Preparation of Monoglycerides from Natural Fats

Franzke, Cl.; Kretzschmann, F.

doi:10.1002/lipi.19630650403

Cited by 4 publications

(2 citation statements)

References 5 publications

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“…A commercial preparation of glyceryl-l-mono-oleate 4 was used (12); it contained traces of diglyceride and 7 to 15% free fatty acid by titration. Glycerol-l-mono-oleate-l-"C was synthesized from glyceryl-trioleate-l-1'C 6 by glycerolysis (13) and then purified by preparative thin layer chromatography. d) Cholesterol.…”

Section: B) Experimental Subjectsmentioning

confidence: 99%

“…Varying ratios of glyceryl-l-mono-oleate to oleic acid were added to achieve the following total concentrations in the final micellar solution: 0.2, 1, 2, and 4 mmoles per L. Oleic acid12 (98% purity by gas-liquid chromatography), glyceryl-1-monooleate 13 (at least 95% purity in class and homologue composition), and cholesterol-2-48H (purified by preparative thin layer chromatography) of known specific activity were added from heptane solution to ampules; solvent was removed by evaporation. The calculated amount of 0.02 N NaOH in 0.13 M NaCl was added to neutralize fatty acid, followed by an appropriate volume of 0.15 M NaCl to make 1.0 ml.…”

Section: Ii) Cholesterol Solubility Studiesmentioning

confidence: 99%

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Absorption of Cholesterol from a Micellar Solution: Intestinal Perfusion Studies in Man*

Simmonds¹,

Hofmann²,

Theodor³

1967

J. Clin. Invest.

183

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Summary. The absorption of cholesterol has been studied in man by perfusing the upper jejunum with a micellar solution of bile salt, 1-monoglyceride, and cholesterol-14C, with a triple lumen tube with collection sites 50 cm apart. The absorption of micellar components between the collection sites was calculated from their concentration changes relative to those of the watersoluble marker, polyethylene glycol. Control experiments were performed with cholesterol-free perfusions of saline or bile salt-monoglyceride solutions. Steady state conditions were obtained.Each of the components of the micelle was absorbed to a different extent during passage through the test segment of jejunum. Bile salt was not absorbed (mean, -3%), but micellar monoglyceride was rapidly hydrolyzed and absorbed almost completely (mean, 98%). Cholesterol radioactivity was absorbed to an intermediate extent (mean, 73%), and the absorption of chemically determined cholesterol (mean, 46%) indicated that much of the disappearance of radioactivity represented true absorption and not simple exchange.The specific activity of the perfused cholesterol fell during passage through the loop. This fall was interpreted as signifying the continuous addition of nonradioactive endogenous cholesterol by the test segment. However, the decrease in specific activity may also be considered to signify exchange, in that nonradioactive molecules entered the lumen as radioactive molecules were absorbed. Plant sterols appeared in the intestinal contents during the perfusion and must have been contributed by the perfused segment.The perfusate and samples taken from the upper and lower collection sites were examined by ultracentrifugation to define the physical state of cholesterol. It was found that cholesterol in the perfusate or upper collection site samples did not sediment, but that 23% of the cholesterol in the lower collection site samples was sedimentable (mean of three experiments); bile salt, as control, was not sedimentable. Solubility experiments in model systems showed that cholesterol possessed low solubility in bile salt solution; its solubility increased markedly and in linear proportion to the amount of

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Section: B) Experimental Subjectsmentioning

confidence: 99%

Section: Ii) Cholesterol Solubility Studiesmentioning

confidence: 99%

Absorption of Cholesterol from a Micellar Solution: Intestinal Perfusion Studies in Man*

Simmonds¹,

Hofmann²,

Theodor³

1967

J. Clin. Invest.

183

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Zur Gleichgewichtseinstellung bei der Glycerinolyse von Triglyceriden I

Schöllner

Läbisch

1967

Fette, Seifen, Anstrichm.

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Die quantitative Bestimmung der bei der Glycerinolyse von Triglyceriden auftretenden Mengen an Glycerin, Mono-, Di-und Triglycerid in Abhangigkeit von der Temperatur, der molaren Zusammensetzung der Ausgangskomponenten Glycerin und Triglycerid sowie der Kettenlange der Fettsaurekomponente wurde saulen-, dunnschicht-und gas-chromatographisch durchgefuhrt. Die Einstellung der Gleichgewichte zwischen 1-und 2-Monoglyceriden sowie zwischen 1,2-und 1,3-Diglyceriden wurde ebenfalls quantitativ bestimmt. Die Verfasser kamen zu dem Ergebnis, daO die Reaktivitat der primaren OH-Gruppen untereinander und ebenfalls die Reaktivitat der sekundaren OH-Gruppen untereinander nicht gleich ist und die Gleichgewichtskonstante K nicht die Berechnung der Einzelgleichgewichte wie 1-und 2-Monoglycerid oder 1,2-und 1,3-Diglycerid gestattet.

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Preparation of partial glycerides by direct esterification1

Gros

Feuge

1964

J Americ Oil Chem Soc

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A previously described procedure for the direct esterification of diglycerides without interesterification occurring has been evaluated for the preparation of mono-and diglycerides. The esterifications were accomplished with p-toluenesulfonic acid catalyst and with continuous removal of water of esterification by azeotropic distillation. The effect of such variables as unsaturation, chain length, mode of addition of solvent and reaction temp on the composition and yield of glycerides was observed. Chemical and chromatographic analyses were used to determine the composition of the glycerides and their component fatty acids and to detect the presence of isomeric glycerides. Simple esterification of 1-monostearin with oleic acid at 80C yielded as much as 72.3% diglycerides, and esterificatiou of glycerol with stearic acid at 100C yielded up to 70.1% monoglycerides, each calculated on a glyceride basis. It is concluded that simple esterifieation predominates with some intra-and interesterification occurring.

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Preparation of Monoglycerides from Natural Fats

Cited by 4 publications

References 5 publications

Absorption of Cholesterol from a Micellar Solution: Intestinal Perfusion Studies in Man*

Absorption of Cholesterol from a Micellar Solution: Intestinal Perfusion Studies in Man*

Zur Gleichgewichtseinstellung bei der Glycerinolyse von Triglyceriden I

Preparation of partial glycerides by direct esterification1

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