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

• ChemBase ID: 70188
• Molecular Formular: C21H24O10
• Molecular Mass: 436.40926
• Monoisotopic Mass: 436.13694697
• SMILES: C(=O)(CCc1ccc(cc1)O)c1c(cc(cc1O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc(O)cc(c2C(=O)CCc2ccc(cc2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
• 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
• InChIKey: IOUVKUPGCMBWBT-QNDFHXLGSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: phlorizin
• Synonyms: Phloridzin; Phlorhizin; Phlorizoside; Phlorizin; Phlorizin

Database IDs

• CAS Number: 60-81-1
• MDL Number: MFCD00006591
• PubChem SID: 162035911
• PubChem CID: 6072

CALCULATED PROPERTIES

• Acid pKa: 7.8697577
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): 0.9756358
• LogD (pH = 7.4): 0.85051596
• Log P: 0.9774724
• Molar Refractivity: 105.8517 cm^3
• Polarizability: 41.671455 Å^3
• Polar Surface Area: 177.14 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• Storage Condition: -20°C
• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%; 98.0
• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2343

Research Area: Cardiovascular Disease
Biological Activity:
Phlorizin (Phloridzin) 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. 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. [1]

REFERENCES

• http://www.bentham.org/prc/samples/prc1-1/Higashi.pdf