Plant extract compositions and methods of preparation thereof

Patent metadata

Field	Value
Publication number	US-11160287-B2
Application number	US-201916684140-A
Country	US
Kind code	B2
Filing date	Nov 14, 2019
Priority date	May 20, 2015
Publication date	Nov 2, 2021
Grant date	Nov 2, 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. 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 1

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

• A23V2200/10

  Preserving against microbes · CPC title

• A23B7/154 Primary

  Organic compounds; Microorganisms; Enzymes · CPC title

• A23V2250/186

  Fatty acids · CPC title

• B01D11/0288

  Applications, solvents · CPC title