Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 66, Issue 47, Pages 12594-12603Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.8b05794
Keywords
6 '-O-acyllactose esters; surfactant properties; practical applications; antimicrobial activity; cytotoxicity
Funding
- National Key Research and Development Program of China [2017YFD040020002]
- Program for Guangdong YangFan Introducing Innovative and Entrepreneurial Teams [2016YT03H132]
- Department of Science and Technology of Guangdong Province [2016A010105010, 2017B090907018, 2014A010107014]
- Guangzhou Science and Technology Project [201508020007]
- Famous Foreign Supervisor Program of the Ministry of Education, People's Republic of China [2018-HWMS001]
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Lactose fatty acid esters are high-value-added derivatives of lactose and represent a class of biodegradable, nonionic, low-molecular-weight surfactants (emulsifiers) that have considerable potential in the food, cosmetic, and pharmaceutical industries. Certain lactose esters have also garnered attention for their biological activities. In this work, we detail syntheses of a homologous series of 6'-O-acyllactose esters of varying alkyl chain length (from 6 to 18 carbons) and report on their activities as surfactants as well as their antimicrobial and cytotoxic properties. The structure property profiles established in this work revealed that while the medium-chain esters displayed excellent emulsifying properties and moderate antimicrobial activities, their longer chain congeners exhibited the highest cytotoxicities. As such, we have established that certain 6'-0-acyllactose esters are superior to their sucrose-derived and commercially exploited counterparts. These results will serve as a useful guide for the development of lactose esters as, inter alia, emulsifiers in the food industry.
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