Coating composition comprising lecithin or a derivative thereof

Abstract

The present disclosure relates to compositions comprising monoglycerides and alkyl esters of fatty acids. Exemplary embodiments include from about 15% to about 99% by weight of one or more C4 to C6 alkyl esters. 28 Monoglycerides of fatty acids, and about 1% to about 75% by weight of one or more C8 to C6 20 The composition contains one or more alkyl esters of fatty acids, C4 to C6, present in a total amount of about 10% to about 90% by weight of the composition. 28 Provided herein are compositions comprising a monoglyceride of a fatty acid, and lecithin present in an amount of about 10% to about 90% by weight of the composition.

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of priority to U.S. Application No. 63 / 427,758, filed November 23, 2022, which is incorporated by reference herein in its entirety.

[0002] Technical Field FIELD OF THE DISCLOSURE The present disclosure relates to coatings for agricultural products. [Background technology]

[0003] background Common agricultural products are susceptible to deterioration and decomposition (i.e., spoilage) when exposed to the environment. Such agricultural products can include, for example, eggs, fruits, vegetables, produce, seeds, nuts, flowers, and / or whole plants (including their processed and semi-processed forms). Non-agricultural products (e.g., vitamins, candy, etc.) are also susceptible to deterioration when exposed to the ambient environment. Deterioration of agricultural products can occur through abiotic means as a result of evaporative water loss from the exterior surface of the agricultural product into the atmosphere, and / or oxidation by oxygen diffusing into the agricultural product from the environment, and / or mechanical damage to the surface, and / or light-induced decomposition (i.e., photodegradation). Additionally, biotic stressors, such as bacteria, fungi, viruses, and / or pests, can also infest and decompose agricultural products.

[0004] Traditional approaches to preventing deterioration, maintaining quality, and extending the shelf life of agricultural produce include refrigeration and / or specialized packaging. Refrigeration requires capital-intensive equipment, requires constant energy consumption, and, if not carefully controlled, can cause product spoilage or quality loss and must be actively managed. Additionally, interruptions in the temperature-controlled supply chain can negate the benefits of refrigeration. Specialized packaging also requires expensive equipment, consumes packaging materials, increases transportation costs, and can require active management. Despite the potential benefits of refrigeration and specialized packaging, handling and transportation of agricultural produce can cause surface abrasions or bruises, which are unsightly to consumers and can serve as entry points for bacteria and fungi. Furthermore, the expenses associated with such approaches can increase the cost of agricultural produce. Summary of the Invention [Means for solving the problem]

[0005] overview One or more C4-C hydroxybenzoates present in a total amount of about 10% to about 90% by weight of the composition 28 Provided herein are compositions comprising a monoglyceride of a fatty acid, and lecithin present in an amount of about 10% to about 90% by weight of the composition.

[0006] One or more types of C4 to C 28 Also provided herein is a composition comprising a monoglyceride of a fatty acid and lecithin, wherein the ratio of the total mass of the one or more monoglycerides to the total mass of the lecithin is from about 10:1 to about 1:10.

[0007] One or more types of C4 to C 28 Monoglycerides of fatty acids, one or more, C4 to C 28Also provided herein is a composition comprising an alkyl ester of a fatty acid and lecithin, wherein the ratio of the total mass of the one or more monoglycerides to the total mass of the one or more alkyl esters is about 20:1 to about 1:1, and the ratio of the total mass of the one or more monoglycerides and the one or more alkyl esters to the total mass of the lecithin is about 10:1 to about 1:10.

[0008] One or more C4-C hydroxybenzoates present in a total amount of about 10% to about 90% by weight of the composition 28 Also provided herein are compositions comprising a monoglyceride of a fatty acid and one or more glycerophospholipids present in an amount of about 4% to about 40% by weight of the composition.

[0009] Also provided herein are mixtures of the compositions described herein and solvents.

[0010] Also provided herein are coated agricultural products comprising an agricultural product and a layer disposed on a surface of the agricultural product, wherein the layer comprises a composition described herein.

[0011] Also provided herein is a method of coating an agricultural produce, the method comprising contacting a surface of the agricultural produce with a mixture comprising a coating agent and a solvent, and removing at least a portion of the solvent to form a coating on the surface of the agricultural produce. The coating agent may be one or more C4-C 28 The monoglycerides of fatty acids and lecithin are included, and the ratio of the total mass of the one or more monoglycerides to the total mass of the lecithin is about 10:1 to about 1:10.

[0012] Also provided herein is a method of coating an agricultural produce, the method comprising contacting a surface of the agricultural produce with a mixture described herein and removing at least a portion of the solvent to form a coating on the surface of the agricultural produce.

[0013] While the disclosed inventive concepts include those defined in the appended claims, it should be understood that the inventive concepts can also be defined according to the following embodiments.

[0014] Embodiment 1 is a composition comprising: One or more C4-C hydroxybenzoates present in a total amount of about 10% to about 90% by weight of the composition. 28 Monoglycerides of fatty acids, and Lecithin present in an amount of about 10% to about 90% by weight of the composition A composition comprising:

[0015] Embodiment 2 is a method for preparing a glyceride-based emulsion, wherein the one or more monoglycerides are present in a total amount of from about 10% to about 50% by weight of the composition; The lecithin is present in an amount of about 50% to about 90% by weight of the composition. The composition of embodiment 1.

[0016] Embodiment 3 is a composition comprising a composition comprising one or more monoglycerides present in a total amount of from about 50% to about 90% by weight of the composition; The lecithin is present in an amount of about 10% to about 50% by weight of the composition. The composition of embodiment 1.

[0017] Embodiment 4 is a method for preparing a glyceride-based emulsion, wherein the one or more monoglycerides are present in a total amount of about 50% to about 65% by weight of the composition; The lecithin is present in an amount of about 35% to about 50% by weight of the composition. The composition of embodiment 3.

[0018] Embodiment 5 is a composition comprising a composition comprising one or more monoglycerides, wherein the one or more monoglycerides are present in an amount from about 65% to about 80% by weight of the composition; The lecithin is present in an amount of about 20% to about 35% by weight of the composition. The composition of embodiment 3.

[0019] Embodiment 6 is a composition comprising a composition comprising one or more monoglycerides, wherein the one or more monoglycerides are present in an amount of about 80% to about 90% by weight of the composition; The lecithin is present in an amount of about 10% to about 20% by weight of the composition. The composition of embodiment 3.

[0020] Embodiment 7 is a method for preparing a glyceride-based glyceride comprising the step of: One or more species of C 16 ~C 28 Monoglycerides of fatty acids, and One or more types of C4 to C 14 Monoglycerides of fatty acids 7. The composition of any one of embodiments 1 to 6, comprising:

[0021] Embodiment 8 is a method for producing one or more of the C4 to C 14 8. The composition of embodiment 7, wherein the monoglycerides of fatty acids are present in a total amount from about 1% to about 15% by weight of the composition.

[0022] Embodiment 9 is a ninth embodiment of the present invention, which comprises one or more C4 to C 28 Monoglycerides of fatty acids, and lecithin wherein the ratio of the total mass of the one or more monoglycerides to the total mass of the lecithin is from about 10:1 to about 1:10.

[0023] Embodiment 10 is the composition of embodiment 9, wherein the ratio of the total weight of the one or more monoglycerides to the total weight of the lecithin is from about 1:1 to about 1:9.

[0024] Embodiment 11 is the composition of embodiment 9, wherein the ratio of the total weight of the one or more monoglycerides to the total weight of the lecithin is from about 9:1 to about 1:1.

[0025] Embodiment 12 is the composition of embodiment 11, wherein the ratio of the total weight of the one or more monoglycerides to the total weight of the lecithin is from about 2:1 to about 1:1.

[0026] Embodiment 13 is the composition of embodiment 11, wherein the ratio of the total weight of the one or more monoglycerides to the total weight of the lecithin is from about 4:1 to about 2:1.

[0027] Embodiment 14 is the composition of embodiment 11, wherein the ratio of the total weight of the one or more monoglycerides to the total weight of the lecithin is from about 9:1 to about 4:1.

[0028] Embodiment 15 is a process for preparing a glyceride-based ... One or more species of C 16 ~C 28 Monoglycerides of fatty acids, and One or more types of C4 to C 14 Monoglycerides of fatty acids 15. The composition of any of embodiments 9 to 14, comprising:

[0029] Embodiment 16 is the composition of any of embodiments 9 to 15, wherein the one or more monoglycerides and the lecithin are present in an amount of at least about 80% by weight of the composition.

[0030] Embodiment 17 is directed to one or more C4 to C6 28 Monoglycerides of fatty acids, One or more types of C4 to C 28 alkyl esters of fatty acids, and lecithin A composition comprising: the ratio of the total mass of the one or more monoglycerides to the total mass of the one or more alkyl esters is about 20:1 to about 1:1; the ratio of the total mass of the one or more monoglycerides and the one or more alkyl esters to the total mass of the lecithin is about 10:1 to about 1:10; It is a composition.

[0031] Embodiment 18 is a method for preparing a composition comprising: a) a glyceride-containing emulsion ... The lecithin is present in an amount of about 50% to about 90% by weight of the composition. 18. The composition of embodiment 17.

[0032] Embodiment 19 is a method for preparing a composition comprising the steps of: The lecithin is present in an amount of about 10% to about 50% by weight of the composition. 18. The composition of embodiment 17.

[0033] Embodiment 20 is the composition of any of embodiments 17 to 19, wherein the one or more monoglycerides, the one or more alkyl esters, and the lecithin are present in an amount of at least about 80% by weight of the composition.

[0034] Embodiment 21 is the composition of any of embodiments 17 to 20, wherein the ratio of the total weight of the one or more monoglycerides to the total weight of the one or more alkyl esters is from about 10:1 to about 2:1.

[0035] Embodiment 22 is the composition of any of embodiments 1 to 21, wherein the lecithin comprises hydrolyzed lecithin.

[0036] Embodiment 23 is a composition according to any one of embodiments 1 to 22, wherein the lecithin comprises soybean lecithin, sunflower lecithin, or rapeseed lecithin.

[0037] Embodiment 24 is a composition of any one of embodiments 1 to 23, wherein the lecithin comprises one or more glycerophospholipids.

[0038] Embodiment 25 is the composition of embodiment 24, wherein the one or more glycerophospholipids are present in an amount from about 20% to about 60% by weight of the lecithin.

[0039] Embodiment 26 is a composition of any one of embodiments 1 to 25, wherein the lecithin comprises one or more triglycerides.

[0040] Embodiment 27 is the composition of embodiment 26, wherein the one or more triglycerides are present in an amount from about 5% to about 50% by weight of the lecithin.

[0041] Embodiment 28 is a composition comprising: One or more C4-C hydroxybenzoates present in a total amount of about 10% to about 90% by weight of the composition. 28 Monoglycerides of fatty acids, and one or more glycerophospholipids present in an amount of about 4% to about 40% by weight of the composition; A composition comprising:

[0042] Embodiment 29 is a method for preparing a glyceride-based emulsion, wherein the one or more monoglycerides are present in a total amount of from about 50% to about 90% by weight of the composition; the one or more glycerophospholipids are present in a total amount of about 4% to about 25% by weight of the composition; 29. The composition of embodiment 28.

[0043] Embodiment 30 is a method for preparing a glyceride-based glyceride comprising the step of: One or more species of C 16 ~C 28 Monoglycerides of fatty acids, and One or more types of C4 to C 14 Monoglycerides of fatty acids 29. The composition of claim 28 or 29, comprising:

[0044] Embodiment 31 is directed to one or more of the C4 to C 14 31. The composition of embodiment 30, wherein the monoglycerides of fatty acids are present in a total amount from about 1% to about 15% by weight of the composition.

[0045] Embodiment 32 is a composition according to any of embodiments 28 to 31, further comprising one or more triglycerides.

[0046] Embodiment 33 is the composition of embodiment 32, wherein the one or more triglycerides are present in a total amount from about 3% to about 35% by weight of the composition.

[0047] Embodiment 34 is the composition of embodiment 32, wherein the one or more triglycerides are present in a total amount from about 3% to about 20% by weight of the composition.

[0048] Embodiment 35 is the composition of any of embodiments 24 to 34, wherein the one or more glycerophospholipids comprise phosphatidylcholine, lysophosphatidylcholine, phosphatidylethanolamine, lysophosphatidylethanolamine, phosphatidylinositol, lysophosphatidylinositol, phosphatidylserine, lysophosphatidylserine, phosphatidic acid, lysophosphatidic acid, or any combination thereof.

[0049] Embodiment 36 is the composition of embodiment 35, wherein the one or more glycerophospholipids comprise phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, and phosphatidic acid.

[0050] Embodiment 37 is the composition of embodiment 35 or embodiment 36, wherein the one or more glycerophospholipids comprise phosphatidylserine.

[0051] Embodiment 38 is an embodiment wherein one or more of the glycerophospholipids independently comprises one or more C8 to C9 22 38. The composition of any of embodiments 24 to 37, comprising a side chain.

[0052] Embodiment 39 is an embodiment wherein one or more of the triglycerides independently comprises one or more C8 to C9 22 The composition of any of embodiments 26, 27, and 32-38, comprising a side chain.

[0053] Embodiment 40 is an embodiment wherein one or more of the glycerophospholipids independently has Formula III: [ka] wherein: Each R P1 are independently -H, [ka] and R P2 and R P3 are each independently -H or -C(O)R H and R P2 and R P3 At least one of the is not -H, Each R H are independently C7~C 21 The side chain is 40. The composition of any one of embodiments 24 to 39.

[0054] Embodiment 41 is an embodiment wherein one or more of the triglycerides independently have the formula IV: [ka] wherein: R G1 , R G2 , and R G3 are each independently -C(O)R H and Each R H are independently C7~C 21 The side chain is The composition of any of embodiments 26, 27, and 32 to 40.

[0055] Embodiment 42 is a method for preparing a compound according to the present invention, H But independently, C 15 or C 17 The composition of embodiment 40 or embodiment 41, wherein the side chain

[0056] Embodiment 43 is a method for preparing a compound according to the present invention, H 43. The composition of any of embodiments 40 to 42, wherein: is an unsubstituted side chain.

[0057] Embodiment 44 is a method for preparing a compound according to the present invention, H is independently a saturated, monounsaturated, diunsaturated, or triunsaturated side chain.

[0058] Embodiment 45 is an embodiment wherein each of the one or more monoglycerides independently has Formula Ii or Formula I-ii: [ka] wherein: R A1 and R A2 are each independently selected from H and C1-C6 alkyl; R H is C3~C 27 The side chain is 45. The composition of any one of embodiments 1 to 44.

[0059] Embodiment 46 is R A1 and R A2 and each is H.

[0060] Embodiment 47 is R H is an unsubstituted saturated side chain.

[0061] Embodiment 48 is R H C 11 ~C 21 48. The composition of any of embodiments 45 to 47, wherein the side chain

[0062] Embodiment 49 is a method for preparing a glycerol-based glyceride comprising the steps of: R H C 15 ~C 27 a first compound of formula Ii or formula I-ii, which is a side chain; and R H C3~C 13 a second compound of formula Ii or formula I-ii which is a side chain 49. The composition of any of embodiments 45 to 48, comprising:

[0063] Embodiment 50 is an embodiment wherein each of the one or more monoglycerides independently has formula IA-i or formula IA-ii: [ka] wherein: R A1 and R A2 are each independently selected from H and C1-C6 alkyl; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R 10A , R 10B , R 11A , and R 11B each occurrence is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R on adjacent carbon atoms1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A , and R 11B any two of can be taken together with the carbon atoms to which they are attached to form a double bond, a 3- to 6-membered heterocycloalkyl, or a C3-C6 cycloalkyl; o is an integer from 0 to 17, p is an integer from 0 to 17, The sum of o and p is 0 to 17. 45. The composition of any one of embodiments 1 to 44.

[0064] Embodiment 51 is R A1 and R A2 and each is H.

[0065] Embodiment 52 is the composition of any of embodiments 17 to 51, wherein the one or more alkyl esters each independently comprise a C1 to C5 alkyl ester.

[0066] Embodiment 53 is the composition of any of embodiments 17 to 51, wherein the one or more alkyl esters each independently comprise a methyl ester, an ethyl ester, a propyl ester, an isopropyl ester, a tert-butyl ester, or an iso-amyl ester.

[0067] Embodiment 54 is the composition of any of embodiments 17 to 53, wherein at least one of the alkyl esters comprises an ethyl ester or a propyl ester.

[0068] Embodiment 55 is an embodiment wherein each of the one or more alkyl esters independently has the formula V: [ka] wherein: R B is a C1-C8 alkyl; R H is C7~C 19 The side chain is 52. The composition of any one of embodiments 17 to 51.

[0069] Embodiment 56 is R B is C1-C5 alkyl.

[0070] Embodiment 57 is R B is a C2 alkyl or a C3 alkyl.

[0071] Embodiment 58 is R H is an unsubstituted saturated side chain.

[0072] Embodiment 59 is R H C 11 ~C 17 59. The composition of any of embodiments 55 to 58, wherein the side chain

[0073] Embodiment 60 is A composition according to any one of embodiments 1 to 59, and solvent It is a mixture comprising:

[0074] Embodiment 61 is the mixture of embodiment 60, wherein the mixture comprises from about 30% to about 99.9% by weight of the solvent.

[0075] Embodiment 62 is the mixture of embodiment 60, wherein the mixture comprises from about 90% to about 99.5% by weight of the solvent.

[0076] Embodiment 63 is a mixture of any of embodiments 60 to 62, wherein the solvent comprises one or more of water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, and methyl tert-butyl ether.

[0077] Embodiment 64 is a coated agricultural product comprising: an agricultural product; and a layer disposed on a surface of the agricultural product, wherein the layer comprises the composition of any of embodiments 1 to 59.

[0078] Embodiment 65 is the coated agricultural product of embodiment 64, wherein the layer is disposed on a cuticular surface of the agricultural product.

[0079] Embodiment 66 is the coated agricultural product of embodiment 64 or embodiment 65, wherein the layer has a thickness of from about 0.1 μm to about 20 μm.

[0080] Embodiment 67 is the coated agricultural product of embodiment 64 or embodiment 65, wherein the layer has a thickness of from about 0.1 μm to about 10 μm.

[0081] Embodiment 68 is a method of coating agricultural produce, the method comprising: contacting the surface of the agricultural produce with a mixture comprising a coating agent and a solvent, the coating agent comprising: One or more types of C4 to C 28 Monoglycerides of fatty acids, and lecithin wherein the ratio of the total mass of the one or more monoglycerides to the total mass of the lecithin is from about 10:1 to about 1:10; and removing at least a portion of the solvent to form a coating on the surface of the agricultural produce. The method includes:

[0082] Embodiment 69 is a method for preparing a glyceride-based glyceride comprising the steps of: One or more species of C 16 ~C 28 Monoglycerides of fatty acids, and One or more types of C4 to C 14 Monoglycerides of fatty acids 69. The method of embodiment 68, comprising:

[0083] Embodiment 70 is the method of embodiment 68 or embodiment 69, wherein the one or more monoglycerides and the lecithin are present in an amount of at least about 80% by weight of the coating.

[0084] Embodiment 71 is the method of any of embodiments 68 to 70, wherein the concentration of the coating agent in the mixture is from about 1 mg / mL to about 200 mg / mL.

[0085] Embodiment 72 is the method of any of embodiments 68 to 70, wherein the concentration of the coating agent in the mixture is from about 25 mg / mL to about 150 mg / mL.

[0086] Embodiment 73 is the method of any of embodiments 68 to 72, wherein the solvent comprises one or more of water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, and methyl tert-butyl ether.

[0087] Embodiment 74 is the method of any of embodiments 68 to 73, wherein the coating agent and the solvent are present in an amount of at least about 98% by weight of the mixture.

[0088] Embodiment 75 is the method of any of embodiments 68 to 74, wherein the surface is a cuticular surface of the agricultural produce.

[0089] Embodiment 76 is a method for contacting the surfaces comprising: spraying the mixture onto the surface; or immersing the agricultural produce in the mixture. 76. The method of any of embodiments 68 to 75, comprising:

[0090] Embodiment 77 is the method of any of embodiments 68 to 76, wherein removing at least a portion of the solvent comprises evaporating at least a portion of the solvent at a temperature of less than 40° C.

[0091] Embodiment 78 is the method of any of embodiments 68 to 76, wherein removing at least a portion of the solvent comprises evaporating at least a portion of the solvent at a temperature of less than 30° C.

[0092] Embodiment 79 is the method of any of embodiments 68 to 76, wherein removing at least a portion of the solvent comprises evaporating at least a portion of the solvent at a temperature between 10°C and 30°C.

[0093] Embodiment 80 is the method of any of embodiments 68 to 79, further comprising combining the coating agent and the solvent to form the mixture.

[0094] Embodiment 81 is a method of coating agricultural produce, the method comprising: Contacting the surface of the agricultural produce with a mixture according to any of embodiments 60 to 63; and removing at least a portion of the solvent to form a coating on the surface of the agricultural produce. The method includes:

[0095] The details of one or more embodiments of the presently disclosed subject matter are set forth in the accompanying drawings and the description. Other features, aspects, and advantages of the present subject matter will become apparent from the description, drawings, and claims. [Brief explanation of the drawings]

[0096] [Figure 1] FIG. 1 is a plot of the differential scanning calorimetry (DSC) curve for certain mixtures described herein.

[0097] [Figure 2] FIG. 2 is a plot of the DSC curve for certain mixtures described herein.

[0098] [Figure 3] FIG. 3 is a plot of predicted mass loss coefficient versus crystallization enthalpy for certain coating mixtures described herein.

[0099] [Figure 4] FIG. 4 shows the initial design space for space-filling mixture design of experiments (DoE) for certain formulations described herein.

[0100] [Figure 5] FIG. 5 is a profile of miscibility results from the space-filling mixture DoE described herein.

[0101] [Figure 6] FIG. 6 is a stability result profile from the space-filling mixture DoE described herein.

[0102] [Figure 7] FIG. 7 shows the initial design space for space-filling mixture Design of Experiments (DoE) for certain formulations described herein.

[0103] [Figure 8]8A-8D show images of coated cherries with residual scores of 0, 0.5, 1, and 2, respectively, determined for the space-filling mixture DoE described herein.

[0104] [Figure 9] FIG. 9 is a ternary plot of the mass loss coefficient results for the space-filling mixture DoE described herein.

[0105] [Figure 10] FIG. 10 is a ternary plot of the residual score results for the space-filling mixture DoE described herein.

[0106] [Figure 11] 11A-11C show images of cherries coated with certain coatings described herein.

[0107] [Figure 12] 12A-12C show images of bananas coated with certain coatings described herein, with peeling indicated by the arrows.

[0108] [Figure 13] 13A and 13B show images of bananas coated with certain coatings described herein.

[0109] [Figure 14] FIG. 14 is a series of plots showing viscosity data collected from certain mixtures described herein.

[0110] [Figure 15] 15A and 15B show images of cherry tomatoes coated with certain coatings described herein.

[0111] [Figure 16] 16A-16F show images of uncoated cherry tomatoes and cherry tomatoes coated with certain coatings described herein. DETAILED DESCRIPTION OF THE INVENTION

[0112] Detailed Description The present disclosure relates to a composition comprising a monoglyceride and lecithin. In some embodiments, the composition further comprises an alkyl ester. In particular, the compositions described herein can be coated on agricultural products and dried at ambient temperatures to provide, for example, an effective barrier against gases or water, and can have improved aesthetic properties (e.g., reduced visible residue).

[0113] Reference will now be made in detail to certain embodiments of the disclosed subject matter. While the disclosed subject matter will be described in conjunction with the enumerated claims, it will be understood that the illustrated subject matter is not intended to limit the claims to the disclosed subject matter.

[0114] definition

[0115] The terms "a," "an," and "the" are used herein to include one or more than one, unless the context clearly dictates otherwise. The term "or" is used to refer to a non-exclusive "or" unless otherwise noted. The statement "at least one of A and B" has the same meaning as "A, B, or A and B." Additionally, it should be understood that phrases or terms utilized in this disclosure, unless otherwise defined, are for descriptive purposes only and not for purposes of limitation. Any use of section headings is intended to aid in the reading of the document and should not be construed as limiting. Information associated with a section heading may occur within or outside the particular section.

[0116] Values ​​expressed in range format should be interpreted in an open manner and should be construed to include not only the numerical values ​​explicitly recited as the limits of the range, but also all individual numerical values ​​or subranges subsumed within the range, as if each numerical value and subrange were explicitly recited. For example, a range such as "about 0.1% to about 5%" or "about 0.1% to 5%" should be interpreted to include not only about 0.1% to about 5%, but also individual values ​​(e.g., 1%, 2%, 3%, and 4%) and subranges (e.g., 0.1% to 0.5%, 1.1% to 2.2%, 3.3% to 4.4%) within the recited range. The statement "about X to Y" has the same meaning as "about X to about Y" unless otherwise indicated. Similarly, the statement "about X, Y, or about Z" has the same meaning as "about X, about Y, or about Z" unless otherwise indicated.

[0117] As used herein, the term "about" allows for a variation of a value or range to within 10% of the stated value or limit of a stated range.

[0118] In the methods described herein, acts may be performed in any order unless a temporal or operational order is explicitly recited. Furthermore, specified acts may be performed simultaneously unless the claim language clearly dictates that they be performed separately. For example, a claimed act of performing X and a claimed act of performing Y may be performed simultaneously in a single operation, and the resulting process would fall within the literal scope of the claimed process.

[0119] As used herein, the term "monoglyceride" refers to the condensation product of one glycerol molecule and one fatty acid, i.e., a glycerol group linked to one fatty acid via an ester bond. Monoglycerides can be, but do not necessarily have to be, derived from a condensation reaction. For example, monoglycerides can be obtained by an esterification reaction between glycerol and a fatty acid, such as by transesterification of a triglyceride with glycerol (glycerolysis). Monoglycerides are also sometimes referred to as glyceryl monoalkanoates. When the glycerol group is linked to the ester bond at the 1-position (e.g., as in 2,3-dihydroxypropan-1-yl octadecanoate), the monoglyceride may be referred to as a 1-monoglyceride or a 1-glyceryl alkanoate (e.g., as in 1-glyceryl octadecanoate). When the glycerol group is attached to the ester bond at the 2-position (e.g., as in 1,3-dihydroxypropan-2-yl hexadecanoate), the monoglyceride may be referred to as a 2-monoglyceride or a 2-glyceryl alkanoate (e.g., as in 2-glyceryl hexadecanoate). The glycerol group of the monoglyceride may be unsubstituted (e.g., as in 2,3-dihydroxypropan-1-yl alkanoate) or may be further substituted with one or more groups other than fatty acids (e.g., as in 1,3-dialkoxypropan-2-yl alkanoate).

[0120] The term "alkyl ester" used in reference to fatty acids refers to the condensation product of an alkanol and a fatty acid, i.e., an alkyl group attached to one fatty acid via an ester bond. Alkyl esters can be, but do not necessarily have to be, derived from a condensation reaction. For example, alkyl esters can be obtained by esterification between an alkanol and a fatty acid, or by transesterification of monoglycerides, triglycerides, etc. Alkyl esters are also sometimes called alkyl alkanoates. For example, the ethyl ester of hexadecanoic acid is sometimes called ethylhexadecanoate.

[0121] As used herein, the term "fatty acid" refers to a carboxylic acid having an aliphatic side chain. Fatty acids can be naturally occurring or non-naturally occurring and can contain branched or unbranched (e.g., straight-chain), substituted or unsubstituted, saturated or unsaturated side chains.

[0122] As used herein, the term "side chain" refers to the aliphatic portion of a fatty acid, or a portion thereof. Unless otherwise indicated, the side chain of a given fatty acid includes the carbon of the carboxylic acid group. For example, dodecanoic acid has a straight-chain saturated C 12 side chains, R H -C(O)OH (where R H is the saturated C 11 Side chains other than fatty acids (e.g., esters or amides) can be present in the compound and can be, but need not be, derived from fatty acids. For example, dodecanamide can be described as an amide of a fatty acid, regardless of whether the compound is actually derived from dodecanoic acid.

[0123] When certain features of the compounds described herein are disclosed as groups or ranges, such disclosure includes any and all individual subcombinations of the members of such groups and ranges. For example, the term "C1-C6 alkyl" includes (without limitation) methyl, ethyl, C3 alkyl, C4 alkyl, C5 alkyl, and C6 alkyl.

[0124] As used herein, the term "n-membered" (where n is an integer) generally describes the number of ring-forming atoms in a moiety where n is the number of ring-forming atoms. For example, piperidinyl is an example of a 6-membered heterocycloalkyl ring, and 1,2,3,4-tetrahydro-naphthalene is an example of a 10-membered cycloalkyl group.

[0125] As used herein, the term "substituted" means that an atom or group of atoms is formally replaced with hydrogen as a "substituent" attached to another group. "Substituted" refers to any level of substitution, for example, mono-, di-, tri-, tetra-, or penta-substitution, unless otherwise specified, where such substitution is permitted. Substituents are independently selected, and substitution may occur at any chemically available position. Substitution at a given atom is limited by valence. Substitution at a given atom results in a chemically stable molecule. The phrase "optionally substituted" means unsubstituted or substituted. A single divalent substituent, for example, oxo, can replace two hydrogen atoms.

[0126] As used herein, "C n ~C m The term "(where n and m are integers and indicate the number of carbons)" denotes a range that includes the endpoints. Examples include C1-C4, C1-C6, etc.

[0127] As used herein, the term "alkyl" refers to a saturated hydrocarbon group which may be straight-chained or branched. n ~C mThe term "alkyl" refers to an alkyl group having n to m carbon atoms. An alkyl group formally corresponds to an alkane in which one C-H bond is replaced by the point of attachment of the alkyl group to the remainder of the compound. Examples of alkyl moieties include, but are not limited to, chemical groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl; higher homologs such as 2-methyl-1-butyl, n-pentyl, 3-pentyl, n-hexyl, 1,2,2-trimethylpropyl, and the like.

[0128] As used herein, the term "alkenyl" refers to a straight-chain or branched hydrocarbon group corresponding to an alkyl group having one or more carbon-carbon double bonds. An alkenyl group formally corresponds to an alkene in which one C-H bond is replaced by the point of attachment of the alkenyl group to the remainder of the compound. n ~C m The term "alkenyl" refers to an alkenyl group having n to m carbons. Exemplary alkenyl groups include, but are not limited to, ethenyl, n-propenyl, isopropenyl, n-butenyl, sec-butenyl, and the like.

[0129] As used herein, the term "alkoxy" refers to a group of formula -O-alkyl, where the alkyl group is as defined above. n ~C m The term "alkoxy" refers to an alkoxy group, wherein the alkyl group of the alkoxy group has n to m carbons. Exemplary alkoxy groups include methoxy, ethoxy, propoxy (e.g., n-propoxy and isopropoxy), t-butoxy, and the like.

[0130] As used herein, the term "cycloalkyl" refers to a non-aromatic hydrocarbon ring system (monocyclic, bicyclic, or polycyclic) and includes cyclized alkyl and cyclized alkenyl groups. n ~C mThe term "cycloalkyl" refers to a cycloalkyl group having n to m ring carbon atoms. Cycloalkyl groups can include fused, bridged, and / or spiro bicyclic or polycyclic ring systems. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cyclohexadienyl, cycloheptatrienyl, norbornyl, norpinyl, norcarnyl, bicyclo[1.1.0]butanyl, bicyclo[1.1.1]pentanyl, bicyclo[2.1.0]pentanyl, bicyclo[2.2.0]hexanyl, bicyclo[3.1.0]hexanyl, bicyclo[3.2.0]heptanyl, and bicyclo[3.3.0]octanyl, bicyclo[2.1.1]hexanyl, bicyclo[2.2.1]heptanyl, and bicyclo[1.1.1]pentanyl.

[0131] As used herein, the term "heterocycloalkyl" refers to a non-aromatic ring system (monocyclic, bicyclic, or polycyclic) that may optionally contain one or more alkenylene groups as part of the ring structure and has at least one heteroatom ring member independently selected from nitrogen, sulfur, oxygen, and phosphorus. The term "nm- to m-membered heterocycloalkyl" refers to a heterocycloalkyl having nm to m ring-forming atoms. Ring-forming carbon atoms and heteroatoms of a heterocycloalkyl group can be optionally oxidized to form oxo or sulfide groups or other oxidized bonds (e.g., C(O), S(O), C(S), S(O), N-oxide, etc.), or the nitrogen atom can be quaternized. A heterocycloalkyl group can be bonded via a ring-forming carbon atom or ring-forming heteroatom. A heterocycloalkyl group can contain double bonds, for example, up to three double bonds.Examples of heterocycloalkyl groups include, but are not limited to, azetidinyl, dihydrofuranyl, dihydrothiophenyl, tetrahydrothiophenyl, tetrahydrofuranyl, tetrahydrotriazinyl, tetrahydropyrazolyl, tetrahydrooxazinyl, tetrahydropyrimidinyl, octahydrobenzofuranyl, octahydrobenzimidazolyl, octahydrobenzothiazolyl, imidazolidinyl, pyrrolidinyl, piperidinyl, piperazinyl, oxazolidinyl, thiazolidinyl, pyrazolidinyl, thiomorpholinyl, tetrahydropyranyl, tetrahydrothiazinyl, tetrahydrothiadiazinyl, tetrahydro-oxazolyl, morpholinyl, oxetanyl, Dioxetanyl, dioxolanyl, dioxanyl, oxapanyl, dioxapanyl, oxacanyl, dioxacanyl, tetrahydrodiazinyl, oxazinyl, oxathiazinyl, quinuclidinyl, chromanyl, isochromanyl, dihydrobenzodioxinyl, benzodioxolyl, benzoxazinyl, indolinyl, dihydrobenzofuranyl, tetrahydroquinolyl, isochromyl, dihydro-1H-isoindolyl, 2-azabicyclo[2.2.1]heptanonyl, 3-azabicyclo[3.1.0]hexanyl, 3-azabicyclo[4.1.0]heptanyl, and the like.Further examples of heterocycloalkyl groups include tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, imidazolidin-1-yl, imidazolidin-2-yl, imidazolidin-4-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, piperazin-1-yl, piperazin-2-yl, 1,3-oxazolidine-3-yl, and the like. yl, 1,4-oxazepan-1-yl, isothiazolidinyl, 1,3-thiazolidin-3-yl, 1,2-pyrazolidin-2-yl, 1,2-tetrahydrothiazin-2-yl, 1,3-thiazinan-3-yl, 1,2-tetrahydrodiazin-2-yl, 1,3-tetrahydrodiazin-1-yl, 1,4-oxazin-4-yl, oxazolidinonyl, 2-oxo-piperidinyl (e.g., 2-oxo-piperidin-1-yl), and the like.

[0132] composition

[0133] One or more types of C4 to C 28 Provided herein are compositions comprising a monoglyceride of a fatty acid and lecithin.

[0134] In some embodiments, the one or more monoglycerides are present in a total amount of about 10% to about 90%, about 10% to about 80%, about 10% to about 65%, about 10% to about 50%, about 50% to about 90% to about 80%, about 50% to about 65%, about 50% to about 65%, about 65% to about 90%, about 65% to about 80%, or about 80% to about 90% by weight of the composition.

[0135] In some embodiments, the lecithin is present in a total amount of about 10% to about 90%, about 10% to about 50%, about 10% to about 35%, about 10% to about 20%, about 20% to about 90%, about 20% to about 50%, about 20% to about 35%, about 35% to about 90%, about 35% to about 50%, or about 50% to about 90% by weight of the composition.

[0136] In some embodiments, the ratio of the total mass of the one or more monoglycerides to the total mass of the lecithin is about 10:1 to about 1:10, e.g., about 10:1 to about 1:9, about 10:1 to about 1:1, about 10:1 to about 2:1, about 10:1 to about 4:1, about 9:1 to about 1:10, about 9:1 to about 1:9, about 9:1 to about 1:1, about 9:1 to about 2:1, about 9:1 to about 4:1, about 4:1 to about 1:10, about 4:1 to about 1:9, about 4:1 to about 1:1, about 4:1 to about 2:1, about 2:1 to about 1:10, about 2:1 to about 1:9, about 2:1 to about 1:1, about 1:1 to about 1:10, or about 1:1 to about 1:9.

[0137] In some embodiments, the one or more monoglycerides are one or more C 16 ~C 28 Monoglycerides of fatty acids, and one or more C4-C 14 In certain such embodiments, the monoglycerides of one or more C4 to C6 fatty acids are 14 The monoglycerides of fatty acids are present in a total amount of about 1% to about 15% by weight of the composition. For example, in some embodiments, one or more C4 to C6 monoglycerides are present in a total amount of about 1% to about 15% by weight of the composition. 14 The monoglycerides of fatty acids are present in a total amount of about 1% to about 10%, about 1% to about 5%, about 2% to about 15%, about 2% to about 10%, or about 2% to about 5% by weight of the composition. As another example, in some embodiments, one or more C4 to C6 monoglycerides are present in a total amount of about 1% to about 10%, about 1% to about 5%, about 2% to about 15%, about 2% to about 10%, or about 2% to about 5% by weight of the composition. 14 The ratio of the total mass of fatty acid monoglycerides to the total mass of lecithin is about 1:1 to about 1:100, for example, about 1:1 to about 1:15, about 1:7 to about 1:100, about 1:7 to about 1:15, or about 1:15 to about 1:100.

[0138] In some embodiments, the one or more monoglycerides are present in a total amount of about 50% to about 65% by weight of the composition, and the lecithin is present in an amount of about 35% to about 50% by weight. 14The monoglycerides of fatty acids are present in a total amount of about 1% to about 5% by weight of the composition. In some embodiments, the one or more monoglycerides are present in an amount of about 65% to about 80% by weight of the composition, and the lecithin is present in an amount of about 20% to about 35% by weight of the composition. In certain such embodiments, one or more C4 to C6 monoglycerides are present in an amount of about 65% to about 80% by weight of the composition. 14 The monoglycerides of fatty acids are present in a total amount of about 1% to about 5% by weight of the composition. In some embodiments, the one or more monoglycerides are present in an amount of about 80% to about 90% by weight of the composition, and the lecithin is present in an amount of about 10% to about 20% by weight of the composition. In certain such embodiments, one or more C4-C6 monoglycerides are present in an amount of about 80% to about 90% by weight of the composition. 14 The monoglycerides of fatty acids are present in a total amount of about 2% to about 15% by weight of the composition.

[0139] In some embodiments, the ratio of the total mass of one or more monoglycerides to the total mass of lecithin is from about 2:1 to about 1:1. In certain such embodiments, one or more C4-C6 monoglycerides 14 The ratio of the total mass of monoglycerides of fatty acids to the total mass of lecithin is about 1:15 to about 1:100. In some embodiments, the ratio of the total mass of one or more monoglycerides to the total mass of lecithin is about 4:1 to about 2:1. In certain such embodiments, the ratio of the total mass of one or more C4-C6 monoglycerides to the total mass of lecithin is about 4:1 to about 2:1. 14 The ratio of the total mass of fatty acid monoglycerides to the total mass of lecithin is from about 1:7 to about 1:100.

[0140] In some embodiments, the one or more monoglycerides and lecithin are present in an amount of at least about 80% by weight of the composition, e.g., at least about 85%, at least about 90%, at least about 95%, at least about 97.5%, at least about 98%, or at least about 99% by weight of the composition.

[0141] One or more types of C4 to C 28 Monoglycerides of fatty acids, one or more, C4 to C 28Also provided herein are compositions comprising alkyl esters of fatty acids and lecithin. In some embodiments, the ratio of the total mass of the one or more monoglycerides to the total mass of the one or more alkyl esters is about 20:1 to about 1:1, e.g., about 20:1 to about 2:1, about 20:1 to about 5:1, about 15:1 to about 1:1, about 15:1 2:1, about 15:1 to about 5:1, about 10:1 to about 1:1, about 10:1 to about 2:1, or about 10:1 to about 5:1. In some embodiments, the ratio of the total mass of the one or more monoglycerides and one or more alkyl esters to the total mass of the lecithin is about 10:1 to about 1:10, e.g., about 10:1 to about 1:5, about 10:1 to about 1:2, about 5:1 to about 1:10, about 5:1 to about 1:5, about 5:1 to about 1:2, about 2:1 to about 1:10, about 2:1 to about 1:5, or about 2:1 to about 1:2.

[0142] In some embodiments, the one or more monoglycerides and another alkyl ester are present in a total amount of about 10% to about 90%, about 10% to about 75%, about 10% to about 50%, about 25% to about 90%, about 25% to about 75%, about 25% to about 50%, about 50% to about 90%, or about 50% to about 75% by weight of the composition. In some embodiments, the lecithin is present in a total amount of about 10% to about 90%, about 10% to about 75%, about 10% to about 50%, about 25% to about 90%, about 25% to about 75%, about 25% to about 50%, about 50% to about 90%, or about 50% to about 75% by weight of the composition.

[0143] In some embodiments, the one or more monoglycerides, one or more alkyl esters, and lecithin are present in an amount of at least about 80% by weight of the composition, e.g., at least about 85%, at least about 90%, at least about 95%, at least about 97.5%, at least about 98%, or at least about 99% by weight of the composition.

[0144] lecithin

[0145] In some embodiments, the lecithin comprises a composition identified by the European Food Safety Authority (EFSA) as E322 (an approved food additive). In some embodiments, the lecithin comprises a composition identified by the US Food and Drug Administration (FDA) as Generally Recognized as Safe (GRAS) and identified as Chemical Abstract Service (CAS) number 8002-43-5. In some embodiments, the lecithin comprises soybean lecithin, sunflower lecithin, or rapeseed lecithin. In some embodiments, the lecithin comprises hydrolyzed lecithin (also called lysolecithin).

[0146] In some embodiments, the lecithin comprises one or more glycerophospholipids. For example, in some embodiments, the lecithin comprises about 20% to about 60%, about 20% to about 50%, about 20% to about 40%, about 30% to about 60%, about 30% to about 50%, about 30% to about 40%, about 40% to about 60%, or about 40% to about 50% by weight of the composition. In some embodiments, the lecithin comprises one or more triglycerides. For example, in some embodiments, lecithin comprises about 5% to about 50%, about 5% to about 50%, about 5% to about 40%, about 5% to about 30%, about 10% to about 50%, about 10% to about 40%, about 10% to about 30%, about 20% to about 50%, about 20% to about 40%, or about 20% to about 30% by weight of the composition.

[0147] One or more types of C4 to C 28Also provided herein are compositions comprising a monoglyceride of a fatty acid and one or more glycerophospholipids. In some embodiments, the composition comprises from about 4% to about 40% by weight of the one or more glycerophospholipids, e.g., from about 4% to about 25%, from about 4% to about 15%, from about 8% to about 40%, from about 8% to about 25%, or from about 8% to about 15% by weight of the one or more glycerophospholipids. In some embodiments, the composition further comprises one or more triglycerides. For example, in some embodiments, the composition comprises from about 3% to about 35%, from about 3% to about 20%, from about 3% to about 15%, from about 6% to about 35%, from about 6% to about 20%, or from about 6% to about 15% by weight of the one or more triglycerides.

[0148] Glycerophospholipids

[0149] In some embodiments, the one or more glycerophospholipids comprise phosphatidylcholine, lysophosphatidylcholine, phosphatidylethanolamine, lysophosphatidylethanolamine, phosphatidylinositol, lysophosphatidylinositol, phosphatidylserine, lysophosphatidylserine, phosphatidic acid, lysophosphatidic acid, or any combination thereof. In some embodiments, the one or more glycerophospholipids comprise phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, and phosphatidic acid. In some embodiments, the one or more glycerophospholipids comprise phosphatidylserine. In some embodiments, the one or more glycerophospholipids independently comprise one or more C8-C9 phospholipids. 22 For example, in some embodiments, one or more glycerophospholipids independently comprise one or more C 16 Side chain, one or more C 18 side chains, or both.

[0150] In some embodiments, one or more of the glycerophospholipids independently has the formula III: [ka] A compound of the formula Each R P1 are independently -H, [ka] and R P2 and R P3 are each independently -H or -C(O)R H and R P2 and R P3 At least one of the is not -H, Each R H are independently C7~C 21 side chain] Includes.

[0151] In some embodiments of Formula III, R P2 and R P3 In some embodiments of Formula III, one of R P2 and R P3 each independently represents -C(O)R H In some embodiments of Formula III, each R H are independently, C 11 ~C 21 In some embodiments of Formula III, each R H are independently, C 15 or C 17 In some embodiments of Formula III, each R H is independently an unsubstituted side chain. In some embodiments of Formula III, each R H is independently a saturated, monounsaturated, diunsaturated, or triunsaturated side chain.

[0152] triglycerides

[0153] In some embodiments, the one or more triglycerides independently comprise one or more C8 to C9 22For example, in some embodiments, one or more triglycerides independently comprise one or more C 16 Side chain, one or more C 18 side chains, or both.

[0154] In some embodiments, one or more of the triglycerides independently have the formula IV: [ka] A compound of the formula R G1 , R G2 , and R G3 are each independently -C(O)R H and Each R H are independently C7~C 21 side chain] Includes.

[0155] In some embodiments of Formula IV, each R H are independently, C 15 or C 17 In some embodiments of Formula IV, each R H is independently an unsubstituted side chain. In some embodiments of Formula IV, each R H is independently a saturated, monounsaturated, diunsaturated, or triunsaturated side chain.

[0156] In some embodiments of Formula III or Formula IV, each R H are, independently, [ka] [ka] [ka] [ka] is.

[0157] C4~C 28 Monoglycerides of fatty acids

[0158] The compositions described herein may comprise one or more C4-C 28 In some embodiments, the composition comprises one of a C4 to C6 monoglyceride of a fatty acid. 28 In some embodiments, the composition comprises two, three or more monoglycerides of fatty acids, C4 to C6. 28 Monoglycerides of fatty acids, e.g., two types, C4-C 28 In certain such embodiments, the composition comprises one or more monoglycerides of fatty acids, 16 ~C 28 Monoglycerides of fatty acids, and one or more C4-C 14 Monoglycerides of Fatty Acids In some embodiments, the monoglycerides comprise monoglycerides of one or more naturally occurring fatty acids.

[0159] The monoglycerides can include one or more 1-monoglycerides, one or more 2-monoglycerides, or mixtures thereof. In some embodiments, the monoglycerides include 2,3-dihydroxypropan-1-yl esters of one or more fatty acids, 1,3-dihydroxypropan-2-yl esters of one or more fatty acids, or mixtures thereof. In some embodiments, the 1-monoglycerides constitute at least about 50%, at least about 70%, at least about 80%, at least about 90%, or about 100% by weight of the monoglycerides present in the composition. In some embodiments, 1-monoglyceride comprises about 70% to about 100%, about 70% to about 90%, about 75% to about 100%, about 75% to about 90%, about 80% to about 100%, or about 80% to about 90% by weight of the monoglycerides present in the composition.

[0160] In some embodiments, the monoglycerides include one or more C6-C 28 fatty acids, C8~C28 Fatty acids, C4~C 24 Fatty acids, C6~C 24 fatty acids, C 12 ~C 24 Fatty acids, C4~C 22 Fatty acids, C6~C 22 Fatty acids, or C 12 ~C 22 In some embodiments, one or more of the monoglycerides have an unsubstituted side chain, e.g., an unsubstituted C 12 ~C 22 In some embodiments, one or more of the monoglycerides comprises a linear side chain, e.g., a linear C 12 ~C 22 In some embodiments, one or more of the monoglycerides comprises a saturated side chain, e.g., a saturated C 12 ~C 22 Contains side chains.

[0161] In some embodiments, the monoglyceride has the formula Ii: [ka] one or more compounds of the formula R A1 and R A2 are each independently selected from H and C1-C6 alkyl; R H is C3~C 27 side chain] Includes.

[0162] In some embodiments, the monoglyceride has the formula I-ii: [ka] one or more compounds of the formula R A1 and R A2 are each independently selected from H and C1-C6 alkyl; R H is C3~C 27 side chain] Includes.

[0163] In some embodiments, each of the one or more monoglycerides independently comprises a compound of Formula Ii or Formula I-ii. In some embodiments of Formula Ii or Formula I-ii, R A1 and R A2 are each H. In some embodiments of Formula Ii or Formula I-ii, R H is a saturated side chain. In some embodiments of Formula Ii or Formula I-ii, R H is an unsubstituted side chain. In some embodiments of Formula Ii or Formula I-ii, R H is a linear side chain. In some embodiments of Formula Ii or Formula I-ii, R H is C5~C 17 In some embodiments of Formula Ii or Formula I-ii, R H is C 11 ~C 21 It is a side chain.

[0164] In some embodiments, the monoglyceride is a first compound of Formula Ii or Formula I-ii, wherein R H is C 15 ~C 27 a side chain) and a second compound of formula Ii or I-ii, H is C3~C 13 In some embodiments, R of the first compound comprises H is C 15 ~C 21 side chain and R of the second compound H is C 11 ~C 13 It is a side chain.

[0165] In some embodiments, the monoglyceride has the formula IA-i: [ka] one or more compounds of the formula R A1 and R A2 are each independently selected from H and C1-C6 alkyl; R1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R 10A , R 10B , R 11A , and R 11B each occurrence is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A , and R 11B any two of can be taken together with the carbon atoms to which they are attached to form a double bond, a 3- to 6-membered heterocycloalkyl, or a C3-C6 cycloalkyl; o is an integer from 0 to 17, p is an integer from 0 to 17 The sum of o and p is 0 to 17. Includes.

[0166] In some embodiments, the monoglyceride has the formula IA-ii: [ka] one or more compounds of the formula R A1 and R A2 are each independently selected from H and C1-C6 alkyl; R 1 , R 2 , R3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R 10A , R 10B , R 11A , and R 11B each occurrence is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A , and R 11B any two of can be taken together with the carbon atoms to which they are attached to form a double bond, a 3- to 6-membered heterocycloalkyl, or a C3-C6 cycloalkyl; o is an integer from 0 to 17, p is an integer from 0 to 17, The sum of o and p is 0 to 17. Includes.

[0167] In some embodiments, each of the one or more monoglycerides independently comprises a compound of formula IA-i or formula IA-ii. In some embodiments of formula IA-i or formula IA-ii, R A1 and R A2 are each H. In some embodiments of Formula IA-i or Formula IA-ii, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8, and R 9 and R 10A , R 10B , R 11A , and R 11B is independently selected from H and OH. In some embodiments of Formula IA-i or Formula IA-ii, R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A , and R 11B In some embodiments of Formula IA-i or Formula IA-ii, any two of R on adjacent carbon atoms together with the carbon atoms to which they are attached form an oxirane. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , and R 10A , R 10B , R 11A , and R 11B In some embodiments of Formula IA-i or Formula IA-ii, two or one pair of R groups on adjacent carbon atoms form a double bond together with the carbon atoms to which they are attached, or none of them form a double bond. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , and R 10A , R 10B , R 11A , and R 11BIn some embodiments of Formula IA-i or Formula IA-ii, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , and R 10A , R 10B , R 11A , and R 11B Two or one of each occurrence of are OH, or none of them are OH.

[0168] In some embodiments of Formula IA-i or Formula IA-ii, the sum of o and p is 0-13, 0-11, 0-9, 0-7, 5-17, 5-13, 5-11, 5-9, 5-7, 7-17, 7-13, 7-11, 7-9, 9-17, 9-13, 9-11, 11-17, or 11-13.

[0169] In some embodiments, the monoglycerides include one or more 1- or 2-monoglycerides (e.g., 2,3-dihydroxypropan-1-yl esters or 1,3-dihydroxypropan-2-yl esters) of heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, or docosanoic acid.

[0170] Alkyl esters

[0171] The compositions described herein may comprise one or more C4-C 28The alkyl esters include alkyl esters of fatty acids. In some embodiments, the alkyl esters include one or more C1-C5 alkyl esters. In some embodiments, each of the alkyl esters is independently a C1-C5 alkyl ester. In some embodiments, the alkyl esters include methyl esters, ethyl esters, propyl esters, isopropyl esters, tert-butyl esters, iso-amyl esters, or any combination thereof. In some embodiments, at least one of the alkyl esters includes an ethyl ester or a propyl ester.

[0172] In some embodiments, the alkyl ester has formula V: [ka] one or more compounds of the formula R B is a C1-C8 alkyl; R H is C7~C 19 side chain] Includes.

[0173] In some embodiments, each of the one or more alkyl esters independently comprises a compound of Formula V. In some embodiments of Formula V, R B is C1-C5 alkyl, C1-C3 alkyl, C2 alkyl, or C3 alkyl. In some embodiments of Formula V, R H is a saturated side chain. In some embodiments of Formula V, R H is an unsubstituted side chain. In some embodiments of Formula V, R H is a linear side chain. In some embodiments of Formula V, R H is C7~C 17 Side chain, C9-C 19 Side chain, C9-C 17 Side chain, C 11 ~C 19 Side chain, or C 11 ~C 17 It is a side chain.

[0174] In some embodiments, the alkyl ester has the formula VA: [ka] one or more compounds of the formula R B is a C1-C8 alkyl; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R 10A , R 10B , R 11A , and R 11B each occurrence is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A , and R 11B any two of can be taken together with the carbon atoms to which they are attached to form a double bond, a 3- to 6-membered heterocycloalkyl, or a C3-C6 cycloalkyl; o is an integer from 0 to 15; p is an integer from 0 to 15, The sum of o and p is 3 to 15. Includes.

[0175] In some embodiments, each of the one or more alkyl esters independently comprises a compound of formula VA. In some embodiments of formula VA, R Bis C1-C5 alkyl, C1-C3 alkyl, C2 alkyl, or C3 alkyl. In some embodiments of Formula VA, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 and R 10A , R 10B , R 11A , and R 11B is independently selected from H and OH. In some embodiments of Formula VA, R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10A , R 10B , R 11A , and R 11B In some embodiments of Formula VA, any two of R on adjacent carbon atoms together with the carbon atoms to which they are attached form an oxirane. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , and R 10A , R 10B , R 11A and R 11B In some embodiments of Formula VA, two or one pair of R groups on adjacent carbon atoms form a double bond together with the carbon atoms to which they are attached, or none of them form a double bond. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R8 , and R 9 , and R 10A , R 10B , R 11A , and R 11B In some embodiments of Formula VA, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , and R 10A , R 10B , R 11A , and R 11B Two or one of each occurrence of are -OH, or none of them are -OH.

[0176] In some embodiments, the one or more alkyl esters include, for example, the methyl, ethyl, propyl, or butyl esters of heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, or docosanoic acid.

[0177] Additional Components

[0178] The compositions described herein can include one or more additional components, such as components that are non-toxic and safe for human and / or animal consumption. For example, the compositions can include a direct or indirect food additive or food contact substance approved by the US Food and Drug Administration (FDA), a component that meets FDA regulatory requirements for use as a food additive or food contact substance, or a component that is Generally Recognized As Safe (GRAS) by the FDA.

[0179] In some embodiments, the compositions described herein comprise one or more fatty acids, e.g., C4-C 22 In some embodiments, the composition comprises less than about 10% by weight, e.g., less than about 5% by weight, less than about 2% by weight, or less than about 1% by weight, of one or more of: triglycerides, diglycerides, acetylated monoglycerides, lactated monoglycerides, succinated monoglycerides, sterols, bile acids, proteins, polysaccharides, phenols, lignans, aromatic acids, terpenoids, flavonoids, carotenoids, alkaloids, alcohols, alkanes, aldehydes, and salts of any thereof, or does not comprise one or more of: triglycerides, diglycerides, acetylated monoglycerides, lactated monoglycerides, succinated monoglycerides, sterols, bile acids, proteins, polysaccharides, phenols, lignans, aromatic acids, terpenoids, flavonoids, carotenoids, alkaloids, alcohols, alkanes, aldehydes, and salts of any thereof.

[0180] mixture

[0181] Also provided herein is a mixture comprising a composition described herein and a solvent. In some embodiments, the mixture is a colloidal dispersion (e.g., emulsion) of the composition described herein in the solvent. In some embodiments, the solvent comprises water, ammonia, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, or any combination thereof. In some embodiments, the solvent comprises water, ethanol, or a combination thereof. In some embodiments, the solvent comprises water and one or more of ammonia, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, and methyl tert-butyl ether. In some embodiments, the solvent comprises water and ammonia.

[0182] In some embodiments, the mixture comprises about 30% to about 99.9%, about 30% to about 99.5%, about 30% to about 99%, about 50% to about 99.9%, about 50% to about 99.5%, about 50% to about 99%, about 90% to about 99.9%, about 90% to about 99.5%, or about 90% to about 99% solvent by weight.

[0183] In some embodiments, the concentration of the composition in the mixture is about 1 mg / mL to about 200 mg / mL, about 1 mg / mL to about 150 mg / mL, about 1 mg / mL to about 125 mg / mL, about 1 mg / mL to about 100 mg / mL, about 25 mg / mL to about 200 mg / mL, about 25 mg / mL to about 150 mg / mL, about 25 mg / mL to about 125 mg / mL, about 25 mg / mL to about 100 mg / mL, about 50 mg / mL to about 200 mg / mL, about 50 mg / mL to about 150 mg / mL, about 50 mg / mL to about 125 mg / mL, or about 50 mg / mL to about 100 mg / mL.

[0184] coating

[0185] Also provided herein is a coated agricultural product comprising a layer formed from a composition or mixture described herein, the layer being disposed on the surface of the agricultural product. In some embodiments, the agricultural product is an edible agricultural product (e.g., fruits, vegetables, edible seeds, nuts, herbs, spices, produce, meat, eggs, dairy products, seafood, grains, or any other consumable item). In other embodiments, the agricultural product is a non-edible agricultural product (e.g., non-edible flowers, seeds, sprouts, stems, leaves, whole plants, etc.). In some embodiments, the layer is disposed on the exterior surface (e.g., cuticle surface) of the agricultural product.

[0186] In some embodiments, the layer has a thickness of about 0.1 μm to about 20 μm, e.g., about 0.1 μm to about 15 μm, about 0.1 μm to about 10 μm, about 0.5 μm to about 20 μm, about 0.5 μm to about 15 μm, about 0.5 μm to about 10 μm, about 1 μm to about 20 μm, about 1 μm to about 15 μm, or about 1 μm to about 10 μm.

[0187] Coating Method

[0188] Also provided herein is a method for coating an agricultural produce, the method comprising contacting a surface of the agricultural produce with a mixture comprising a coating agent and a solvent, and removing at least a portion of the solvent to form a coating on the surface of the agricultural produce. The coating agent may be one or more C4-C 28 The coating agent comprises a monoglyceride of a fatty acid and lecithin. In some embodiments, the coating agent is a composition described herein. For example, in some embodiments, the ratio of the total mass of the one or more monoglycerides to the total mass of the lecithin is about 10:1 to about 1:10. In some embodiments, the coating agent comprises one or more C4-C monoglycerides. 28 The monoglycerides of fatty acids are present in a total amount of about 10% to about 90% by weight of the composition, and the lecithin is present in an amount of about 10% to about 90% by weight of the composition. In some embodiments, the coating agent comprises one or more C8 to C9 monoglycerides of fatty acids.20 Further comprising an alkyl ester of a fatty acid. In certain such embodiments, the ratio of the total weight of the one or more monoglycerides to the total weight of the one or more alkyl esters is from about 20:1 to about 1:1. In some embodiments, the one or more monoglycerides and the other alkyl ester are present in a total amount of from about 10% to about 90% by weight of the composition.

[0189] In some embodiments of the coating method, the agricultural product is an edible agricultural product (including, for example, fruits, vegetables, edible seeds, and nuts, herbs, spices, produce, meat, eggs, dairy products, seafood, grains, or any other consumable item). In other embodiments of the coating method, the agricultural product is a non-edible agricultural product (including, for example, non-edible flowers, seeds, sprouts, stems, leaves, whole plants, etc.). In some embodiments, the method comprises contacting an exterior surface (e.g., cuticle surface) of the agricultural product with a mixture containing a coating agent.

[0190] In some embodiments of the coating method, contacting the surface of the agricultural produce comprises spraying the mixture onto the surface of the agricultural produce. The mixture can be sprayed, for example, from a commercially available sprayer. In some embodiments, the mixture is aerosol sprayed onto the surface of the agricultural produce. In some embodiments of the coating method, contacting the surface of the agricultural produce comprises immersing the agricultural produce in the mixture. In other embodiments of the coating method, the mixture can be brushed, dripped, drop-cast, rolled, tapped, or poured onto the surface of the agricultural produce.

[0191] In some embodiments of the coating method, the solvent comprises water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, or any combination thereof. In some embodiments of the coating method, the solvent comprises water, ethanol, or a combination thereof. In some embodiments, the solvent comprises water and one or more of ammonia, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, and methyl tert-butyl ether. In some embodiments, the solvent comprises water and ammonia.

[0192] In some embodiments of the coating method, the concentration of the coating agent in the mixture is about 1 mg / mL to about 200 mg / mL, about 1 mg / mL to about 150 mg / mL, about 1 mg / mL to about 125 mg / mL, about 1 mg / mL to about 100 mg / mL, about 25 mg / mL to about 200 mg / mL, about 25 mg / mL to about 150 mg / mL, about 25 mg / mL to about 125 mg / mL, about 25 mg / mL to about 100 mg / mL, about 50 mg / mL to about 200 mg / mL, about 50 mg / mL to about 150 mg / mL, about 50 mg / mL to about 125 mg / mL, or about 50 mg / mL to about 100 mg / mL.

[0193] In some embodiments of the coating method, removing at least a portion of the solvent comprises evaporating at least a portion of the solvent. In some embodiments, the evaporation may be passive. In other embodiments, the evaporation may be active, such as in the case of convective drying. In some embodiments, removing at least a portion of the solvent comprises evaporating at least a portion of the solvent at a temperature below 40°C, e.g., below 35°C, or below 30°C. In some embodiments, removing at least a portion of the solvent comprises evaporating at least a portion of the solvent at a temperature between 10°C and about 40°C, or between about 10°C and about 30°C. In some embodiments, removing at least a portion of the solvent comprises evaporating at least a portion of the solvent at ambient temperature. [Example]

[0194] Example

[0195] Example 1 Crystallinity of lecithin-containing mixtures

[0196] Coating agents A to E having the compositions shown in Table 1 were prepared.

[0197] [Table 1]

[0198] Mixtures 1 to 6 of coating agents A to E dispersed in water at the concentrations shown in Table 2 were prepared.

[0199] [Table 2]

[0200] An 8-12 mg sample of each mixture was placed on a sealed sample pan and analyzed using a differential scanning calorimeter (DSC). The samples were subjected to two heating and cooling cycles: heating cycle 1: 20°C → 70-80°C, rate: 10°C / min; cooling cycle 1: 70-80°C → 10°C, rate: -10°C / min; heating cycle 2: 10°C → 70-80°C, rate: 10°C / min; cooling cycle 2: 70-80°C → 10°C, rate: -10°C / min. The results of the second cooling cycle were identical to those of the first. The DSC results for mixtures 1-5 are shown in Figure 1, which indicated that the degree of crystallinity increased as the lecithin content decreased. Figure 2 compares the DSC curves for mixtures 1 and 6 and shows no correlation between the crystallization peak and the concentration present.

[0201] The mass loss coefficients (MLF; the ratio of the average mass loss rate of untreated produce to the average mass loss rate of coated produce over a given period of time) of produce coated with each of Mixes 1-5 were predicted using a model based on the space-filling mixture design of experiments (DoE) in Example 3 below, and then plotted against the respective crystallization enthalpies (calculated by integrating the peaks shown in Figure 1). The resulting graph is shown in Figure 3. A linear fit of the points (y = 0.2223x + 1.0962; R 2 =0.9525), demonstrating a correlation between barrier performance and coating crystallinity.

[0202] Example 2 Stability / compatibility mapping of lecithin-containing formulations

[0203] A space-filling mixture design of experiments (DoE) was conducted on coatings containing combinations of sunflower lecithin (mass fractions 0-1), glyceryl monostearate (mass fractions 0-1), and glyceryl monolaurate (mass fractions 0-1) dispersed in water (50 g / L). The initial design space is shown in Figure 4. Each formulation shown in Figure 4 (filled circles) was tested for miscibility and stability.

[0204] The resulting profiles for the miscibility (1 = miscible; 0 = unmiscible) and stability (1 = stable for more than 1 day; 0 = stable for less than 1 day) of the colloidal dispersions as a function of the mass fraction of lecithin, glycerol monostearate, and glycerol monolaurate are shown in Figures 5 and 6, respectively. The results showed that a lecithin content greater than 10 wt% and a glycerol monolaurate content less than 15 wt% resulted in acceptable miscibility and stability.

[0205] Example 3 Performance mapping of lecithin-containing compositions

[0206] A space-filling mixture Design of Experiments (DoE) was conducted on coatings formed from coatings containing combinations of sunflower lecithin (mass fractions 0-1), glyceryl monostearate (mass fractions 0-0.8), and glyceryl monolaurate (mass fractions 0-0.15) dispersed in water (50 g / L). The initial design space is shown in Figure 7. Cherries were coated with each formulation (block dot) shown in Figure 7 by dipping into a bowl containing the colloidal dispersion and then allowed to dry at room temperature. The coated cherries were then tested to determine the mass loss coefficient (averaged over 100 cherries per formulation) and visually evaluated to determine the retention score (averaged over 40 cherries per formulation). Examples of coated cherries with retention scores of 0, 0.5, 1, and 2 are shown in Figures 8A, 8B, 8C, and 8D, respectively. A residue score of less than 0.5 indicated that the residue was barely noticeable or not present.

[0207] Triangular plots of the mass loss factor and residue score across the design space are shown in Figures 9 and 10, respectively. As shown in Figure 11, (A) a coating containing 12.1 wt% lecithin, 78.1 wt% glycerol monostearate, and 9.8 wt% glycerol monolaurate, and (B) a coating containing 54.1 wt% lecithin, 39.1 wt% glycerol monostearate, and 6.7 wt% glycerol monolaurate each had acceptable mass loss factors (1.79 and 1.33, respectively) and produced coatings with less visible residue compared to (C) a comparative coating containing 95 wt% glycerol monostearate and 5 wt% sodium stearate (mass loss factor of 1.91).

[0208] Coating bananas

[0209] Coating agents F to I having the compositions shown in Table 3 were prepared.

[0210] [Table 3]

[0211] Mixtures 7-10 were prepared of coating agents F-H dispersed in water at the concentrations shown in Table 4. For each of Mixtures 7-10, bananas were coated by dipping them into a bowl containing the mixture and then allowed to dry at room temperature. The coated bananas were visually inspected for peeling and residue formation.

[0212] [Table 4]

[0213] Images of bananas coated with Mixtures 7, 9, and 10 are shown in Figures 12A, 12B, and 12C, respectively. As shown in Figures 12A-C, no delamination was observed for bananas coated with the lecithin-containing formulations (delamination is indicated by the white arrow in Figure 12A).

[0214] Images of bananas coated with Blends 8 and 10 are shown in Figures 13A and 13B, respectively. As shown in Figures 13A and 13B, less residue formation was observed for the coatings formed from the lecithin-containing formulations.

[0215] Coating cherry tomatoes

[0216] Coating agents J to R having the compositions shown in Tables 5 and 6 were prepared.

[0217] [Table 5]

[0218] [Table 6]

[0219] Mixtures 11-19 were prepared of Coating Agents J-R dispersed in water at the concentrations shown in Table 7. Mixture 13 did not emulsify properly. Samples of each mixture were analyzed using a differential scanning calorimeter (DSC) following the procedure described in Example 1 above. DSC results for Mixtures 11-19 showed no difference in crystallinity due to the inclusion of alkyl esters, with monoglyceride to alkyl ester weight ratios ranging from 9:1 to approximately 2:1. In a rheometer (TA instruments Discovery HR-3), the mixtures were run in a double-walled concentric cylinder (inner bob diameter 32.01 mm; outer bob diameter 35.01 mm) using a shear flow ramp (20°C; 0.0 immersion time; 60-second duration; shear rate range 1.74-500 s). -1) was also used to determine the viscosities of Mixtures 11-19. The results, shown in Figure 14, indicated that the change in viscosity due to the inclusion of alkyl esters was only minimal at weight ratios of monoglyceride to alkyl esters from 9:1 to approximately 2:1. At a weight ratio of approximately 2:1, the mixtures had 30-40 wt% higher viscosities compared to the corresponding mixtures without alkyl esters.

[0220] For each of mixtures 11-19, a group of 80 cherry tomatoes was coated by dipping them into a bowl of the mixture and then allowed to dry at room temperature. The mass loss of the coated cherry tomatoes and a control group of uncoated cherry tomatoes was then measured on a flat tray.

[0221] [Table 7]

[0222] Images of cherry tomatoes one day after coating with Mixtures 11 and 16 are shown in Figures 15A and 15B, respectively. Images of untreated cherry tomatoes and cherry tomatoes coated with Mixtures 11, 14, 16, 17, and 19 after 14 days of storage at ambient temperature are shown in Figures 16A, 16B, 16C, 16D, 16E, and 16F, respectively. As demonstrated in Table 7, Figures 14, 15A, and 15B, and Figures 16A-16F, lecithin-containing coatings further comprising alkyl esters can provide improved barrier properties without significantly affecting the properties of the coating mixture, including residue formation.

[0223] While the present disclosure includes details of many specific embodiments, these should not be construed as limiting the scope of the present subject matter or the scope of what can be claimed, but rather as descriptions of features that may be specific to particular embodiments. Certain features described in this disclosure in the context of separate embodiments can also be implemented in combination in a single embodiment. Conversely, various features described in the context of a single embodiment can also be implemented separately or in any suitable subcombination in multiple embodiments. Furthermore, the features described above may be described as working in certain combinations, and even if originally claimed as such, one or more features from a claimed combination may in some cases be excluded from the combination, and a claimed combination may also be directed to a subcombination or variations of the subcombination.

[0224] Specific embodiments of the present subject matter have been described. Other embodiments, modifications, and permutations of the described embodiments, as will be apparent to those skilled in the art, are within the scope of the following claims. Although operations are shown in a particular order in the drawings or claims, this should not be understood as requiring such operations to be performed in the particular order or sequential order shown, or as requiring all illustrated operations to achieve desirable results (although some operations may be considered optional).

[0225] Therefore, the exemplary embodiments set forth above do not define or bind this disclosure. Other changes, substitutions, and alterations may also occur without departing from the spirit and scope of this disclosure.

Claims

1. 1. A composition comprising: One or more C present in a total amount of about 10% to about 90% by weight of the composition ４ ~C ２８ Monoglycerides of fatty acids, and Lecithin present in an amount of about 10% to about 90% by weight of the composition A composition comprising:

2. the one or more monoglycerides are present in a total amount of from about 10% to about 50% by weight of the composition; the lecithin is present in an amount of about 50% to about 90% by weight of the composition; The composition of claim 1.

3. the one or more monoglycerides are present in a total amount of from about 50% to about 90% by weight of the composition; the lecithin is present in an amount of about 10% to about 50% by weight of the composition; The composition of claim 1.

4. the one or more monoglycerides are present in a total amount of from about 50% to about 65% by weight of the composition; the lecithin is present in an amount of about 35% to about 50% by weight of the composition; The composition of claim 3.

5. the one or more monoglycerides are present in an amount from about 65% to about 80% by weight of the composition; the lecithin is present in an amount of about 20% to about 35% by weight of the composition; The composition of claim 3.

6. the one or more monoglycerides are present in an amount from about 80% to about 90% by weight of the composition; the lecithin is present in an amount of about 10% to about 20% by weight of the composition; The composition of claim 3.

7. the one or more monoglycerides One or more C １６ ~C ２８ Monoglycerides of fatty acids, and One or more C ４ ~C １４ Monoglycerides of fatty acids 7. The composition of claim 1, comprising:

8. The one or more C ４ ~C １４ 8. The composition of claim 7, wherein the monoglycerides of fatty acids are present in a total amount of from about 1% to about 15% by weight of the composition.

9. One or more C ４ ~C ２８ Monoglycerides of fatty acids, and lecithin wherein the ratio of the total weight of the one or more monoglycerides to the total weight of the lecithin is from about 10:1 to about 1:

10.

10. 10. The composition of claim 9, wherein the ratio of the total mass of the one or more monoglycerides to the total mass of the lecithin is from about 1:1 to about 1:

9.

11. 10. The composition of claim 9, wherein the ratio of the total mass of the one or more monoglycerides to the total mass of the lecithin is from about 9:1 to about 1:

1.

12. 12. The composition of claim 11, wherein the ratio of the total mass of the one or more monoglycerides to the total mass of the lecithin is from about 2:1 to about 1:

1.

13. 12. The composition of claim 11, wherein the ratio of the total mass of the one or more monoglycerides to the total mass of the lecithin is from about 4:1 to about 2:

1.

14. 12. The composition of claim 11, wherein the ratio of the total mass of the one or more monoglycerides to the total mass of the lecithin is from about 9:1 to about 4:

1.

15. the one or more monoglycerides One or more C １６ ~C ２８ Monoglycerides of fatty acids, and One or more C ４ ~C １４ Monoglycerides of fatty acids 15. The composition of any of claims 9 to 14, comprising:

16. 16. The composition of any of claims 9 to 15, wherein the one or more monoglycerides and the lecithin are present in an amount of at least about 80% by weight of the composition.

17. One or more C ４ ~C ２８ Monoglycerides of fatty acids, One or more C ４ ~C ２８ alkyl esters of fatty acids, and lecithin A composition comprising: the ratio of the total weight of the one or more monoglycerides to the total weight of the one or more alkyl esters is from about 20:1 to about 1:1; the ratio of the total weight of the one or more monoglycerides and the one or more alkyl esters to the total weight of the lecithin is from about 10:1 to about 1:10; composition.

18. the one or more monoglycerides and the one or more alkyl esters are present in a total amount of from about 10% to about 50% by weight of the composition; the lecithin is present in an amount of about 50% to about 90% by weight of the composition; 18. The composition of claim 17.

19. the one or more monoglycerides and the one or more alkyl esters are present in a total amount of from about 50% to about 90% by weight of the composition; the lecithin is present in an amount of about 10% to about 50% by weight of the composition; 18. The composition of claim 17.

20. 20. The composition of any of claims 17-19, wherein the one or more monoglycerides, the one or more alkyl esters, and the lecithin are present in an amount of at least about 80% by weight of the composition.

21. 21. The composition of any of claims 17 to 20, wherein the ratio of the total mass of the one or more monoglycerides to the total mass of the one or more alkyl esters is from about 10:1 to about 2:

1.

22. 22. The composition of any of claims 1 to 21, wherein the lecithin comprises hydrolyzed lecithin.

23. 23. The composition of any of claims 1 to 22, wherein the lecithin comprises soybean lecithin, sunflower lecithin, or rapeseed lecithin.

24. 24. The composition of any of claims 1 to 23, wherein the lecithin comprises one or more glycerophospholipids.

25. 25. The composition of claim 24, wherein the one or more glycerophospholipids are present in an amount of about 20% to about 60% by weight of the lecithin.

26. 26. The composition of any of claims 1 to 25, wherein the lecithin comprises one or more triglycerides.

27. 27. The composition of claim 26, wherein the one or more triglycerides are present in an amount from about 5% to about 50% by weight of the lecithin.

28. 1. A composition comprising: One or more C present in a total amount of about 10% to about 90% by weight of the composition ４ ~C ２８ Monoglycerides of fatty acids, and One or more glycerophospholipids present in an amount of about 4% to about 40% by weight of the composition A composition comprising:

29. the one or more monoglycerides are present in a total amount of from about 50% to about 90% by weight of the composition; the one or more glycerophospholipids are present in a total amount of from about 4% to about 25% by weight of the composition; 29. The composition of claim 28.

30. the one or more monoglycerides One or more C １６ ~C ２８ Monoglycerides of fatty acids, and One or more C ４ ~C １４ Monoglycerides of fatty acids 30. The composition of claim 28 or claim 29, comprising:

31. The one or more C ４ ~C １４ 31. The composition of claim 30, wherein the monoglycerides of fatty acids are present in a total amount of from about 1% to about 15% by weight of the composition.

32. 32. The composition of any of claims 28 to 31, further comprising one or more triglycerides.

33. 33. The composition of claim 32, wherein the one or more triglycerides are present in a total amount of from about 3% to about 35% by weight of the composition.

34. 33. The composition of claim 32, wherein the one or more triglycerides are present in a total amount of from about 3% to about 20% by weight of the composition.

35. 35. The composition of any of claims 24 to 34, wherein the one or more glycerophospholipids comprise phosphatidylcholine, lysophosphatidylcholine, phosphatidylethanolamine, lysophosphatidylethanolamine, phosphatidylinositol, lysophosphatidylinositol, phosphatidylserine, lysophosphatidylserine, phosphatidic acid, lysophosphatidic acid, or any combination thereof.

36. 36. The composition of claim 35, wherein the one or more glycerophospholipids comprise phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, and phosphatidic acid.

37. 37. The composition of claim 35 or claim 36, wherein the one or more glycerophospholipids comprise phosphatidylserine.

38. One or more of the glycerophospholipids independently comprises one or more C ８ ~C ２２ 38. The composition of any one of claims 24 to 37, comprising a side chain.

39. One or more of the triglycerides independently comprise one or more C ８ ~C ２２ 39. The composition of any of claims 26, 27, and 32-38, comprising a side chain.

40. One or more of the glycerophospholipids independently have the formula III: 【Chemistry 20】 wherein: Each R Ｐ１ are independently -H, 【Chemistry 21】 and R Ｐ２ and R Ｐ３ are each independently —H or —C(O)R Ｈ and R Ｐ２ and R Ｐ３ at least one of is not -H, Each R Ｈ are independently ７ ~C ２１ The side chain is 40. The composition of any one of claims 24 to 39.

41. One or more of the triglycerides independently have the formula IV: 【Chemistry 22】 wherein: R Ｇ１ , R Ｇ２ , and R Ｇ３ are each independently —C(O)R Ｈ and Each R Ｈ are independently ７ ~C ２１ The side chain is 41. The composition of any one of claims 26, 27, and 32-40.

42. Each R Ｈ But independently, C １５ or C １７ 42. The composition of claim 40 or claim 41, which is a side chain.

43. Each R Ｈ 43. The composition of any of claims 40 to 42, wherein is an unsubstituted side chain.

44. Each R Ｈ is independently a saturated side chain, a monounsaturated side chain, a diunsaturated side chain, or a triunsaturated side chain.

45. Each of the one or more monoglycerides independently has the formula I-i or I-ii: 【Chemistry 23】 wherein: R Ａ１ and R Ａ２ are each independently H and C １ ~C ６ alkyl, R Ｈ is C ３ ~C ２７ The side chain is 45. The composition of any one of claims 1 to 44.

46. R Ａ１ and R Ａ２ 46. ​​The composition of claim 45, wherein each is H.

47. R Ｈ is an unsubstituted saturated side chain.

48. R Ｈ is C １１ ~C ２１ 48. The composition of any one of claims 45 to 47, which is a side chain.

49. the one or more monoglycerides R Ｈ is C １５ ~C ２７ a first compound of formula I-i or formula I-ii, which is a side chain; and R Ｈ is C ３ ~C １３ a second compound of formula I-i or I-ii which is a side chain 49. The composition of any of claims 45 to 48, comprising:

50. Each of the one or more monoglycerides independently has formula IA-i or formula IA-ii: 【Chemistry 24】 wherein: R Ａ１ and R Ａ２ are each independently H and C １ ~C ６ alkyl, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , and R ９ are each independently H, OH, C １ ~C ６ Alkyl, C ２ ~C ６ alkenyl, and C １ ~C ６ alkoxy; R １０Ａ , R １０Ｂ , R １１Ａ , and R １１Ｂ Each occurrence of is independently H, OH, C １ ~C ６ Alkyl, C ２ ~C ６ alkenyl, and C １ ~C ６ alkoxy; R on the adjacent carbon atom １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０Ａ , R １０Ｂ , R １１Ａ , and R １１Ｂ Any two of, together with the carbon atoms to which they are attached, form a double bond, a 3- to 6-membered heterocycloalkyl, or C ３ ~C ６ can form a cycloalkyl, o is an integer from 0 to 17; p is an integer from 0 to 17; The sum of o and p is 0 to 17.

45. The composition of any one of claims 1 to 44.

51. R Ａ１ and R Ａ２ 51. The composition of claim 50, wherein each is H.

52. The one or more alkyl esters are each independently selected from the group consisting of: １ ~C ５ 52. The composition of any of claims 17 to 51, comprising an alkyl ester.

53. 52. The composition of any of claims 17 to 51, wherein the one or more alkyl esters each independently comprise a methyl ester, an ethyl ester, a propyl ester, an isopropyl ester, a tert-butyl ester, or an iso-amyl ester.

54. 54. The composition of any of claims 17 to 53, wherein at least one of the alkyl esters comprises an ethyl ester or a propyl ester.

55. Each of the one or more alkyl esters independently has the formula V: 【Chemistry 25】 wherein: R Ｂ is C １ ~C ８ is alkyl, R Ｈ is C ７ ~C １９ The side chain is 52. The composition of any one of claims 17 to 51.

56. R Ｂ is C １ ~C ５ 56. The composition of claim 55, wherein the alkyl is alkyl.

57. R Ｂ is C ２ Alkyl or C ３ 56. The composition of claim 55, wherein the alkyl is alkyl.

58. R Ｈ 58. The composition of any of claims 55-57, wherein is an unsubstituted saturated side chain.

59. R Ｈ is C １１ ~C １７ 59. The composition of any one of claims 55 to 58, which is a side chain.

60. A composition according to any one of claims 1 to 59, and solvent A mixture comprising:

61. 61. The mixture of claim 60, wherein the mixture comprises from about 30% to about 99.9% by weight of the solvent.

62. 61. The mixture of claim 60, wherein the mixture comprises from about 90% to about 99.5% by weight of the solvent.

63. 63. The mixture of any of claims 60 to 62, wherein the solvent comprises one or more of water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, and methyl tert-butyl ether.

64. 60. A coated agricultural product comprising an agricultural product and a layer disposed on a surface of the agricultural product, the layer comprising the composition of any of claims 1 to 59.

65. 65. The coated agricultural produce of claim 64, wherein the layer is disposed on a cuticular surface of the agricultural produce.

66. 66. The coated agricultural product of claim 64 or claim 65, wherein the layer has a thickness of from about 0.1 μm to about 20 μm.

67. 66. The coated agricultural product of claim 64 or claim 65, wherein the layer has a thickness of from about 0.1 μm to about 10 μm.

68. 1. A method of coating an agricultural product, said method comprising: contacting the surface of the agricultural produce with a mixture comprising a coating agent and a solvent, the coating agent comprising: One or more C ４ ~C ２８ Monoglycerides of fatty acids, and lecithin wherein the ratio of the total mass of the one or more monoglycerides to the total mass of the lecithin is from about 10:1 to about 1:10; and removing at least a portion of the solvent to form a coating on the surface of the agricultural produce. A method comprising:

69. the one or more monoglycerides One or more C １６ ~C ２８ Monoglycerides of fatty acids, and One or more C ４ ~C １４ Monoglycerides of fatty acids 69. The method of claim 68, comprising:

70. 70. The method of claim 68 or claim 69, wherein the one or more monoglycerides and the lecithin are present in an amount of at least about 80% by weight of the coating.

71. 71. The method of any of claims 68 to 70, wherein the concentration of the coating agent in the mixture is from about 1 mg / mL to about 200 mg / mL.

72. 71. The method of any of claims 68 to 70, wherein the concentration of the coating agent in the mixture is from about 25 mg / mL to about 150 mg / mL.

73. 73. The method of any of claims 68 to 72, wherein the solvent comprises one or more of water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, and methyl tert-butyl ether.

74. 74. The method of any of claims 68 to 73, wherein the coating agent and the solvent are present in an amount of at least about 98% by weight of the mixture.

75. 75. The method of any of claims 68 to 74, wherein the surface is a cuticular surface of the agricultural produce.

76. contacting the surfaces comprises: spraying the mixture onto the surface; or immersing the agricultural produce in the mixture.

76. The method of any of claims 68 to 75, comprising:

77. 77. The method of any of claims 68 to 76, wherein removing at least a portion of the solvent comprises evaporating at least a portion of the solvent at a temperature of less than 40°C.

78. 77. The method of any of claims 68 to 76, wherein removing at least a portion of the solvent comprises evaporating at least a portion of the solvent at a temperature of less than 30°C.

79. 77. The method of any of claims 68 to 76, wherein removing at least a portion of the solvent comprises evaporating at least a portion of the solvent at a temperature of from 10°C to 30°C.

80. 80. The method of any of claims 68 to 79, further comprising combining the coating agent and the solvent to form the mixture.

81. 1. A method of coating an agricultural product, said method comprising: contacting the surface of the agricultural produce with a mixture according to any of claims 60 to 63; and removing at least a portion of the solvent to form a coating on the surface of the agricultural produce. A method comprising:

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