Production and properties of 7,10,12-trihydroxy-8(E)-octadecenoic acid from ricinoleic acid conversion by Pseudomonas aeruginosa

This study was undertaken to produce a novel antifungal compound, 7,10,12-trihydroxy-8(E)-octadecenoic acid (7,10,12-THOD), in large quantities for determining its, properties by use of crude ricinoleic acid as converted by Pseudomonas aeruginosa NRRL B-23260. A useful reactor process was developed by employing a unique aeration mechanism and a new agitation device. The aeration mechanism involved a filtered airflow constantly supplied from the top through two ports on the headplate at 220 mL/min and at varied rates as needed and regulated through a bottom sparger, to control foaming. The agitation device combined a marine impeller and an open turbine to overcome the early phase of oxygen depletion and enhance production yields. A yield of 40% was achieved after 77 h of reaction when down-stream processing of the bioproduct was most suitable. 7,10,12-THOD was crystallized from ethyl acetate extracts of the reactor broth following a sequential cooling process to -20 degreesC. The melting point of 7,10,12-THOD was 94.5-95.0 degreesC. The H-1- and C-13-NMR signals of all protons and carbons in the 2(E)-ene-1,4,6-triol moiety of 7,10,12-THOD were now assigned, also with the aid of various 2D techniques. 7,10,12-THOD was found to exhibit a unique surface-active property. This study provides basic information and process technology for potential new uses of 7,10,12-THOD.