2- O-Monoalkyl isosorbide ethers with C8, C10, C12 and C14 chain lengths

Acta Crystallogr E Crystallogr Commun. 2020 May 29;76(Pt 6):924-928. doi: 10.1107/S2056989020006647. eCollection 2020 Jun 1.

Abstract

The title compounds, 6-(octyloxy)hexa-hydro-furo[3,2-b]furan-3-ol, C14H26O4, 6-(decyl-oxy)hexa-hydro-furo[3,2-b]furan-3-ol, C16H30O4, 6-(do-decyl-oxy)hexa-hydro-furo[3,2-b]furan-3-ol, C18H34O4, and 6-(tetra-decyl-oxy)hexa-hydro-furo[3,2-b]furan-3-ol, C20H38O4, consist of a polar headgroup (isosorbide) and a lipophilic alkyl chain linked via an ether bridge. Isosorbide is a biobased diol, containing two fused furan rings. One inter-molecular hydrogen bond connects the mol-ecules between the free endo hy-droxy group and the opposing ether oxygen of the V-shaped head group. Thus the mol-ecule layers inter-lock like in a herringbone pattern parallel to the bc plane.

Keywords: carbohydrate derivate; crystal structure; isorbide; short-chain amphiphiles.