Phloretic acid

Phloretic acid

Names
IUPAC name 3-(4-Hydroxyphenyl)propanoic acid
Other names 3-(4-Hydroxyphenyl)propanoic acid Desaminotyrosine Hydro-p-coumaric acid Phloretate
Identifiers
CAS Number	501-97-3
ChEBI	CHEBI:32980
ChemSpider	9965
EC Number	207-931-3
Jmol interactive 3D	Image
KEGG	C01744
MeSH	C008869
PubChem	10394
InChI InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12) Key: NMHMNPHRMNGLLB-UHFFFAOYSA-N InChI=1/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12) Key: NMHMNPHRMNGLLB-UHFFFAOYAT
SMILES C1=CC(=CC=C1CCC(=O)O)O
Properties
Chemical formula	C9H10O3
Molar mass	166.18 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Phloretic acid is a phenolic compound.

Metabolism

The enzyme phloretin hydrolase uses phloretin and H₂O to produce phloretate and phloroglucinol.

It is found in the rumen of sheep fed with dried grass and is produced by hydrogenation of the 2-propenoic side chain of p-coumaric acid.^[1] It is also an urinary metabolite of tyrosine in rats.^[2]

Uses

It can be used to produce polyesters based on phloretic acid and gallic acid.^[3]

References

1. Chesson, A; Stewart, CS; Wallace, RJ (1982). "Influence of plant phenolic acids on growth and cellulolytic activity of rumen bacteria". Applied and Environmental Microbiology 44 (3): 597–603. PMC 242064. PMID 16346090.
2. Booth A N, Masri M S, Robbins D J, Emerson O H, Jones F T and Deeds F (1960). "Urinary phenolic acid metabolities of tyrosine". Journal of Biological Chemistry 235 (9): 2649–2652.
3. Reina, Antonio; Gerken, Andreas; Zemann, Uwe; Kricheldorf, Hans R. (1999). "New polymer syntheses, 101. Liquid-crystalline hyperbranched and potentially biodegradable polyesters based on phloretic acid and gallic acid". Macromolecular Chemistry and Physics 200 (7): 1784–1791. doi:10.1002/(SICI)1521-3935(19990701)200:7<1784::AID-MACP1784>3.0.CO;2-B.