Phlorizin

Phlorizin

Names
IUPAC name 1-[2,4-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-3-(4-hydroxyphenyl)propan-1-one
Other names Isosalipurposide
Identifiers
CAS Number	60-81-1 Y
ChEBI	CHEBI:8113 N
ChEMBL	ChEMBL245067 N
ChemSpider	16498836 N
IUPHAR/BPS	4757
Jmol 3D model	Interactive image
PubChem	6072
UNII	CU9S17279X Y
InChI InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1 N Key: IOUVKUPGCMBWBT-QNDFHXLGSA-N N InChI=1/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1 Key: IOUVKUPGCMBWBT-QNDFHXLGBL
SMILES c1cc(ccc1CCC(=O)c2c(cc(cc2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
Properties
Chemical formula	C21H24O10
Molar mass	436.41 g·mol−1
Appearance	White to yellow crystalline solid
Melting point	106 to 109 °C (223 to 228 °F; 379 to 382 K)
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

Phlorizin is a 2'-glucoside of phloretin. It belongs to the group of dihydrochalcones, a type of flavonoids.

Occurrence

Phlorizin, or phloridzin is a naturally occurring flavonoid produced in some plants. It is found primarily in Malus (apple) species although trace amounts exist in other species. In Malus it is most abundant in vegetative tissues (leaves, bark, etc...) and seeds. Closely related species, such as pear (Pyrus communis), cherry and other fruit trees in the Rosaceae do not contain phloridzin. Trace amounts have been reported in strawberry and it is responsible for the petal color in Dianthus caryophyllus. Phloridzin, a phytocemical belongs to a class of polyphenols. It may be present with other polyphenols such as quercetin, catechin, epicatechin, procynidins, rutin etc. These polyhydroxy compounds have been proved to be potent antioxidants.

Properties

Phlorizin is a white to yellow crystalline solid with a melting point of 106–109 °C. It is of sweet taste and contains four molecules of water in the crystal. Above 200 °C, it decomposes. It is poorly soluble in ether and cold water, but soluble in ethanol and hot water. Upon prolonged exposure to aqueous solutions phlorizin hydrolyzes to phloretin and glucose.

Pharmacology

Phlorizin is a competitive inhibitor of SGLT1 and SGLT2 because it competes with D-glucose for binding to the carrier; this reduces renal glucose transport, lowering the amount of glucose in the blood. Phlorizin was studied as a potential pharmaceutical treatment for type II diabetes, but has since been superseded by more selective and more promising synthetic analogs, such as canagliflozin and dapagliflozin. Orally consumed phlorizin is nearly entirely converted into phloretin by hydrolytic enzymes in the small intestine. Apart from conventional antidiabetic activity, phlorizin is also studied for its antioxidant activity.