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;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:32980;
ChemSpider	9965;
ECHA InfoCard	100.007.211
EC Number	207-931-3
KEGG	C01744;
MeSH	C008869
PubChem CID	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
Melting point	129 °C (264 °F; 402 K)
	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

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

References

↑ 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.
↑ Booth AN, Masri MS, Robbins DJ, Emerson OH, Jones FT, Deeds F (1960). "Urinary phenolic acid metabolities of tyrosine". Journal of Biological Chemistry. 235 (9): 2649–2652.
↑ 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.

External links

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[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 AN, Masri MS, Robbins DJ, Emerson OH, Jones FT, 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.