An improved method for preparing squalene from a squalene-containing composition, said method comprising the steps of (a) a purification distillation carried out at a temperature T.sub.1 (b) a denaturing distillation carried out at a temperature T.sub.2; wherein steps (a) and (b) may be performed in either order; T.sub.1 and T.sub.2 are sufficient to cause squalene to boil; T.sub.2>T.sub.1; and T.sub.2>200 C.

Provided are enhanced high yield production systems for producing terpenes in plants via the expression of fusion proteins comprising various combinations of geranyl diphosphate synthase large and small subunits and limonene synthases. Also provided are engineered oilseed plants that accumulate monoterpene and sesquiterpene hydrocarbons in their seeds, as well as methods for producing such plants, providing a system for rapidly engineering oilseed crop production platforms for terpene-based biofuels.

Provided are enhanced high yield production systems for producing terpenes in plants via the expression of fusion proteins comprising various combinations of geranyl diphosphate synthase large and small subunits and limonene synthases. Also provided are engineered oilseed plants that accumulate monoterpene and sesquiterpene hydrocarbons in their seeds, as well as methods for producing such plants, providing a system for rapidly engineering oilseed crop production platforms for terpene-based biofuels.

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.

The present invention provides a process for preparing a 4-substituted 3-methyl-1,3-butadiene compound of the following general formula (A), wherein R represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms and optionally having an unsaturated bond(s), the process comprising steps of subjecting a primary allylsulfone compound of the following general formula (D), wherein R represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms and optionally having an unsaturated bond(s), X represents a halogen atom, and W represents an arenesulfonyl group, to a reductive removal of the arenesulfonyl group, W, to form a halide compound of the following general formula (B), wherein R represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms and optionally having an unsaturated bond(s), and X represents a halogen atom; and subjecting the aforesaid halide compound (B) to an elimination reaction of a hydrogen halide, HX, to form the aforesaid 4-substituted 3-methyl-1,3-butadiene compound (A).

##STR00001##

The present invention provides a process for preparing a 4-substituted 3-methyl-1,3-butadiene compound of the following general formula (A), wherein R represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms and optionally having an unsaturated bond(s), the process comprising steps of subjecting a primary allylsulfone compound of the following general formula (D), wherein R represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms and optionally having an unsaturated bond(s), X represents a halogen atom, and W represents an arenesulfonyl group, to a reductive removal of the arenesulfonyl group, W, to form a halide compound of the following general formula (B), wherein R represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms and optionally having an unsaturated bond(s), and X represents a halogen atom; and subjecting the aforesaid halide compound (B) to an elimination reaction of a hydrogen halide, HX, to form the aforesaid 4-substituted 3-methyl-1,3-butadiene compound (A).

##STR00001##

The present invention provides a process for preparing a 2-(3-alkenyl)-1,3-butadiene compound of the following general formula (A), wherein R.sup.1 and R.sup.2 represent, independently of each other, a hydrogen atom or a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms and optionally having an unsaturated bond(s), the process comprising the step of subjecting a secondary allylsulfone compound of the following general formula (G), wherein R.sup.1 and R.sup.2 represent, independently of each other, a hydrogen atom or a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms and optionally having an unsaturated bond(s), W represents an arenesulfonyl group, and Z represents a halogen atom, to a reductive removal of an arenesulfonyl group, W, at an allyl position, and then subjecting the secondary allylsulfone compound (G) to an elimination reaction of a hydrogen halide, HZ, in this order or in reverse order, to form the 2-(3-alkenyl)-1,3-butadiene compound (A).

##STR00001##

The present invention provides a process for preparing a 2-(3-alkenyl)-1,3-butadiene compound of the following general formula (A), wherein R.sup.1 and R.sup.2 represent, independently of each other, a hydrogen atom or a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms and optionally having an unsaturated bond(s), the process comprising the step of subjecting a secondary allylsulfone compound of the following general formula (G), wherein R.sup.1 and R.sup.2 represent, independently of each other, a hydrogen atom or a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms and optionally having an unsaturated bond(s), W represents an arenesulfonyl group, and Z represents a halogen atom, to a reductive removal of an arenesulfonyl group, W, at an allyl position, and then subjecting the secondary allylsulfone compound (G) to an elimination reaction of a hydrogen halide, HZ, in this order or in reverse order, to form the 2-(3-alkenyl)-1,3-butadiene compound (A).

##STR00001##

A synthetic chiral composition comprising (i) pinene isomers; (ii) linalool isomers; and (iii) a terpene or terpenoid, and formulations comprising the synthetic chiral composition, in addition to methods for preparing, creating, populating, and querying databases pertaining to, and kits comprising, the synthetic chiral composition are disclosed herein. The composition further includes one or more modifiers. The composition includes organoleptic properties (e.g. aroma) of a plant cultivar (e.g. Cannabis).