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. A coated agricultural product comprising:
an agricultural product; and
a coating over the agricultural product,
wherein the coating is formed from a mixture comprising:
a solvent; and
a composition comprising at least one monoacylglyceride of Formula I:
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 heteroaryl, wherein each hetereroaryl is independently a 5- to 10-membered ring heteroaryl, and 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 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 heteroaryl, wherein each hetereroaryl is independently a 5- to 10-membered ring heteroaryl, and 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 heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; wherein:
R 3 and R 4 are optionally combined with carbon atoms to which they are attached to form a 3 to 6-membered ring, and/or
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 at least one monoacylglyceride is formed by esterification or transesterification of a fatty acid.
2. The coated agricultural product of claim 1 , wherein the at least one monoacylglyceride of Formula I comprises a glycerol ester of hexadecanoic acid, a glycerol ester of 16-hydroxyhexadecanoic acid, a glycerol ester of 9,16-dihydroxyhexadecanoic acid, a glycerol ester of 10,16-dihydroxyhexadecanoic acid, a glycerol ester of 9,10,16-trihydroxyhexadecanoic acid, or any combination thereof.
3. The coated agricultural product of claim 1 , wherein the at least one monoacylglyceride of Formula I comprises a glycerol ester of octadecanoic acid, a glycerol ester of 18-hydroxyoctadecanoic acid, a glycerol ester of 9,18-dihydroxyoctadecanoic acid, a glycerol ester of 10,18-dihydroxyoctadecanoic acid, a glycerol ester of 9,10,18-trihydroxyoctadecanoic acid, or any combination thereof.
4. The coated agricultural product of claim 1 , wherein the composition further comprises an emulsifier.
5. The coated agricultural product of claim 1 , wherein the composition further comprises a salt.
6. The coated agricultural product of claim 1 , wherein the composition further comprises a weak acid.
7. The coated agricultural product of claim 1 , wherein the solvent comprises one or both of water and ethanol.
8. The coated agricultural product of claim 1 , wherein the agricultural product is edible.
9. The coated agricultural product of claim 8 , wherein the agricultural product is a fruit or a vegetable.
10. The coated agricultural product of claim 1 , wherein the agricultural product is inedible.
11. The coated agricultural product of claim 1 , wherein the coating prevents diffusion of gaseous species.
12. The coated agricultural product of claim 1 , wherein the coating reduces moisture loss from the product.
13. The coated agricultural product of claim 1 , wherein the coating reduces a rate of mass loss in the agricultural product.
14. The coated agricultural product of claim 1 , wherein the coating is transparent to the human eye.
15. The coated agricultural product of claim 1 , wherein a thickness of the coating is less than about 1500 nm.
16. A coated agricultural product comprising:
an agricultural product; and
a coating over the agricultural product,
wherein the coating is formed from a composition comprising:
about 15 wt % to about 100 wt % of one or more first monoacylglycerides formed by:
esterification of C 16 hydroxy fatty acids,
transesterification of C 16 hydroxy fatty esters, or both; and
up to about 85 wt % of one or more second monoacylglycerides formed by:
esterification of C 18 hydroxy fatty acids,
transesterification of C 18 hydroxy fatty esters, or both.
17. The coated agricultural product of claim 16 , wherein the composition comprises:
about 50 wt % to about 100 wt % of the one or more first monoacylglycerides; and
up to about 35 wt % of the one or more second monoacylglycerides.
18. The coated agricultural product of claim 16 , wherein the one or more first monacylglycerides comprise a glycerol ester of 16 hydroxyhexadecanoic acid, a glycerol ester of 9,16-dihydroxyhexadecanoic acid, a glycerol ester of 10,16-dihydroxyhexadecanoic acid, a glycerol ester of 9,10,16-trihydroxyhexadecanoic acid, a glycerol ester of 16-hydroxy-10-oxohexadecanoic acid, or any combination thereof.
19. The coated agricultural product of claim 16 , wherein the composition comprises about 50 wt % to about 100 wt % of the one or more one or more first monacylglycerides.
20. The coated agricultural product of claim 16 , wherein the one or more second monacylglycerides comprise a glycerol ester of 18-hydroxyoctadecanoic acid, a glycerol ester of 9,18-dihydroxyoctadecanoic acid, a glycerol ester of 10,18-dihydroxyoctadecanoic acid, a glycerol ester of 9,10,18-trihydroxy-octadecanoic acid, a glycerol ester of 18-hydroxy-9,10-epoxy-octadecanoic acid, or any combination thereof.
21. The coated agricultural product of claim 16 , wherein the composition further comprises one or both of an emulsifier and a salt.
22. The coated agricultural product of claim 16 , wherein the agricultural product is a fruit or a vegetable.