G.. "Cytochrome P450 CYP199A4 from Rhodopseudomonas palustris Catalyzes Heteroatom Dealkylations, Sulfoxidation, and Amide and Cyclic Hemiacetal Formation". . p. 5915 - 5927. Retrieved 2018.
• 9、 Meti,Lamani,Naikar,Sutar,Nandibewoor,Chimatadar. "Kinetic and mechanistic investigations and thermodynamic quantities for different steps involved in the mechanism of oxidation of procainamide by hexacyanoferrate(III) in aqueous alkaline medium: a spectrophotometric study". . p. 1485 - 1493. Retrieved 2015.
• 10、 Srinivasa Rao,Srivani,Dhana Lakshmi,Lingaiah. "Selective Hydration of Nitriles to Amides Over Titania Supported Palladium Exchanged Vanadium Incorporated Molybdophosphoric Acid Catalysts". . p. 2025 - 2031. Retrieved 2016.