Phlorizin
Chemical compound
From Wikipedia, the free encyclopedia
Phlorizin is a glucoside of phloretin, a dihydrochalcone. A white solid when pure, samples often appear yellow due to impurities. It is of sweet taste and contains four molecules of water in the crystal. 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]
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| Names | |
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| 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 | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.443 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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 |
| water, low MW alcohols | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Occurrence
Phlorizin is found primarily in unripe Malus (apple)[2] root bark of apple,[3] and trace amounts have been found in strawberry.[4] In Malus, 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
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the blood.[6][7] Phlorizin was studied as a potential pharmaceutical treatment for type 2 diabetes, but has since been superseded by more selective and more promising synthetic analogs, such as empagliflozin, canagliflozin and dapagliflozin.[8] Phlorizin is not an effective drug because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]