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Title: PRODUCTION AND PROPERTIES OF 7,10,12-TRIHYDROXY-8(E)-OCTADECENOIC ACID FROM RICINOLEIC ACID CONVERSION BY PSEUDOMONAS AERUGINOSA

Author
item Kuo, Tsung Min
item Knothe, Gerhard

Submitted to: European Journal of Lipid Science and Technology
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 4/19/2004
Publication Date: 6/1/2004
Citation: Kuo, T., Knothe, G.H. 2004. Production and properties of 7,10,12-trihydroxy-8(e)-octadecenoic acid from ricinoleic acid conversion by pseudomonas aeruginosa. European Journal Lipid Science Technology. 106:405-411.

Interpretive Summary: Surplus vegetable oils represent attractive renewable resources for the production of useful chemicals. We are investigating microbial conversion of vegetable oils and their component fatty acids for producing value-added products. Previously, we found a new bioconversion reaction that produced a novel new compound that possessed anti-fungicidal activity for rice. In this study, we further examined a reactor process for producing sufficient quantities of this new compound for determining its properties and further testing of industrial uses. The results led to the production of this compound in gram quantity, the determination of melting point, and the finding of its new surface-active property. The impact of this study provides new basic information for scientists to develop production processes suitable for commercial uses of this compound.

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) 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.