Plant extract compositions and methods of preparation thereof

• US 10,517,310 B2
• Filed: 07/26/2017
• Issued: 12/31/2019
• Est. Priority Date: 05/20/2015
• Status: Active Grant

• Current Assignee: Apeel Technology, Inc.
• Original Assignee: Apeel Technology, Inc.
• Inventors: Perez, Louis, Rogers, James, Bakus, II, Ronald C., Holland, Chance, Du, Jenny
• Primary Examiner(s): Drodge, Joseph W
• Application Number:
  US15/660,260
• Publication Number:
  US 20170318827A1
• Time in Patent Office: 888 Days
• Field of Search: 210634, 210639, 210806, 426 89, 426 90, 426302, 426303, 426310, 426615, 554 8, 554 20, 554 21, 554 29, 554 30, 554174, 554175
• CPC Class Codes: A23B 7/154 Organic compounds; Microorganisms; Enzymes
• CPC Class Codes: A23B 7/16 Coating with a protective layer; Compositions or apparatus therefor A23B7/08 takes precedence
• CPC Class Codes: A23L 3/3517 Carboxylic acid esters
• CPC Class Codes: A23V 2002/00 Food compositions, function of food ingredients or processes for food or foodstuffs
• CPC Class Codes: A23V 2200/10 Preserving against microbes
• CPC Class Codes: A23V 2250/186 Fatty acids
• CPC Class Codes: A23V 2300/14 Extraction
• CPC Class Codes: B01D 11/0284 Multistage extraction
• CPC Class Codes: B01D 11/0288 Applications, solvents
• CPC Class Codes: B01D 37/00 Processes of filtration processes specially adapted for filtering gases B01D46/00

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.

Claims

1. A method of treating an agricultural product, comprising:

obtaining a composition comprising plant-derived fatty acids;

functionalizing the fatty acids by esterification to form fatty acid esters, the fatty acid esters comprising monoacylglycerides;

causing the monoacylglycerides 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 a protective coating from the monoacylglycerides over the agricultural product.

2. The method of claim 1, further comprising causing an emulsifier to be added to the solvent.

3. The method of claim 2, wherein the solvent is water.

4. The method of claim 1, wherein the forming of the protective coating further comprises causing the solvent to be removed from the surface of the product.

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

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

7. The method of claim 1, wherein the protective coating is formulated to prevent diffusion of gaseous species.

8. 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.

9. 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.

10. The method of claim 1, wherein the agricultural product is a fruit or a vegetable.

11. The method of claim 1, wherein the monoacylglycerides are compounds of Formula I, wherein Formula I is:

12. A method of treating an agricultural product, comprising:

obtaining a composition comprising a first group of plant-derived fatty acid esters;

transesterifying the first group of fatty acid esters to form a second group of fatty acid esters different from the first group of fatty acid esters, the second group of fatty acid esters comprising monoacylglycerides; and

causing the monoacylglycerides to be applied to a surface of the agricultural product to form a protective coating from the monoacylglycerides over the agricultural product.

13. The method of claim 12, wherein the agricultural product is an edible product, and the protective coating serves to reduce moisture loss from the product.

14. The method of claim 12, wherein the agricultural product is a fruit or a vegetable.

15. The method of claim 12, wherein the monoacylglycerides are compounds of Formula I, wherein Formula I is:

16. A method of treating an agricultural product, 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 agricultural product to form a protective coating from the monoacylglycerides over the agricultural product.

17. The method of claim 16, 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.

18. The method of claim 16, 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.

19. The method of claim 16, wherein the composition further comprises a salt.

20. The method of claim 19, wherein the mixture further comprises a weak acid.

21. The method of claim 16, wherein the agricultural product is a fruit or a vegetable.

22. The method of claim 16, wherein the monoacylglycerides are compounds of Formula I, wherein Formula I is:

23. A method of treating an agricultural product, comprising:

obtaining a composition comprising monoacylglycerides, wherein the monoacylglycerides are formed by transesterification of plant-derived fatty acid esters; and

causing the composition to be applied to a surface of the agricultural product to form a protective coating from the monoacylglycerides over the agricultural product.

24. The method of claim 23, wherein the protective coating serves to reduce a rate of mass loss in the agricultural product.

25. The method of claim 23, wherein the agricultural product is a fruit or a vegetable.

26. The method of claim 23, wherein the monoacylglycerides are compounds of Formula I, wherein Formula I is: