The broader impact/commercial potential of this Small Business Innovation Research (SBIR) Phase I project is the development of a new scalable manufacturing capability for producing bio-based chemicals for surfactants, lubricants, and polymers. This manufacturing platform will utilize biologically derived sugar carbon-source and transform this carbon to higher value products via microbial fermentation. At the core of this new manufacturing platform is a re-designed microorganism that will deliver homogeneous preparations of individual fatty acids of defined carbon-chain length that contain a single carbon-carbon double bond. This contrasts with current sources of oleochemicals, which are complex mixtures of fatty acids of different carbon chain lengths ranging between 12 and 18 carbon atoms, and may contain 0-3 carbon-carbon double bonds. The complex mixtures that occur in these oleochemicals limit the types of products that can be generated from fats and oils, or adds considerable separations cost to the manufacture of homogeneous products. The project will take advantage of unprecedented technological capability to produce homogeneous preparations of a single monounsaturated fatty acid, which is a platform feedstock for producing many chemicals that impact surfactant, lubricant, and polymer markets, currently valued at $40B per annum, and predicted to grow to $150B per annum in the next 5-years. This SBIR Phase I project proposes to develop new transformational technology that is based on the discovery and fundamental understanding of the biocatalytic mechanism that terminates the elongation cycle of Type II fatty acid synthase, the enzyme acyl-ACP thioesterase. The project will harness this technology for the production of near homogeneous preparations (~60%) of the monounsaturated fatty acid, 7-tetradecenoic acid, and proposes to optimize the system to produce over 80% homogeneous preparations of this fatty acid. This monounsaturated fatty acid is not currently available in the marketplace at a reasonable cost. The unprecedented availability of 7-tetradecenoic acid makes it a platform biochemical for subsequent chemical conversion to numerous biorenewable chemicals that have applications in surfactants, lubricants, and polymers. In the long-term, this platform technology can be expanded to produce alternative homogeneous preparations of monounsaturated fatty acids of different chain lengths, with carbon-carbon double bonds at different but defined places in the molecule.