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Polyhydroxy Fatty Acids Derived from Sophorolipids
Author(s) -
Zerkowski Jonathan A.,
Solaiman Daniel K. Y.
Publication year - 2007
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-007-1054-4
Subject(s) - dihydroxylation , chemistry , organic chemistry , hydroxylation , allylic rearrangement , catalysis , enantioselective synthesis , enzyme
Starting from 17‐hydroxyoleic acid, which is readily available from acid alcoholysis of sophorolipids, several new polyhydroxy fatty acids have been synthesized. These compounds contain from 2 to 4 hydroxy groups, in some instances combined with other functional groups. The added hydroxy groups can be incorporated in the C 18 chain in a variety of geometries, for example spaced widely throughout the chain at C1, C8, and C17. This regiochemical control will be of use in structure/function studies involving materials constructed from these hydroxy fatty acids. A further benefit is that the hydroxy groups can be present in protected or free states. The principal reactions used to introduce extra hydroxy groups are selenium oxide‐mediated allylic hydroxylation, osmium‐catalyzed dihydroxylation, and borohydride reduction of a carboxylic ester. These new compounds are expected to be of use in a number of areas, but particularly as building blocks for polymers or components of lubricant formulations.