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
CAS Number	156-38-7  Y
3D model (JSmol)	Interactive image
Beilstein Reference	1448766
ChEBI	CHEBI:18101  Y
ChEMBL	ChEMBL1772  Y
ChemSpider	124  Y
ECHA InfoCard	100.005.321
EC Number	205-851-3
KEGG	C00642  Y
PubChem CID	127
UNII	3J9SHG0RCN  Y
CompTox Dashboard (EPA)	DTXSID5059745
InChI InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11) Y Key: XQXPVVBIMDBYFF-UHFFFAOYSA-N Y
SMILES O=C(O)Cc1ccc(O)cc1
Properties
Chemical formula	C8H8O3
Molar mass	152.149 g·mol−1
Appearance	white 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). Y  verify  (what is  YN ?) Infobox references

4-Hydroxyphenylacetic acid is an organic compound with the formula HOC₆H₄CH₂CO₂H. It is a colorless or white solid but commercial samples can appear beige. It is 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 to 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. 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.