Described herein are methods of stabilizing the beta hydrogen of glycerol based esters by the insertion of alkoxy groups to significantly improve the thermal, oxidative, and hydrolytic stability of the ester and allow for controlling the molar density of esters bonds in the lubricants to maximize hydrolytic stability while maintaining biodegradability and further improving performance properties.

Plant oil-based compounds are provided which possess both low viscosity and high reactive functionality. These compounds are useful in coating and composite applications, as well as related methods. Exemplary compounds can be produced by transesterification of a plant oil triglyceride with a nucleophile reactant, such as a vinyl-functional alcohol, to yield reactive fatty acid-containing monomers.

Plant oil-based compounds are provided which possess both low viscosity and high reactive functionality. These compounds are useful in coating and composite applications, as well as related methods. Exemplary compounds can be produced by transesterification of a plant oil triglyceride with a nucleophile reactant, such as a vinyl-functional alcohol, to yield reactive fatty acid-containing monomers.

Succinic acid esters of resveratrol and topical compositions containing the esters.

Succinic acid esters of resveratrol and topical compositions containing the esters.

Provided herein are processes of preparing sulfonated estolide compounds, and the removal of sulfonate residues from those compounds to provide desulfonated estolide base oils. Exemplary sulfonated estolide compounds include those selected from the formula: ##STR00001##
wherein z is an integer selected from 0 to 15; q is an integer selected from 0 to 15; x is, independently for each occurrence, an integer selected from 0 to 20; y is, independently for each occurrence, an integer selected 0 to 20; n is equal to or greater than 0; R.sub.6 is selected from —OH, optionally substituted alkyl, and optionally substituted aryl; and R.sub.2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched, wherein each fatty acid chain residue of said compounds is independently optionally substituted.

Provided herein are processes of preparing sulfonated estolide compounds, and the removal of sulfonate residues from those compounds to provide desulfonated estolide base oils. Exemplary sulfonated estolide compounds include those selected from the formula: ##STR00001##
wherein z is an integer selected from 0 to 15; q is an integer selected from 0 to 15; x is, independently for each occurrence, an integer selected from 0 to 20; y is, independently for each occurrence, an integer selected 0 to 20; n is equal to or greater than 0; R.sub.6 is selected from —OH, optionally substituted alkyl, and optionally substituted aryl; and R.sub.2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched, wherein each fatty acid chain residue of said compounds is independently optionally substituted.

Disclosed are compounds of formula (I)
(R.sup.1OOC).sub.a—R.sup.2(OH).sub.c—COO—(C.sub.nH.sub.2n—O).sub.m—OC—R.sup.3(OH).sub.d—(COOR.sup.4).sub.b  (I)
wherein R.sup.1 and R.sup.4 independently of one another are hydrogen, a metal cation, an ammonium cation, C.sub.1-C.sub.6-alkyl, cycloalkyl with three to nine ring carbon atoms, aryl with five to ten ring carbon atoms, aryl that is substituted with one or two alkyl groups, aryl that is connected via an alkylene group with the carboxyl group, —(C.sub.nH.sub.2n—O).sub.m—H or —O—R.sup.2(COOR1).sub.a+1,
R.sup.2 and R.sup.3 independently of one another are aliphatic hydrocarbon residues with one to eight carbon atoms,
a and b independently of one another are integers from 1 to 4,
c is an integer from 0 to 4,
d is an integer from 1 to 4,
n is 2, 3 or 4, and
m is 1, 2, 3 or 4, with the proviso that
R.sup.1 and R.sup.4 may be different within a molecule within the given definitions. These compounds are characterized by a very good complexation power for metal cations and can be used in detergents and cleaning agents, in oil extraction and for water softening.

Disclosed are compounds of formula (I)
(R.sup.1OOC).sub.a—R.sup.2(OH).sub.c—COO—(C.sub.nH.sub.2n—O).sub.m—OC—R.sup.3(OH).sub.d—(COOR.sup.4).sub.b  (I)
wherein R.sup.1 and R.sup.4 independently of one another are hydrogen, a metal cation, an ammonium cation, C.sub.1-C.sub.6-alkyl, cycloalkyl with three to nine ring carbon atoms, aryl with five to ten ring carbon atoms, aryl that is substituted with one or two alkyl groups, aryl that is connected via an alkylene group with the carboxyl group, —(C.sub.nH.sub.2n—O).sub.m—H or —O—R.sup.2(COOR1).sub.a+1,
R.sup.2 and R.sup.3 independently of one another are aliphatic hydrocarbon residues with one to eight carbon atoms,
a and b independently of one another are integers from 1 to 4,
c is an integer from 0 to 4,
d is an integer from 1 to 4,
n is 2, 3 or 4, and
m is 1, 2, 3 or 4, with the proviso that
R.sup.1 and R.sup.4 may be different within a molecule within the given definitions. These compounds are characterized by a very good complexation power for metal cations and can be used in detergents and cleaning agents, in oil extraction and for water softening.

The present invention provides: novel compounds capable of producing monomethyl fumarate after the compounds are administered; pharmaceutical compositions comprising same as active ingredients; and pharmaceutical uses thereof for treating or alleviating various diseases including immune system abnormalities, neurodegeneration, and/or inflammatory diseases.