Structure and polymorphism of 18-carbon fatty acyl triacylglycerols: Effect of unsaturation and substitution in the 2-position

D. R. Kodali, D. Atkinson, T. G. Redgrave, D. M. Small

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Abstract

The polymorphic behavior of symmetric diacid triacylglycerols (TGs), 1,3-dioleoyl-2-stearoyl (OSO), 2-elaidoyl (OEO), and 2-vaccinoyl (OVO) glycerols were studied by differential scanning colorimetry (DSC) and X-ray diffraction and compared with the corresponding monoacid TGs triolein (OOO), tristearin (SSS), trielaidin (EEE), and trivaccinin (VVV). The monoacid TGs formed a bilayered structure in all the polymorphic forms. On quenching from the melt, the diacid TGs OEO and OVO formed a bilayered (D = 45 Å) β'-phase with the exception of OSO, which formed a hexagonally packed bilayered (D = 52 Å) α-phase. At -7°C, the α-phase of OSO quickly transformed to a bilayered (D = 45 Å) β'-phase. Incubation at the β'-phase melting temperature transformed OVO, OEO, and OSO into a trilayered (D = 65 Å) β-phase, where the 1,3-dioleoyl chains are segregated from the vaccinoyl, elaidoyl, or stearoyl chains into alternating layers. In summary, when all the acyl chains in a TG are the same (saturated, cis or trans unsaturated), the stable β-phase packs into a bilayered structure. However, when the 1- and 3-acyl chains are cis unsaturated (bent) and the 2-acyl chain is either saturated or trans-unsaturated (straight), a bilayered β'-phase can form, but transforms to a stable trilayered β-phase, where the 2-acyl chains form a layer between two different layers of 1,3-oleoyl chains.

Original languageEnglish (US)
Pages (from-to)403-413
Number of pages11
JournalJournal of Lipid Research
Volume28
Issue number4
StatePublished - Jan 1 1987

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Polymorphism
Triglycerides
Substitution reactions
Carbon
Triolein
Colorimetry
X-Ray Diffraction
Glycerol
Freezing
Melting point
Quenching
Scanning
X ray diffraction
Temperature

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Structure and polymorphism of 18-carbon fatty acyl triacylglycerols : Effect of unsaturation and substitution in the 2-position. / Kodali, D. R.; Atkinson, D.; Redgrave, T. G.; Small, D. M.

In: Journal of Lipid Research, Vol. 28, No. 4, 01.01.1987, p. 403-413.

Research output: Contribution to journalArticle

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abstract = "The polymorphic behavior of symmetric diacid triacylglycerols (TGs), 1,3-dioleoyl-2-stearoyl (OSO), 2-elaidoyl (OEO), and 2-vaccinoyl (OVO) glycerols were studied by differential scanning colorimetry (DSC) and X-ray diffraction and compared with the corresponding monoacid TGs triolein (OOO), tristearin (SSS), trielaidin (EEE), and trivaccinin (VVV). The monoacid TGs formed a bilayered structure in all the polymorphic forms. On quenching from the melt, the diacid TGs OEO and OVO formed a bilayered (D = 45 {\AA}) β'-phase with the exception of OSO, which formed a hexagonally packed bilayered (D = 52 {\AA}) α-phase. At -7°C, the α-phase of OSO quickly transformed to a bilayered (D = 45 {\AA}) β'-phase. Incubation at the β'-phase melting temperature transformed OVO, OEO, and OSO into a trilayered (D = 65 {\AA}) β-phase, where the 1,3-dioleoyl chains are segregated from the vaccinoyl, elaidoyl, or stearoyl chains into alternating layers. In summary, when all the acyl chains in a TG are the same (saturated, cis or trans unsaturated), the stable β-phase packs into a bilayered structure. However, when the 1- and 3-acyl chains are cis unsaturated (bent) and the 2-acyl chain is either saturated or trans-unsaturated (straight), a bilayered β'-phase can form, but transforms to a stable trilayered β-phase, where the 2-acyl chains form a layer between two different layers of 1,3-oleoyl chains.",
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