GLYCERIDE SYNTHESIS: I. SYNTHESIS OF SYMMETRICAL DIGLYCERIDES FROM DIHYDROXY ACETONE AND ALLYL ALCOHOL

1955 ◽  
Vol 33 (4) ◽  
pp. 716-721 ◽  
Author(s):  
P. J. Barry ◽  
B. M. Craig

1,3-Distearoxy acetone and 1,3-dipalmitoxy acetone were prepared by interesterification of the methyl esters of the fatty acids with 1,3-dipropionoxy acetone diethyl mercaptal. The 1,3-diglycerides were obtained by hydrogenation of the ketone group. Allyl tetrahydropyranyl ether was oxidized to 1-tetra-hydropyranyl glycerol which was acetylated and interesterified with methyl esters of fatty acids to produce 1,3-diglycerides.

2019 ◽  
Vol 56 (4) ◽  
pp. 279-286 ◽  
Author(s):  
Tomasz Wasilewski ◽  
Yong-Qiang Sun ◽  
Wiesław Hreczuch ◽  
Artur Seweryn ◽  
Tomasz Bujak

1972 ◽  
Vol 128 (5) ◽  
pp. 1057-1067 ◽  
Author(s):  
E. D Saggerson

1. 0.5mm-Palmitate stimulated incorporation of [U-14C]glucose into glyceride glycerol and fatty acids in normal fat cells in a manner dependent upon the glucose concentration. 2. In the presence of insulin the incorporation of 5mm-glucose into glyceride fatty acids was increased by concentrations of palmitate, adrenaline and 6-N-2′-O-dibutyryladenosine 3′:5′-cyclic monophosphate up to 0.5mm, 0.5μm and 0.5mm respectively. Higher concentrations of these agents produced progressive decreases in the rate of glucose incorporation into fatty acids. 3. The effects of palmitate and lipolytic agents upon the measured parameters of glucose utilization were similar, suggesting that the effects of lipolytic agents are mediated through increased concentrations of free fatty acids. 4. In fat cells from 24h-starved rats, maximal stimulation of glucose incorporation into fatty acids was achieved with 0.25mm-palmitate. Higher concentrations of palmitate were inhibitory. In fat cells from 72h-starved rats, palmitate only stimulated glucose incorporation into fatty acids at high concentrations of palmitate (1mm and above). 5. The ability of fat cells to incorporate glucose into glyceride glycerol in the presence of palmitate decreased with increasing periods of starvation. 6. It is suggested that low concentrations of free fatty acids stimulate fatty acid synthesis from glucose by increasing the utilization of ATP and cytoplasmic NADH for esterification of these free fatty acids. When esterification of free fatty acids does not keep pace with their provision, inhibition of fatty acid synthesis occurs. Provision of free fatty acids far in excess of the esterification capacity of the cells leads to uncoupling of oxidative phosphorylation and a secondary stimulation of fatty acid synthesis from glucose.


1998 ◽  
Vol 4 (6) ◽  
pp. 401-405 ◽  
Author(s):  
V.J. Robles ◽  
H.S. García ◽  
J.A. Monroy ◽  
O. Angulo

Menhaden oil was hydrolyzed using a lipase from Pseudomonas sp. The hydrolysate was cold frac tionated at-72°C. Glyceride synthesis was performed using the same lipase under different reaction environments. The best conditions for the esterification reaction were 39 °C for 18 h in a reaction mixture containing anhydrous glycerol, n-3 polyunsaturated fatty acids (PUFA) enriched solution (2% lipids in hexane), hexane, and phosphate buffer-lipase solution (1% w/v). Product composition was 81.33% triacylglycerides and 18.67% of free fatty acids (w/w). Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) accounted for 36.18% of the esterified fatty acids, of which 58% was EPA and 42% was DHA. This method offers an alternative to produce glycerides rich in n-3 PUFA.


2003 ◽  
Vol 783 (2) ◽  
pp. 443-451 ◽  
Author(s):  
M.M. Keinänen ◽  
L.K. Korhonen ◽  
P.J. Martikainen ◽  
T. Vartiainen ◽  
I.T. Miettinen ◽  
...  

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