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4-Hydroxymandelic acid

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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
3D model (JSmol)
Beilstein Reference 2365374
ChemSpider
ECHA InfoCard 100.013.490 Edit this at Wikidata
EC Number
  • 214-839-7
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)Key: YHXHKYRQLYQUIH-UHFFFAOYSA-N
SMILES
  • C1=CC(=CC=C1C(C(=O)O)O)O
Properties
Chemical formula C8H8O4
Molar mass 168.148 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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

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:

HOC6H5 + CHOCO2H → HOC6H4CH(OH)CO2H

See also

References

  1. ^ Mattioda, Georges & Christidis, Yani (2000). Glyoxylic Acid. p. 2. doi:10.1002/14356007.a12_495. ISBN 978-3527306732. {{cite book}}: |journal= ignored (help)
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