Stabilization of compounds as cyclodextrin complexes

A composition comprising a complex of a cyclodextrin with an active compound, wherein the active compound is:

• a nitroalkene is a structure of formula I:
• wherein R1 is hydrogen, C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl;
• R2, R3, R7, and R8 are each independently, hydrogen, oxygen, C1-C24 alkyl, NO2, OH, or OOH;
• R4 is a terminal COOR6 group, wherein R6 is hydrogen, or a C1-C24 alkyl;
• R5 is hydrogen, C1-C24 alkyl, or R4 and R5 collectively form ═C(R9)(R10), wherein R9 comprises C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl, or wherein R9 is a terminal COOR6 group, and R10 is hydrogen, NO2, OH, or OOH;
• n is from 1 to 24;
• and
• wherein the nitroalkene fatty acid includes at least one NO2 group;
• a nitroalkene is a structure of formula II:
• wherein R1 is hydrogen, C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl;
• R2, R4, R5 and R6 are each hydrogen;
• R7 is a terminal COORS group, wherein R9 is hydrogen or a C1-C24 alkyl;
• and
• R3 and R8 are each independently, hydrogen, oxygen, C1-C24 alkyl, NO2, OH, ONO2, NO, ONO or OOH, provided at least one of R3 or R8 is NO2 and the other of R3 or R8 is hydrogen, ONO or ONO2;
• a nitro group-containing compound is a structure of formula III:
• wherein R1 is hydrogen, C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl;
• R2 and R5 are each hydrogen;
• R7 is a terminal COOR6 group, wherein R6 is hydrogen or a C1-C24 alkyl;
• and
• R3 and R4 are each independently, hydrogen, oxygen, C1-C24 alkyl, NO2, OH, ONO2, NO, ONO or OOH, provided at least one of R3 or R4 is NO2 and the other of R3 or R4 is hydrogen, ONO or ONO2;
• a compound comprising a dicarboxylic acid of a structure of formula IV:
• wherein X is an electron-withdrawing group selected from acyl, carboxylic acid, an ester, a halogen, fluoromethyl, —CN, sulfonyl, sulfone, sulfonic acid, primary ammonium, secondary ammonium, tertiary ammonium, or —NO2,
• m is from 1 to 10;
• and
• n is from 1 to 10;
• a compound comprising a dicarboxylic acid of a structure of formula V:
• wherein X is an electron-withdrawing group selected from acyl, carboxylic acid, an ester, a halogen, fluoromethyl, —CN, sulfonyl, sulfone, sulfonic acid, primary ammonium, secondary ammonium, tertiary ammonium, or —NO2;
• Y and Z are each, independently, hydrogen or a C1 to C10 alkyl;
• m is from 1 to 10;
• and
• n is from 1 to 10;
• or
• a compound comprising a dicarboxylic acid of a structure of formula VI:
• wherein X is an electron-withdrawing group selected from acyl, carboxylic acid, an ester, a halogen, fluoromethyl, —CN, sulfonyl, sulfone, sulfonic acid, primary ammonium, secondary ammonium, tertiary ammonium, or —NO2;
• Y and Z are each, independently, hydrogen or C1 to C10 alkyl;
• p and t are each, independently, 1 to 10;
• s is absent or 1 to 10, and
• r is 1.

A liquid composition comprising (a) water and (b) suspended or dissolved in the water, a solid powder comprising a complex of a cyclodextrin with an active compound, wherein the active compound is:

• a nitroalkene is a structure of formula I:
• wherein R1 is hydrogen, C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl;
• R2, R3, R7, and R8 are each independently, hydrogen, oxygen, C1-C24 alkyl, NO2, OH, or OOH;
• R4 is a terminal COOR6 group, wherein R6 is hydrogen, or a C1-C24 alkyl;
• R5 is hydrogen, C1-C24 alkyl, or R4 and R5 collectively form ═C(R9)(R10), wherein R9 comprises C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl, or wherein R9 is a terminal COOR6 group, and R10 is hydrogen, NO2, OH, or OOH;
• n is from 1 to 24;
• and
• wherein the nitroalkene fatty acid includes at least one NO2 group;
• a nitroalkene is a structure of formula II:
• wherein R1 is hydrogen, C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl;
• R2, R4, R5 and R6 are each hydrogen;
• R7 is a terminal COOR9 group, wherein R9 is hydrogen or a C1-C24 alkyl;
• and
• R3 and R8 are each independently, hydrogen, oxygen, C1-C24 alkyl, NO2, OH, ONO2, NO, ONO or OOH, provided at least one of R3 or R8 is NO2 and the other of R3 or R8 is hydrogen, ONO or ONO2;
• a nitro group-containing compound is a structure of formula III:
• wherein R1 is hydrogen, C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl;
• R2 and R5 are each hydrogen;
• R7 is a terminal COOR6 group, wherein R6 is hydrogen or a C1-C24 alkyl;
• and
• R3 and R4 are each independently, hydrogen, oxygen, C1-C24 alkyl, NO2, OH, ONO2, NO, ONO or OOH, provided at least one of R3 or R4 is NO2 and the other of R3 or R4 is hydrogen, ONO or ONO2;
• a compound comprising a dicarboxylic acid of a structure of formula IV:
• wherein X is an electron-withdrawing group selected from acyl, carboxylic acid, an ester, a halogen, fluoromethyl, —CN, sulfonyl, sulfone, sulfonic acid, primary ammonium, secondary ammonium, tertiary ammonium, or —NO2,
• m is from 1 to 10;
• and
• n is from 1 to 10;
• a compound comprising a dicarboxylic acid of a structure of formula V:
• wherein X is an electron-withdrawing group selected from acyl, carboxylic acid, an ester, a halogen, fluoromethyl, —CN, sulfonyl, sulfone, sulfonic acid, primary ammonium, secondary ammonium, tertiary ammonium, or —NO2;
• Y and Z are each, independently, hydrogen or a C1 to C10 alkyl;
• m is from 1 to 10;
• and
• n is from 1 to 10;
• or
• a compound comprising a dicarboxylic acid of a structure of formula VI:
• wherein X is an electron-withdrawing group selected from acyl, carboxylic acid, an ester, a halogen, fluoromethyl, —CN, sulfonyl, sulfone, sulfonic acid, primary ammonium, secondary ammonium, tertiary ammonium, or —NO2;
• Y and Z are each, independently, hydrogen or C1 to C10 alkyl;
• p and t are each, independently, 1 to 10;
• s is absent or 1 to 10, and
• r is 1.

A method comprising contacting a cyclodextrin with an active compound under conditions resulting in forming a complex of the cyclodextrin with the active compound, wherein the active compound is:

• a nitroalkene is a structure of formula I:
• wherein R1 is hydrogen, C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl;
• R2, R3, R7, and R8 are each independently, hydrogen, oxygen, C1-C24 alkyl, NO2, OH, or OOH;
• R4 is a terminal COOR6 group, wherein R6 is hydrogen, or a C1-C24 alkyl;
• R5 is hydrogen, C1-C24 alkyl, or R4 and R5 collectively form ═C(R9)(R10), wherein R9 comprises C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl, or wherein R9 is a terminal COOR6 group, and R10 is hydrogen, NO2, OH, or OOH;
• n is from 1 to 24;
• and
• wherein the nitroalkene fatty acid includes at least one NO2 group;
• a nitroalkene is a structure of formula II:
• wherein R1 is hydrogen, C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl;
• R2, R4, R5 and R6 are each hydrogen;
• R7 is a terminal COORS group, wherein R9 is hydrogen or a C1-C24 alkyl;
• and
• R3 and R8 are each independently, hydrogen, oxygen, C1-C24 alkyl, NO2, OH, ONO2, NO, ONO or OOH, provided at least one of R3 or R8 is NO2 and the other of R3 or R8 is hydrogen, ONO or ONO2;
• a nitro group-containing compound is a structure of formula III:
• wherein R1 is hydrogen, C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl;
• R2 and R5 are each hydrogen;
• R7 is a terminal COOR6 group, wherein R6 is hydrogen or a C1-C24 alkyl;
• and
• R3 and R4 are each independently, hydrogen, oxygen, C1-C24 alkyl, NO2, OH, ONO2, NO, ONO or OOH, provided at least one of R3 or R4 is NO2 and the other of R3 or R4 is hydrogen, ONO or ONO2;
• a compound comprising a dicarboxylic acid of a structure of formula IV:
• wherein X is an electron-withdrawing group selected from acyl, carboxylic acid, an ester, a halogen, fluoromethyl, —CN, sulfonyl, sulfone, sulfonic acid, primary ammonium, secondary ammonium, tertiary ammonium, or —NO2,
• m is from 1 to 10;
• and
• n is from 1 to 10;
• a compound comprising a dicarboxylic acid of a structure of formula V:
• wherein X is an electron-withdrawing group selected from acyl, carboxylic acid, an ester, a halogen, fluoromethyl, —CN, sulfonyl, sulfone, sulfonic acid, primary ammonium, secondary ammonium, tertiary ammonium, or —NO2;
• Y and Z are each, independently, hydrogen or a C1 to C10 alkyl;
• m is from 1 to 10;
• and
• n is from 1 to 10;
• or
• a compound comprising a dicarboxylic acid of a structure of formula VI:
• wherein X is an electron-withdrawing group selected from acyl, carboxylic acid, an ester, a halogen, fluoromethyl, —CN, sulfonyl, sulfone, sulfonic acid, primary ammonium, secondary ammonium, tertiary ammonium, or —NO2;
• Y and Z are each, independently, hydrogen or C1 to C10 alkyl;
• p and t are each, independently, 1 to 10;
• s is absent or 1 to 10, and
• r is 1.