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.

In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I ##STR00001##
with a metathesis reaction partner according to Formula IIb ##STR00002##
in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: ##STR00003##
and
b) converting the metathesis product to the fatty olefin derivative. Each R.sup.1 is independently selected from H, C.sub.1-18 alkyl, and C.sub.2-18 alkenyl; R.sup.2b is C.sub.1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.

In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I ##STR00001##
with a metathesis reaction partner according to Formula IIb ##STR00002##
in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: ##STR00003##
and
b) converting the metathesis product to the fatty olefin derivative. Each R.sup.1 is independently selected from H, C.sub.1-18 alkyl, and C.sub.2-18 alkenyl; R.sup.2b is C.sub.1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.

The present disclosure provides novel polypeptides with 3-buten-2-ol dehydratase activity, polypeptides with catalytic activity in the conversion of 3-methyl-3-buten-2-ol to isoprene, and crystal structure data for one of such polypeptides. Methods of making and using the polypeptides and their related crystal structure data are also provided.

The present disclosure provides novel polypeptides with 3-buten-2-ol dehydratase activity, polypeptides with catalytic activity in the conversion of 3-methyl-3-buten-2-ol to isoprene, and crystal structure data for one of such polypeptides. Methods of making and using the polypeptides and their related crystal structure data are also provided.

The invention provides a method of alkene metathesis comprising contacting at least a first alkene, which is cardanol and/or anacardic acid, with an alkylidene ruthenium alkene metathesis catalyst comprising two ligands P.sup.1 and P.sup.2, which may be the same or different and of formula P(R.sup.1).sup.3, in which P is a phosphorus atom coordinated to the ruthenium ion and each R.sup.1 is independently an optionally substituted alkyl or alkoxy group; or two R.sup.1 groups within one P.sup.1 or P.sup.2 ligand constitute an optionally substituted bicycloalkyl.

The invention provides a method of alkene metathesis comprising contacting at least a first alkene, which is cardanol and/or anacardic acid, with an alkylidene ruthenium alkene metathesis catalyst comprising two ligands P.sup.1 and P.sup.2, which may be the same or different and of formula P(R.sup.1).sup.3, in which P is a phosphorus atom coordinated to the ruthenium ion and each R.sup.1 is independently an optionally substituted alkyl or alkoxy group; or two R.sup.1 groups within one P.sup.1 or P.sup.2 ligand constitute an optionally substituted bicycloalkyl.

This invention describes processes to make products by cross metathesis of functionalized or non-functionalized olefins with poly-branched poly-olefins such as terpenes (e.g., farnesene(s), -farnesene, -farnesene, -myrcene, etc.) and compositions made by such methods. More particularly, the present invention relates to methods of making (i) cross metathesis products by a cross metathesis reaction between at least one hydrovinylated olefinic substrate and at least one hydrovinylated cross metathesis substrate in the presence of at least one olefin metathesis catalyst; (ii) cross metathesis products by a cross metathesis reaction between at least one hydrovinylated olefinic substrate and at least one cross metathesis substrate in the presence of at least one olefin metathesis catalyst; and (iii) cross metathesis products by a cross metathesis reaction between at least one olefinic substrate and at least one hydrovinylated cross metathesis substrate in the presence of at least one olefin metathesis catalyst; as well as compositions made by such methods.

This invention describes processes to make products by cross metathesis of functionalized or non-functionalized olefins with poly-branched poly-olefins such as terpenes (e.g., farnesene(s), -farnesene, -farnesene, -myrcene, etc.) and compositions made by such methods. More particularly, the present invention relates to methods of making (i) cross metathesis products by a cross metathesis reaction between at least one hydrovinylated olefinic substrate and at least one hydrovinylated cross metathesis substrate in the presence of at least one olefin metathesis catalyst; (ii) cross metathesis products by a cross metathesis reaction between at least one hydrovinylated olefinic substrate and at least one cross metathesis substrate in the presence of at least one olefin metathesis catalyst; and (iii) cross metathesis products by a cross metathesis reaction between at least one olefinic substrate and at least one hydrovinylated cross metathesis substrate in the presence of at least one olefin metathesis catalyst; as well as compositions made by such methods.