Identification of trans-diene isomers in hydrogenated soybean oil by gas chromatography, silver nitrate thin-layer chromatography, and carbon-13 NMR spectroscopy

McDonald, Roderick P.; Kreishman, George P.

doi:10.1021/jf00087a013

Cited by 23 publications

(12 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Correction factors for relating the IR and GLC responses. As indicated above and elsewhere (1,2,5,16,23,24,26), within each of the trans groups, namely transoctadecenoate (18:lt),c/s, trans or trans, cis-octadecadienoate [hereafter referred to as mono-trans-octadecadienoate (18:2t) ], trans, trans-octadecadienoate (i 8:2tt) and mono-trans-octadecatrienoate (18:3t), various isomers are present, and in developing the mathematical formula it is assumed that there is no variation in the absorption between the various isomers within a trans group.…”

Section: Resultsmentioning

confidence: 74%

“…Some of the margarines contained as much as 5-6% 18:2 trans isomers (5,16,25). The major diethylenic trans acids in partially hydrogenated vegetable oils have been well characterized as c/s-9, trans-12-octadecadienoic (18:2A9c,12t), trans-9, c/s-12octadecadienoic (18:2A9t,12c)( and trans-9, trans-12octadecadienoic (18:2A9t,12t) (16,23,24,26). It has been reported (26) that another major diethylenic trans isomer is present in the Cls region.…”

Section: Resultsmentioning

confidence: 99%

“…It has been reported (26) that another major diethylenic trans isomer is present in the Cls region. Recently (16,23,24), this has been partially characterized as a cis, trans and/ or trans, cis nonmethylene interrupted octadecadienoic acid. The exact position of the two double bonds and the respective geometries are yet to be determined.…”

Section: Resultsmentioning

confidence: 99%

“…The various FAME fractions isolated were analyzed by GLC. The FAME of these fractions and the starting margarines were identified or characterized by comparing the GLC retention times with authentic standards, comparing the elution patterns or equivalent chain lengths (ECL) on columns of similar polarity published in the literature (22)(23)(24) and through GLC ECL calculations. The relative positions of the MBM-adducts on TLC and the FAME on AgNo3-TLC further helped to established their identifications.…”

Section: Methodsmentioning

confidence: 99%

See 3 more Smart Citations

Determination ofcis andtrans‐Octadecenoic acids in margarines by gas liquid chromatography‐infrared spectrophotometry

Ratnayake

Hollywood

O'Grady

et al. 1990

J Americ Oil Chem Soc

View full text Add to dashboard Cite

A combined capillary gas liquid chromatography (GLC) and infrared spectrophotometry (IR) method is described for the determination of c/s and transoctadecenoic acids in margarines made from partially hydrogenated vegetable oils. The total trans-unsaturation of margarine fatty acid methyl esters determined by IR, with methyl elaidate as the external standard, was correlated to the capillary GLC weight percentages of the component trans fatty acid methyl esters by the mathematical formula: IR trans = %18:1t + 0.84 X %18.2t + 1.74 X %18:2tt + 0.84 X %18:3t where 0.84, 1.74 and 0.84 are the correction factors which relate the GLC weight percentages to the IR trans-equivalents for mono-transoctadecadienoic (18:2t), trans, trans-octadecadienoic (18:2tt) and mono-trans-octadecatrienoic (18:3t) acids, respectively. This formula forms the basis for the determination of total trans-and c/s-octadecenoic acids in partially hydrogenated vegetable oils. From the weight percentages of 18:2t, 18:2tt and 18:3t determined by capillary GLC on a cyanosilicone liquid phase and the total trans-unsaturation by IR, the percentage of the total trans-octadecenoic acids (18:1t) is calculated using the formula. The difference between the total octadecenoic acids (18:1), determined by capillary GLC, and the 18:1t gives the total c/s-octadecenoic acids.

show abstract

Section: Resultsmentioning

confidence: 74%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Determination ofcis andtrans‐Octadecenoic acids in margarines by gas liquid chromatography‐infrared spectrophotometry

Ratnayake

Hollywood

O'Grady

et al. 1990

J Americ Oil Chem Soc

View full text Add to dashboard Cite

show abstract

“…According to a preliminary study, the configuration of double bonds in compound LLX‐1 could be determined by the chemical shifts of C‐7′ ( δ 27.8), C‐10′ ( δ 25.6) and C‐13′ ( δ 27.8) in the 13 C NMR, and those chemical shifts were the same as the cis configuration of the conjugated diene (McDonald et al. ). Therefore, the structure of compound LLX‐1 was deduced to be β‐sitosterol ‐3‐ O ‐heptadeca‐8 Z , 11 Z ‐dienoate.…”

Section: Resultsmentioning

confidence: 99%

Effect of the extract and compound from Solanum nigrum Linn on Tetranychus cinnabarinus

Chen

Dai

2016

J Applied Entomology

View full text Add to dashboard Cite

The carmine spider mite Tetranychus cinnabarinus (Boisduval) is a serious pest affecting various glasshouse vegetables, fruits and crops and causes significant damage to crop yields and quality by piercing and sucking foliar tissues. The control of this mite primarily involves the application of synthetic chemical pesticides. In this study, a Solanum nigrum L. extract was evaluated for its potential acaricidal activity against adult female T. cinnabarinus in laboratory conditions, and the S. nigrum extract showed marked efficacy in controlling the carmine spider mite both in vitro and in potted seedlings. Furthermore, the active compound, a phytostanol ester (β‐sitosterol‐3‐O‐heptadeca‐8Z, 11Z‐dienoate), was isolated from the petroleum ether‐soluble fraction of S. nigrum extract via repeated column chromatography and identified based on its physiochemical properties and spectral data. At 7 days after treatment in a potted seedling experiment, the LC50 values of the S. nigrum extract and active compound were found to be 4.70 and 1.85 g/l, respectively. All of these results demonstrated that the S. nigrum extract and its active component exhibit the potential for use as new natural acaricides for controlling carmine spider mites.

show abstract

¹³C nuclear magnetic resonance spectroscopic analysis of the triacylglycerol composition of some margarines

Jie

Lam

Pasha

et al. 1996

J Americ Oil Chem Soc

View full text Add to dashboard Cite

The triacylglycerol fraction of three samples of margarine, namely “Flora” (Holland), “Kaliakra” (Bulgaria), and “Corona” (Holland), were studied by13C nuclear magnetic resonance spectroscopy. By examining the various carbon chemical shifts of the saturated and unsaturated carbon nuclei, “Flora” margarine was shown to contain a mixture of hydrogenated and unhydrogenated vegetable oils. This technique allowed all major acyl groups (saturated, oleate, linoleate, and linolenate) and minor acyl components [different positional isomers of long‐chain (E)‐ and (Z)‐monoenoic moieties, arising as by‐products during catalytic hydrogenation] to be identified. The amount of each fatty acid present in the margarine was also estimated from the relative intensities of the corresponding signals. “Kaliakra” margarine consisted of a blend of unhydrogenated natural fats and oils that contained saturated fatty acids, oleate, and linoleate. There were no signs in the spectrum of “Kaliakra” of any (E)‐isomers, nor signals associated with positional unsaturated acyl groups (other than oleate and linoleate). The sample of “Corona” margarine consisted of a mixture of hydrogenated and unhydrogenated vegetable oils and butter (1.3%). The presence of butter in this sample was identified by the characteristic carbon shifts of the C‐1 to C‐4 carbon atoms of butyrate. The distribution of the fatty acids on the glycerol “backbone” also was estimated by this technique.

show abstract

Identification of trans-diene isomers in hydrogenated soybean oil by gas chromatography, silver nitrate thin-layer chromatography, and carbon-13 NMR spectroscopy

Cited by 23 publications

References 16 publications

Determination ofcis andtrans‐Octadecenoic acids in margarines by gas liquid chromatography‐infrared spectrophotometry

Determination ofcis andtrans‐Octadecenoic acids in margarines by gas liquid chromatography‐infrared spectrophotometry

Effect of the extract and compound from Solanum nigrum Linn on Tetranychus cinnabarinus

¹³C nuclear magnetic resonance spectroscopic analysis of the triacylglycerol composition of some margarines

Contact Info

Product

Resources

About

Identification of trans-diene isomers in hydrogenated soybean oil by gas chromatography, silver nitrate thin-layer chromatography, and carbon-13 NMR spectroscopy

Cited by 23 publications

References 16 publications

Determination ofcis andtrans‐Octadecenoic acids in margarines by gas liquid chromatography‐infrared spectrophotometry

Determination ofcis andtrans‐Octadecenoic acids in margarines by gas liquid chromatography‐infrared spectrophotometry

Effect of the extract and compound from Solanum nigrum Linn on Tetranychus cinnabarinus

13C nuclear magnetic resonance spectroscopic analysis of the triacylglycerol composition of some margarines

Contact Info

Product

Resources

About

¹³C nuclear magnetic resonance spectroscopic analysis of the triacylglycerol composition of some margarines