Adverse effects of cyclopropenoid fatty acids

Self Cite

Various concentrations of cyclopropene fatty acids have been determined down to 0.2% by the use of gas liquid chromatographic (GLC) analysis of the methyl esters of fatty acids that have been quantitatively hydrogenated using a homogeneous transition metal complex catalyst. The effectiveness of the use of bromotris(triphenylphosphine)-rhodium(I), Br(P(C~ H s)3)3 Rh, as a homogeneous hydrogenation catalyst to convert the cyclopropene ring to a cyclopropane ring has been evaluated and compared with the analogous chloro-and iodo-complexes. The hydrogenation/GLC method of analysis has been compared with the method of titration with hydrogen bromide in benzene and with the method involving the use of high resolution nuclear magnetic resonance (NMR).

Section: Total Phenolic Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Homogeneously catalyzed hydrogenation and gas‐liquid chromatographic analysis of the methyl esters of cyclopropene fatty acids

Bland

Dine

Jobanputra

et al. 1984

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“…Their cyclopropane derivatives, dihydromalvalic and dihydrosterculic acids, are the biological precursors of the corresponding cyctopropene fatty acids (3,4). Because both cyclopropene and cyclopropane fatty acids shown unusual physiological activity (1,5,6), it was of interest to obtain them in pure form to determine their thermal properties.…”

Section: Introductionmentioning

confidence: 99%

Some thermal properties of methyl malvalate, methyl sterculate, and their dihydro derivatives

White

Zariņš

Feuge

1977

Methyl ABSTRACT AND SUMMARYMethyl esters of cyclopropene acids, malvalic and sterculic, and their dihydro derivatives, were highly purified and examined for melting points, polymorphic behavior, heats of fusion, and dilatometric behavior. Results revealed that the quickly chilled forms of the unsaturated methyl esters underwent a r a p i d m o n o t r o p i c transformation. The dihydro derivatives exhibited no detectable polymorphism. The melting dilation for methyl malvalate was significantly below the previously reported dilations of other fatty acid methyl esters.

The rearrangement of fatty cyclopropenoids in the presence of boron trifluoride

Gilkison

Shone

1993

The destruction of the cyclopropenoid ring system of methyl 9,10 methyleneoctadec‐9‐enoate (methyl sterculate) with boron trifluoride etherate has been shown to give a complex mixture of products, including methyl esters of C19 allenes (12%), a C18 alkyne (11%) and a variety of C19 and C20 conjugated dienes containing either a methyl or methylene branch. The methylene group lost from the methyl sterculate reactant in the formation of methyl octadec‐9‐ynoate is incorporated into a second molecule of reactant to yield a mixture of methyl 9‐methylene‐trans‐nonadec‐10‐enoate and the 11‐methylene‐trans‐9‐isomer.