Phloretic acid is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

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

phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...

and

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...

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 non-essential amino acid with a polar side group. The word "tyrosine" is from the Gr ...

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. Together with

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

, 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 ...

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 an urinary metabolite of

in rats.

Polyester Polyester is a category of polymers that contain the ester functional group 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 natural ...

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 guts.

References

External links

*{{Commonscat-inline Phenylpropanoids Animal metabolites Carboxylic acids