Edible plasticizers for food and food packaging films
View Patent ↗Disclosed are plasticizers, salts thereof, chelates thereof and cleavage derivatives thereof, that exhibit a superior combination of properties. The plasticizers can be used for a variety of purposes, including food preparation, cosmetics, beverages and polymeric matrices. The plasticizers can be prepared by esterifying gallic acid, fulvic acid, or tannic acid.
1. A plasticizing composition comprising a compound of formula I:
a salt thereof, a chelate thereof, or a combination thereof,
wherein R 1A , R 1B , and R 1C are independently selected from hydrogen, —(C═O)—(C 8 -C 16 )alkyl, or —(C═O)—(C 8 -C 16 )alkenyl, wherein at least two of R 1A , R 1B , and R 1C are not hydrogen;
R 2 is —(C 8 -C 16 )alkyl, —(C 8 -C 16 )alkenyl, -mannitosyl, -sorbitolyl, or -sucrosyl.
2. The composition of claim 1 , wherein R 2 is —(C 8 -C 16 )alkyl or —(C 8 -C 16 )alkenyl.
3. The composition of claim 1 , wherein R 2 is -mannitosyl, -sorbitolyl, or -sucrosyl.
4. The composition of claim 1 , wherein R 2 is selected from the group consisting of:
5. The composition of claim 1 , wherein R 2 is selected from the group consisting of:
6. The composition of claim 1 , wherein R 1A , R 1B , and R 1C are independently selected from —(C═O)—(C 8 -C 16 )alkyl and —(C═O)—(C 8 -C 16 )alkenyl.
7. The composition of claim 1 , wherein the at least one compound comprises a sodium salt, an ammonium salt, a potassium salt, a calcium salt, a magnesium salt, a manganese salt, a zinc salt, an iron salt, or a combination thereof.
8. The composition of claim 1 , wherein the at least one compound comprises a transition metal ion chelate.
9. A method of preparing a plasticizing compound, the method comprising esterifying gallic acid to form a plasticizing compound of formula I:
a salt thereof, a chelate thereof, or a combination thereof,
wherein R 1A , R 1B , and R 1C are independently selected from hydrogen, —(C═O)—(C 8 -C 16 )alkyl, and —(C═O)—(C 8 -C 16 )alkenyl, wherein at least two of R 1A , R 1B , and R 1C are not hydrogen;
R 2 is —(C 8 -C 16 )alkyl, —(C 8 -C 16 )alkenyl, -mannitosyl, -sorbitolyl, or -sucrosyl.
10. The method of claim 9 , wherein the method includes esterifying the gallic acid to form at least one compound of formula I, wherein R 1A , R 1B , and R 1C are independently selected from hydrogen, —(C═O)—(C 8 -C 16 )alkyl, and —(C═O)—(C 8 -C 16 )alkenyl, wherein at least two of R 1A , R 1B , and R 1C are not hydrogen;
wherein R 2 is selected from the group consisting of:
11. The method of claim 9 , wherein the method includes esterifying the gallic acid to form at least one compound of formula I, wherein R 2 is selected from the group consisting of
12. The method of claim 9 , wherein R 1A , R 1B , and R 1C are independently selected from —(C═O)—(C 8 -C 16 )alkyl and —(C═O)—(C 8 -C 16 )alkenyl.
13. The method of claim 9 , wherein the method comprises esterifying the gallic acid to form at least one compound of formula I, wherein the compound is a sodium salt, an ammonium salt, a potassium salt, a calcium salt, a magnesium salt, a manganese salt, a zinc salt, an iron salt, or a combination thereof.
14. The method of claim 9 , wherein the method comprises esterifying the gallic acid to form at least one compound of formula I, wherein the compound is a transition metal ion chelate.
15. A treated food product comprising at least one of the plasticizing compound of formula I of claim 1 , wherein the food product comprises a dairy product, fat, oil, fat emulsion, edible ice, fruit, vegetable, fungi, seaweed, nuts, seeds, confectionery, cereal, cereal product derived from cereal grains, bakery ware, meat, meat byproduct, fish, fish product, egg product, sugar, artificial sweetener, spices, condiment, soup, sauce, salad, protein mix, non-dairy beverage, savory snack, or combinations thereof.