Compositions formed from plant extracts and methods of preparation thereof

• US 10,843,997 B2
• Filed: 05/16/2019
• Issued: 11/24/2020
• Est. Priority Date: 11/17/2016
• Status: Active Grant

• Current Assignee: Apeel Technology, Inc.
• Original Assignee: Apeel Technology, Inc.
• Inventors: Bakus, II, Ronald C., Rodriguez, Gabriel, Mol, Camille, Perez, Louis
• Primary Examiner(s): Cutliff, Yate' K
• Application Number:
  US16/414,735
• Publication Number:
  US 20190269145A1
• Time in Patent Office: 558 Days
• CPC Class Codes: A23B 7/16 Coating with a protective layer; Compositions or apparatus therefor A23B7/08 takes precedence
• CPC Class Codes: A23B 9/14 Coating with a protective layer; Compositions or apparatus therefor
• 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: C07C 67/02 by interreacting ester groups, i.e. transesterification
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• CPC Class Codes: C08J 11/16 by treatment with inorganic material C08J11/14 takes precedence
• CPC Class Codes: C08J 2367/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds; C08J2367/06 takes precedence
• CPC Class Codes: C08J 3/00 Processes of treating or compounding macromolecular substances
• CPC Class Codes: C11C 3/00 Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F
• CPC Class Codes: C11C 3/003 by esterification of fatty acids with alcohols C11C3/02 takes precedence

Abstract

Embodiments described herein relate generally to plant extract compositions and methods to isolate fatty acid esters derived from crosslinked polyesters. Particular embodiments are directed to methods of preparing compositions of fatty acid esters by treating crosslinked polyesters or other crosslinked networks with an acid and an alcohol.

Claims

1. A method of preparing a composition comprising fatty acid esters, the method comprising:

providing a crosslinked polyester comprising polymerized mono- or polyhydroxy fatty acids;

treating the crosslinked polyester with an acid and an alcohol at a temperature from 78°

C. to 120°

C., wherein the acid is combined with the alcohol in superstoichiometric amounts;

removing the acid and the alcohol to form a mixture comprising the fatty acid esters; and

purifying the mixture to isolate the fatty acid esters.

2. The method of claim 1, wherein the crosslinked polyester is naturally occurring.

3. The method of claim 1, wherein the crosslinked polyester is derived from plant matter.

4. The method of claim 1, wherein the crosslinked polyester is cutin.

5. The method of claim 4, wherein the cutin is derived from plant skins.

6. The method of claim 1, wherein the crosslinked polyester contains endogenous water.

7. The method of claim 6, wherein the method is characterized as only requiring a single step to obtain the mixture comprising the fatty acid esters from the crosslinked polyester.

8. The method of claim 1, wherein the alcohol comprises ethanol, methanol, propanol, glycerol, or isopropanol.

9. The method of claim 1, wherein removing the acid comprises neutralizing the acid.

10. The method of claim 1, wherein removing the alcohol comprises evaporating the alcohol.

11. The method of claim 1, wherein the acid is sulfuric acid, triflic acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, para-toluenesulfonic acid, or a combination thereof.

12. The method of claim 1, wherein the fatty acids of the crosslinked polymer comprise 16-hydroxyhexadecanoic acid, 9,16-dihydroxyhexadecanoic acid, 10,16-dihydroxyhexadecanoic acid, 18-hydroxyoctadecanoic acid, 18-hydroxy-(9Z)-octadec-9-enoic acid, 9,10-epoxy-18-hydroxyoctadecanoic acid, 9,10,18-trihydroxyoctadecanoic acid, or a combination thereof.

13. The method of claim 1, wherein the isolated fatty acid esters comprise ethyl 16-hydroxyhexadecanoate, ethyl 9,16-dihydroxyhexadecanoate, ethyl 10,16-dihydroxyhexadecanoate, ethyl 18-hydroxyoctadecanoate, ethyl 18-hydroxy-(9Z)-octadec-9-enoate, ethyl 9,10-epoxy-18-hydroxyoctadecanoate, ethyl 9,10,18-trihydroxyoctadecanoate, or a combination thereof.

14. The method of claim 1, where the composition is in the form of a solid powder.

15. The method of claim 14, wherein the powder has no substantial coloration.

29. The method of claim 1, wherein crosslinked polyester is treated with the acid and the alcohol at a temperature from 100°

C. to 120°

C.

16. A method of preparing a composition comprising cutin-derived monomeric or oligomeric esters, the method comprising:

adding cutin to a solvent comprising an acid and an alcohol, wherein the acid is combined with the alcohol in superstoichiometric amounts;

heating the solvent to a temperature from 78°

C. to 120°

C.;

removing the solvent to form a mixture comprising the cutin-derived monomeric or oligomeric esters; and

purifying the mixture to isolate the cutin-derived monomeric or oligomeric esters;

wherein

the cutin-derived monomeric or oligomeric esters comprise one or more compounds of Formula I;

17. The method of claim 16, wherein the cutin contains endogenous water.

18. The method of claim 17, wherein the method is characterized as only requiring a single step to obtain the mixture comprising the cutin-derived monomeric or oligomeric esters from the cutin.

19. The method of claim 16, wherein the alcohol comprises ethanol, methanol, propanol, glycerol, or isopropanol.

20. The method of claim 16, where the composition is in the form of a solid powder.

21. The method of claim 20, wherein the powder has no substantial coloration.

30. The method of claim 16, wherein the solvent is heated to a temperature from 100°

C. to 120°

C.

22. A method of forming a protective coating on a substrate, comprising:

obtaining fatty acid esters, the obtaining of the fatty acid esters comprising;

treating a crosslinked polyester comprising polymerized mono- or polyhydroxy fatty acids with an acid and an alcohol at a temperature from 78°

C. to 120°

C., wherein the acid is combined with the alcohol in superstoichiometric amounts;

removing the acid and the alcohol to form a mixture; and

purifying the mixture to isolate the resulting fatty acid esters; and

causing the fatty acid esters to be applied to a surface of the substrate to form the protective coating.

23. The method of claim 22, where the composition is in the form of a solid powder.

24. The method of claim 23, wherein the powder has no substantial coloration.

25. The method of claim 22, wherein the crosslinked polyester comprises cutin.

26. The method of claim 22, wherein the substrate is an edible substrate.

27. The method of claim 22, wherein the substrate comprises produce.

28. The method of claim 22, wherein the substrate comprises plant matter.