Contents

Phlorizin

Phlorizin

Names
IUPAC name 1-[2-(β-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
Systematic IUPAC name 1-(2,4-Dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one
Other names Isosalipurposide
Identifiers
CAS Number	60-81-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8113 N
ChEMBL	ChEMBL245067 N
ChemSpider	16498836 N
ECHA InfoCard	100.000.443
IUPHAR/BPS	4757
PubChem CID	6072
UNII	CU9S17279X Y
CompTox Dashboard (EPA)	DTXSID3075339
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
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	436.413 g·mol−1
Appearance	White solid
Melting point	106 to 109 °C (223 to 228 °F; 379 to 382 K)
Boiling point	200 °C (392 °F; 473 K) decomposition
Solubility in water	water, low MW alcohols
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

Chemical compound

Phlorizin is a glucosideofphloretin, a dihydrochalcone. A white solid, samples often appear yellowing to impurities. It is of sweet taste and contains four molecules of water in the crystal. Above 200 °C, it decomposes to give rufin. 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. ^[1]

Occurrence[edit]

Phlorizin is found primarily in unripe Malus (apple)^[2] root bark of apple,^[3] and trace amounts have been found in strawberry.^[4]InMalus, it is most abundant in vegetative tissues (such as leaves and bark) and seeds. Closely related species, such as pear (Pyrus communis), cherry, and other fruit trees in the Rosaceae do not contain phlorizin.^[5] Phlorizin is a phytochemical that belongs to the class of polyphenols. In natural sources, it may occur with other polyphenols such as quercetin, catechin, epicatechin, procyanidins, and rutin.

Pharmacology[edit]

Phlorizin is an inhibitor of SGLT1 and SGLT2 because it competes with D-glucose for binding to the carrier; this action reduces renal glucose transport, lowering the amount of glucose in the blood.^[6][7] Phlorizin was studied as a potential pharmaceutical treatment for type 2 diabetes, but has since been superseded by more selective and more promising synthetic analogs, such as empagliflozin, canagliflozin and dapagliflozin.^[8] Phlorizin is not an effective drug because when orally consumed, it is nearly entirely converted into phloretin by hydrolytic enzymes in the small intestine.^[9][10]

References[edit]