Fundamental Characterization of the Micellar Self-Assembly of Sophorolipid Esters

Langmuir : the ACS Journal of Surfaces and Colloids
Amanda KohRichard Gross

Abstract

Surfactants are ubiquitous constituents of commercial and biological systems that function based on complex structure-dependent interactions. Sophorolipid (SL) n-alkyl esters (SL-esters) comprise a group of modified naturally derived glycolipids from Candida bombicola. Herein, micellar self-assembly behavior as a function of SL-ester chain length was studied. Surface tensions as low as 31.2 mN/m and critical micelle concentrations (CMCs) as low as 1.1 μM were attained for diacetylated SL-decyl ester (dASL-DE) and SL-octyl ester, respectively. For deacetylated SL-esters, CMC values reach a lower limit at SL-ester chains above n-butyl (SL-BE, 1-3 μM). This behavior of SL-esters with increasing hydrophobic tail length is unlike other known surfactants. Diffusion-ordered spectroscopy (DOSY) and T1 relaxation NMR experiments indicate this behavior is due to a change in intramolecular interactions, which impedes the self-assembly of SL-esters with chain lengths above SL-BE. This hypothesis is supported by micellar thermodynamics where a disruption in trends occurs at n-alkyl ester chain lengths above those of SL-BE and SL-hexyl ester (SL-HE). Diacetylated (dA) SL-esters exhibit an even more unusual trend in that CMC increases from 1....Continue Reading

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May 10, 2016·Langmuir : the ACS Journal of Surfaces and Colloids·Amanda KohRichard Gross

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Citations

Sep 27, 2018·Organic & Biomolecular Chemistry·Shekar MekalaRichard A Gross
Jan 25, 2019·Gels·Krishnamoorthy LalithaSubbiah Nagarajan
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Filbert TotsinganRichard A Gross
Jun 25, 2021·Biotechnology Advances·Sven DierickxWim K Soetaert

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