Granted Patent B2

US 12,245,605 · App. 16/427,219 · Granted Mar 11, 2025

Inventors: Carlos Hernandez (Goleta, CA); Chance Holland (Goleta, CA); Stephen Kaun (Goleta, CA); Louis Perez (Santa Barbara, CA); Charles Frazier (Goleta, CA)

Assignee: Apeel Technology, Inc.

A23B7/154A23B7/16A23L3/3517A23V2002/00

Abstract

Claims (88)

1. An edible coating composition, comprising:

(i) from 70% to 99% by mass of a first group of one or more compounds, wherein each compound of the first group is a compound of Formula I; and

(ii) from 1% to 30% by mass of a second group of one or more compounds, wherein each compound of the second group is a salt of Formula II, wherein Formulas I and II are:

wherein for each of the formulas:

R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently, at each occurrence, —H, —(C═O)R 14 , —(C═O)H, —(C═O)OH, —(C═O)OR 14 , —(C═O)—O—(C═O)R 14 , —O(C═O)R 14 , —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, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;

R 3 , R 4 , R 7 and R 8 are each independently, at each occurrence, —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, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or

R 3 and R 4 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or

R 7 and R 8 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring;

R 14 and R 15 are each independently, at each occurrence, —H, aryl, heteroaryl, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, or —C 2 -C 6 alkynyl;

the symbol represents a single or cis or trans double bond;

n is 0, 1, 2, 3, 4, 5, 6, 7, or 8;

m is 0, 1, 2, or 3;

q is 0, 1, 2, 3, 4, or 5;

r is 0, 1, 2, 3, 4, 5, 6, 7, or 8;

R is -glyceryl; and

X is a cationic moiety.

2. The composition of claim 1 , wherein each compound of the first group of compounds has a carbon chain length of at least 14.

3. The composition of claim 2 , wherein each compound of the second group of compounds has a carbon chain length of at least 14.

4. The composition of claim 1 , wherein the second group of compounds comprises SA-Na, PA-Na, MA-Na, SA-K, PA-K, or MA-K.

5. The composition of claim 1 , wherein the composition comprises less than 10% by mass of diglycerides.

6. The composition of claim 1 , wherein the composition comprises less than 10% by mass of triglycerides.

7. The composition of claim 1 , wherein the first group of one or more compounds comprises at least two compounds of Formula (I).

8. The composition of claim 1 , comprising from 80% to 99% by mass of the first group of one or more compounds and from 1% to 20% by mass of the second group of one or more compounds.

9. A mixture comprising an edible coating composition in a solvent, the composition comprising:

(i) from 70% to 99% by mass of a first group of one or more compounds, wherein each compound of the first group is a compound of Formula I;

(ii) from 1% to 30% by mass of a second group of one or more compounds, wherein each compound of the second group is a salt of Formula II, wherein Formulas I and II are:

wherein for each of the formulas:

R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently, at each occurrence, —H, —(C═O)R 14 , —(C═O)H, —(C═O)OH, —(C═O)OR 14 , —(C═O)—O—(C═O)R 14 , —O(C═O)R 14 , —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, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;

R 3 , R 4 , R 7 and R 8 are each independently, at each occurrence, —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, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or

R 3 and R 4 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or

R 7 and R 8 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring;

R 14 and R 15 are each independently, at each occurrence, —H, aryl, heteroaryl, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, or —C 2 -C 6 alkynyl;

the symbol represents a single or cis or trans double bond;

n is 0, 1, 2, 3, 4, 5, 6, 7, or 8;

m is 0, 1, 2, or 3;

q is 0, 1, 2, 3, 4, or 5;

r is 0, 1, 2, 3, 4, 5, 6, 7, or 8;

R is -glyceryl; and

X is a cationic moiety.

10. The mixture of claim 9 , wherein the solvent is water.

11. The mixture of claim 9 , wherein the solvent is at least 50% water by volume.

12. The mixture of claim 9 , wherein the first group of compounds comprises one or more compounds selected from the group consisting of:

13. The mixture of claim 12 , wherein the second group of compounds comprises SA-Na, PA-Na, MA-Na, SA-K, PA-K, or MA-K.

14. The mixture of claim 9 , wherein a concentration of the composition in the mixture is in a range of 0.5 to 200 mg/mL.

15. The composition of claim 9 , wherein the first group of one or more compounds comprises at least two compounds of Formula (I).

16. An edible coating composition, comprising:

(i) from 70% to 99% by mass of a first group of one or more compounds, wherein each compound of the first group is a compound of Formula I; and

(ii) from 1% to 30% by mass of a second group of one or more compounds, wherein each compound of the second group is a compound of Formula III, wherein Formula I and Formula III are:

wherein for each of the formulas:

R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently, at each occurrence, —H, —(C═O)R 14 , —(C═O)H, —(C═O)OH, —(C═O)OR 14 , —(C═O)—O—(C═O)R 14 , —O(C═O)R 14 , —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, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;

R 3 , R 4 , R 7 and R 8 are each independently, at each occurrence, —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, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or

R 3 and R 4 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or

R 7 and R 8 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring;

R 14 and R 15 are each independently, at each occurrence, —H, aryl, heteroaryl, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, or —C 2 -C 6 alkynyl;

the symbol represents a single or cis or trans double bond;

n is 0, 1, 2, 3, 4, 5, 6, 7, or 8;

m is 0, 1, 2, or 3;

q is 0, 1, 2, 3, 4, or 5;

r is 0, 1, 2, 3, 4, 5, 6, 7, or 8;

R is -glyceryl; and

X p+ is a cationic counter ion having a charge state p, and p is 2 or 3.

17. The composition of claim 16 , wherein the first group of compounds comprises one or more compounds selected from the group consisting of:

18. The composition of claim 16 , wherein the second group of compounds comprises (SA) 2 -Mg, (PA) 2 -Mg, (MA) 2 -Mg, (SA) 2 -Ca, (PA) 2 -Ca, or (MA) 2 -Ca.

19. The composition of claim 16 , wherein the first group of one or more compounds comprises at least two compounds of Formula (I).

20. A mixture comprising an edible coating composition in a solvent, the composition comprising:

(i) from 70% to 99% by mass of a first group of one or more compounds, wherein each compound of the first group is a compound of Formula I;

(ii) from 1% to 30% by mass of a second group of one or more compounds, wherein each compound of the second group is a compound of Formula III, wherein Formula I and Formula III are:

wherein for each of the formulas:

R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently, at each occurrence, —H, —(C═O)R 14 , —(C═O)H, —(C═O)OH, —(C═O)OR 14 , —(C═O)—O—(C═O)R 14 , —O(C═O)R 14 , —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, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;

R 3 , R 4 , R 7 and R 8 are each independently, at each occurrence, —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, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or

R 3 and R 4 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or

R 7 and R 8 can combine with the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl, a C 4 -C 6 cycloalkenyl, or 3- to 6-membered ring;

R 14 and R 15 are each independently, at each occurrence, —H, aryl, heteroaryl, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, or —C 2 -C 6 alkynyl;

the symbol represents a single or cis or trans double bond;

n is 0, 1, 2, 3, 4, 5, 6, 7, or 8;

m is 0, 1, 2, or 3;

q is 0, 1, 2, 3, 4, or 5;

r is 0, 1, 2, 3, 4, 5, 6, 7, or 8;

R is -glyceryl; and

X p+ is a cationic counter ion having a charge state p, and p is 2 or 3.

21. The mixture of claim 20 , wherein the solvent is water.

22. The mixture of claim 20 , wherein the solvent is at least 50% water by volume.

23. The mixture of claim 20 , wherein each compound of the first group of compounds has a carbon chain length of at least 14.

24. The mixture of claim 23 , wherein each compound of the second group of compounds has a carbon chain length of at least 14.

25. The mixture of claim 20 , wherein the second group of compounds comprises (SA) 2 -Mg, (PA) 2 -Mg, (MA) 2 -Mg, (SA) 2 -Ca, (PA) 2 -Ca, or (MA) 2 -Ca.

26. The mixture of claim 20 , wherein the composition comprises less than 10% by mass of diglycerides.

27. The mixture of claim 20 , wherein the composition comprises less than 10% by mass of triglycerides.

28. The composition of claim 20 , wherein the first group of one or more compounds comprises at least two compounds of Formula (I).

Assignments (3)

Continuity (2)

References Cited (400)