Phloretic acid is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula HOC₆H₄(CH₂)₂CO₂H. It is a white solid. The compound contains both

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

and

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...

functional groups. It is sometimes called Desaminotyrosine (DAT) because it is identical to the common alpha amino acid

tyrosine -Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a conditionally essential amino acid with a polar side group. The word "tyrosine" is ...

except for the absence of the amino functional group on the alpha carbon.

Production and occurrence

Phloretic acid is produced by reduction of the unsaturated side chain of

p-coumaric acid ''p''-Coumaric acid is an organic compound with the formula HOC6H4CH=CHCO2H. It is one of the three isomers of coumaric acid. It is a white solid that is only slightly soluble in water but very soluble in ethanol and diethyl ether. Natural occur ...

. Together with

phloroglucinol Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the organic synthesis, synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isom ...

, it is produced by the action of the enzyme

phloretin hydrolase In enzymology, a phloretin hydrolase () is an enzyme that catalyzes the chemical reaction :phloretin + H2O \rightleftharpoons phloretate + phloroglucinol Thus, the two substrates of this enzyme are phloretin and H2O, whereas its two products a ...

phloretin Phloretin is a dihydrochalcone, a type of natural phenol. It can be found in apple tree leaves and the Manchurian apricot. Metabolism In rats, ingested phlorizin is converted into phloretin by hydrolytic enzymes in the small intestine. Ph ...

. It is found in olives. It is found in the rumen of sheep fed with dried grass. It is also a urinary metabolite of

in rats.

Polyester Polyester is a category of polymers that contain one or two ester linkages in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include some natura ...

s have been prepared from phloretic acid. It is one of the products of

flavonoid Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...

metabolism performed by the bacterium ''Clostridium orbiscindens'', a resident of some human intestinal tracts.

Drug uses

Phloretic acid is used in the synthesis of

Esmolol Esmolol, sold under the brand name Brevibloc, is a cardio selective beta-blocker, beta1 receptor blocker with rapid Onset of action, onset, a very short duration of action, and no significant intrinsic sympathomimetic or membrane stabilising acti ...

References

External links

*{{Commonscat-inline Phenylpropanoids Animal metabolites Carboxylic acids