Glycolipids from natural sources: dry liquid crystal properties, hydrogen bonding and molecular mobility of Palm Kernel oil mannosides

ABSTRACT

Glycolipids prepared from palm kernel oil, PKO, in tropical regions represent an excellent opportunity to develop new surfactant formulations for cosmeceutical and pharmaceutical applications while contributing to sustainable economies. Here we report the synthesis of a new mannoside obtained from palm kernel oil, aManPKO, and we characterise its thermotropic properties by using DSC, POM, SAXS, WAXS, FT-IR and broadband dielectric spectroscopy. aManPKO exhibits a monotropic smectic phase with a partially interdigitated bilayer structure, similar to its major unsaturated component, the oleyl mannoside with a C18:1 monounsaturated alkyl chain. The smectic phase of aManPKO vitrifies below room temperature, which is associated to the C18:1 component, but also to the activation of short-range motions, ~4 Å, by cleavage of strong hydrogen bonding between the polar heads of the mannosides. The stability of the liquid crystal phase, on the other hand, is linked to the presence of weak hydrogen bonding, whose breakage leads to the activation of long rate motions in the range of the layer distances, ~39 Å.

Graphical Abstract

KEYWORDS:

• Glycolipid
• Palm kernel oil
• hydrogen bond
• carbohydrate liquid crystals
• FT-IR
• dielectric spectroscopy

Acknowledgments

AMF and TS would like to acknowledge the financial support provided by University Malaya for the Visiting Lecturer fellowship.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Supplementary material

Supplemental data of this article can be accessed here.

Additional information

Funding

This work was supported by the Ministry of Education of Malaysia [600-RMI/RAGS 5/3 (140/2014), 2014]; University Malaya [RP038B-17AFR, 2017]; Royal Academy of Engineering, U.K., and Academy of Science, Malaysia [NRCP1516/4/61, 2016] and the University of Aberdeen [SF10192, 2018].