Determination of cyclopropenoic fatty acids by reversed-phase liquid chromatography and gas chromatography

Gaydou, Émile M.; Bianchini, Jean‐Pierre; Ralaimanarivo, A.

doi:10.1021/ac00264a025

Cited by 15 publications

(9 citation statements)

References 17 publications

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“…The percentages of 18:CE, 19:CE and 19:CA were found to be 8.3, 4.7 and 1.7, respectively. These results are quite similar to kapok seed oil analyses recently reported by other workers(6,7).Previous workers…”

supporting

confidence: 93%

“…Various plant families such as Malvaceae, Sterculiaceae and Bombacaceae have been found to contain CPEFA (4,5). Cottonseed (Gossypium birsutum) oil contains small amounts (0.4-1.3%)of CPEFA (6)(7)(8), while greater amounts (8.7-14.4%) have been found in kapok (Ceiba pentandra) seed oils (6,7). Since these oils are of importance in developing countries, it is essential to have an unsophisticated, simple technique to accurately determine their CPEFA content.…”

Section: Introductionmentioning

confidence: 99%

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Hydrazine reduction in the gas liquid chromatographic analysis of the methyl esters of cyclopropenoic fatty acids

Conway

Ratnayake

Ackman

1985

J Americ Oil Chem Soc

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supporting

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Hydrazine reduction in the gas liquid chromatographic analysis of the methyl esters of cyclopropenoic fatty acids

Conway

Ratnayake

Ackman

1985

J Americ Oil Chem Soc

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“…AgNO 3 -chromatography is not suitable for the separation of cyclopropenoic fatty acids because of ring opening and other derivatization reactions catalyzed by silver ions (17,18). Methods used for the preparative isolation of cyclopropenoic fatty acids in good purity include repeated urea fractionations and crystallizations (9,19,20) as well as countercurrent distribution (19). We report here a simple method involving preparative RP-HPLC for the preparation of highly pure cyclopropenoic fatty acids, e.g., malvalic and sterculic acids, in appropriate quantities that could be of interest for chemical, biochemical, and analytical purposes.…”

Section: Resultsmentioning

confidence: 99%

“…The presence of cyclopropene fatty acids in seed oils can be roughly checked by the Halphen test (8). Identification by gas chromatography (GC) and high-performance liquid chromatography (HPLC) analysis (9,10) is difficult, however, because no cyclopropene fatty acid standards are commercially available. This paper presents a simple method for the preparation of both methyl malvalate and methyl sterculate of high purity, which may be useful for GC and HPLC comparison as well as biochemical and enzymatic studies.…”

mentioning

confidence: 99%

Preparation of malvalic and sterculic acid methyl esters from Bombax munguba and Sterculia foetida seed oils

Fehling¹,

Schönwiese²,

Klein³

et al. 1998

J Americ Oil Chem Soc

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A method has been developed for the preparation of highly pure malvalic (cis-8,9-methyleneheptadec-8-enoic) and sterculic (cis-9,10-methyleneoctadec-9-enoic) acid methyl esters starting from Bombax munguba and Sterculia foetida seed oils. The methyl esters of these oils were prepared by sodium methylate-catalyzed transmethylation followed by cooling (6°C) the hexane solution of crude methyl esters and separation of insoluble fatty acid methyl esters by centrifugation in the case of B. munguba and by column chromatography in the case of S. foetida. Subsequently, the saturated straightchain fatty acid methyl esters were almost quantitatively removed by urea adduct formation. Finally, methyl malvalate and methyl sterculate were separated from the remaining unsaturated fatty acid methyl esters, in particular methyl oleate and methyl linoleate, by preparative high-performance liquid chromatography on C 18 reversed-phase using acetonitrile isocratically. Methyl malvalate and methyl sterculate were obtained with purities of 95-97 and 95-98%, respectively. JAOCS 75, 1757-1760 (1998). KEY WORDS:Bombax munguba oil, cyclopropene fatty acids, malvalic acid methyl ester, preparative HPLC, Sterculia foetida oil, sterculic acid methyl ester, urea fractionation.Cyclopropene fatty acids are widely distributed in the seed oils of many plant families of the order Malvales (1,2). Small proportions of cyclopropene fatty acids, e.g., malvalic (cis-8,9-methyleneheptadec-8-enoic) and sterculic (cis-9,10-methyleneoctadec-9-enoic) acids, which are present in crude cottonseed oil, are of special interest owing to their harmful biological effects when fed to animals (3-7).The presence of cyclopropene fatty acids in seed oils can be roughly checked by the Halphen test (8). Identification by gas chromatography (GC) and high-performance liquid chromatography (HPLC) analysis (9,10) is difficult, however, because no cyclopropene fatty acid standards are commercially available. This paper presents a simple method for the preparation of both methyl malvalate and methyl sterculate of high purity, which may be useful for GC and HPLC comparison as well as biochemical and enzymatic studies. The starting materials were seeds of Bombax munguba (11) and Sterculia foetida (1,2), which are known to be good sources of cyclopropene fatty acids. EXPERIMENTAL PROCEDURESMaterials. Distilled solvents were used throughout. HPLCgrade acetonitrile was purchased from Rathburn Chemicals (Walkerburn, Scotland). Silica gel, urea, and sodium methylate were products of E. Merck (Darmstadt, Germany). Bombax munguba Mart. seeds were collected at University of Paraiba, João Pessoa, Brazil (11); S. foetida L. seeds were a gift from Professor Helmut K. Mangold, Münster, Germany.Preparation of fatty acid methyl esters (FAME). Seeds of B. munguba (10 g) were ground in an electric coffee grinder and the meal extracted in a Soxhlet extractor for 6 h with 200 mL hexane. The hexane was evaporated and the oil transmethylated with sodium methylate in methanol (11). After addition of...

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“…This is almost twice as sensitive as the method of Fisher and Schuller (1981) with packed column. The present method is also simpler and almost ten times more sensitive than the parallel GC-HPLC method of Gaydou et al (1983) which cannot be extended below CPEFA concentrations of about 0.15%. It should, therefore, find application in the analysis of cottonseed oils containing CPEFAs as low as 0.017%.…”

Section: Quantitation Of Cpefasmentioning

confidence: 89%

A Capillary GC Determination of Cyclopropenoid Fatty Acids in Cottonseed Oils

Park

Rhee

1988

Journal of Food Science

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A capillary gas chromatography (GC) method was studied for direct analysis for cyclopropenoid fatty acids (CPEFAs) as methyl esters. No thermal alterations were indicated in CPEFA methyl esters on a Supelcowax IO or a DB-5 capillary column like other fatty acid methyl esters (FAMES), which obviated a second derivatization. GC conditions are described for a complete separation and quantitation of CPEFAs in cottonseed oils. CPEFAs of cottonseed oils from various refining steps were analyzed by the method. The reliability of the method was demonstrated with over 95% recoveries of CPEFA methyl esters diluted in corn oil FAMES at various levels as low as 0.017%.

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Determination of cyclopropenoic fatty acids by reversed-phase liquid chromatography and gas chromatography

Cited by 15 publications

References 17 publications

Hydrazine reduction in the gas liquid chromatographic analysis of the methyl esters of cyclopropenoic fatty acids

Hydrazine reduction in the gas liquid chromatographic analysis of the methyl esters of cyclopropenoic fatty acids

Preparation of malvalic and sterculic acid methyl esters from Bombax munguba and Sterculia foetida seed oils

A Capillary GC Determination of Cyclopropenoid Fatty Acids in Cottonseed Oils

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