4-Hydroxymandelic acid
Appearance
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Names | |
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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 | |
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3D model (JSmol)
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2365374 | |
ChemSpider | |
ECHA InfoCard | 100.013.490 |
EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
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).
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4-Hydroxymandelic acid is a chemical compound used to synthesize atenolol.[1] 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:[1]
- HOC6H5 + CHOCO2H → HOC6H4CH(OH)CO2H
See also
References
- ^ a b Mattioda, Georges & Christidis, Yani (2000). Glyoxylic Acid. p. pg. 2. doi:10.1002/14356007.a12_495. ISBN 978-3527306732.
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