Phlorizin

Phlorizin
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
PubChem 6072
ChemSpider 5847 Y
UNII CU9S17279X Y
ChEMBL CHEMBL245067 N
Jmol-3D images Image 1
Properties
Molecular formula C21H24O10
Molar mass 436.41 g mol−1
Exact mass 436.136947 u
Appearance White to yellow crystalline solid
Melting point

106–109 °C
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Phlorizin is a toxic 2'-glucoside of phloretin. It belongs to the group of dihydrochalcones, a type of flavonoids. It is a competitive inhibitor of renal glucose transport.[1][2]

Phlorizin is naturally occurring in some plants. It could be found in the bark of pear (Pyrus communis), apple, cherry and other fruit trees (Rosaceae) and is responsible for the petal color in Dianthus caryophyllus.[3]

Properties

The crystalline substance is white to yellow. It is of sweet taste and contains four molecules of water in the crystal.

References

  1. ^ Rossetti, L. .; Smith, D. .; Shulman, I. .; Papachristou, D. .; Defronzo, A. . (May 1987). "Correction of hyperglycemia with phlorizin normalizes tissue sensitivity to insulin in diabetic rats" (Free full text). The Journal of clinical investigation 79 (5): 1510–1515. doi:10.1172/JCI112981. ISSN 0021-9738. PMC 424427. PMID 3571496. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=424427.  edit
  2. ^ Tatoń, J; Piatkiewicz, P; Czech, A. (May-Jun 2010). "Molecular physiology of cellular glucose transport - a potential area for clinical studies in diabetes mellitus". Endokrynol Pol 61 (3): 303–10. PMID 20602306. 
  3. ^ Isosalipurposide on PubChem
Dihydrochalcones and their glycosides
Dihydrochalcones:
3′,5′-dihydroxy-2′,4′,6′-trimethoxydihydrochalcone | 2′-hydroxy-3′,4′,5′,6′-tetramethoxydihydrochalcone (dihydrokanakugiol) | 2′-hydroxy-3′,4′,5′,6′-tetramethoxychalcone (kanakugiol) | 5-hydroxy-6,7,8-trimethoxyflavone (alnetin) | methyl linderone | 2′,3′,4′,5′,6′-pentamethoxychalcone (pedicellin) | Phloretin | Pinocembrin chalcone
Dihydrochalcone glycosides: