The present invention relates to a new process for the production of vitamin A and/or its derivatives.

The present invention relates to a new process for the production of vitamin A and/or its derivatives.

Compounds of the formula 1

##STR00001##

wherein, R is hydrogen, alkyl or substituted alkyl, aryl or substituted aryl, are useful intermediates in the synthesis of fragrance ingredients such as Ambrox 2

##STR00002##

Compounds of the formula 1

##STR00001##

wherein, R is hydrogen, alkyl or substituted alkyl, aryl or substituted aryl, are useful intermediates in the synthesis of fragrance ingredients such as Ambrox 2

##STR00002##

Methods are provided for synthesis of abscisic acid and 8 analogues thereof (including an enantiopure 8-acetylene analogue) including methods wherein the previously reported first step of oxidation of 2,6-dimethylphenol (VI) to 2,6-dimethylbenzoquinone, mono ketal (VII) is replaced by a novel two step process comprising (i) oxidation of 2,6-dimethylphenol (VI) using potassium peroxymonosulfate with a catalytic amount of iodobenzene to produce 2,6-dimethylbenzoquinone (XVI) and (ii) ketalization of 2,6-dimethylbenzoquinone (XVI) using ethylene glycol, trimethylorthoformate with a catalytic amount of p-toluenesulfonic acid to produce 2,6-dimethylbenzoquinone, mono ketal (VII).

Methods are provided for synthesis of abscisic acid and 8 analogues thereof (including an enantiopure 8-acetylene analogue) including methods wherein the previously reported first step of oxidation of 2,6-dimethylphenol (VI) to 2,6-dimethylbenzoquinone, mono ketal (VII) is replaced by a novel two step process comprising (i) oxidation of 2,6-dimethylphenol (VI) using potassium peroxymonosulfate with a catalytic amount of iodobenzene to produce 2,6-dimethylbenzoquinone (XVI) and (ii) ketalization of 2,6-dimethylbenzoquinone (XVI) using ethylene glycol, trimethylorthoformate with a catalytic amount of p-toluenesulfonic acid to produce 2,6-dimethylbenzoquinone, mono ketal (VII).

Compositions of and methods for using synthetic retinal derivatives as retinoid replacements and opsin agonists are provided.

Esters of O-substituted hydroxy carboxylic acids are provided having Formula 1, or 2, or both Formulas 1 and 2: ##STR00001##
wherein R and R.sup.1 are independently selected from the group consisting of substituted and unsubstituted, branched- and straight-chain, saturated, unsaturated, and polyunsaturated C.sub.1-C.sub.22 alkyl, substituted and unsubstituted C.sub.3-C.sub.8 cycloalkyl, substituted and unsubstituted C.sub.6-C.sub.20 carbocyclic aryl, and substituted and unsubstituted C.sub.4-C.sub.20 heterocyclic; wherein the heteroatoms are selected from sulfur, nitrogen, and oxygen; and wherein n is 1-6. Process of producing esters of O-substituted hydroxy carboxylic acids are also provided.

Esters of O-substituted hydroxy carboxylic acids are provided having Formula 1, or 2, or both Formulas 1 and 2: ##STR00001##
wherein R and R.sup.1 are independently selected from the group consisting of substituted and unsubstituted, branched- and straight-chain, saturated, unsaturated, and polyunsaturated C.sub.1-C.sub.22 alkyl, substituted and unsubstituted C.sub.3-C.sub.8 cycloalkyl, substituted and unsubstituted C.sub.6-C.sub.20 carbocyclic aryl, and substituted and unsubstituted C.sub.4-C.sub.20 heterocyclic; wherein the heteroatoms are selected from sulfur, nitrogen, and oxygen; and wherein n is 1-6. Process of producing esters of O-substituted hydroxy carboxylic acids are also provided.

A nanosized complex includes a nucleic acid and a compound comprising formula (I):

##STR00001## wherein R.sup.1 is an alkylamino group or a group containing at least one aromatic group; R.sup.2 and R.sup.3 are independently an aliphatic group or hydrophobic group; R.sup.4 and R.sup.5 are independently H, a substituted or unsubstituted alkyl group, an alkenyl group, an acyl group, or an aromatic group, or a polymer, a targeting group, a detectable moiety, or a linker, or a combination thereof, and at least one of R.sup.4 and R.sup.5 includes a retinoid or retinoid derivative that targets and/or binds to an interphotoreceptor retinoid binding protein; a, b, c, and d are independently an integer from 1 to 10; and pharmaceutically acceptable salts thereof.