1-(2,4-dihydroxy-6-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one

• ChemBase ID: 176677
• Molecular Formular: C21H24O10
• Molecular Mass: 436.40926
• Monoisotopic Mass: 436.13694697
• SMILES: O([C@@H]1OC([C@@H](O)C([C@H]1O)O)CO)c1c(c(cc(c1)O)O)C(=O)CCc1ccc(cc1)O
• Canonical SMILES: OCC1O[C@@H](Oc2cc(O)cc(c2C(=O)CCc2ccc(cc2)O)O)[C@@H](C([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-VOUWZBHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2,4-dihydroxy-6-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one
• IUPAC Traditional name: 1-(2,4-dihydroxy-6-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one
• Synonyms: 1-[2-(β-D-Glucopyranosyl-oxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone; Phlorhizin; Phlorizin; Phlorrhizen; Phloretin-2’-β-glucoside; Phloridzin

Database IDs

• CAS Number: 60-81-1
• PubChem SID: 164232587
• PubChem CID: 45040243

CALCULATED PROPERTIES

• Acid pKa: 7.8912544
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): 0.97572434
• LogD (pH = 7.4): 0.8561777
• 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

• Solubility: Acetone; Aniline; Ethyl Acetate; Methanol; Pyridine
• Apperance: Light Yellow to Tan Solid
• Melting Point: >110°C (dec.)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P339500

It is a dihydrochalcone occurring in all parts of the apple tree except the mature fruit. Once thought to occur in pear, plum, cherry trees and other Rosaceae.

REFERENCES

• Moelwyn-Hughes, J., et al.: Gen. Physiol., 13,807 (1930)
• Bridel, K., et al.: Bull. Soc. Chim. Biol., 15, 544 (1930)