9,12,15-Octadecatrienoic acid, sodium salt, (Z,Z,Z)- synthesis

Yield:822-18-4 83%

Reaction Conditions:

Stage #1: (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acidwith sodium carbonate in water at 55; for 3 h;
Stage #2: with Dowex 50W-X₈ (H+ form) in water;

Steps:

1.3

3. Preparation of Sodium Salt of α-Linolenic Acid The starting material α-linolenic acid has an extremely low solubility in water, so to facilitate action as an enzyme substrate, the α-linolenic acid was converted to a sodium salt. That is, 530 mg of sodium carbonate was dissolved in 10 ml of purified water and warmed to 55°C, 278 mg of α-linolenic acid (made by Nacalai Tesque) was dropwise added thereto and the mixture was stirred for 3 hours. After the end of the reaction, an ion exchange resin (Dowex 50W-X8 (H⁺form) (made by Dow Chemical)) was used for neutralization, whereby a precipitate was produced. The resultant product was filtered to separate the resin which was then dissolved by MeOH, the solvent was then distilled off under reduced pressure. The product obtained was recrystallized with isopropanol to obtain a desired sodium salt of α-linolenic acid (250 mg,83%).

References:

EP1741338,2007,A1 Location in patent:Page/Page column 14