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Profiling the Triacylglyceride Contents in Bat Integumentary Lipids by Preparative Thin Layer Chromatography and MALDI-TOF Mass Spectrometry
Published on: September 5, 2013
Structure of mono-acid even-numbered beta-triacylglycerols
van Langevelde A1, van Malssen K, Hollander
1Laboratory for Crystallography, Institute for Molecular Chemistry (IMC), Universiteit van Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands. arjen@crys.chem.uva.nl
Abstract:
The crystal structure of the beta polymorph of tripalmitin (1,2,3-trihexadecanoylglycerol, beta-PPP) has been determined by single-crystal X-ray diffraction. The molecules crystallize in space group P1; in an asymmetric tuning-fork conformation. This structure and the already-known crystal structures of beta-tricaprin (beta-CCC) and beta-trilaurin (beta-LLL) could be matched in an overlap model. Apart from a difference in chain length, the three structures are almost identical. The overlap model can be used to predict the crystal structure of the other members of the C(n)C(n)C(n)-type (n = even) TAG series reasonably accurately. This is demonstrated by predicting the crystal structure for beta-trimyristin (beta-MMM) and successively comparing the experimental and calculated X-ray powder diagrams.
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For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
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The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
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Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
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