Synthesis, thermal properties, and cytotoxicity evaluation of hydrocarbon and fluorocarbon alkyl β-d-xylopyranoside surfactants

Wenjin Xu, Gifty Osei-Prempeh, Carolina Lema, E. Davis Oldham, Renato J. Aguilera, Sean Parkin, Stephen E. Rankin, Barbara L. Knutson, Hans Joachim Lehmler

Research output: Contribution to journalArticlepeer-review

34 Scopus citations


Alkyl β-d-xylopyranosides are highly surface active, biodegradable surfactants that can be prepared from hemicelluloses and are of interest for use as pharmaceuticals, detergents, agrochemicals, and personal care products. To gain further insights into their structure-property and structure-activity relationships, the present study synthesized a series of hydrocarbon (-C 6H 13 to -C 16H 33) and fluorocarbon (-(CH 2) 2C 6F 13) alkyl β-d-xylopyranosides in four steps from d-xylose by acylation or benzoylation, bromination, Koenigs-Knorr reaction, and hydrolysis, with the benzoyl protecting group giving better yields compared to the acyl group in the Koenigs-Knorr reaction. All alkyl β-d-xylopyranosides formed thermotropic liquid crystals. The phase transition of the solid crystalline phase to a liquid crystalline phase increased linearly with the length of the hydrophobic tail. The clearing points were near constant for alkyl β-d-xylopyranosides with a hydrophobic tail ≥8, but occurred at a significantly lower temperature for hexyl β-d-xylopyranoside. Short and long-chain alkyl β-d- xylopyranosides displayed no cytotoxicity at concentration below their aqueous solubility limit. Hydrocarbon and fluorocarbon alkyl β-d-xylopyranosides with intermediate chain length displayed some toxicity at millimolar concentrations due to apoptosis.

Original languageEnglish
Pages (from-to)12-23
Number of pages12
JournalCarbohydrate Research
StatePublished - Feb 15 2012

Bibliographical note

Funding Information:
This work was supported by the National Science Foundation (CBET-0967381/0967390), the U.S. Department of Agriculture Biomass Research and Development Initiative (Grant Agreement 68-3A75-7-608) and the Department of Energy Development and Independence, Energy and Environment Cabinet of The Commonwealth of Kentucky. The cell culture work was supported by Grant 5G12RR008124 to the Border Biomedical Research Center (BBRC), granted to the University of Texas at El Paso from the National Center for Research Resources (NCRR) of the NIH.


  • Koenigs-Knorr reaction
  • Next-generation surfactants
  • Renewable precursors
  • Structure-activity relationship
  • Structure-property relationship
  • Xylose

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry


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