DOI QR코드

DOI QR Code

The Crystal and Molecular Structure of Phlorizin Dihydrate

  • Shin, Whan-Chul (Department of Chemistry, College of Natural Sciences, Seoul National University)
  • Published : 1985.02.20

Abstract

The crystal structure of phlorizin, a ${\beta}$ -D-glucopyranoside of a flavonoid dihydrochalcone phloretin, has been determined by single crystal diffraction methods using diffractometer data obtained by the ${\omega}-2{\theta}$ scan technique with Cu $K{\alpha}$ radiation from a crystal with space group symmetry $P2_12_12_1$ and unit cell parameters a = 4.9094 (2), b = 19.109 (1), c = 23.275 (4) $\AA$. The structure was solved by direct methods and refined by full-matrix least-squares to a final R = 0.047 for the 1697 observed reflections. The dihydrochalcone moiety is flat and fully extended. The glucose ring has the $^4C_1$ chair conformation and the conformation of the primary alcohol group is gauche-gauche. The crystal packing is dominated by an extensive hydrogen bonding pattern. There are one strong and two weak intramolecular hydrogen bonds in the phlorizin molecule.

Keywords

References

  1. J. Agric. Food Chem. v.17 R. M. Horowitz;B. Gentili
  2. Acta Cryst. v.B33 G. A. Geffrey;S. Takagi
  3. Acta Cryst. v.B35 W. P. J. Gaykema;J. A. Kanters
  4. Acta Cryst. v.B36 D. C. Rohrer;A. Sarko;T. L. Bluhm;Y. N. Lee
  5. J. Am. Chem. Soc. v.100 G. A. Jeffrey;J. A. Pople;J. S. Binkley;S. Vishveshwara
  6. J. Am. Chem. Soc. v.97 D. Cremer;J. A. Pople
  7. Carbohydr. Res. v.38 G. A. Jeffrey;J. A. Pople;L. Radom
  8. PLUTO. Program for Plotting Molecular and Crystal Structure W. D. S. Motherwell;W. Clegg
  9. J. Agric. Food Chem. v.29 G. E. DuBois;G. A. Crosby;J. F. Lee;R. A. Stephenson;P. C. Wang
  10. J. Med. Chem. v.24 G. E. DuBois;G. A. Crosby;R. A. Stephenson
  11. SHELX. A Program for X-ray Crystal Structure Determination G. M. Sheldrick
  12. International Tables for X-ray Crystallography v.IV
  13. Acta Cryst. v.B31 A. Domenicano;A. Vaciago;C. A. Coulson
  14. Acta Cryst. v.B35 A. Domenicano;A. Vaciago
  15. Acta Cryst. v.19 K. Maartmann-Moe
  16. Acta Cryst. v.16 W. G. Ferrier