Crystal Structure of β-Tricaprin

Jensen, L. H.; Mabis, A. J.

doi:10.1038/197681d0

Cited by 64 publications

(37 citation statements)

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“…These results also suggest the importance of considering that water molecules in different locations have different , ρ s represents the density of the lipophilic groups (0.84 g/cm 3 according to a reported value for stearyl alcohol in a supercooled state), φ w and φ s represent the total weight fraction of water and the surfactant and higher alcohol in the system, and represents the monolayer thickness of the lipophilic group (assumed to be ~2 nm). Compositions A, B, C, and D correspond to those in the phase diagram (Fig.…”

Section: Resultsmentioning

confidence: 94%

“…where d represents the interlayer spacing, ρ w represents the density of water 1 g/cm 3 , ρ s represents the density of the lipophilic group 0.84 g/cm 3 according to a reported value for stearyl alcohol in the supercooled state 13 , φ w and φ s represent the total weight fraction of water and the surfactant and higher alcohol in the system, respectively, and represents the monolayer thickness of the lipophilic group assumed to be 2 nm .…”

Section: Resultsmentioning

confidence: 99%

“…The phase transition temperature of the α-crystalline phase in a hexadecanol/octadecyl trimethyl ammonium chloride OTAC /water system was studied in detail using differential scanning calorimeter DSC . The results revealed that the melting point of the α-crystalline phase increases with increasing hexadecanol/ OTAC mole ratio and reaches a maximum at a ratio of 3/1 3 .…”

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α-Gel Prepared in Sodium Methyl Stearoyl Taurate/Behenyl Alcohol/Water System-Characterization of Structural Changes with Water Concentration

et al. 2012

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

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confidence: 98%

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α-Gel Prepared in Sodium Methyl Stearoyl Taurate/Behenyl Alcohol/Water System-Characterization of Structural Changes with Water Concentration

et al. 2012

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“…Only two structures on single-chain triacylglycerols, tricaprin by Jensen and Mabis in 1963 (4) and trilaurin by Larsson in 1964 (5), have been published. A single complex triacylglyceride structure, 2-(11-bromoundecanoyl)-1,1'-dicaprin, was published (6), but its structure, especially the conformation of the glycerol and the chain orientation, are quite similar to the structure of single-chain triacylglycerols (4,5). Our understanding of the structure and polymorphism of acylglycerols would be greatly enhanced by knowing the crystal structures of some of the forms of mixed-chain triacylglycerols.…”

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confidence: 99%

“…The general structure of saturated 1,2-diacyl-sn-glycerols has been reported (11) and the crystal structure of 1,2-dilauroyl-sn-glycerol (12) and 1,2-dipalmitoyl-sn-glycerol (13) have been solved. We have synthesized the three acetyl derivative of 1,2-dipalmitoyl-sn-glycerol and defined its crystal structure.$ The structure of this triacylglycerol with an acetate in position 3 differs considerably around the glycerol backbone from 1,2-diacylglycerols (12)(13)(14) or simple acid triacylglycerols such as trilaurin (4,5). The glycerol conformation is, however, quite similar to one of the two conformers of dimyristoyl phosphatidylcholine (15 The coordinates of the non-H atoms are given in Table 1.…”

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Single crystal structure of a mixed-chain triacylglycerol: 1,2-dipalmitoyl-3-acetyl-sn-glycerol.

Goto¹,

Kodali²,

Small³

et al. 1992

Proc. Natl. Acad. Sci. U.S.A.

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The mixed chain triacylglycerol 1,2-dipalmitoyl-3-acetyl-sn-glycerol was synthesized and its crystal structure was determined to a rinal reliability factor (R) of 0.11. Two molecules are present in the monoclinic unit cell: space group P21; a = 5.375(1), b = 8.286(2), c = 42.96(1) i; 13 = 93.30(2)°, V = 1910 A3, p = 1.065 g/cm3, and jt = 5.7 cm-'. The structure is a trilayer: a bilayer of palmitate chains packed in the (3 mode (T//) and an interdigitated monolayer of acetates. The glycerol backbone and acetate extend roughly linearly from the sn-i chain. The sn-2 chain bends around the C-2 carbon to lie next to the sn-i chain. Analysis of the torsion angles indicate that the glycerol conformation of 1,2-dipalmitoyl-3-acetyl-sn-glycerol is markedly different from single acid triacylglycerols and from 1,2-diacyl-sn-glycerols but very similar to 1,2-dimyristoyl-sn-glycero-3-phosphocholine.Acylglycerols are ubiquitous and highly prevalent biological molecules. Triacylglycerols are the major form of lipids stored in tissues of both plants and animals. Although their physical properties such as polymorphic forms, melting and transition temperatures, volumes, and viscosity are generally known (1-3), specific detailed crystal structures are largely lacking. Only two structures on single-chain triacylglycerols, tricaprin by Jensen and Mabis in 1963 (4) and trilaurin by Larsson in 1964 (5), have been published. A single complex triacylglyceride structure, 2-(11-bromoundecanoyl)-1,1'-dicaprin, was published (6), but its structure, especially the conformation of the glycerol and the chain orientation, are quite similar to the structure of single-chain triacylglycerols (4, 5). Our understanding of the structure and polymorphism of acylglycerols would be greatly enhanced by knowing the crystal structures of some of the forms of mixed-chain triacylglycerols. Diacylglycerols are intermediates in the metabolism of triacylglycerols and phospholipids. Diacylglycerols are also membrane-oriented (7) second messengers participating in signal transduction across membranes (8, 9). The biologically active form of diacylglycerols are the membrane-bound 1,2-diacyl-sn-glycerols (10). The general structure of saturated 1,2-diacyl-sn-glycerols has been reported (11) and the crystal structure of 1,2-dilauroyl-sn-glycerol (12) and 1,2-dipalmitoyl-sn-glycerol (13) have been solved. We have synthesized the three acetyl derivative of 1,2-dipalmitoyl-sn-glycerol and defined its crystal structure.$ The structure of this triacylglycerol with an acetate in position 3 differs considerably around the glycerol backbone from 1,2-diacylglycerols (12-14) or simple acid triacylglycerols such as trilaurin (4, 5). The glycerol conformation is, however, quite similar to one of the two conformers of dimyristoyl phosphatidylcholine (15). 11 MATERIALS AND METHODS 1,2-Dipalmitoyl-3-acetyl-sn-glycerol (PP2) was synthesized as described by Kodali et al. (16). After several trials of crystallization, a fairly good crystal with dimensions of 0.02 x 0.06 x 0.5 ...

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Raman Spectroscopy for the Study of Molecular Order, Thermodynamics, and Solid–Liquid Transitions in Triacylglycerols

Silva

Rousseau

2001

Handbook of Vibrational Spectroscopy

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The use of Raman spectroscopy for the study of the molecular order in triglycerides is explored, with emphasis placed on three key spectroscopic fingerprints: (i) the CH stretching region at 3000–2700 cm −1 , (ii) the ester carbonyl (CO) stretching region at 1780–1700 cm −1 , and the CC stretching region at ∼1200–1100 cm −1 . Triglyceride polymorph and phase‐dependent changes related to the aliphatic chain and glycerol backbone conformation and packing, as well as changes in local environment, are ascertained on the basis of shifts in these bands. In particular, the ester carbonyl stretching region demonstrates clear differences between triglycerides polymorphs, as changes are seen in the number, stretching frequency, and size of the modes present. Besides, phase transition enthalpies are extracted from the Raman spectra of triglycerides studied. This chapter demonstrates that Raman spectroscopy is a viable tool for the characterization of triglycerides.

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Crystal Structure of β-Tricaprin

Cited by 64 publications

References 4 publications

α-Gel Prepared in Sodium Methyl Stearoyl Taurate/Behenyl Alcohol/Water System-Characterization of Structural Changes with Water Concentration

α-Gel Prepared in Sodium Methyl Stearoyl Taurate/Behenyl Alcohol/Water System-Characterization of Structural Changes with Water Concentration

Single crystal structure of a mixed-chain triacylglycerol: 1,2-dipalmitoyl-3-acetyl-sn-glycerol.

Raman Spectroscopy for the Study of Molecular Order, Thermodynamics, and Solid–Liquid Transitions in Triacylglycerols

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