4-Hydroxyphenylacetic acid

4-Hydroxyphenylacetic acid
Chemical structure of 4-hydroxyphenylacetic acid
Names
Preferred IUPAC name
(4-Hydroxyphenyl)acetic acid
Other names
p-Hydroxyphenylacetic acid
Identifiers
3D model (JSmol)
1448766
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.321 Edit this at Wikidata
EC Number
  • 205-851-3
KEGG
UNII
  • InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11) checkY
    Key: XQXPVVBIMDBYFF-UHFFFAOYSA-N checkY
  • O=C(O)Cc1ccc(O)cc1
Properties
C8H8O3
Molar mass 152.149 g·mol−1
Appearance Beige powder
Melting point 150 °C (302 °F; 423 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-Hydroxyphenylacetic acid is a chemical compound found in olive oil[1] and beer.[2]

Synthesis

4-Hydroxyphenylacetic acid is obtained by reducing 4-hydroxymandelic acid with elemental phosphorus and iodine.[3]

Uses

In industry, 4-hydroxyphenylacetic acid is an intermediate used to synthesize atenolol,[3] 3,4-dihydroxyphenylacetic acid,[4] and coclaurine.

References

  1. ^ Papadopoulos, George; Boskou, Dimitrios (1991). "Antioxidant effect of natural phenols on olive oil". Journal of the American Oil Chemists' Society. 68 (9): 669. doi:10.1007/BF02662292. S2CID 85234954.
  2. ^ Determination of free and bound phenolic acids in beer. M. Nardini and A. Ghiselli, Food Chemistry, January 2004, Volume 84, Issue 1, Pages 137–143, doi:10.1016/S0308-8146(03)00257-7
  3. ^ a b Mattioda, Georges; Christidis, Yani (2000). Glyoxylic Acid. p. 2. doi:10.1002/14356007.a12_495. ISBN 978-3527306732. {{cite book}}: |journal= ignored (help)
  4. ^ Sutton, Peter; Whittall, John (2012). Practical Methods for Biocatalysis and Biotransformations 2. Chichester, West Sussex: John Wiley & Sons, Ltd. pp. 150–153. ISBN 9781119991397.