4-Hydroxyphenylacetic acid

4-Hydroxyphenylacetic acid

Names
IUPAC name 2-(4-Hydroxyphenyl)acetic acid
Other names p-Hydroxyphenylacetic acid
Identifiers
CAS Number	156-38-7
Beilstein Reference	1448766
ChEBI	CHEBI:18101
ChEMBL	ChEMBL1772
ChemSpider	124
EC Number	205-851-3
Jmol interactive 3D	Image
PubChem	127
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	152.15 g·mol^−1
Appearance	Beige powder
Melting point	150 °C (302 °F; 423 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4-Hydroxyphenylacetic acid is a chemical compound found in olive oil^[1] and beer.^[2] In industry the chemical is an intermediate used to synthesize atenolol^[3] and 3,4-dihydroxyphenylacetic acid.^[4]

Synthesis

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

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.
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 and Christidis, Yani (2000). "Glyoxylic Acid". Ullmann's Encyclopedia of Industrial Chemistry: pg. 2. doi:10.1002/14356007.a12_495. Retrieved 27 December 2013.
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.