Mandelate

Mandelate is the conjugate base or salt of mandelic acid, an alpha-hydroxyphenylacetic acid. It occurs in two enantiomeric forms, R- and S-, and mandelate can be encountered as enantiopure salts (for example, sodium or potassium mandelate) or as the racemic mixture. The mandelate anion has the formula C6H5-CH(OH)-COO−, featuring a chiral benzylic carbon.

In chemistry and biochemistry, mandelate is notable as a metabolite and a substrate in various pathways. Mandelic acid and mandelate are associated with natural sources such as bitter almonds and certain fruits. In several bacteria, mandelate serves as a carbon source via the mandelate pathway, which includes enzymes such as mandelate racemase, mandelate dehydrogenase, and benzoylformate decarboxylase. Mandelate racemase interconverts the R- and S- forms, enabling racemization, while mandelate dehydrogenase oxidizes mandelate to benzoylformate, feeding into downstream metabolism.

Applications of mandelate and mandelic acid derivatives include their use as chiral building blocks in asymmetric synthesis and pharmaceutical production. The ability to resolve or selectively transform one mandelate enantiomer makes mandelate-derived materials valuable in enantioselective chemistry. In biocatalysis, mandelate-related enzymes are studied and exploited for the enantioselective transformation of mandelate substrates and related compounds.

See also: mandelic acid, mandelate racemase, mandelate dehydrogenase, benzoylformate.