Synthesis and characterization of dioctanoyl glycerate as water-soluble trypsin inhibitor

Shun Sato, Shota Nagata, Tomohiro Imura, Tokuma Fukuoka, Tomotake Morita, Yutaka Takahashi, Yukishige Kondo, Dai Kitamoto, Hiroshi Habe

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)


Glyceric acids (GAs) esterified with long acyl chains (> C16) exhibit antitrypsin activity (Folia Microbiol. 46, 21-23 (2001)). However, their hydrophobic nature, derived from the long acyl chains, has limited the number of studies on their physical and biological properties. To improve the water solubility of diacyl GAs, GA was esterified with octanoyl groups (C8), and its physical properties were investigated. Synthesized dioctanoyl GA was not water-soluble, whereas its sodium salt was. Surface tension measurements of dioctanoyl GA sodium salt (diC8GA-Na) in water revealed that the critical micelle concentration (CMC) was 0.82 mM, and surface tension at the CMC was 25.5 mN/m. Additionally, diC8GANa inhibited casein digestion by trypsin to a greater extent than dioleoyl GA. These data suggest that watersoluble diacyl GAs may have utility as surfactants and bioactive compounds.

Original languageEnglish
Pages (from-to)251-256
Number of pages6
JournalJournal of oleo science
Issue number3
Publication statusPublished - 2016 Mar 1
Externally publishedYes


  • Antitrypsin activity
  • Diacyl glyceric acid
  • Glyceric acid
  • Glycerol
  • Surfactant

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)


Dive into the research topics of 'Synthesis and characterization of dioctanoyl glycerate as water-soluble trypsin inhibitor'. Together they form a unique fingerprint.

Cite this