(E)-Ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate: a natural polymorph extracted from Aristotelia chilensis (Maqui)

Acta Crystallogr C. 2013 Jul;69(Pt 7):765-9. doi: 10.1107/S0108270113013991. Epub 2013 Jun 8.

Abstract

The natural title compound, C11H12O4, extracted from the Chilean native tree Aristotelia chilensis (Maqui), is a polymorph of the synthetic E form reported by Xia, Hu & Rao [Acta Cryst. (2004), E60, o913-o914]. Both rotational conformers are identical from a metrical point of view, and only differ in the orientation of the 3,4-dihydroxyphenyl ring with respect to the rest of the molecule, which leads to completely different crystal structure arrangements and packing efficiencies. The reasons behind both reside in the different hydrogen-bonding interactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Elaeocarpaceae / chemistry*
  • Hydrogen Bonding
  • Molecular Structure
  • Phenylpropionates / chemical synthesis
  • Phenylpropionates / chemistry*
  • Plant Leaves / chemistry*

Substances

  • (E)-ethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
  • Phenylpropionates