Keto fatty acids form<i>Cuspidaria pterocarpa</i> seed oil

Smith, C. R.

doi:10.1007/bf02531614

Cited by 18 publications

(5 citation statements)

References 14 publications

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“…Hydrogenation was done in methanol with H2/PtO2 (12). The products obtained were reduced with sodium borohydride in methanol solution (13). Both reaction products were examined by gas chromatography/mass spectrometry (GC/MS).…”

Section: Preparation Of the Dimethyl Disulfide (Dmds) Adducts Of The mentioning

confidence: 99%

Identification of conjugated fatty acids in the seed oil of Acioa edulis (Prance) syn. Couepia edulis (Chrysobalanaceae)

Spitzer

Marx

Maia

et al. 1991

J Americ Oil Chem Soc

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The oil ofAcioa edulis has the fatty acid composition: palmitic acid 28.3%, palmitoleic acid 1.3%, stearic acid 6.8%, oleic acid 26.5%, vaccenic acid 1.3%, linoleic acid 8.8%, arachidic acid 0.7%, a-eleostearic acid 7.3% and a-licanic acid 19%. The oil was analyzed and components were identified by ultraviolet (UV), infrared (IR), nuclear magnetic resonance (IH-NMR, 13C-NMR), gas chromatography/mass spectrometry (GC/ MS) and chemical methods. For transesterification the tetramethylguanidine reagent was used and it was shown that the method is very suitable for co~ugated fatty acids. The equivalent chain lengths of aeleostearic acid and ~-licanic acid and their all-trans isomers were determined on DB 23 and OV-1. The electron impact (EI) and chemical ionization (CI) (with isobutane) mass spectra of Hcanic acid, eleostearic acid and the EI mass spectrum of 4-oxo-azelalc acid are presented and discussed. Furthermore, a comparison of literature data of seeds with the same common name is presented. KEY WORDS: Acioa edulis, Chrysobalanaceae, conjugated fatty acids, eleostearic acid, gas chromatography/mass spectrometry (GC/MS), licanic acid, 4-oxo-azelaic acid.Acioa edulis syn. Couepia edulis is a member of the family Chrysobalanaceae found in the basin of the Rio Purus and the central Solimoes of Amazonia, Brazil. The tree is 25 m tall and its stone-fruits are 8-9 cm long and 4.5-cm broad. The kernel is eaten raw by the habitants of the described region or is crushed and added to tapioca cakes. The oil of the seeds is used for cooking and soapmaking (1).The common name "Cotia Chestnut (Castanha de Cotia)" obviously is not unique for this fruit. This curious designation is derived from the name of a tailless animal called "Cotia, "which feeds on these kernels (2). There obtained by argentation thin-layer chromatography was converted to the bis-(methylthio) derivates as described previously (10).

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Section: Preparation Of the Dimethyl Disulfide (Dmds) Adducts Of The mentioning

confidence: 99%

Identification of conjugated fatty acids in the seed oil of Acioa edulis (Prance) syn. Couepia edulis (Chrysobalanaceae)

Spitzer

Marx

Maia

et al. 1991

J Americ Oil Chem Soc

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“…In 1966, Smith reported the presence of an interesting homologous series of unsaturated keto-acids in the seed oil of Cuspidaria pterocarpa (21). The major keto-ester derived from the oil was methyl 17-oxo-cis-20-hexacosenoate.…”

Section: Keto Fatty Estersmentioning

confidence: 99%

Gas chromatography‐mass spectrometry of methyl esters of unsaturated oxygenated fatty acids

Kleiman

Spencer

1973

J Americ Oil Chem Soc

199

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Silylation of hydroxyl groups in methyl esters of unsaturated hydroxy acids provides compounds that give mass spectra which can be readily interpreted, whereas spectra of underivatized esters are extremely difficult to evaluate. The relationship of the double bond(s) to the trimethylsiloxy (TMS) group results in specific mass spectral patterns. In esters that have the TMS group separated from the double bond by one methylene group, the ions caused by a-cleavage at the TMS group on the side closest to the olefinic group are much more abundant than those produced from a-cleavage on the other side of the TMS group. In esters that have the TMS group and the double bond separated by two methylene groups, a-cleavage ions are approximately equal. When the TMS group and the double bond are allylic, no fragmentation results between them. Cleavage does occur on either side of thig system, and those ions resulting from cleavage

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“…Aside from the work on milk fat and rumen lipids, relatively few OFA have been identified in biological material: lactarinic (6-oxostearic) acid from the mushroom fungus Lactarius refus (6,7); 13-oxodotriacontanoic acid from the cochineal insect, coccerin (8); licanic (4-oxo-9,1 I,I 3-octadectrienoic) acid in the seed fat of Licania rigida (9) and other species of this genus (1 0); 9-oxo-trans-2-decenoic acid, socalled Queen Substance from bees (11), which also has been considered to be the sex attractant for drones (12); 8-oxohexadecanoic acid which occurs in small amounts in the oil of the spores of Lycopodium species of the clubmoss Lycopodium (13); 6-oxotetradecanoic acid from hydrolized lac resin (14); 10-oxooctadecanoic acid from the Iipids of the Tubercle bacillus (15); and 17-oxo-cis-20-hexacosenoic, 15-oxocis-1 8-tetracosenoic, and 19-oxo-cis-octacosenoic acid from the seed oil of Cuspidaria pterocarpa (16). OFA of milk fat using new, improved wet microchemical techniques and mass spectrometry.…”

Section: Introductionmentioning

confidence: 99%

Trace constituents in milk fat: Isolation and identification of oxofatty acids

Weihrauch

Brewington

Schwartz

1974

Lipids

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Ca. 1% of the glycerides of milk fat contain oxofatty acids. The isolation, fractionation, and characterization of oxofatty acids were accomplished using the following sequence of steps: (A) transmethylation, (B) conversion into 2,4‐dinitrophenylhydrazones, (C) adsorption of the 2,4‐dinitrophenylhydrazones on magnesium oxide to eliminate the colorless lipid, (D) fractionation of the 2,4‐dinitrophenylhydrazones into non‐oxofatty acid and oxofatty acid fractions on alumina, (E) separation of the oxofatty acid 2,4‐dinitrophenylhydrazones into saturated and unsaturated classes by argentation column chromatography, (F) separation of these classes by chain length using liquid‐liquid column and thin layer partition chromatography, (G) resolution of positional isomers by thin layer chromatography, (H) regeneration of the positional isomer 2,4‐dinitrophenylhydrazones, and (I) analysis of the parent oxofatty acids by gas liquid chromatographymass spectrometry. In this manner, 36 saturated and 11 unsaturated oxofatty acids were identified tentatively or positively. The saturated oxofatty acids ranged in chain length from C10–C24, predominantly C18 and C16, and generally contained an even number of carbon atoms. The unsaturated oxofatty acids ranged from C14–C18, with C18 predominating.

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Keto fatty acids formCuspidaria pterocarpa seed oil

Cited by 18 publications

References 14 publications

Identification of conjugated fatty acids in the seed oil of Acioa edulis (Prance) syn. Couepia edulis (Chrysobalanaceae)

Identification of conjugated fatty acids in the seed oil of Acioa edulis (Prance) syn. Couepia edulis (Chrysobalanaceae)

Gas chromatography‐mass spectrometry of methyl esters of unsaturated oxygenated fatty acids

Trace constituents in milk fat: Isolation and identification of oxofatty acids

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