Plant extract compositions and methods of preparation thereof
Embodiments described herein relate generally to plant extract compositions and methods to isolate cutin-derived monomers, oligomers, and mixtures thereof for application in agricultural coating formulations, and in particular, to methods of preparing plant extract compositions that include functionalized and non-functionalized fatty acids and fatty esters (as well as their oligomers and mixtures thereof), which are substantially free from accompanying plant-derived compounds (e.g., proteins, polysaccharides, phenols, lignans, aromatic acids, terpenoids, flavonoids, carotenoids, alkaloids, alcohols, alkanes, and aldehydes) and can be used in agricultural coating formulations.
1. An agricultural product having a protective coating thereover, the protective coating formed from monoacylglycerides, wherein the monoacylglycerides are compounds of Formula I, wherein Formula I is:
wherein:
R is a 1-glyceryl or a 2-glyceryl;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently —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, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl, wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 and R 8 are each independently —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, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 are optionally combined with carbon atoms to which they are attached to form a 3 to 6-membered ring;
R 7 and R 8 are optionally combined with carbon atoms to which they are attached to form a 3 to 6-membered ring;
R 14 and R 15 are each independently —H, —C 1 -C 6 alkyl, —C 1 -C 6 alkenyl, or —C 1 -C 6 alkynyl;
the symbol represents a single bond or cis or trans double bond;
n is an integer between 0 and 8;
m is an integer between 0 and 3;
q is an integer between 0 and 5; and
r is an integer between 0 and 8;
wherein the protective coating is formed by a process comprising:
obtaining a composition comprising the monoacylglycerides, wherein the monoacylglycerides are formed by esterification of plant-derived fatty acids;
causing the composition to be added to a solvent, thereby forming a mixture; and
causing the mixture to be applied to a surface of the agricultural product to form the protective coating over the agricultural product.
2. The agricultural product of claim 1 , wherein the forming of the protective coating further comprises causing an emulsifier to be added to the solvent.
3. The agricultural product of claim 2 , wherein the solvent comprises water or ethanol.
4. The agricultural product of claim 1 , wherein the forming of the protective coating further comprises causing the solvent to be removed from the surface of the agricultural product.
5. The agricultural product of claim 1 , wherein the agricultural product is an edible product.
6. The agricultural product of claim 1 , wherein the agricultural product is an inedible product.
7. The agricultural product of claim 1 , wherein the protective coating is formulated to prevent diffusion of gaseous species.
8. The agricultural product of claim 1 , wherein the fatty acids comprise at least one of hexadecanoic acid, 16-hydroxyhexadecanoic acid, 9,16-dihydroxyhexadecanoic acid, 10,16-dihydroxyhexadecanoic acid, or 9,10,16-trihydroxyhexadecanoic acid.
9. The agricultural product of claim 1 , wherein the fatty acids comprise at least one of octadecanoic acid, 18-hydroxyoctadecanoic acid, 9,18-dihydroxyoctadecanoic acid, 10,18-dihydroxyoctadecanoic acid, or 9,10,18-trihydroxyoctadecanoic acid.
10. An agricultural product having a protective coating thereover, the protective coating formed from monoacylglycerides, wherein the monoacylglycerides are compounds of Formula I, wherein Formula I is:
wherein:
R is a 1-glyceryl or a 2-glyceryl;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently —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, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl, wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 and R 8 are each independently —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, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 are optionally combined with carbon atoms to which they are attached to form a 3 to 6-membered ring;
R 7 and R 8 are optionally combined with carbon atoms to which they are attached to form a 3 to 6-membered ring;
R 14 and R 15 are each independently —H, —C 1 -C 6 alkyl, —C 1 -C 6 alkenyl, or —C 1 -C 6 alkynyl;
the symbol represents a single bond or cis or trans double bond;
n is an integer between 0 and 8;
m is an integer between 0 and 3;
q is an integer between 0 and 5; and
r is an integer between 0 and 8;
wherein the protective coating is formed by a process comprising:
obtaining a composition comprising the monoacylglycerides, wherein the monoacylglycerides are formed by transesterification of plant-derived fatty acid esters;
causing the composition to be added to a solvent, thereby forming a mixture; and
causing the mixture to be applied to a surface of the agricultural product to form the protective coating over the agricultural product.
11. The agricultural product of claim 10 , wherein the forming of the protective coating further comprises causing an emulsifier to be added to the solvent.
12. The agricultural product of claim 11 , wherein the solvent comprises water or ethanol.
13. The agricultural product of claim 10 , wherein the agricultural product is an edible product, and the protective coating serves to reduce moisture loss from the product.
14. The agricultural product of claim 10 , wherein the agricultural product is a fruit or a vegetable.
15. An agricultural product having a protective coating thereover, the protective coating formed from monoacylglycerides, wherein the monoacylglycerides are compounds of Formula I, wherein Formula I is:
wherein:
R is a 1-glyceryl or a 2-glyceryl;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently —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, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl, wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 and R 8 are each independently —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, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 are optionally combined with carbon atoms to which they are attached to form a 3 to 6-membered ring;
R 7 and R 8 are optionally combined with carbon atoms to which they are attached to form a 3 to 6-membered ring;
R 14 and R 15 are each independently —H, —C 1 -C 6 alkyl, —C 1 -C 6 alkenyl, or —C 1 -C 6 alkynyl;
the symbol represents a single bond or cis or trans double bond;
n is an integer between 0 and 8;
m is an integer between 0 and 3;
q is an integer between 0 and 5; and
r is an integer between 0 and 8;
wherein the protective coating is formed by a process comprising:
obtaining a mixture comprising a composition in a solvent, the composition comprising the monoacylglycerides, wherein the monoacylglycerides are formed by esterification of plant-derived fatty acids; and
causing the mixture to be applied to a surface of the agricultural product to form the protective coating over the agricultural product.
16. The agricultural product of claim 15 , wherein the fatty acids comprise at least one of hexadecanoic acid, 16-hydroxyhexadecanoic acid, 9,16-dihydroxyhexadecanoic acid, 10,16-dihydroxyhexadecanoic acid, or 9,10,16-trihydroxyhexadecanoic acid.
17. The agricultural product of claim 15 , wherein the fatty acids comprise at least one of octadecanoic acid, 18-hydroxyoctadecanoic acid, 9,18-dihydroxyoctadecanoic acid, 10,18-dihydroxyoctadecanoic acid, or 9,10,18-trihydroxyoctadecanoic acid.
18. The agricultural product of claim 15 , wherein the composition further comprises a salt.
19. The agricultural product of claim 18 , wherein the mixture further comprises a weak acid.
20. An agricultural product having a protective coating thereover, the protective coating formed from monoacylglycerides, wherein the monoacylglycerides are compounds of Formula I, wherein Formula I is:
wherein:
R is a 1-glyceryl or a 2-glyceryl;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently —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, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl, wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 and R 8 are each independently —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, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 are optionally combined with carbon atoms to which they are attached to form a 3 to 6-membered ring;
R 7 and R 8 are optionally combined with carbon atoms to which they are attached to form a 3 to 6-membered ring;
R 14 and R 15 are each independently —H, —C 1 -C 6 alkyl, —C 1 -C 6 alkenyl, or —C 1 -C 6 alkynyl;
the symbol represents a single bond or cis or trans double bond;
n is an integer between 0 and 8;
m is an integer between 0 and 3;
q is an integer between 0 and 5; and
r is an integer between 0 and 8;
wherein the protective coating is formed by a process comprising:
obtaining a mixture comprising a composition in a solvent, the composition comprising the monoacylglycerides, wherein the monoacylglycerides are formed by transesterification of plant-derived fatty acid esters; and
causing the mixture to be applied to a surface of the agricultural product to form the protective coating over the agricultural product.
21. The agricultural product of claim 20 , wherein the protective coating serves to reduce a rate of mass loss in the agricultural product.
22. The agricultural product of claim 20 , wherein the agricultural product is a fruit or a vegetable.
23. The agricultural product of claim 20 , wherein the forming of the protective coating further comprises causing the solvent to be removed from the surface of the agricultural product.
24. The agricultural product of claim 20 , wherein the composition further comprises a salt.
25. The agricultural product of claim 24 , wherein the mixture further comprises a weak acid.
26. The agricultural product of claim 20 , wherein the protective coating is formulated to prevent diffusion of gaseous species.