Precursor compounds for molecular coatings
Presented are compositions that can be used as protective coatings for agricultural (e.g., food) substrates. The compositions can comprise a compound of Formula I: and an additive, wherein the variables m, n, q, r, R a , R b , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are defined herein. The protective coatings formed from the compositions can be used to prevent food spoilage due to, for instance, moisture loss, oxidation, or infection by a foreign pathogen.
1. A composition consisting of:
a compound of Formula I:
and
one or more additives, wherein at least one of the one or more additives comprises a compound of Formula II:
wherein for each formula:
each R a is independently —H or —C 1 -C 6 alkyl;
each R b is independently selected from —H, —C 1 -C 6 alkyl, or —OH;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 , and R 8 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or
R 7 and R 8 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle;
R 14 and R 15 are each independently, at each occurrence, —H, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, or —C 2 -C 6 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;
wherein a molar ratio of the one or more additives to the compound of Formula I is in a range of 0.1 to 1, and the composition is formulated such that coatings formed from the composition are substantially free of visible residues.
2. The composition of claim 1 , wherein a carbon chain length of the compound of Formula I is the same as a carbon chain length of the compound of Formula II.
3. The composition of claim 1 , wherein a carbon chain length of the compound of Formula I is different from a carbon chain length of the compound of Formula II.
4. The composition of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
5. The composition of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
6. The composition of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are each —H.
7. The composition of claim 1 , wherein the one or more additives comprise a first additive and a second additive different from the first additive.
8. The composition of claim 7 , wherein the first additive is a fatty acid and the second additive is the compound of Formula II.
9. The composition of claim 1 , wherein the one or more additives comprise a fatty acid having a carbon chain length that is the same as a carbon chain length of the compound of Formula I.
10. The composition of claim 1 , wherein the one or more additives comprise a fatty acid having a carbon chain length that is different from a carbon chain length of the compound of Formula I.
11. A mixture comprising a composition in a solvent, the composition consisting of:
a compound of Formula I:
and
one or more additives, wherein at least one of the one or more additives comprises a compound of Formula II:
wherein for each formula:
each R a is independently —H or —C 1 -C 6 alkyl;
each R b is independently selected from —H, —C 1 -C 6 alkyl, or —OH;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 , and R 8 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or
R 7 and R 8 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle;
R 14 and R 15 are each independently, at each occurrence, —H, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, or —C 2 -C 6 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;
wherein a molar ratio of the one or more additives to the compound of Formula I is in a range of 0.1 to 1, and the composition is formulated such that coatings formed from the composition are substantially free of visible residues; and
wherein the composition has a concentration in the solvent of at least 0.5 mg/mL.
12. The mixture of claim 11 , wherein the solvent comprises water or ethanol.
13. The composition of claim 1 , wherein the molar ratio of the one or more additives to the compound of Formula I is in a range of about 0.1 to about 0.5.
14. The composition of claim 13 , wherein the molar ratio of the one or more additives to the compound of Formula I is in a range of about 0.2 to about 0.4.
15. The mixture of claim 11 , wherein a carbon chain length of the compound of Formula I is the same as a carbon chain length of the compound of Formula II.
16. The mixture of claim 11 , wherein a carbon chain length of the compound of Formula I is different from a carbon chain length of the compound of Formula II.
17. The mixture of claim 11 , wherein the compound of Formula I is selected from the group consisting of:
18. The mixture of claim 11 , wherein the compound of Formula I is selected from the group consisting of:
19. The mixture of claim 11 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 are each —H.
20. The mixture of claim 11 , wherein the one or more additives further comprise a fatty acid.
21. The mixture of claim 11 , wherein the one or more additives comprise a fatty acid having a carbon chain length that is the same as a carbon chain length of the compound of Formula I.
22. The mixture of claim 11 , wherein the one or more additives comprise a fatty acid having a carbon chain length that is different from a carbon chain length of the compound of Formula I.
23. The mixture of claim 11 , wherein the molar ratio of the one or more additives to the compound of Formula I is in a range of about 0.1 to about 0.5.
24. The mixture of claim 11 , wherein the molar ratio of the one or more additives to the compound of Formula I is in a range of about 0.2 to about 0.4.
25. A composition consisting of:
a compound of Formula I:
and
an additive comprising one or more additives, wherein at least one of the one or more additives comprises a compound of Formula II:
wherein for each formula:
each R a is independently —H or —C 1 -C 6 alkyl;
each R b is independently selected from —H, —C 1 -C 6 alkyl, or —OH;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 , and R 8 are each independently, at each occurrence, —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or
R 7 and R 8 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle;
R 14 and R 15 are each independently, at each occurrence, —H, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, or —C 2 -C 6 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; wherein
a molar ratio of the one or more additives to the compound of Formula I is in a range of 0.1 to 1;
the compound of Formula I is selected from the group consisting of 2-glycero palmitate, 2-glycero stearate, 2-glycero myristate, and 2-glycero oleate; and
the compound of Formula II is selected from the group consisting of 1-glycero palmitate, 1-glycero stearate, 1-glycero myristate, and 1-glycero oleate.