Structure via PubChem · Public domain (PubChem)
phlorizin
Sign in to saveAlso known as Phloridzin, Phlorhizin, Floridzin, Phlorizoside, Phloretin 2'-glucoside
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.
Chemical data
- Formula
- C21H24O10
- Molecular weight
- 436.4 g/mol
- IUPAC name
- 1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
- SMILES
- C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
- InChIKey
- IOUVKUPGCMBWBT-QNDFHXLGSA-N
- XLogP
- 1.2
- Polar surface area
- 177 Ų
- H-bond donors
- 7
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2,940 papers- Phlorizin from Lithocarpus litseifolius [Hance] Chun ameliorates FFA-induced insulin resistance by regulating AMPK/PI3K/AKT signaling pathway.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2024
- Phlorizin, an Important Glucoside: Research Progress on Its Biological Activity and Mechanism.Molecules (Basel, Switzerland) · 2024
- Phlorizin: a review.Diabetes/metabolism research and reviews · 2005
- Phlorizin Protects Against Oxidative Stress and Inflammation in Age-Related Macular Degeneration Model.Biomolecules · 2025
- Phlorizin attenuates postoperative gastric ileus in rats.Neurogastroenterology and motility · 2023
via PubMed
Wikidata facts
- Mass
- 436.136947
Show 6 more facts
- found in taxon
- Eucalyptus globulus
- chemical formula
- C₂₁H₂₄O₁₀
- canonical SMILES
- C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2OC3C(C(C(C(O3)CO)O)O)O)O)O)O
- isomeric SMILES
- C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
- has characteristic
- bitterness
- Commons category
- Phlorizin
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Occurrence
- Pharmacology
- References
{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464204632 | ImageFile = Phlorhizin.svg | ImageSize = 200px | IUPACName = 1-[2-(β-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one | SystematicName = 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 | OtherNames = Isosalipurposide
| Section1 =
Excerpted from Wikipedia’s “phlorizin” article, available under the CC BY-SA 4.0 licence.