Resting cell suspensions of seven Nocardia species catalyzed the production of 10-hydroxystearic acid from oleic acid. Nocardia cholesterolicum N R R L 5767 gave a good yield with optimum conditions at pH 6.5 and 40 ° C. Yields exceeding 90% can be obtained within 6 h with 0.1 g cells (dry weight) and 178 mg oleic acid in 10 ml of 0.05 M sodium phosphate buffer (pH 6.5). In addition, minor amounts of 10-ketostearic acid were formed as a by-product. The reaction proceeded via hydration of the double bond as shown by labeling experiments with deuterium oxide and 180-labeled water. The system was specific for fatty acids with cis unsaturation at the 9 positon.
Sixty‐two cultures from the Agricultural Research Service (ARS) Culture Collection and 10 cultures isolated from soil and water samples in Illinois were screened for their ability to convert agricultural oils to value‐added industrial chemicals. A new compound, 7,10‐dihydroxy‐8(E)‐octadecenoic acid (DOD), was produced from oleic acid at a yield of greater than 60% by bacterial strain PR3 which was isolated from a water sample in Morton, IL. To our knowledge, DOD has not been previously reported. The optimum time, pH and temperature for the production of DOD were 2 days, 7.0, and 30°C, respectively. The production of DOD is unique in that it involves hydroxylation at two positions and rearrangement of the double bond of the substrate molecule.
Over 100 different strains of bacteria, actinomycetes, fungi and yeasts were incubated at 28 C for five days in the presence of soybean oil. Some soybean oil was consumed by many microorganisms, and some was also hydrolyzed to free fatty acids.Aspergillus oryzae, two different strains ofAmylomyces rouxii andRhizopus oligosporus hydrolyzed the oil completely (95%). The fatty acids fromAspergillus flavus fermentation contained less linolenic acid than the original soybean oil. Lipase was found intra‐ and extracellularly when microorganisms were grown in the presence of soybean oil.
Soybean oil was partially hydrogenated at 170 and 200C with 0.5 and 0.1% copper‐chromium catalysts, respectively. The reaction proceeded selectively at both temperatures, although selectivity was better at the lower temperature. Both commercial and laboratory‐prepared catalysts reduced the linolenic acid to less than 1% and with selectivity ratios (KLe/KLo) ranging from 6 to 13. Since stearate did not increase, linoleate selectivity (KLo/KOl) was extremely high. About 80% or more of the original linoleic acid remained in the hydrogenated products as measured by the alkali‐isomerization method. More conjugated dienes were formed at 200 than at 170C.
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