4-Hydroxyphenylacetic acid
{{chembox
| verifiedrevid = 456503066
| Name = 4-Hydroxyphenylacetic acid
| ImageFile = 4-Hydroxyphenylacetic acid.svg
| ImageSize = 200px
| ImageName = Chemical structure of 4-hydroxyphenylacetic acid
| ImageAlt = Chemical structure of 4-hydroxyphenylacetic acid
| PIN = (4-Hydroxyphenyl)acetic acid
| OtherNames = p-Hydroxyphenylacetic acid
|Section1= {{Chembox Identifiers
| CASNo = 156-38-7
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3J9SHG0RCN
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00642
| EINECS = 205-851-3
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1772
| PubChem = 127
| Beilstein = 1448766
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 124
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 18101
| SMILES = O=C(O)Cc1ccc(O)cc1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XQXPVVBIMDBYFF-UHFFFAOYSA-N
| MeSHName =
}}
|Section2= {{Chembox Properties
| C=8|H=8|O=3
| Appearance = Beige powder
| Density =
| MeltingPtC = 150
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| ExternalSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=H50004&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2Fh50004%3Flang%3Den MSDS at Sigma Aldrich]
}}
}}
4-Hydroxyphenylacetic acid is a chemical compound found in olive oil{{cite journal | last1 = Papadopoulos | first1 = George | last2 = Boskou | first2 = Dimitrios | title = Antioxidant effect of natural phenols on olive oil | journal = Journal of the American Oil Chemists' Society | volume = 68 | pages = 669 | year = 1991 | doi = 10.1007/BF02662292 | issue = 9| s2cid = 85234954 }} and beer.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}}
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,{{Ullmann|last1=Mattioda|first1=Georges|last2=Christidis|first2=Yani|title=Glyoxylic Acid|year=2000|page=2|doi=10.1002/14356007.a12_495|isbn=978-3527306732}} 3,4-dihydroxyphenylacetic acid,{{cite book|author1=Sutton, Peter |author2=Whittall, John |title=Practical Methods for Biocatalysis and Biotransformations 2|date=2012|publisher=John Wiley & Sons, Ltd.|location=Chichester, West Sussex|isbn=9781119991397|pages=150–153|url=https://books.google.com/books?id=WlODZ-WX8vIC&q=9781119991397}} and coclaurine.