ARS | Publication request: PRODUCTION AND USES OF 7,10,12-TRIHYDROXY-8(E)-OCTADECENOIC ACID FROM RICINOLEIC ACID CONVERSION BY PSEUDOMONAS AERUGINOSA

Submitted to: American Oil Chemists' Society Meeting
Publication Type: Abstract Only
Publication Acceptance Date: May 12, 2004
Publication Date: N/A

Technical Abstract: Pseudomonas aeruginosa NRRL B-18602 was previously found to convert ricinoleic acid in small shake flasks to 7,10,12-trihydroxy-8(E)-octadecenoic acid (TOD), a novel fungicide active against the rice blast fungus. The objectives of this study were to develop a scale-up process to produce TOD in large quantities sufficient for testing of industrial uses and to determine its properties for new uses. The bioconversion was carried out in a 2-L reactor using crude ricinoleic acid prepared from saponification of castor oil and a new strain of P. aeruginosa (NRRL B-23260) was found more suitable for the reaction. The reactor process employed a unique aeration mechanism that involved a filtered airflow constantly supplied from the top through two ports on the headplate at 220 ml/min and, when needed, at varied rates as regulated through a bottom sparger. The yield of TOD production was 27% after 60 h of reaction. TOD was crystallized from ethyl acetate extracts of the reactor broth following a sequential cooling process to about - 20 degrees C. TOD had a much higher melting point (94.5 - 95.0 degrees C) than 7,10-dihydroxy-8(E)-octadecenoic acid (63.5 - 64.0 degrees C), a multihydroxy monounsaturated fatty acid resulting from bioconversion of oleic acid. TOD was found to exhibit a unique surface-active property. This study has provided basic information useful for further developing production processes suitable for commercial uses of TOD.