Mandelic acid

Mandelic acid
IUPAC name	2-Phenyl-2-hydroxyacetic acid
Other names	Mandelic acid Phenylglycolic acid
Identifiers
CAS number	90-64-2
SMILES	OC(C(O)c1ccccc1)=O
Properties
Molecular formula	C8H8O3
Molar mass	152.14 g/mol
Density	1.30 g/cm3
Melting point	119 °C
Boiling point	°C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C₈H₈O₃. It is a white crystalline solid that is soluble in water and most common organic solvents.

Discovery and name

Mandelic acid was discovered while heating an extract of bitter almonds with diluted hydrochloric acid. The name is derived from the German "Mandel" for "almond".

Chemistry

It is an isomer of cresotinic acid (2-hydroxy-3-methylbenzoic acid) and oxymethylbenzoic acid (2-methoxybenzoic acid). Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-o-methyl transferase. It is also present in certain skin care products, is an intermediate molecule in the production of other biochemicals, may be used as an analytical reagent and is a precursor in the manufacture of dyes. Since the molecule contains a chiral carbon atom, the acid exists in either of two optically active forms. The racemic mixture of the two is known as paramandelic acid. It may be prepared by the action of hydrochloric acid on the addition compound of benzaldehyde and hydrocyanic acid, by boiling phenylchloracetic acid with alkalis, by heating benzoyl formaldehyde with alkalis or by the action of dilute alkalis on ω-dibromacetophenone.

References

• Merck Index, 11th Edition, 5599.
• This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.

See also

• Amygdalin
• Vanillylmandelic acid