On methylation of unsaturated acids using boron trihalide-methanol reagents.

Paper

On methylation of unsaturated acids using boron trihalide-methanol reagents.

Published Nov 1, 1971 · W. E. Klopfenstein

Journal of lipid research

Q1 SJR score

65

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0

Influential Citations

Semantic Scholar

Abstract

Methanolysis of unsaturated fatty acids and triglycerides was carried out with boron trihalide-methanol reagents of various ages. Boron trichloride-methanol produced esters apparently free from contaminants; boron trifluoride caused some loss of highly unsaturated esters after 90 min at 100 or 120 degrees C in Teflon-lined screw-cap vials and at 120 degrees C in ampoules. The losses were more marked when the reactions were carried out in vinyl-lined screw-cap vials. Noticeable losses did not occur with any of the vessel types when BCl(3)-CH(3)OH was the methylating agent. Long-term studies at 80 degrees C further demonstrated that BCl(3)-CH(3)OH caused less loss of unsaturated acid than did BF(3)-CH(3)OH.

Study Snapshot

Boron trihalide-methanol reagents can produce unsaturated fatty acids and triglycerides, with BCl(3)-CH(3)OH causing less loss of unsaturated acid than BF(3)-CH(3)OH.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

On methylation of unsaturated acids using boron trihalide-methanol reagents.

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References

Production of an artifact during methanolysis of lipids by boron trifluoride-methanol.

Artifacts can be produced during methanolysis of lipids with boron trifluoride-methanol, but no artifacts were produced with sodium methoxide.

Lipid oxidation in flour doughs—observations involving the boron trifluoride interesterification reaction

Lipid oxidation in flour doughs is a reversible stage involved in natural and chemical flour maturing, with methyl methoxy stearate as an artifact of the interesterification process.

Characterization of unsaturated fatty acids by gas-liquid chromatography

The equivalent chain length (ECL) of unsaturated fatty acids can be determined using gas-liquid chromatography, with ethyl esters of 18 and 20 carbon acids having greater ECL values than methyl esters.

QUANTITATIVE PREPARATION OF METHYL ESTERS OF SHORT-CHAIN AND LONG-CHAIN FATTY ACIDS FOR GAS CHROMATOGRAPHIC ANALYSIS.

This paper presents a method for quantitative preparation of methyl esters of both short- and long-chain fatty acids for gas chromatographic analysis, improving fatty acid analysis methods.

PREPARATION OF FATTY ACID METHYL ESTERS AND DIMETHYLACETALS FROM LIPIDS WITH BORON FLUORIDE--METHANOL.

This study developed a simple, rapid, and generally applicable method for preparing fatty acid methyl esters and dimethylacetals from lipids for gas chromatographic analysis.

A source of contamination in the ultramicro analysis of methyl esters of fatty acids by gas-liquid chromatography.

Contaminants in ultramicro analysis of methyl esters of fatty acids can be traced to anhydrous methanolic HCl used for methanolysis, which are not esters of carboxylic acids but mimic them on GLC analysis.

Citations

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A critical assessment of transmethylation procedures for n-3 long-chain polyunsaturated fatty acid quantification of lipid classes.

The sodium methoxide and sulfuric acid method is effective for accurately quantifying long-chain n-3 polyunsaturated fatty acids in lipid classes, ensuring accurate fatty acid composition.

Determination of fatty acid methyl esters derived from algae Scenedesmus dimorphus biomass by GC-MS with one-step esterification of free fatty acids and transesterification of glycerolipids.

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Quantitative analysis of 3-OH oxylipins in fermentation yeast.

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Associations between omega-3 fatty acids and 25(OH)D and psychological distress among Inuit in Canada

Low levels of 25(OH)D and long-chain n-3 FAs are associated with higher odds of psychological distress in Inuit in Canada, suggesting the potential impact of traditional foods on mental health and wellbeing.

Survey of the total fatty acid and triacylglycerol composition and content of 30 duckweed species and cloning of a Δ6-desaturase responsible for the production of γ-linolenic and stearidonic acids in Lemna gibba

Duckweed species show diverse fatty acid composition, with 6-desaturase LgDes playing a key role in producing GLA and SDA, but polyunsaturated FA is underrepresented in triacylglycerol.