Provided herein are compounds, compositions, and methods for recovery of one or more water-immiscible compounds from microbial biomass.

Methods and compositions for stabilization and subsequent hydrogenation of a microbial-derived immiscible olefin are described. The methods comprise separating immiscible olefin from a mixture comprising an aqueous solution, microbial cells and immiscible olefin thereby forming a crude olefin composition; purifying the crude olefin composition thereby forming a purified olefin composition; and adding a phenolic antioxidant to the purified olefin composition wherein the phenolic antioxidant is a phenol derivative containing an unfused phenyl ring with one or more hydroxyl substituents. The methods further comprise reacting the purified olefin composition with hydrogen in the presence of a hydrogen catalyst such that hydrogen saturates at least one double bond in the olefin. Hydrogenated compositions produced by the methods are further provided.

Methods and compositions for stabilization and subsequent hydrogenation of a microbial-derived immiscible olefin are described. The methods comprise separating immiscible olefin from a mixture comprising an aqueous solution, microbial cells and immiscible olefin thereby forming a crude olefin composition; purifying the crude olefin composition thereby forming a purified olefin composition; and adding a phenolic antioxidant to the purified olefin composition wherein the phenolic antioxidant is a phenol derivative containing an unfused phenyl ring with one or more hydroxyl substituents. The methods further comprise reacting the purified olefin composition with hydrogen in the presence of a hydrogen catalyst such that hydrogen saturates at least one double bond in the olefin. Hydrogenated compositions produced by the methods are further provided.

Methods and compositions for stabilization and subsequent hydrogenation of a microbial-derived immiscible olefin are described. The methods comprise separating immiscible olefin from a mixture comprising an aqueous solution, microbial cells and immiscible olefin thereby forming a crude olefin composition; purifying the crude olefin composition thereby forming a purified olefin composition; and adding a phenolic antioxidant to the purified olefin composition wherein the phenolic antioxidant is a phenol derivative containing an unfused phenyl ring with one or more hydroxyl substituents. The methods further comprise reacting the purified olefin composition with hydrogen in the presence of a hydrogen catalyst such that hydrogen saturates at least one double bond in the olefin. Hydrogenated compositions produced by the methods are further provided.

A method for squalene extraction from a seed oil includes converting fatty acids of the seed oil into soap by subjecting the seed oil to a saponification reaction to obtain a saponified product, and adsorbing the fatty acids of the seed oil on surfaces of iron oxide nanoparticles to obtain iron oxide nanoparticles coated with fatty acids. The method may further include washing the iron oxide nanoparticles coated with fatty acids with a polar solvent to obtain a third mixture including a polar phase and the iron oxide nanoparticles coated with fatty acids, separating the iron oxide nanoparticles coated with fatty acids from the third mixture by a magnetic field, mixing the polar phase with a non-polar solvent and distilled water to obtain a two-phase solution, the two-phase solution including a non-polar phase and an aqueous phase, and separating and drying the non-polar phase to obtain squalene.

A method for squalene extraction from a seed oil includes converting fatty acids of the seed oil into soap by subjecting the seed oil to a saponification reaction to obtain a saponified product, and adsorbing the fatty acids of the seed oil on surfaces of iron oxide nanoparticles to obtain iron oxide nanoparticles coated with fatty acids. The method may further include washing the iron oxide nanoparticles coated with fatty acids with a polar solvent to obtain a third mixture including a polar phase and the iron oxide nanoparticles coated with fatty acids, separating the iron oxide nanoparticles coated with fatty acids from the third mixture by a magnetic field, mixing the polar phase with a non-polar solvent and distilled water to obtain a two-phase solution, the two-phase solution including a non-polar phase and an aqueous phase, and separating and drying the non-polar phase to obtain squalene.

A method for squalene extraction from a seed oil includes converting fatty acids of the seed oil into soap by subjecting the seed oil to a saponification reaction to obtain a saponified product, and adsorbing the fatty acids of the seed oil on surfaces of iron oxide nanoparticles to obtain iron oxide nanoparticles coated with fatty acids. The method may further include washing the iron oxide nanoparticles coated with fatty acids with a polar solvent to obtain a third mixture including a polar phase and the iron oxide nanoparticles coated with fatty acids, separating the iron oxide nanoparticles coated with fatty acids from the third mixture by a magnetic field, mixing the polar phase with a non-polar solvent and distilled water to obtain a two-phase solution, the two-phase solution including a non-polar phase and an aqueous phase, and separating and drying the non-polar phase to obtain squalene.

Methods for preparing isotopically modified 1,4-diene systems from non-isotopically modified 1,4-dienes involve selective oxidation of one or more bis-allylic position(s), or the preparation of isotopically modified 1,4-diene systems via trapping pi-allylic complexes with a source of deuterium or tritium. Such methods are useful for preparing isotopically modified polyunsaturated lipid including polyunsaturated fatty acids and polyunsaturated fatty acid derivatives.

Methods for preparing isotopically modified 1,4-diene systems from non-isotopically modified 1,4-dienes involve selective oxidation of one or more bis-allylic position(s), or the preparation of isotopically modified 1,4-diene systems via trapping pi-allylic complexes with a source of deuterium or tritium. Such methods are useful for preparing isotopically modified polyunsaturated lipid including polyunsaturated fatty acids and polyunsaturated fatty acid derivatives.

Disclosed is a method for removing benzo[]pyrene from a liposoluble natural extract. The method of the present invention comprises adding a suitable solvent to a crude natural extract product so as to obtain a mixed material; heating the mixed material, stirring until uniform, cooling and layering, and then separating the upper layer from the lower layer so as to obtain a precipitate and a filtrate; washing the precipitate with a small amount of a solvent so as to obtain a washed product and a washing solution; removing the solvent from the washed product at a low temperature so as to obtain a finished product; and directly recycling the filtrate and the washing solution as solvents. The present method achieves the purification of the crude natural extract product and the removal of benzo[]pyrene in one step, and is a novel method which is simple, highly efficient, feasible and easy for industrial applications.