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The reaction of methyl 11, 12-E-epoxy-9Z-octadecenoate (1) with boron trifluoride etherate furnished a mixture of methyl 12-oxo-10E-octadecenoate (3a) and methyl 11-oxo-9E-octadecenoate (3b) in 66% yield. Methyl 9, 10-Z-epoxy-11 E-octadecenoate (2) with boron trifluoride etherate furnished a mixture of methyl 9-oxo-10 E-octadecenoate (4a, 45%) and methyl 10-oxo-11 E-octadecenoate (4b, 19%). A plausible...
A methylene-interrupted C18 keto-acetylenic fatty ester (methyl 12-oxo-9-octadecynoate) was obtained from methyl ricinoleate by bromination-dehydrobromination followed by oxidation. Reaction of methyl 12-oxo-9-octadecynoate with bis(benzonitrile) palladium(II) chloride, allyl bromide, or methyl-allyl bromide furnished methyl 8-[5-hexyl-3-allyl-furan-2-yl]-octanoate (1, 56%) or methyl 8-[5-hexyl-3-(2-methyl-allyl)-furan-2-yl]-octanoate...
Reactions of methyl 6-azido-hexanoate, 8-azido-octanoate, and 12-azido-dodecanoate with [60]fullerene (1) gave the corresponding aza-[60]fullerene ester derivatives (2a-2c, 22–35% based on the amount of [60]fullerene reacted). The nitrogen atom is bonded to the [60]fullerene cage to yield a “[5,6]-open” type aza substructure. This was confirmed by the appearance of 30–31 sp2 signals at δC 133–147...
Reaction of methyl 9,10-dioxostearate (1) and 9,12-dioxostearate (2) with 1,2-diaminoethane under concomitant ultrasonic irradiation (10–15 min, 60°C) in water furnished the corresponding 2,3-dihydropyrazine (4, 79%) and 1,2,3,4-tetrahydro-1,4-diazocine (5, 70%) derivatives, respectively. Reaction of methyl 10,12-dioxostearate (3) with 1,2-diaminoethane was successful only when glacial acetic acid...
Some 1,2- and 1,3-diacyl glycerols (with acyl groups as stearyl, oleyl, linoleyl, or stearolyl) were synthesized by conventional methods. The diacyl glycerols were esterified with 6-bromo-hexanoic acid to give the corresponding bromotriacylglycerols (of the type AAB and ABA containing a bromo group at the distal part of the hexanoate chain). The bromo function was transformed to an azide group by...
Primary amines (ammonia, methyl, propyl, octyl, octadecyl, phenyl, benzyl, phenethyl) including methyl esters of amino acids (glycine, dl-alanine, l-valine, l-leucine, L-tyrosine, and l-methionine), and secondary amines (dimethyl, diethyl, dipropyl, diisopropyl, dioctyl, and diphenyl) attack regiospecifically the central carbon atom of the allene system of methyl 12-keto-9,10-octadecadienoate (1)...
Tris(hydroxymethyl)aminomethane was successfully esterified with saturated and unsaturated long-chain fatty acids. The resulting amino-triester intermediates were successively reacted with chloroacetyl chloride, sodium azide, and C60 fullerene. Spectral evidence showed that the aziridine ring is joined to the junction of [6,6]-fused rings of the fullerene. The structures of the various C60 fullerene...
Reduction of methyl 8-hydroxy-11-E/Z-octadecen-9-ynoate (1) with zinc in either aqueous n-propanol or water under concomitant ultrasound irradiation furnished a mixture of methyl 8-hydroxy-9Z,11E-octadecadienoate (3a) and methyl 8-hydroxy-9Z, 11Z-octadecadienoate (3b) (96% yield). Reduction of methyl 8-oxo-11-E/Z-octadecen-9-ynoate (2) under similar conditions gave methyl 8-oxo-10-Z-octadecenoate...
The esterification of five medium- and long-chain acetylenic alcohols (2-nonyn-1-ol, 10-undecyn-1-ol, 6-octadecyn-1-ol, 9-octadecyn-1-ol, and 13-docosyn-1-ol), seven olefinic alcohols (cis-3-nonen-1-ol, 10-undecen-1-ol, cis-6-octadecen-1-ol, cis-9-octadecen-1-ol, trans-9-octadecen-1-ol, trans-9, trans-11-octadecadien-1-ol, cis-9, cis-12-octadecadien-1-ol), and four short-chain unsaturated alcohols...
Esterification of five positional isomers of acetylenic fatty acids [viz. 9:1(2a), 11:1(10a), 18:1(6a), 18:1(9a) and 22:1(13a)] of different chain lengths with n-butanol in n-hexane in the presence of eight different lipases [Lipozyme IM 20 (Rhizomucor miehei), Lipolase 100T (R. miehei), Novozyme 435 (Candida antarctica), PPL (porcine pancreatic lipase), CCL (C. cylindracea), PS-D (Pseudomonas cepacia...
Epoxidation of the double bond in methyl oleate, octadec-11E-en-9-ynoate, ricinoleate (12-hydroxy-octadec-9Z-enoate), iso-ricinoleate (9-hydroxy-octadec-12Z-enoate), and 12-oxo-octadec-9Z-enoate with potassium peroxomonosulfate (oxone, 2 KHSO5.K2SO4) in the presence of trifluoroacetone or methyl pyruvate gave the corresponding monoepoxy derivatives. Reaction of Oxone® with methyl linoleate and octadeca-9...
Reaction of C60 fullerene with dialkyl bromomalonate (where the alkyl groups consist of short-, medium-, and long-saturated chains or unsaturated long chains) in the presence of sodium hydride gives [6,6]-bridged mono-adducts of methanofullerene. The spectroscopic properties of such fullerenoid lipids are reported.
Reaction of methyl undec-10-ynoate (1) with selenium dioxide/tert-butyl hydroperoxide (TBHP) in aqueous dioxane gave methyl 9-oxo-undec-10-ynoate (2, 9%) and 9-hydroxy-undec-10-ynoate (3, 60%), while methyl octadec-9-ynoate (4) yielded mixtures of positional isomers of mono-keto (viz. methyl 8-oxo- and 11-oxo-octadec-9-ynoate, 5, 5%), hydroxy-keto (viz. methyl 8-hydroxy-11-oxo-and 11-hydroxy-8-oxo-octadec-9-ynoate,...
Gas-liquid chromatographic analyses of three complete series of synthetic positional isomers of methyl thia, selena, and tellura laurate analogs were carried on a nonpolar (SE-30) and a polar (SP-2330) stationary phase. The average ECL (equivalent chain length) values of the thia, selena, and tellura laurate on SE-30 stationary phase were 13.8, 14,8, and 15.7, respectively, while on SP-2330 the average...
Pure geometric isomers of conjugated linoleic acid were prepared from castor oil as the primary starting material. Methyl octadeca-9Z, 11E-dienoate (2) and methyl octadeca-9Z, 11Z-dienoate (4) were obtained by zinc reduction of methyl santalbate (1, methyl octadec-11E-en-9-ynoate) and methyl octadec-11 Z-en-9-ynoate (3), respectively, as the key intermediates. Methyl octadeca-9E, 11E-dienoate (8)...
During the past two decades, nuclear magnetic resonance spectroscopy (NMR) has played an ever-increasing role in the structural determination of fatty acids, fatty acid derivatives and analogues, and in the analysis of the structures of triacylglycerols including the quantitative analysis of lipid mixtures. This article discusses some of the results obtained through the application of the NMR technique...
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