Plant extract compositions for forming protective coatings

A method of preparing cutin-derived monomers, oligomers, or combinations thereof from cutin-containing plant matter, comprising:

• obtaining cutin from the cutin-containing plant matter;
• adding the cutin to a solvent to form a first mixture, the solvent having a boiling point at a first temperature at a pressure of one atmosphere;
• and
• heating the first mixture to a second temperature and second pressure, the second temperature being higher than the first temperature and the second pressure being higher than one atmosphere, to form a second mixture comprising a first group of compounds 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, —C1-C6 alkenyl, —C1-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, —C1-C6 alkenyl, or —C1-C6 alkynyl;
• R11 is —H, -glyceryl, —C1-C6 alkyl, —C1-C6 alkenyl, —C1-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;
• R12 is —OH, —H, —C1-C6 alkyl, —C1-C6 alkenyl, —C1-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;
• and
• m, n, and o are each independently an integer in the range of 0 to 30, and 0≤m+n+o≤30.

A method of preparing cutin-derived monomers, oligomers, or combinations thereof from cutin-containing plant matter, comprising:

• obtaining cutin from the cutin-containing plant matter;
• adding the cutin to a solvent to form a first mixture, the solvent having a boiling point at a first temperature at a pressure of one atmosphere;
• and
• heating the first mixture to a second temperature and second pressure, the second temperature being higher than the first temperature and the second pressure being higher than one atmosphere, to form a second mixture comprising a first group of compounds 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;
• or
• 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;
• 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;
• and
• R is selected from —H, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C7 cycloalkyl, aryl, 1-glycerol, 2-glycerol, or heteroaryl.

A method of preparing cutin-derived monomers, oligomers, or combinations thereof from cutin-containing plant matter, comprising:

• obtaining cutin from the cutin-containing plant matter;
• adding the cutin to a solvent to form a first mixture;
• and
• heating the first mixture to a temperature of at least 498K and a pressure of at least 360 psi, thereby forming a second mixture comprising the cutin-derived monomers, oligomers, or combinations thereof.