Cyclic fatty esters: Synthesis, characterization, and lipolysis of isomeric triglycerides of 9-(6-propyl-3-cyclohexenyl)(Z)-8-nonenoic acid

✍ Scribed by R.A. Awl; E.N. Frankel; D.D. Brooks; D. Weisleder

• Publisher: Elsevier Science
• Year: 1986
• Tongue: English
• Weight: 675 KB
• Volume: 41
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(86)90125-8

✦ Synopsis

Triglycerides of a model cyclic fatty acid (CFA) 9-(6-propyl-3-cyclohexenyl)-(Z)8-nonenoic acid (la) were synthesized for biological and toxicity evaluations. The monoacid triglyceride I1 {CyCyCy) was interesterified with triolein (OOO) to obtain mixtures of diacid triglycerides: Ill (OOCy), IV (OCyO), V (OCyCy), and VI (CyOCy). The interesterification mixtures were separated by preparative HPLC into two 'critical pairs' of isomeric triglycerides. Triglycerides III-VI were synthesized and a a3C-NMR method was developed to estimate 'critical pairs'. CFA-triglycerides were characterized by IR, NMR, HPLC and capillary GLC, and their relative rates of hydrolysis by !ipase were compared. Although tricyclin (It) was completely resistant to lipolysis, triglycerides Ill and VI hydrolyzed significantly slower than triolein, and the 'critical pairs' hydrolyzed as readily as triolein. Therefore, partial CFA-triglycerides formed in heatabused fats can undergo lipolysis and likely be absorbed like normal dietary fats.