Formula C8H8O3 Molar mass 152.1473 g/mol Density 1.3 g/cm³ | Melting point 119 °C Boiling point 321.8 °C Appearance White crystalline powder | |
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Mandelic acid medicated toner
Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C6H5CH(OH)CO2H. It is a white crystalline solid that is soluble in water and polar organic solvents. It is a useful precursor to various drugs. The molecule is chiral. The racemic mixture is known as paramandelic acid.
Contents
- Mandelic acid medicated toner
- Melanopeel s mandelic acid peel how to use
- Isolation synthesis occurrence
- Uses
- References
Melanopeel s mandelic acid peel how to use
Isolation, synthesis, occurrence
Mandelic acid was discovered in 1831 by the German pharmacist Ferdinand Ludwig Winckler (1801–1868) while heating amygdalin, an extract of bitter almonds, with diluted hydrochloric acid. The name is derived from the German "Mandel" for "almond". Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-O-methyl transferase.
Mandelic acid is usually prepared by the acid-catalysed hydrolysis of mandelonitrile, which is the cyanohydrin of benzaldehyde. Mandelonitrile can also be prepared by reacting benzaldehyde with sodium bisulfite to give the corresponding adduct, forming mandelonitrile with sodium cyanide, which is hydrolyzed:
Alternatively, it can be prepared by base hydrolysis of phenylchloroacetic acid and dibromacetophenone. It also arises by heating phenylglyoxal with alkalis.
It arises from the biodegradation of styrene, as detected in urine.
Uses
Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections. It has also been used as an oral antibiotic, and as a component of "chemical face peels", along with other alpha-hydroxy acids (AHAs).
- The drugs cyclandelate and homatropine are esters of mandelic acid.
- Pemoline is synthesized by the condensation of the ethyl ester of mandelic acid with guanidine.
- Amolanone
