Compositions and methods of preparation thereof

The method of claim 19, wherein the cutin-derived monomers comprise at least one compound of Formula I:

• wherein:
• R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 are each independently —H, —OR13, —NR13R14, —SR13, halogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR13, —NR13R14, —SR13, or halogen;
• R13 and R14 are each independently —H, —C1-C6 alkyl, —C2-C6 alkenyl, or —C2-C6 alkynyl;
• R12 is —OH, —H, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR13, —NR13R14, —SR13, halogen, —COOH, or —COOR11;
• m, n, and o are each independently an integer in the range of 0 to 30;
• and
• the sum of m, n, and o is 0 to 30.

The method of claim 19, wherein the cutin-derived monomers comprise at least one compound of Formula II:

• wherein:
• R1, R2, R4, and R5 are each independently —H, —OR11, —NR11R12, —SR11, halogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR11, —NR11R12, —SR11,or halogen;
• R11 and R12 are each independently —H, —C1-C6 alkyl, —C2-C6 alkenyl, or —C2-C6 alkynyl;
• the symbol represents an optionally single or cis or trans double bond;
• R3 is —OH and R3′ is selected from —H, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, and aryl when between R3 and R3′ is a single bond, and R3 and R3′ are absent when between R3 and R3′ represents a double bond;
• R6 is —OH and R6′ is selected from —H, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, and —C6-C10 aryl when between R6 and R6′ is a single bond, and R6 and R6′ are absent when between R6 and R6′ represents a double bond;
• n is an integer in the range of 0 to 11;
• m is an integer in the range of 0 to 25;
• and
• the sum of m and n is 0 to 25.

The method of claim 19, wherein the cutin-derived monomers comprise at least one compound of Formula III:

• wherein:
• R1, R2, R5, R6, R9, R10, R11, R12, and R13 are each independently, at each occurrence, —H, —OR14, —NR14R15, —SR14, halogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR14, —NR14R15, —SR14, or halogen;
• R3, R4, R7, and R8 are each independently, at each occurrence, —H, —OR14, —NR14R15, —SR14, halogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR14, —NR14R15, —SR14, or halogen, wherein:
• R3 and R4 can combine with the carbon atoms to which they are attached to form a C3-C6 cycloalkyl, a C4-C6 cycloalkenyl, or 3- to 6-membered ring heterocycle, and/or
• R7 and R8 can combine with the carbon atoms to which they are attached to form a C3-C6 cycloalkyl, a C4-C6 cycloalkenyl, or 3- to 6-membered ring heterocycle;
• R14 and R15 are each independently, at each occurrence, —H, —C1-C6 alkyl, —C2-C6 alkenyl, or —C2-C6 alkynyl;
• the symbol represents a single bond or a cis or trans double bond;
• the symbol represents a cis or trans double bond;
• n is 0, 1, 2, 3, 4, 5, 6, 7, or 8;
• m is 0, 1, 2, or 3;
• q is 0, 1, 2, 3, 4, or 5;
• and
• r is 0, 1, 2, 3, 4, 5, 6, 7, or 8.

A method of producing cutin-derived monomers, oligomers, or both from plant-matter, the method comprising:

• obtaining cutin from a cutin-containing portion of plant matter;
• contacting the cutin with a nucleophile to form a first mixture;
• and
• subjecting the first mixture to mechanochemical processing to decompose at least a portion of the cutin, thereby yielding a second mixture comprising cutin-derived monomers, oligomers, or both.

A method of producing constituent monomers from at least a portion of triglycerides of seed, bean, nut, kernel, or pulp material of plant matter comprising:

• obtaining at least partially separated seed, bean, nut, kernel, or pulp material from other portions of plant matter;
• optionally extracting oil from the seed, bean, nut, kernel, or pulp material;
• contacting the separated seed, bean, nut, kernel or pulp material, or the optionally extracted oil therefrom, with a nucleophile to form a first mixture;
• and
• subjecting the first mixture to mechanical processing to produce a second mixture comprising constituent monomers derived from the triglycerides.