Phloretin

Phloretin

Names
IUPAC name 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
Other names Dihydronaringenin Phloretol
Identifiers
CAS Number	60-82-2 Y
ChEBI	CHEBI:17276 N
ChemSpider	4624 N
IUPHAR/BPS	4285
Jmol 3D model	Interactive image
PubChem	4788
UNII	S5J5OE47MK Y
InChI InChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2 N Key: VGEREEWJJVICBM-UHFFFAOYSA-N N InChI=1/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2 Key: VGEREEWJJVICBM-UHFFFAOYAB
SMILES C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O)O)O)O
Properties
Chemical formula	C15H14O5
Molar mass	274.26 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Phloretin is a dihydrochalcone, a type of natural phenols. It can be found in apple tree leaves and the Manchurian apricot.

Pharmacology

Phloretin inhibits the active transport of glucose into cells by SGLT1 and SGLT2, though the inhibition is weaker than by its glycoside phlorizin. Orally consumed phlorizin is nearly entirely converted into phloretin by hydrolytic enzymes in the small intestine. An important effect of this is the inhibition of glucose absorption by the small intestine and the inhibition of renal glucose reabsorption. Phloretin also inhibits a variety of urea transporters. It induces urea loss and diuresis when coupled with high protein diets.

Phloretin has been found to inhibit GLUT2.

Metabolism

Phloretin hydrolase uses phloretin and water to produce phloretate and phloroglucinol.

Glycosides

• Phlorizin is the 2'-glucoside of phloretin.
• Naringin dihydrochalcone is a diglycoside of phloretin.

See also

• Phloretin-glucosidase