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4-Hydroxyphenylacetic acid

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4-Hydroxyphenylacetic acid
Chemical structure of 4-hydroxyphenylacetic acid
Names
Preferred IUPAC name (4-Hydroxyphenyl)acetic acid
Other names p-Hydroxyphenylacetic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1448766
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.321 Edit this at Wikidata
EC Number
  • 205-851-3
KEGG
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: XQXPVVBIMDBYFF-UHFFFAOYSA-N
SMILES
  • O=C(O)Cc1ccc(O)cc1
Properties
Chemical formula C8H8O3
Molar mass 152.149 g·mol
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 , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

4-Hydroxyphenylacetic acid is a chemical compound found in olive oil and beer.

Synthesis

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

Uses

In industry, 4-hydroxyphenylacetic acid is an intermediate used to synthesize atenolol, 3,4-dihydroxyphenylacetic acid, 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. ^ Mattioda, Georges; Christidis, Yani (2000). "Glyoxylic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 2. doi:10.1002/14356007.a12_495. ISBN 978-3527306732.
  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.
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