4-Hydroxymandelic acid

4-Hydroxymandelic acid is a chemical compound used to synthesize atenolol.^[1] The compound typically occurs as a monohydrate.

4-Hydroxymandelic acid

Chemical structure of 4-Hydroxymandelic acid
Names
Preferred IUPAC name Hydroxy(4-hydroxyphenyl)acetic acid
Other names 2-Hydroxy-2-(4-hydroxyphenyl)acetic acid 4-Hydroxyphenylglycolic acid p-Hydroxymandelic acid 4-Hydroxymandelate
Identifiers
CAS Number	1198-84-1 Y 184901-84-6 (hydrate)
3D model (JSmol)	Interactive image
Beilstein Reference	2365374
ChemSpider	321 Y
ECHA InfoCard	100.013.490
EC Number	214-839-7
PubChem CID	328
UNII	HV52GS53BA Y
CompTox Dashboard (EPA)	DTXSID70862596
InChI InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11) Y Key: YHXHKYRQLYQUIH-UHFFFAOYSA-N Y
SMILES C1=CC(=CC=C1C(C(=O)O)O)O
Properties
Chemical formula	C8H8O4
Molar mass	168.148 g·mol−1
Appearance	Light red powder
Melting point	89 °C (192 °F; 362 K)
Hazards
Safety data sheet (SDS)	MSDS at Sigma Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis and occurrence

It is produced from 4-hydroxypyruvic acid by the action of the enzyme (S)-p-hydroxymandelate synthase:

HOC₆H₄CH₂C(O)CO₂H + O₂ → HOC₆H₄CH(OH)CO₂H + CO2

4-Hydroxymandelic acid can be synthesized by the condensation reaction of phenol and glyoxylic acid:^[1]

HOC₆H₅ + CHOCO₂H → HOC₆H₄CH(OH)CO₂H

See also

• Vanillyl mandelic acid
• 4-Hydroxyphenylacetic acid