TRILINOLENIN synthesis
- Product Name:TRILINOLENIN
- CAS Number:14465-68-0
- Molecular formula:C57H92O6
- Molecular Weight:873.34
54562-14-0
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Yield:14465-68-0 96.3%
Reaction Conditions:
with pyridine;dmap in dichloromethane at 20 - 35;
Steps:
1.1
Example 1: synthesis OF TRIGAMMALINOLENIN 1) Acid chloride method 2.0 g (7.2 mmol, 3.1 equiv) GLA95 (95% pure y-linolenic acid) was dissolved in 10 ml DCM. L. Olg (0.71 ml, 8.0 mmol, 3.4 equiv) oxalyl chloride in 5 ml DCM added dropwise over 2-3 min under nitrogen. Stirred at RT overnight. Reaction mixture concentrated in vacuo to remove DCM and excess oxalyl chloride. This acid chloride was then added dropwise over 2-3 min to a stirred mixture of 215 mg (2.3 mmol, 1 equiv) of glycerol, 0.58 ml (3.1 equiv) pyridine and 10 ml DCM under nitrogen. The mixture was stirred at RT overnight. The pyridine hydrochloride formed was then filtered off and washed with DCM. The solution was washed 1 x 4 ml water, 0. 1N HC1, 5% sodium bicarbonate and 5% NaCl. Dried over magnesium sulphate, filtered and concentrated in vacuo to a yellow oil. This oil was purified on a silica column using 10% ether in hexane as eluting solvent. A clear colourless oil was obtained, a sample of which was trans- esterified and subsequently analysed by GC. The product contained 96.3% GLA
References:
WO2005/18632,2005,A1 Location in patent:Page/Page column 22-23
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