4-Hydroxymandelic acid
(Redirected from 4-hydroxymandelate)
| 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 | |
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3D model (JSmol)
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| 2365374 | |
| ChemSpider | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| EC Number |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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| UNII | |
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
[edit | edit source]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
