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Synthesis of α-Hydroxy Fatty Acids from Fatty Acids by Intermediate α-Chlorination with TCCA under Solvent-Free Conditions: A Way to Valorization of Waste Fat Biomasses.

ABSTRACT: Within food wastes, including edible and inedible parts, fat biomasses represent a significant portion, often uneconomically used or improperly disposed causing pollution issues. Interesting perspectives for their management and valorization could be opened by conversion of fatty acids (FAs), which are their main constituents, into α-hydroxy FAs (α-HFAs), fine chemicals of great, but largely untapped potential, possibly due to current poor availability. Here, a simple and efficient procedure is reported to α-chlorinate FAs with trichloroisocyanuric acid (TCCA), a green halogenating agent, under solvent-free conditions and to directly convert the resultant α-chloro FAs, without previous purification, into α-HFAs. The procedure was applied to stearic, palmitic, and myristic acid and, with analogous success, to their mixture, ad hoc created to simulate a FAs mixture obtainable from a fat biomass.

SUBMITTER: Bertolini V

PROVIDER: S-EPMC8637944 | biostudies-literature |

REPOSITORIES: biostudies-literature

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RNASeq of Developing Arabidopsis Seeds Producing Hydroxy-Fatty Acids

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2014-01-10 | E-GEOD-53952 | biostudies-arrayexpress

TEMPO-Catalyzed Direct Conversion of Primary Alcohols to α-Chloroacetals with TCCA Both as an Oxidant and a Chlorination Reagent.

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Project description:3-Hydroxy fatty acids have attracted the interest of researchers, since some of them may interact with free fatty acid receptors more effectively than their non-hydroxylated counterparts and their determination in plasma provides diagnostic information regarding mitochondrial deficiency. We present here the development of a convenient and general methodology for the asymmetric synthesis of 3-hydroxy fatty acids. The enantioselective organocatalytic synthesis of terminal epoxides, starting from long chain aldehydes, is the key-step of our methodology, followed by ring opening with vinylmagnesium bromide. Ozonolysis and subsequent oxidation leads to the target products. MacMillan's third generation imidazolidinone organocatalyst has been employed for the epoxide formation, ensuring products in high enantiomeric purity. Furthermore, a route for the incorporation of deuterium on the carbon atom carrying the hydroxy group was developed allowing the synthesis of deuterated derivatives, which may be useful in biological studies and in mass spectrometry studies. In addition, the synthesis of fatty γ-lactones, corresponding to 4-hydroxy fatty acids, was also explored.

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2014-07-23 | E-GEOD-53947 | biostudies-arrayexpress

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