Description
4-Acetamidobenzoic acid (PAcBA) is a naturally occurring acetylated metabolite of 4-aminobenzoic acid and is a component of the antiviral and immunostimulatory drug inosine pranobex (Inosiplex; Isoprinosine; Methisoprinol).
Chemical Properties
white or off-white powder or crystals
Originator
4-Acetamidobenzoic acid ,ARIAC
Uses
Acedoben is the acetylated derivative of p-aminobenzoic acid (PABA). Acedoben is a metabolite of the anesthetic Benzocaine (B202970).
Uses
immune stimulant (component)
Definition
ChEBI: 4-acetamidobenzoic acid is a amidobenzoic acid that consists of benzoic acid bearing an acetamido substituent at position 4. It is functionally related to a 4-aminobenzoic acid. It is a conjugate acid of a 4-acetamidobenzoate.
Manufacturing Process
Into a 2 L, 3-necked flask set in a tub and equipped with a stirrer, an air
condenser (drying tube), thermometer, was placed 860 ml of water, 43.0 g of
MgSO4 and 43.0 g of sodium acetate and heated on water bath. Into heated
solution to 70°C stirring 43.0 g of N-p-tolylacetamide were added. Then 136.0
g of KMnO4 by small portions were added at 75°-80°C. The reaction mixture
allow to stand for 6 h and stirring was continue till the solution became
colorless. Hot solution was filtered and filtrate treated hydrochloric acid to
slightly acidic pH. After that 44.0 g (85%) of p-acetoaminobenzoic acid was
obtained as white precipitate, melting point 250°C.
Therapeutic Function
Antiviral
General Description
Needles or off-white powder.
Air & Water Reactions
Water insoluble.
Reactivity Profile
Simultaneously an amide and a carboxylic acid.
Fire Hazard
Flash point data for p-Acetylamino benzoic acid are not available; however, p-Acetylamino benzoic acid is probably combustible.
reaction suitability
reaction type: solution phase peptide synthesis
References
[1] Synthetic Communications, 2008, vol. 38, # 7, p. 1028 - 1035
[2] Applied Catalysis A: General, 2013, vol. 456, p. 118 - 125
[3] Green Chemistry, 2012, vol. 14, # 3, p. 847 - 854
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 9, p. 1274 - 1281
[5] Synthetic Communications, 2008, vol. 38, # 17, p. 2929 - 2940
