4-Hydroxymandelic acid is a
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
used to synthesize
atenolol.
The compound typically occurs as a
monohydrate
In chemistry, a hydrate is a substance that contains water or its constituent elements. The chemical state of the water varies widely between different classes of hydrates, some of which were so labeled before their chemical structure was underst ...
.
Synthesis and occurrence
It is produced from
4-hydroxypyruvic acid by the action of the enzyme
(''S'')-''p''-hydroxymandelate synthase:
:HOC
6H
4CH
2C(O)CO
2H + O
2 → HOC
6H
4CH(OH)CO
2H + CO2
4-Hydroxymandelic acid can be synthesized by the condensation reaction of
phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...
and
glyoxylic acid:
:HOC
6H
5 + CHOCO
2H → HOC
6H
4CH(OH)CO
2H
See also
*
Vanillyl mandelic acid
Vanillylmandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings and is an end-stage metabolite of the catecholamines (dopamine, epinephrine, and norepinephrine). It is produced via intermediary metabolites. ...
*
4-Hydroxyphenylacetic acid
4-Hydroxyphenylacetic acid is a chemical compound found in olive oil and beer.
Synthesis
4-Hydroxyphenylacetic acid is obtained by reducing 4-Hydroxymandelic acid, 4-hydroxymandelic acid with elemental phosphorus and iodine.
Uses
In industry, ...
References
{{DEFAULTSORT:Hydroxymandelic acid, 4-
Phenols
Acetic acids
Alpha hydroxy acids