Preparation of 2,5,6-trihydroxy-3-hexenoic acid and 2,5-dihydroxy-3-pentenoic acid and esters thereof from C6 and C5 sugars in the presence of a Lewis Acid material, wherein the yield of the 2,5,6-trihydroxy-3-hexenoic acid or 2,5-dihydroxy-3-pentenoic acid or esters thereof exceeds 15%. The process including the steps of contacting a saccharide composition including one or more C6 and/or C5 saccharide units with a Lewis Acid material; and recovering 2,5,6-trihydroxy-3-hexenoic acid and/or 2,5-dihydroxy-3-pentenoic acid or the esters thereof.

Preparation of 2,5,6-trihydroxy-3-hexenoic acid and 2,5-dihydroxy-3-pentenoic acid and esters thereof from C6 and C5 sugars in the presence of a Lewis Acid material, wherein the yield of the 2,5,6-trihydroxy-3-hexenoic acid or 2,5-dihydroxy-3-pentenoic acid or esters thereof exceeds 15%. The process including the steps of contacting a saccharide composition including one or more C6 and/or C5 saccharide units with a Lewis Acid material; and recovering 2,5,6-trihydroxy-3-hexenoic acid and/or 2,5-dihydroxy-3-pentenoic acid or the esters thereof.

The disclosure relates to the field of specialty chemicals and methods for their synthesis. In embodiments, the disclosure provides novel multifunctional fatty acid derivative molecules such as e.g., fatty triols, fatty tetrols, dihydroxy fatty acids, etc. The disclosure further provides derivatives of the disclosed multifunctional molecules which are useful e.g., in the production of personal care products, surfactants, detergents, polymers, paints, coatings, and as emulsifiers, emollients, and thickeners in cosmetics and foods, as industrial solvents and plasticizers, etc. The disclosure further provides biochemical pathways, recombinant microorganisms and methods for the biological production of various multifunctional fatty acid derivatives.

Described herein are methods of preparing cutin-derived monomers, oligomers, or combinations thereof from cutin-containing plant matter. The methods can include heating the cutin-derived plant matter in a solvent at elevated temperature and pressure. In some preferred embodiments, the methods can be carried out without the use of additional acidic or basic species.

Described herein are methods of preparing cutin-derived monomers, oligomers, or combinations thereof from cutin-containing plant matter. The methods can include heating the cutin-derived plant matter in a solvent at elevated temperature and pressure. In some preferred embodiments, the methods can be carried out without the use of additional acidic or basic species.

The present invention relates to compounds of Formulas I-IV, which are salts of special lipid mediators of inflammation, compositions containing same, and methods of using same in the treatment of various diseases and disorders characterized by chronic or excessive inflammation, or both. Provided are pharmaceutical compositions adapted to deliver the compounds the lower gastrointestinal tract and methods of using same as monotherapy in the treatment of inflammatory diseases or disorders of the lower gastrointestinal tract, and in combination therapy with 5-aminosalicylate.

The present invention relates to compounds of Formulas I-IV, which are salts of special lipid mediators of inflammation, compositions containing same, and methods of using same in the treatment of various diseases and disorders characterized by chronic or excessive inflammation, or both. Provided are pharmaceutical compositions adapted to deliver the compounds the lower gastrointestinal tract and methods of using same as monotherapy in the treatment of inflammatory diseases or disorders of the lower gastrointestinal tract, and in combination therapy with 5-aminosalicylate.

This disclosure concerns fatty acid derivatives, pharmaceutical compositions comprising the fatty acid derivatives, and methods of using the fatty acid derivatives, for example, to treat inflammation, chronic itch, chronic pain, an autoimmune disorder, atherosclerosis, a skin disorder, arthritis, a neurodegenerative disorder, or a psychiatric disorder in a subject. In some embodiments, the fatty acid derivative is a compound, or a stereoisomer, tautomer, or pharmaceutically acceptable salt thereof, having a structure according to:

##STR00001##

wherein X is from 1-16 carbons in length, Z is aliphatic from 1-16 carbons in length, or is not present, Y is selected from:

##STR00002##

R.sup.1, R.sup.2, and R.sup.3 are independently hydrogen or lower alkyl, R.sup.4 is lower alkyl, hydroxyl, carboxyl, or amine, R.sup.5 is hydrogen, lower alkyl, or halide, R.sup.6 is hydroxyl or substituted thiol, and each R.sup.7 is independently hydrogen or fluoride or is not present and the adjacent carbons form alkyne.

This disclosure concerns fatty acid derivatives, pharmaceutical compositions comprising the fatty acid derivatives, and methods of using the fatty acid derivatives, for example, to treat inflammation, chronic itch, chronic pain, an autoimmune disorder, atherosclerosis, a skin disorder, arthritis, a neurodegenerative disorder, or a psychiatric disorder in a subject. In some embodiments, the fatty acid derivative is a compound, or a stereoisomer, tautomer, or pharmaceutically acceptable salt thereof, having a structure according to:

##STR00001##

wherein X is from 1-16 carbons in length, Z is aliphatic from 1-16 carbons in length, or is not present, Y is selected from:

##STR00002##

R.sup.1, R.sup.2, and R.sup.3 are independently hydrogen or lower alkyl, R.sup.4 is lower alkyl, hydroxyl, carboxyl, or amine, R.sup.5 is hydrogen, lower alkyl, or halide, R.sup.6 is hydroxyl or substituted thiol, and each R.sup.7 is independently hydrogen or fluoride or is not present and the adjacent carbons form alkyne.

The present invention provides a synthetic chemical method for preparing ω-hydroxylated polyunsaturated fatty acids (PUFAs) including 20-hydroxyeicosatetraenoic acid (20-HETE), 20-hydroxyeicosapentaenoic acid (20-HEPE), and 22-hydroxydocosahexaenoic acid (22-HDoHE) and a method of use thereof for treating cancer and macular degeneration.