Plant extract compositions and methods of preparation thereof

Patent metadata

Field	Value
Publication number	US-10959442-B2
Application number	US-202016749735-A
Country	US
Kind code	B2
Filing date	Jan 22, 2020
Priority date	May 20, 2015
Publication date	Mar 30, 2021
Grant date	Mar 30, 2021

Abstract

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.

First claim

The invention claimed is:

1. A method of forming a protective coating on a product, the product being pre-harvest and comprising a plant, a portion of a plant, or an agricultural product, the method comprising:
obtaining a composition comprising 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 product to form the protective coating over the product, and
wherein the method further comprises causing the solvent to be removed from the surface of the agricultural product.

2. The method of claim 1 , wherein the product is a fruit, a vegetable, produce, a seed, a nut, or a flower.

3. The method of claim 1 , wherein the product is an edible product.

4. The method of claim 1 , wherein the product is an inedible product.

5. The method of claim 1 , wherein the protective coating prevents diffusion of gaseous species.

6. The method 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.

7. The method 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.

8. A method of forming a protective coating on a product, the product being pre-harvest and comprising a plant, a portion of a plant, or an agricultural product, the method comprising:
obtaining a composition comprising 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 product to form a protective coating over the product, and
wherein the method further comprises causing the solvent to be removed from the surface of the agricultural product.

9. The method of claim 8 , wherein the product is a fruit, a vegetable, produce, a seed, a nut, or a flower.

10. The method of claim 8 , wherein the protective coating prevents diffusion of gaseous species.

11. A method of treating forming a protective coating on a product, the product being pre-harvest and comprising a plant, a portion of a plant, or an agricultural product, the method comprising:
obtaining a composition comprising monoacylglycerides, wherein the monoacylglycerides are formed by esterification of plant-derived fatty acids; and
causing the composition to be applied to a surface of the product to form a protective coating over the product,
wherein the obtaining of the composition comprises obtaining a mixture comprising the composition in a solvent, and
wherein the method further comprises causing the solvent to be removed from the surface of the agricultural product.

12. The method of claim 11 , wherein the fatty acids comprise at least one of hexadecanoic acid, 16-hydroxyhexadecanoic acid, 9,16-dihydroxyhexadecanoic acid, 10,16-dihydroxyhexadecanoic acid, 9,10,16-trihydroxyhexadecanoic acid, octadecanoic acid, 18-hydroxyoctadecanoic acid, 9,18-dihydroxyoctadecanoic acid, 10,18-dihydroxyoctadecanoic acid, or 9,10,18-trihydroxyoctadecanoic acid.

13. The method of claim 11 , wherein the product is a fruit, a vegetable, produce, a seed, a nut, or a flower.

14. A method of forming a protective coating on a product, the product being pre-harvest and comprising a plant, a portion of a plant, or an agricultural product, the method comprising:
obtaining a composition comprising monoacylglycerides, wherein the monoacylglycerides are formed by transesterification of plant-derived fatty acids; and
causing the composition to be applied to a surface of the product to form a protective coating on the product,
wherein the obtaining of the composition comprises obtaining a mixture comprising the composition in a solvent, and
wherein the method further comprises causing the solvent to be removed from the surface of the agricultural product.

15. The method of claim 1 , 8 , 11 or 14 wherein the mixture further comprises an emulsifier.

16. The method of claim 1 , 8 , 11 or 14 , wherein the solvent comprises water or ethanol.

17. The method of claim 8 , 11 or 14 , 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 the carbon atoms to which they are attached to form a 3 to 6-membered ring, such as a cyclic ether;
R 7 and R 8 are optionally combined with the carbon atoms to which they are attached to form a 3 to 6-membered ring, such as a cyclic ether;
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 an optionally single 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.

18. The method of claim 1 , 8 , 11 or 14 , wherein the composition further comprises a salt of a fatty acid.

19. The method of claim 1 , 8 , 11 or 14 , wherein the mixture further comprises a weak acid.

20. The method of claim 14 , wherein the product is a fruit, a vegetable, produce, a seed, a nut, or a flower.

21. The method of claim 14 , wherein the protective coating prevents diffusion of gaseous species.

22. The method of claim 14 , wherein the product is an edible product.

23. The method of claim 14 , wherein the product is an inedible product.

Assignees

• Apeel Tech Inc

Inventors

• Perez Louis
• Rogers James
• Bakus Ii Ronald C
• Holland Chance
• Du Jenny

Classifications

• A23B2/758

  Carboxylic acid esters · CPC title

• B01D11/0284

  Multistage extraction · CPC title

• A23B7/154 Primary

  Organic compounds; Microorganisms; Enzymes · CPC title

• B01D11/0288

  Applications, solvents · CPC title

• A23V2300/14

  Extraction · CPC title