Glyceryl trioleate

Problem 27.2 Draw structures of glyceryl tripalmitate and glyceryl trioleate. Which would you expect to have a higher melting point ... 

Show the products you would expect to obtain from reaction of glyceryl trioleate with the following reagents ... 

A typical fat in the body is glyceryl trioleate, C57H104CV When it is metabolized in the body, it combines with oxygen to produce carbon dioxide, water, and 3.022 X 104 kj ofheat per mole of fat. 

Platford, R.F. (1979) Glyceryl trioleate-water partition coefficients for three simple organic compounds. Bull. Environ. Contam. Toxicol. 21, 68. 

Chiou chose glyceryl trioleate (triolein) as model lipid because of its similarity to triglycerides which are abundant in organisms [109], Triolein is also a bulk lipid and the good correlation with the bioconcentration factor is restricted to neutral compounds of moderate hydrophobicity. No attempts were made to measure partitioning of ionogenic compounds with the glyceryl trioleate-water partition system. 

Other lipids include steroids, such as cholesterol, and terpenes, which are plant oils such as oil of turpentine, or oil of cedar. Figure 2.22 shows the lipid glyceryl trioleate, which is present in olive oil. 

Chiou, C.T. and Manes, M. Application of the Flory-Huggins theory to the solubility of solids in glyceryl trioleate, / Chem. Soa, Faraday Trans. 1, 82(l) 243-246, 1986. 

VLCFAs arise from both dietary and endogenous synthetic sources, so treatment is mainly supportive. -Feeding a 4 1 mixture of glyceryl trioleate and glyceryl trierucate (Lorenzo s Oil) can reduce plasma... 

Pharmacokinetics. Seed oil, administered intramuscularly to dogs at a dose of 1 mL/kg labeled glyceryl trioleate injected with the oil, was distributed primarily to iliac nodes, heart, liver, and lungs 5 Phytotoxic effect. Ethanol (95%) extract of the dried seed oil, at a concentration of 500 ppm, was inactive. The biological activity reported has been patented " k Prostaglandin induction. Seed oil, administered subcutaneously to rats at a dose of 1 g/day for 14 days, stimulated PGl-2 synthesis in the thoracic aorta . ... 

Representative esters of oleic add are methyl oleate, C17H33COOCH3, bp 190 C at 10 millimeters pressure ethyl oleate. CnH COOCiHs, bp 205°C at 10 millimeters pressure glyceryl trioleate (triolein), (jj, bp 240°C at 18 millimeters pressure. 

PROBLEM 24.16 Show the structure of glyceryl trioleate, a fat molecule whose components are glycerol and three oleic acid units. 

Lorenzo s oil is a 4 1 mixture of glyceryl trioleate and glyceryl trierucate. It is used in patients with adreno-leukodystrophy. The dyslipidemia in patients with adre-noleukodystrophy consists of increased blood concentrations of very-long-chain saturated fatty acids, particularly hexacosaenoic acid (C26 0). Treatment with Lorenzo s oil has tended to normalize the abnormality in the blood while the patient deteriorates. Neurological changes are unrelated to the fatty acid changes in the blood, and, moreover, erucic acid does not seem to enter the brain. It is not known whether it works. 

Moser HW, Raymond GY Koehler W, et al. Evaluation of the preventive effect of glyceryl trioleate-trierucate ( Lorenzo s oil ) therapy in X-linked adrenoleukodystrophy results of two concurrent trials. Adv Exp Med Biol. 544 369-387,2003. 

We have already seen how oils such as glyceryl trioleate form thin layers on water while soaps from the alkaline hydrolysis of glycerides form micelles. Phosphatidyl choline forms yet another structure—it spontaneously forms a membrane in water. The hydrophobic hydrocarbon chains line up together on the inside of the membrane with the hydrophilic choline residues on the outside. 

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