4-Hydroxymandelic acid (original) (raw)
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4-Hydroxymandelic acid
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| Names | |
| Preferred IUPAC name Hydroxy(4-hydroxyphenyl)acetic acid | |
| Other names2-Hydroxy-2-(4-hydroxyphenyl)acetic acid4-Hydroxyphenylglycolic acid_p_-Hydroxymandelic acid4-Hydroxymandelate | |
| Identifiers | |
| CAS Number | 1198-84-1  Y184901-84-6 (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) YKey: YHXHKYRQLYQUIH-UHFFFAOYSA-N Y |
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| 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 |
Chemical compound
4-Hydroxymandelic acid is a chemical compound used to synthesize atenolol.[1] The compound typically occurs as a monohydrate.
Synthesis and occurrence
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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
- ^ a b Mattioda, Georges & Christidis, Yani (2000). Glyoxylic Acid. p. 2. doi:10.1002/14356007.a12_495. ISBN 978-3527306732.