Tentative identification of an unusual naturally-occurring polyenoic fatty acid by calculations from precision open-tubular GLC and structural element retention data

Ackman, R. G.; Manzer, A.; Joseph, Jeanne D.

doi:10.1007/bf02269820

Cited by 24 publications

(16 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It can also be noted in Tab The ECL of a dienoic acid depends in principle on the contribution of the two constitutive ethylenic bonds and of a "dienoic adjustment" that is function of the distance (the number of methylene groups) between the double bonds, and also slightly on their position along the hydrocarbon chain. Several applications of this principle have been developed in pioneering studies by Ackman and coworkers [73][74][75][76]. This is not valid for conjugated ethylenic bonds, but such an arrangement does not occur in gymnosperms.…”

Section: Experimental and Calculated Equivalent Chain Lengths (Ecl) Omentioning

confidence: 99%

“…This is not valid for conjugated ethylenic bonds, but such an arrangement does not occur in gymnosperms. Arithmetically, the ECL of a dienoic acid is the sum of the fractional chain lengths (FCL: ECL minus base value) of the two corresponding monoenoic acids, plus the base value, plus a dienoic adjustment ∆x (x representing the number of methylene groups between the ethylenic bonds) [73][74][75][76]. Most often, the value of the latter parameter may be high, but it cannot be predicted on a theoretical basis and must be experimentally determined with known components.…”

Section: Experimental and Calculated Equivalent Chain Lengths (Ecl) Omentioning

confidence: 99%

See 1 more Smart Citation

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

Wolff

Christie

2002

Eur. J. Lipid Sci. Technol.

View full text Add to dashboard Cite

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis ∆ ∆5-olefinic acidsIn view of the increasing interest of lipid researchers in the biological effects of all-cis ∆5-unsaturated polymethylene-interrupted fatty acids (∆5-UPIFA) from vegetable origin, this paper is concerned with their occurrence in practical sources (gymnosperm seeds), structures, and identification by gas-liquid chromatography (GLC) and mass spectrometry (MS). The use of equivalent chain lengths (ECL) determined by calculations based on available standards, in close agreement with data determined with easily available commercial gymnosperm seeds specific for each ∆5-UPIFA, allows identification of all ∆5-UPIFA. These tentative identifications are supported by GLC-MS of the appropriate (4,4-dimethyloxazoline and picolinyl ester) derivatives. ECL are particularly useful to identify ∆5-UPIFA in tissue lipids from animals experimentally fed oils containing these acids, with no interference with polyunsaturated fatty acids of endogenous origin.

show abstract

Section: Experimental and Calculated Equivalent Chain Lengths (Ecl) Omentioning

confidence: 99%

Section: Experimental and Calculated Equivalent Chain Lengths (Ecl) Omentioning

confidence: 99%

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

Wolff

Christie

2002

Eur. J. Lipid Sci. Technol.

View full text Add to dashboard Cite

show abstract

“…The molecular weights of most of the fatty acids were confirmed by gas-liquid chromatography/mass spectrometry (GUMS) using a Finnigan MAT 700 ITD (Ion Trap Detector, Finnigan MAT, San Jose, California). The procedures for AgN03-TLC of the original esters, the hydrazine reduction of the isolated bands, and the comparative GLC have been described elsewhere (Ackman et al 1974).…”

Section: Fatty Acid Identijkationmentioning

confidence: 99%

Fatty Acid Composition of Three Cultured Algal Species (Isochvysis galbana, Chaetoceros gracilis and Chaetoceros calcitrans) Used as Food for Bivalve Larvae

Napolitano

Ackman

Ratnayake

1990

J World Aquaculture Soc

View full text Add to dashboard Cite

Fatty acids of three cultured unicellular algae wldely used in aquaculture (Isochrysis galbana, clone T‐iso, Chaetoceros calcitrans, and Chaetoceros gracilis) were analyzed in detail by gas‐liquid chromatography and mass spectrometry. Fatty acid compositions of the individual species, harvested at monthly intervals during a four month period, showed a very consistent pattern. Shorter chain (C16) fatty acids accounted for more than 70% of total fatty acids in the diatoms but less than 20% in I. galbana. Medium chain (C18) and the long chain 22:6w3 unsaturated fatty acids represented more than 50% of the total fatty acids in I. galbana but less than 10% of the total In the Chaetoceros spp. However, in the latter, 20:5w3 replaced 22:6w3 at an equivalent level. Fatty acid profiles of c. calcitrans and c. gracilis were similar, except that the latter contained lower levels of 16:2w4, 16:3w4 and 16:4w1, and higher levels of 18:2w6 and 18:3w6. In particular C. gracilis contained a higher proportion of the biochemically important fatty acid 20:4w6 (arachldonic acid). One of the salient features of I. galbana lipids was the presence of the fatty acid 18:5w3. This fatty acid is not generally reported in algae or invertebrate lipid analyses, but is a typical component of I. galbana and of other marine photosynthetic flagellates. Its potential for utilization by aquatic organisms is unknown.

show abstract

“…2), it was initially impossible to identify all the fatty acids formed in the mixture of total oil methyl esters on either polar or nonpolar columns. The experimental and calculated equivalent chain lengths (23,24) predict limits within which groups of certain structures occur, but there are overlaps, e.g., between esters of fatty acids with two and three ethylenic bonds, even in the case of all-cis polyethylenic acid isomers (4). In anticipation of this problem of overlap, the TLC separation of the MBM adducts into fatty acid classes (monoene, diene, triene, etc.)…”

Section: Transformation Of Fatw Acids During Hydrogenationmentioning

confidence: 99%

Hydrogenation of a menhaden oil: I. Fatty acid and C₂₀monoethylenic isomer compositions as a function of the degree of hydrogenation

Sébédio

Ackman

1983

J Americ Oil Chem Soc

Self Cite

View full text Add to dashboard Cite

US menhaden oil is rich in long‐chain polyethylenic fatty acids, chiefly C20 (eicosapentaenoic) and C22 (docosahexaenoic) fatty acids, unlike Canadian herring oil, which is rich in long‐chain (C20 and C22) monoethylenic fatty acids. An examination of the product fatty acids from hydrogenation of menhaden oil therefore comple‐ments studies previously published for herring oil. During a commer‐cial hydrogenation of menhaden oil, iodine value (IV) 159.0, on nickel catalyst, samples were collected at IV 150.0, 140.0, 131.5, 120.5, 96.5, 90.0 and 84.5. The fatty acid compositions were deter‐mined using a combination of mercuric adduct fractionation and gas liquid chromatographic (GLC) analyses, and the totaltrans content by infrared spectroscopy. The partial hydrogenation resulted in the disappearance of the pentaenoic and hexaenoic fatty acids, a de‐crease in tetraenes, and a definite increase in trienes, 8.3% at IV 84.5 compared to 4.2% at IV 159.0. The dienoic fatty acids in‐creased to 13.2% at IV 84.5 compared to 4.1% at IV 159.0, and the monoenoic fatty acids increased to 34.2% from 24.0%. No impor‐tant changes in the saturated acids were observed, 43.8% at IV 84.5 compared to 41.6% at IV 159.0. The totaltrans content varied from 3.4% at IV 150.0 to 45.1% at an IV of 84.5. The isomer composi‐tions of thecis andtrans C20 monoethylenic fatty acids were deter‐mined using a combination of preparative GLC, AgNO3 thin layer chromatography and ozonolysis. Thecis 20:1 acids at IV 84.5 still retained 27.5% of the major isomer (All) originally present at 72%. The parent A5, A8, All, A14 and A17 bonds of the 20:5 originally present could be detected in thecis 20:1 isomers at IV 96.5 but not at IV 84.5. At IV 84.5, 58% of the 20:1was trans, the major isomer being All (9.4% of total 20.1), accompanied by important quanti‐ties of Δ10 and Δ12, respectively, 6.9% and 6.6% of the total 20:1.

show abstract

Tentative identification of an unusual naturally-occurring polyenoic fatty acid by calculations from precision open-tubular GLC and structural element retention data

Cited by 24 publications

References 18 publications

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

Fatty Acid Composition of Three Cultured Algal Species (Isochvysis galbana, Chaetoceros gracilis and Chaetoceros calcitrans) Used as Food for Bivalve Larvae

Hydrogenation of a menhaden oil: I. Fatty acid and C₂₀monoethylenic isomer compositions as a function of the degree of hydrogenation

Contact Info

Product

Resources

About

Tentative identification of an unusual naturally-occurring polyenoic fatty acid by calculations from precision open-tubular GLC and structural element retention data

Cited by 24 publications

References 18 publications

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

Fatty Acid Composition of Three Cultured Algal Species (Isochvysis galbana, Chaetoceros gracilis and Chaetoceros calcitrans) Used as Food for Bivalve Larvae

Hydrogenation of a menhaden oil: I. Fatty acid and C20monoethylenic isomer compositions as a function of the degree of hydrogenation

Contact Info

Product

Resources

About

Hydrogenation of a menhaden oil: I. Fatty acid and C₂₀monoethylenic isomer compositions as a function of the degree of hydrogenation