|Jmol-3D images||Image 1
|Molar mass||138.121 g/mol|
|Melting point||214.5 °C; 418.1 °F; 487.6 K|
|Solubility in water||0.5 g/100 mL|
|Solubility||soluble in alcohol, ether, acetone
slightly soluble in chloroform
negligible in CS2
|Autoignition temperature||250 °C; 482 °F; 523 K|
|LD50||2200 mg/kg (oral, mouse)|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
4-Hydroxybenzoic acid is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin.
Occurrences in food
4-Hydroxybenzoic acid can be found naturally in Cocos nucifera. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine and in vanilla.
4-Hydroxybenzoic acid is produced commercially from potassium phenoxide and carbon dioxide in the Kolbe-Schmitt reaction. It can also be produced in the laboratory by heating potassium salicylate with potassium carbonate to 240 °C, followed by treating with acid.
- HOC6H4CO2H HOC6H4CO2− + H+
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- Edwin Ritzer and Rudolf Sundermann “Hydroxycarboxylic Acids, Aromatic” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a13_519
- C. A. Buehler and W. E. Cate (1943), "p-Hydroxybenzoic acid", Org. Synth.; Coll. Vol. 2: 341