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Phloretic acid

Chemical compound From Wikipedia, the free encyclopedia

Phloretic acid is an organic compound with the formula HOC6H4(CH2)2CO2H. It is a white solid. The compound contains both phenol and carboxylic acid functional groups. It is sometimes called Desaminotyrosine (DAT) because it is identical to the common alpha amino acid tyrosine except for the absence of the amino functional group on the alpha carbon.

Quick facts Names, Identifiers ...
Phloretic acid
Chemical structure of phloretic acid
Names
Preferred IUPAC name
3-(4-Hydroxyphenyl)propanoic acid
Other names
Desaminotyrosine
Hydro-p-coumaric acid
Phloretate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.211 Edit this at Wikidata
EC Number
  • 207-931-3
KEGG
MeSH C008869
UNII
  • 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
  • C1=CC(=CC=C1CCC(=O)O)O
Properties
C9H10O3
Molar mass 166.176 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).
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Production and occurrence

Phloretic acid is produced by reduction of the unsaturated side chain of p-coumaric acid. Together with phloroglucinol, it is produced by the action of the enzyme phloretin hydrolase on phloretin.

It is found in olives.[1] It is found in the rumen of sheep fed with dried grass.[2] It is also a urinary metabolite of tyrosine in rats.[3]

Polyesters have been prepared from phloretic acid.[4]

It is one of the products of flavonoid metabolism performed by the bacterium Clostridium orbiscindens, a resident of some human intestinal tracts. [5]

Drug uses

Phloretic acid is used in the synthesis of Esmolol.

References

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