Coating composition comprising monoglycerides of C4 to C28 fatty acids and alkyl esters of C8 to C20 fatty acids

Abstract

The present disclosure relates to compositions comprising monoglycerides and alkyl esters of fatty acids. Exemplary embodiments include C4-C 28 About 15 wt% to about 99 wt% of one or more monoglycerides of fatty acids and C8 to C 20 and about 1 wt % to about 75 wt % of one or more alkyl esters of fatty acids.

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of priority to U.S. Application No. 63 / 408,964, filed September 22, 2022, the contents of which are incorporated herein by reference in their entirety.

[0002] Technical Field

[0002] The present disclosure relates to coatings for agricultural products. [Background technology]

[0003] background

[0003] 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 vulnerable to deterioration when exposed to the ambient environment. Produce deterioration can occur via abiotic means as a result of evaporative moisture loss from the exterior surface of the produce to the atmosphere, and / or oxidation by oxygen diffusing into the produce from the environment, and / or mechanical damage to the surface, and / or light-induced degradation (i.e., photodegradation). Furthermore, biotic stressors, such as bacteria, fungi, viruses, and / or pests, can also attach to and degrade agricultural products.

[0004]

[0004] Traditional approaches to preventing deterioration, maintaining quality, and increasing the shelf life of produce include refrigeration and / or special packaging. Refrigeration requires capital-intensive equipment, demands constant energy expenditure, and can cause produce spoilage or quality loss if not carefully controlled and actively managed. Additionally, the benefits of refrigeration are lost if the temperature-controlled supply chain is interrupted. Special packaging also requires expensive equipment, consumes packaging materials, increases transportation costs, and can require active management. Despite the benefits that refrigeration and special packaging can confer, handling and transporting produce can cause surface wear or blemishes that are aesthetically unpleasant to consumers and can serve as entry points for bacteria and fungi. Furthermore, the expenses associated with such approaches can increase the cost of produce. Summary of the Invention [Means for solving the problem]

[0005] overview

[0005] The present invention provides a C4 to C6 copolymer, which is present in a total amount of about 15 wt% to about 99 wt% of the composition. 28 one or more monoglycerides of fatty acids, C8-C, present in a total amount of about 1 wt% to about 75 wt% of the composition; 20 and one or more alkyl esters of fatty acids.

[0006]

[0006] In addition, in this specification, C4 to C 28 One or more monoglycerides of fatty acids C8 to C 20 and one or more alkyl esters of fatty acids, wherein the ratio of the total number of moles of the one or more monoglycerides to the total number of moles of the one or more alkyl esters is from about 100:1 to about 1:5.

[0007] Also provided herein are mixtures of the compositions described herein with solvents.

[0008]

[0008] Also provided herein is a coated produce comprising a produce and a layer disposed on a surface of the produce, the layer comprising the composition described herein.

[0009] Also provided herein is a method of coating 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 is selected from the group consisting of C4 to C6 28 One or more monoglycerides of fatty acids C8 to C 20 and one or more alkyl esters of fatty acids. The ratio of the total number of moles of the one or more monoglycerides to the total number of moles of the one or more alkyl esters is about 100:1 to about 1:5.

[0010]

[0010] Also provided herein is a method for coating 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.

[0011]

[0011] The inventive concepts of the present disclosure include those defined in the appended claims, but it should be understood that the inventive concepts may also be defined according to the following embodiments.

[0012]

[0012] In addition to the embodiments in the accompanying claims and described above, the following numbered embodiments are also innovative.

[0013]

[0013] Embodiment 1 is C4 to C6 present in a total amount of about 15 wt% to about 99 wt% of the composition 28 one or more monoglycerides of fatty acids; C8-C present in a total amount of about 1 wt% to about 75 wt% of the composition 20 one or more alkyl esters of fatty acids; A composition comprising:

[0014]

[0014] Embodiment 2 is the one or more monoglycerides are present in a total amount of about 70% to about 99% by weight of the composition; and 2. The composition of embodiment 1, wherein the one or more alkyl esters are present in a total amount of about 1% to about 15% by weight of the composition.

[0015]

[0015] Embodiment 3 is the composition of embodiment 2, wherein the one or more alkyl esters are present in a total amount of about 1 wt % to about 10 wt % of the composition.

[0016]

[0016] Embodiment 4 is the one or more monoglycerides are present in a total amount of about 15% to about 85% by weight of the composition; and The composition of embodiment 1, wherein the one or more alkyl esters are present in a total amount of about 15% to about 75% by weight of the composition.

[0017]

[0017] Embodiment 5 is the composition of any one of Embodiments 1-4, wherein the one or more monoglycerides and one or more alkyl esters comprise from about 70% to about 98% by weight of the composition.

[0018]

[0018] Embodiment 6 is a C4 to C6 polyol present in a total amount of 0.1 wt% to about 30 wt% of the composition. 28 6. The composition of any of embodiments 1-5, further comprising one or more salts of fatty acids.

[0019]

[0019] Embodiment 7 is the composition of embodiment 6, wherein the one or more salts are present in a total amount of about 1% to about 20% by weight of the composition.

[0020]

[0020] Embodiment 8 is the composition of embodiment 6, wherein the one or more salts are present in a total amount of about 1% to about 10% by weight of the composition.

[0021]

[0021] Embodiment 9 is C4~C 28 one or more monoglycerides of fatty acids; C8~C 20 one or more alkyl esters of fatty acids; Including, The composition has a ratio of the total number of moles of the one or more monoglycerides to the total number of moles of the one or more alkyl esters of about 100:1 to about 1:5.

[0022]

[0022] Embodiment 10 is the composition of embodiment 9, wherein the ratio of the total number of moles of the one or more monoglycerides to the total number of moles of the one or more alkyl esters is from about 50:1 to about 6:1.

[0023]

[0023] Embodiment 11 is the composition of embodiment 9, wherein the ratio of the total number of moles of the one or more monoglycerides to the total number of moles of the one or more alkyl esters is from about 3:1 to about 1:3.

[0024]

[0024] Embodiment 12 is the composition of any of embodiments 9-11, wherein the one or more monoglycerides and one or more alkyl esters comprise from about 70% to about 98% by weight of the composition.

[0025]

[0025] Embodiment 13 is C4 to C 28 13. The composition of any of embodiments 9-12, further comprising one or more salts of fatty acids.

[0026]

[0026] Embodiment 14 is a composition described in embodiment 13, in which the ratio of the total number of moles of one or more monoglycerides and one or more alkyl esters to the total number of moles of one or more salts is from about 100:1 to about 4:1.

[0027]

[0027] Embodiment 15 is a composition described in embodiment 13, in which the ratio of the total number of moles of one or more monoglycerides and one or more alkyl esters to the total number of moles of one or more salts is from about 50:1 to about 6:1.

[0028]

[0028] Embodiment 16 is the composition of any of embodiments 13-15, wherein the one or more monoglycerides, one or more alkyl esters, and one or more salts comprise at least 80 wt% of the composition.

[0029]

[0029] Embodiment 17 is the composition of any of embodiments 1-16, wherein the one or more alkyl esters each independently comprise a C1 to C5 alkyl ester.

[0030]

[0030] Embodiment 18 is the composition of any of embodiments 1-16, 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.

[0031]

[0031] Embodiment 19 is the composition of any of embodiments 1-16, wherein at least one of the alkyl esters comprises an ethyl ester or a propyl ester.

[0032]

[0032] Embodiment 20 is an embodiment wherein each of the one or more alkyl esters independently has Formula III: [ka] (In the formula, R B is C1-C8 alkyl, and R H is C7~C 19 side chain) 17. The composition of any of embodiments 1-16, comprising a compound of formula:

[0033]

[0033] Embodiment 21 is R B is C1-C5 alkyl.

[0034]

[0034] Embodiment 22 is R B is a C2 alkyl or a C3 alkyl.

[0035]

[0035] Embodiment 23 is R H 23. The composition of any of embodiments 20-22, wherein is a saturated unsubstituted side chain.

[0036]

[0036] Embodiment 24 is R H C 11 ~C 17 24. The composition of any of embodiments 20-23, wherein the side chain.

[0037]

[0037] Embodiment 25 is an embodiment wherein each of the one or more alkyl esters independently has the formula IIIA: [ka] (In 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; Each R that exists 10A , R 10B , R 11A , and R 11B 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 11Bany 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, and The sum of o and p is 3 to 15. 17. The composition of any of embodiments 1-16, comprising a compound of formula:

[0038]

[0038] Embodiment 26 is R B is a C1-C5 alkyl.

[0039]

[0039] Embodiment 27 is R B is a C2 alkyl or a C3 alkyl.

[0040]

[0040] Embodiment 28 is an embodiment wherein each of the one or more monoglycerides independently has formula Ii or formula I-ii: [ka] (In the formula, R A1 and R A2 are each independently selected from H and C1-C6 alkyl, and R H is C3~C 27 side chain) 28. The composition of any of embodiments 1-27, comprising a compound of formula:

[0041]

[0041] Embodiment 29 is R A1 and R A2 and each is H.

[0042]

[0042] Embodiment 30 is R H is a saturated unsubstituted side chain.

[0043]

[0043] Embodiment 31 is R H C 11 ~C 21 31. The composition of any of embodiments 28-30, wherein the side chain.

[0044]

[0044] Embodiment 32 is directed to a method for preparing a glycerol-based glyceride comprising the steps of: a first compound of formula Ii or formula I-ii, wherein R H is C 15 ~C 27 side chain) and a second compound of formula Ii or I-ii, wherein R H is C3~C 13 side chain) and 32. The composition of any of embodiments 28-31, comprising:

[0045]

[0045] Embodiment 33 is an embodiment wherein each of the one or more monoglycerides independently has formula IA-i or formula IA-ii: [ka] (In the formula, 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; Each R that exists 10A , R 10B , R 11A , and R 11B 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, and The sum of o and p is 0 to 17. 28. The composition of any of embodiments 1-27, comprising a compound of formula:

[0046]

[0046] Embodiment 34 is R A1 and R A2 and each is H.

[0047]

[0047] Embodiment 35 is an embodiment wherein each of the one or more salts present in the composition independently represents Formula II: [ka] (In the formula, R H is C3~C 27 is a side chain, and X n+ is a cationic moiety with a formal charge n 35. The composition of any of embodiments 1-34, comprising a compound of formula:

[0048]

[0048] Embodiment 36 is X n+ But Li + , Na + , K. + , Cs + , Ag + , Ca 2+ , Mg 2+ , Zn 2+ , Cu2+ , and (R D )4N + and each R D is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl; Each C1-C6 alkyl is selected from 1 to 3 R independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl. E and Optionally, R D 36. The composition of embodiment 35, wherein one or more instances of are taken together with the nitrogen atom to which they are attached to form a C3-C6 heterocycloalkyl.

[0049]

[0049] Embodiment 37 is R H is a saturated unsubstituted side chain.

[0050]

[0050] Embodiment 38 is an embodiment wherein the one or more salts present in the composition each independently represent Formula IIA: [ka] (In the formula, 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; Each R that exists 10A , R 10B , R 11A , and R 11B is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R on adjacent carbon atoms 1 , R2 , 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, and X n+ is a cationic moiety with a formal charge n 38. The composition of any of embodiments 1-37, comprising a compound of formula:

[0051]

[0051] Embodiment 39 is X n+ But Li + , Na + , K. + , Cs + , Ag + , Ca 2+ , Mg 2+ , Zn 2+ , Cu 2+ , and (R D )4N + and each R D is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl; Each C1-C6 alkyl is selected from 1 to 3 R independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl. E and Optionally, R D 39. The composition of embodiment 38, wherein one or more instances of are taken together with the nitrogen atom to which they are attached to form a C3-C6 heterocycloalkyl.

[0052]

[0052] Embodiment 40 is The composition of any one of embodiments 1 to 39; a solvent; It is a mixture containing

[0053]

[0053] Embodiment 41 is the mixture of embodiment 40, wherein the mixture comprises from about 30 wt% to about 99.9 wt% of the solvent.

[0054]

[0054] Embodiment 42 is the mixture of embodiment 40, wherein the mixture comprises about 90 wt% to about 99.5 wt% solvent.

[0055]

[0055] Embodiment 43 is a mixture of any of embodiments 40-42, 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.

[0056]

[0056] Embodiment 44 is a coated produce comprising a produce and a layer disposed on a surface of the produce, wherein the layer comprises the composition of any of embodiments 1-39.

[0057]

[0057] Embodiment 45 is the coated produce of embodiment 44, wherein the layer is disposed on a cuticular surface of the produce.

[0058]

[0058] Embodiment 46 is the coated produce of embodiment 44 or embodiment 45, wherein the layer thickness is from about 0.1 μm to about 20 μm.

[0059]

[0059] Embodiment 47 is the coated produce of any of embodiments 44-46, wherein the layer has a thickness of from about 0.1 μm to about 10 μm.

[0060] Embodiment 48 is a method of coating produce, the method comprising: contacting a surface of the produce with a mixture comprising a coating agent and a solvent, the coating agent comprising: C4~C 28 one or more monoglycerides of fatty acids; C8~C 20 one or more alkyl esters of fatty acids; wherein the ratio of the total number of moles of the one or more monoglycerides to the total number of moles of the one or more alkyl esters is from about 100:1 to about 1:5; removing at least a portion of the solvent to form a coating on the surface of the produce; The method includes:

[0061]

[0061] Embodiment 49 is the method of embodiment 48, wherein the surface is a cuticular surface of an agricultural product.

[0062] Embodiment 50 is directed to a method for contacting the surfaces comprising: spraying the mixture onto the surface; or Immersing the produce in the mixture; 49. The method of any one of embodiments 48 to 48, comprising:

[0063]

[0063] Embodiment 51 is the method of any of embodiments 48-50, wherein removing at least a portion of the solvent comprises evaporating at least a portion of the solvent.

[0064]

[0064] Embodiment 52 is the method of any of embodiments 48-51, 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.

[0065]

[0065] Embodiment 53 is the method of any of embodiments 48-52, further comprising adding the coating agent to a solvent to form a mixture.

[0066]

[0066] Embodiment 54 is a method for preparing a solvent and a C4-C 28 A premix containing one or more monoglycerides of fatty acids C8 to C 20 54. The method of any of embodiments 48-53, further comprising adding one or more alkyl esters of fatty acids to form a mixture.

[0067]

[0067] Embodiment 55 is the method of any of embodiments 48-54, wherein the concentration of the coating agent in the mixture is from about 1 mg / mL to about 200 mg / mL.

[0068]

[0068] Embodiment 56 is the method of any of embodiments 48-54, wherein the concentration of the coating agent in the mixture is from about 25 mg / mL to about 150 mg / mL.

[0069]

[0069] Embodiment 57 is the one or more monoglycerides are present in a total amount of about 70 wt% to about 99 wt% of the coating; and 57. The method of any of embodiments 48-56, wherein the one or more alkyl esters are present in a total amount of about 1 wt % to about 15 wt % of the coating.

[0070]

[0070] Embodiment 58 is the one or more monoglycerides are present in a total amount of about 15% to about 85% by weight of the coating; and 57. The method of any of embodiments 48-56, wherein the one or more alkyl esters are present in a total amount of about 15 wt% to about 75 wt% of the coating.

[0071]

[0071] Embodiment 59 is the method of any of embodiments 48-59, wherein the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more alkyl esters is from about 50:1 to about 6:1.

[0072]

[0072] Embodiment 60 is the method of any of embodiments 48-59, wherein the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more alkyl esters is from about 3:1 to about 1:3.

[0073]

[0073] Embodiment 61 is the method of any of embodiments 48-60, wherein the one or more alkyl esters each independently comprise a C1 to C5 alkyl ester.

[0074]

[0074] Embodiment 62 is the method of any of embodiments 48-60, wherein each of the one or more alkyl esters independently comprises a methyl ester, an ethyl ester, a propyl ester, an isopropyl ester, a tert-butyl ester, or an iso-amyl ester.

[0075]

[0075] Embodiment 63 is the method of any of embodiments 48-60, wherein at least one of the alkyl esters comprises an ethyl ester or a propyl ester.

[0076]

[0076] In embodiment 64, the coating agent is C4 to C 28 64. The method of any of embodiments 48-63, further comprising one or more salts of fatty acids, wherein the ratio of the total moles of the one or more monoglycerides and one or more alkyl esters to the total moles of the one or more salts is from about 100:1 to about 4:1.

[0077]

[0077] Embodiment 65 is the method of embodiment 64, wherein the one or more monoglycerides, one or more alkyl esters, and one or more salts comprise at least 80 wt% of the coating agent.

[0078]

[0078] Embodiment 66 is the method of any of embodiments 48-65, wherein the one or more monoglycerides and one or more alkyl esters comprise about 70 wt% to about 98 wt% of the coating agent.

[0079]

[0079] Embodiment 67 is the method of any of embodiments 48-66, wherein the coating agent and solvent comprise at least 95 wt% of the mixture.

[0080]

[0080] Embodiment 68 is a method of coating produce, comprising: contacting a surface of an agricultural product with a mixture of any of embodiments 40-43; removing at least a portion of the solvent to form a coating on the surface of the produce; The method includes:

[0081] The details of one or more embodiments of the subject matter of this disclosure are set forth in the accompanying drawings and the description. Other features, aspects, and advantages of the subject matter will become apparent from the description, drawings, and claims. [Brief explanation of the drawings]

[0082] BRIEF DESCRIPTION OF THE DRAWINGS [Figure 1]

[0082] Figure 1 is a graph showing small angle X-ray scattering (SAXS) / wide angle X-ray scattering (WAXS) data collected from monoglyceride films. [Figure 2]

[0083] 1 is a graph showing SAXS / WAXS data collected from films of compositions described herein. [Figure 3]

[0084] 1 is a graph showing SAXS / WAXS data collected from alkyl ester films. [Figure 4]

[0085] 1 is a plot showing viscosity data collected from certain compositions described herein. DETAILED DESCRIPTION OF THE INVENTION

[0083] Detailed Description

[0086] The present disclosure relates to compositions comprising monoglycerides and alkyl esters of fatty acids. Specifically, the compositions described herein can be coated onto produce to provide an improved barrier to gases, water, and the like. Such coatings can better limit mass loss and / or CO2 production from produce compared to those lacking the alkyl esters of fatty acids.

[0084]

[0087] Reference will now be made in detail to certain embodiments of the presently disclosed subject matter. While the presently disclosed subject matter will be described in conjunction with the recited claims, it will be understood that the illustrated subject matter is not intended to limit the claims to the presently disclosed subject matter.

[0085]

[0088] definition

[0089] The terms "a," "an," and "the" are used herein to include one or more, unless the context clearly dictates otherwise. The term "or" is used to mean a non-exclusive "or" unless otherwise indicated. The statement "at least one of A and B" has the same meaning as "A, B, or A and B." In addition, any phrases or terms used in this disclosure without a specific definition should be understood to be for descriptive purposes only, not limiting. Any use of section headings is intended to aid in the reading of the document and should not be construed as limiting that the information associated with the section heading may be found within or outside of that particular section.

[0086]

[0090] Values ​​expressed in range format should be interpreted flexibly to include not only the explicitly stated numerical values ​​as range limits but also all individual numerical values ​​or subranges subsumed within that range as if each numerical value and subrange were explicitly stated. For example, a range of "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 indicated range. A statement "about X to Y" has the same meaning as "about X to about Y" unless otherwise indicated. Similarly, a statement "about X, Y, or about Z" has the same meaning as "about X, about Y, or about Z" unless otherwise indicated.

[0087]

[0091] As used herein, the term "about" allows for variability in a value or range within 10% of the stated value or stated range limit.

[0088]

[0092] In the methods described herein, acts may be performed in any order, except when explicitly recited as a temporal or operational sequence. Furthermore, specifically recited acts may be performed in parallel, unless express claim language recites them 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 may fall within the literal scope of the claimed process.

[0089]

[0093] As used herein, the term "monoglyceride" refers to the condensation product of one glycerol molecule with one fatty acid—i.e., a glycerol group attached to one fatty acid via an ester linkage. Monoglycerides can be, but need not necessarily be, derived from a condensation reaction. For example, monoglycerides can be obtained by an esterification reaction between glycerol and a fatty acid, by transesterification of a triglyceride with glycerol (glycerolysis), etc. Monoglycerides can also be referred to as glyceryl monoalkanoates. When the glycerol group is attached to the ester linkage at the 1-position (e.g., as in 2,3-dihydroxypropan-1-yl octadecanoate), the monoglyceride can be referred to as a 1-monoglyceride or 1-glyceryl alkanoate (e.g., as in 1-glyceryl octadecanoate). When the glycerol group is attached to the ester linkage at the 2-position (e.g., as in 1,3-dihydroxypropan-2-yl hexadecanoate), the monoglyceride can 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 can be unsubstituted (e.g., as in 2,3-dihydroxypropan-1-yl alkanoate) or can be further substituted with one or more groups other than fatty acids (e.g., as in 1,3-dialkoxypropan-2-yl alkanoates).

[0090]

[0094] The term "alkyl ester" as used with reference to fatty acids refers to the condensation product of an alkanol and a fatty acid—i.e., an alkyl group attached to a fatty acid via an ester linkage. Alkyl esters can be, but need not necessarily be, derived from a condensation reaction. For example, alkyl esters can be obtained by an esterification reaction between an alkanol and a fatty acid, by transesterification of monoglycerides, triglycerides, etc. Alkyl esters can also be referred to as alkylalkanoates. For example, the ethyl ester of hexadecanoic acid can also be referred to as ethylhexadecanoate.

[0091]

[0095] 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 include branched or unbranched (e.g., linear), substituted or unsubstituted, and saturated or unsaturated side chains.

[0092]

[0096] As used herein, the term "side chain" refers to the aliphatic portion of a fatty acid or a portion thereof. Unless otherwise specified, the side chain of a given fatty acid includes the carbon of the carboxylic acid group. For example, dodecanoic acid can be described as including a linear saturated C12 side chain and R H -C(O)OH(wherein, R H is a linear saturated C11 side chain). The side chain can be present in compounds other than fatty acids, such as esters and amides, 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 in fact derived from dodecanoic acid.

[0093]

[0097] The term "salt" as used with reference to the disclosed compounds (e.g., fatty acids) refers to derivatives of the compounds obtained by modifying the parent compound by converting an acid or base moiety into its salt form. Examples of such salts include, but are not limited to, mineral or organic acid salts of basic residues such as amines, or inorganic (e.g., alkali) or organic salts of acidic residues such as carboxylic acids.

[0094]

[0098] While certain features of the compounds described herein are disclosed in groups or ranges, such disclosure includes each and every individual subcombination of the members of such groups and ranges. For example, the term "C1-C6 alkyl" includes (but is not limited to) methyl, ethyl, C3 alkyl, C4 alkyl, C5 alkyl, and C6 alkyl.

[0095]

[0099] As used herein, the term "n-membered" (where n is an integer) typically 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.

[0096]

[0100] As used herein, the term "substituted" means that an atom or group of atoms formally replaces hydrogen as a "substituent" attached to another group. "Substituted" refers to any level of substitution, for example, mono-, di-, tri-, tetra-, penta-substitution, and the like, unless otherwise indicated, and such substitution is permitted. Substituents are independently selected, and substitution may occur at any chemically accessible position. Substitution of a given atom is limited by valency. Substitution of a given atom results in a chemically stable molecule. The phrase "optionally substituted" means unsubstituted or substituted. A single divalent substituent, such as oxo, can replace two hydrogen atoms.

[0097]

[0101] As used herein, "C n ~C mThe term "n" or "m" implies a range inclusive of the endpoints, where n and m are integers and imply the number of carbon atoms. Examples include C1-C4, C1-C6, etc.

[0098]

[0102] As used herein, the term "alkyl" means a saturated hydrocarbon group which may be straight-chained or branched. n ~C m The term "alkyl" refers to an alkyl group having n to m carbon atoms. An alkyl group formally corresponds to an alkane compound in which one C-H bond has been replaced by the alkyl group's point of attachment 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.

[0099]

[0103] 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 with one C-H bond replaced by the point of attachment of the alkenyl group to the remainder of the compound. n ~C m The term "alkenyl" means an alkenyl group having n to m carbons. Examples of alkenyl groups include, but are not limited to, ethenyl, n-propenyl, isopropenyl, n-butenyl, sec-butenyl, and the like.

[0100]

[0104] As used herein, the term "alkoxy" means a group of formula -O-alkyl, where alkyl is as defined above. n ~C mThe term "alkoxy" means an alkoxy group in which the alkyl group has n to m carbons. Examples of alkoxy groups include methoxy, ethoxy, propoxy (e.g., n-propoxy and isopropoxy), t-butoxy, and the like.

[0101]

[0105] As used herein, the term "cycloalkyl" refers to a non-aromatic hydrocarbon ring system (monocyclic, bicyclic, polycyclic), including cyclized alkyl and alkenyl groups. n ~C m The term "cycloalkyl" means 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.

[0102]

[0106] As used herein, the term "heterocycloalkyl" refers to a non-aromatic ring system (monocyclic, bicyclic, or polycyclic) having at least one heteroatom ring member independently selected from nitrogen, sulfur, oxygen, and phosphorus, and which may optionally contain one or more alkenylene groups as part of the ring structure. The term "nm- to m-membered heterocycloalkyl" refers to a heterocycloalkyl having nm to m ring-forming atoms. The ring-forming carbon atoms and heteroatoms of a heterocycloalkyl group can be optionally oxidized to form oxo or sulfido groups or other oxidized linkages (e.g., C(O), S(O), C(S), S(O), N-oxide, etc.), or the nitrogen atom can be quaternized. The heterocycloalkyl group can be attached via a ring-forming carbon atom or a ring-forming heteroatom. The heterocycloalkyl group can contain, 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, tetrahydropyranyl, tetrahydropyranyl, tetrahydrothiazinyl, tetrahydropyrazole ... Examples of the dihydrobenzoxazolyl include 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, and 3-azabicyclo[4.1.0]heptanyl.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.

[0103]

[0107] composition

[0108] In this specification, C4 to C 28 One or more monoglycerides of fatty acids C8 to C 20 and one or more alkyl esters of fatty acids.

[0104]

[0109] In some embodiments, the one or more monoglycerides are present in a total amount of about 15 wt% to about 99 wt% of the composition, e.g., about 15 wt% to about 85 wt%, about 15 wt% to about 65 wt%, about 25 wt% to about 85 wt%, about 25 wt% to about 65 wt%, about 35 wt% to about 85 wt%, about 35 wt% to about 65 wt%, about 70 wt% to about 99 wt%, about 70 wt% to about 96 wt%, about 80 wt% to about 99 wt%, or about 80 wt% to about 96 wt% of the composition.

[0105]

[0110] In some embodiments, the one or more alkyl esters are present in a total amount of about 1 wt% to about 75 wt% of the composition, e.g., about 1 wt% to about 15 wt%, about 1 wt% to about 10 wt%, about 2.5 wt% to about 15 wt%, about 2.5 wt% to about 10 wt%, about 5 wt% to about 15 wt%, about 5 wt% to about 10 wt%, about 15 wt% to about 75 wt%, about 15 wt% to about 55 wt%, about 25 wt% to about 75 wt%, about 25 wt% to about 55 wt%, about 35 wt% to about 75 wt%, or about 35 wt% to about 55 wt%.

[0106]

[0111] In some embodiments, the ratio of the total number of moles of the one or more monoglycerides to the total number of moles of the one or more alkyl esters is about 100:1 to about 1:5, e.g., about 100:1 to about 5:1, about 100:1 to about 7:1, about 50:1 to about 5:1, about 50:1 to about 7:1, about 25:1 to about 5:1, about 25:1 to about 7:1, about 5:1 to about 1:5, about 5:1 to about 1:2, about 3:1 to about 1:5, about 3:1 to about 1:2, about 2:1 to about 1:5, or about 2:1 to about 1:2.

[0107]

[0112] In some embodiments, the one or more monoglycerides and one or more alkyl esters comprise from about 70 wt% to about 99 wt% of the composition, e.g., from about 70 wt% to about 96 wt%, from about 80 wt% to about 99 wt%, from about 80 wt% to about 96 wt%, from about 85 wt% to about 99 wt%, or from about 85 wt% to about 96 wt% of the composition.

[0108]

[0113] In some embodiments, the composition is 28Further comprising one or more salts of a fatty acid, in some embodiments, the one or more salts are present in a total amount of about 0.1 wt% to about 30 wt% of the composition, about 0.1 wt% to about 15 wt%, about 0.1 wt% to about 10 wt%, about 1 wt% to about 30 wt%, about 1 wt% to about 15 wt%, about 1 wt% to about 10 wt%, about 2 wt% to about 30 wt%, about 2 wt% to about 15 wt%, or about 2 wt% to about 10 wt% of the composition. In some embodiments, the ratio of the total number of moles of the one or more monoglycerides and the one or more alkyl esters to the total number of moles of the one or more salts is from about 100:1 to about 4:1, e.g., from about 100:1 to about 8:1, from about 75:1 to about 4:1, from about 75:1 to about 4:1, from about 50:1 to about 4:1, or from about 50:1 to about 8:1. In some embodiments, the one or more monoglycerides, the one or more alkyl esters, and the one or more salts comprise at least about 80 wt% of the composition, e.g., at least about 85 wt%, at least about 90 wt%, at least about 95 wt%, or at least about 99 wt% of the composition.

[0109]

[0114] C4~C 28 Monoglycerides of fatty acids

[0115] The compositions described herein are C4 to C 28 In some embodiments, the composition comprises one or more monoglycerides of fatty acids. 28 In some embodiments, the composition comprises a monoglyceride of one of the fatty acids C4 to C6. 28 Monoglycerides of two, three or more fatty acids, e.g., C4-C 28 In some embodiments, the monoglyceride comprises one or more monoglycerides of a naturally occurring fatty acid.

[0110]

[0116] The monoglycerides can include one or more 1-monoglycerides, one or more 2-monoglycerides, or mixtures thereof. In some embodiments, the monoglycerides include one or more 2,3-dihydroxypropan-1-yl esters of fatty acids, one or more 1,3-dihydroxypropan-2-yl esters of fatty acids, or mixtures thereof. In some embodiments, the 1-monoglycerides comprise at least about 50 wt%, at least about 70 wt%, at least about 80 wt%, at least about 90 wt%, or about 100 wt% of the monoglycerides present in the composition. In some embodiments, the 1-monoglyceride comprises between about 70 wt% and about 100 wt%, between about 70 wt% and about 90 wt%, between about 75 wt% and about 100 wt%, between about 75 wt% and about 90 wt%, between about 80 wt% and about 100 wt%, or between about 80 wt% and about 90 wt% of the monoglycerides present in the composition.

[0111]

[0117] In some embodiments, the monoglyceride is a C6-C 28 fatty acids, C8~C 28 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 comprises 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.

[0112]

[0118] In some embodiments, the monoglyceride has the formula Ii: [ka] (In the formula, R A1 and R A2 are each independently selected from H and C1-C6 alkyl, and R H is C3~C 27 side chain) It contains one or more compounds of the formula:

[0113]

[0119] In some embodiments, the monoglyceride has the formula I-ii: [ka] (In the formula, R A1 and R A2 are each independently selected from H and C1-C6 alkyl, and R H is C3~C 27 side chain) It contains one or more compounds of the formula:

[0114]

[0120] 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.

[0115]

[0121] 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 formula I-ii, wherein R H is C3~C 13 In some embodiments, R of the first compound includes H is C 15 ~C 21 is a side chain of the second compound, and R H is C 11 ~C 13 It is a side chain.

[0116]

[0122] In some embodiments, the monoglyceride has the formula IA-i: [ka] (In the formula, 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; Each R that exists 10A , R 10B , R 11A , and R 11B 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 , R9 , 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, and The sum of o and p is 0 to 17. It contains one or more compounds of the formula:

[0117]

[0123] In some embodiments, the monoglyceride has the formula IA-ii: [ka] (In the formula, 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; Each R that exists 10A , R 10B , R 11A , and R 11B 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 , R10B , 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, and The sum of o and p is 0 to 17. It contains one or more compounds of the formula:

[0118]

[0124] 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 each 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 each R 10A , R 10B , R 11A , and R 11B In some embodiments of Formula IA-i or Formula IA-ii, two pairs or one pair of R 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 each R 10A , R 10B , R 11A , and R 11B In some embodiments of Formula IA-i or Formula IA-ii, one pair of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , and each R 10A , R 10B , R 11A , and R 11B Two or one of them are OH, or none of them are OH.

[0119]

[0125] In some embodiments of Formula IA-i or Formula IA-ii, the sum of o and p is 0 to 13, 0 to 11, 0 to 9, 0 to 7, 5 to 17, 5 to 13, 5 to 11, 5 to 9, 5 to 7, 7 to 17, 7 to 13, 7 to 11, 7 to 9, 9 to 17, 9 to 13, 9 to 11, 11 to 17, or 11 to 13.

[0120]

[0126] In some embodiments, the monoglyceride comprises one or more 1- or 2-monoglycerides, such as 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.

[0121]

[0127] C4~C 28 Salts of fatty acids

[0128] The compositions described herein are C4 to C 28 In some embodiments, the composition may include one or more salts of a fatty acid. 28 In some embodiments, the composition comprises a salt of one of the C4 to C6 fatty acids. 28 Salts of two, three or more fatty acids, e.g., C4-C 28 In some embodiments, the salt comprises one or more salts of a naturally occurring fatty acid.

[0122]

[0129] In some embodiments, the salt is a C-C 28 fatty acids, C8~C 28 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, the salt comprises one or more salts of a fatty acid. 12 ~C 22 Fatty acids, two salts of e.g., C 16 Fatty acids and C 18 In some embodiments, one or more of the salts may have an unsubstituted side chain, e.g., an unsubstituted C 12 ~C 22In some embodiments, one or more of the salts comprises a linear side chain, e.g., a linear C 12 ~C 22 In some embodiments, one or more of the salts comprises a saturated side chain, e.g., a saturated C 12 ~C 22 Contains side chains.

[0123]

[0130] In some embodiments, the salt has Formula II: [ka] (In the formula, R H is C3~C 27 is a side chain, and X n+ is a cationic moiety with a formal charge n It contains one or more compounds of the formula:

[0124]

[0131] In some embodiments, each of the one or more salts independently comprises a compound of Formula II. In some embodiments of Formula II, X n+ Li + , Na + , K. + , Cs + , Ag + , Ca 2+ , Mg 2+ , Zn 2+ , Cu 2+ , and (R D )4N + where each R D is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl, and each C1-C6 alkyl is followed by 1 to 3 R independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl. E In some embodiments, X n+ (R D )4N + and R Dtogether with the nitrogen atom to which they are attached form a C3-C6 heterocycloalkyl. In some embodiments of Formula II, X n+ Na + , K. + , Ca 2+ , Mg 2+ , and Zn 2+ In some embodiments of Formula II, R H is a saturated side chain. In some embodiments of Formula II, R H is an unsubstituted side chain. In some embodiments of Formula II, R H is a linear side chain. In some embodiments of Formula II, R H is C5~C 17 In some embodiments of Formula II, R H is C 11 ~C 21 It is a side chain.

[0125]

[0132] In some embodiments, the salt has formula IIA: [ka] (In the formula, 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; Each R that exists 10A , R 10B , R 11A , and R 11B 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 , R6 , 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, and X n+ is a cationic moiety with a formal charge n It contains one or more compounds of the formula:

[0126]

[0133] In some embodiments, each of the one or more salts independently comprises a compound of Formula IIA. In some embodiments of Formula IIA, X n+ Li + , Na + , K. + , Cs + , Ag + , Ca 2+ , Mg 2+ , Zn 2+ , Cu 2+ , and (R D )4N + where each R D is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl, and each C1-C6 alkyl is followed by 1 to 3 R independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl. E In some embodiments, X n+ (R D )4N + and R D together with the nitrogen atom to which they are attached form a C3-C6 heterocycloalkyl. In some embodiments of Formula II, Xn+ Na + , K. + , Ca 2+ , Mg 2+ , and Zn 2+ is selected from.

[0127]

[0134] In some embodiments of Formula IIA, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , and each R 10A , R 10B , R 11A , and R 11B is independently selected from H and OH. In some embodiments of Formula IIA, 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 IIA, any two of R on adjacent carbon atoms together form an oxirane. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , and each R 10A , R 10B , R 11A , and R 11B In some embodiments of Formula IIA, two pairs or one pair of R 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 , R2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , and each R 10A , R 10B , R 11A , and R 11B In some embodiments of Formula IIA, one pair of R together with the carbon atom to which they are attached form an oxirane, or none of them form an oxirane. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , and each R 10A , R 10B , R 11A , and R 11B Two or one of them are OH, or none of them are OH.

[0128]

[0135] In some embodiments of Formula IIA, 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.

[0129]

[0136] In some embodiments, the salt comprises one or more salts, such as the sodium, potassium, silver, calcium, magnesium, or zinc salts of a saturated, linear, unsubstituted fatty acid. In some embodiments, the salt comprises one or more salts, such as the sodium, potassium, silver, calcium, magnesium, or zinc salts 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.

[0130]

[0137] Alkyl esters

[0138] The compositions described herein are C4 to C 28 The fatty acid may comprise one or more alkyl esters of the fatty acid. In some embodiments, the alkyl ester comprises 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 ester comprises a methyl ester, an ethyl ester, a propyl ester, an isopropyl ester, a tert-butyl ester, an iso-amyl ester, or any combination thereof. In some embodiments, at least one of the alkyl esters comprises an ethyl ester or a propyl ester.

[0131]

[0139] In some embodiments, the alkyl ester has Formula III: [ka] (In the formula, R B is a C1-C8 alkyl, and R H is C7~C 19 side chain) It contains one or more compounds of the formula:

[0132]

[0140] In some embodiments, each of the one or more alkyl esters independently comprises a compound of Formula III. In some embodiments of Formula III, R B is C1-C5 alkyl, C1-C3 alkyl, C2 alkyl, or C3 alkyl. In some embodiments, R H is a saturated side chain. In some embodiments, R H is an unsubstituted side chain. In some embodiments, R H is a linear side chain. In some embodiments, 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.

[0133]

[0141] In some embodiments, the alkyl ester has formula IIIA: [ka] (In 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; Each R that exists 10A , R 10B , R 11A , and R 11B 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 , R4 , 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, and The sum of o and p is 3 to 15. It contains one or more compounds of the formula:

[0134]

[0142] In some embodiments, each of the one or more alkyl esters independently comprises a compound of Formula IIIA. In some embodiments of Formula IIIA, R B is C1-C5 alkyl, C1-C3 alkyl, C2 alkyl, or C3 alkyl. In some embodiments of Formula IIIA, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , and each R 10A , R 10B , R 11A , and R 11B is independently selected from H and OH. In some embodiments of Formula IIIA, 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 11BIn some embodiments of Formula IIIA, 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 each R 10A , R 10B , R 11A , and R 11B In some embodiments of Formula IIIA, two pairs or one pair of R 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 each R 10A , R 10B , R 11A , and R 11B In some embodiments of Formula IIIA, one pair of R together with the carbon atom to which they are attached form an oxirane, or none of them form an oxirane. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , and each R 10A , R 10B , R 11A , and R 11B Two or one of them are OH, or none of them are OH.

[0135]

[0143] In some embodiments, the monoglyceride is one or more alkyl esters of, for example, 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, 9-hydroxyhexadecanoic acid, 10-hydroxyhexadecanoic acid, or the like. Acid, 9,10-dihydroxyhexadecanoic acid, 16-hydroxyhexadecanoic acid, 9,16-dihydroxyhexadecanoic acid, 10,16-dihydroxyhexadecanoic acid, 9,10,16-trihydroxyhexadecanoic acid, 9,10-epoxyhexadecanoic acid, (9Z)-hexadec-9-enoic acid, (9E)-hexadec-9-enoic acid, 9,10-epoxy-16-hydroxyhexadecanoic acid, 16-hydroxy Oxy-(9Z)-hexadec-9-enoic acid, 16-hydroxy-(9E)-hexadec-9-enoic acid, 9-hydroxyoctadecanoic acid, 10-hydroxyoctadecanoic acid, 9,10-dihydroxyoctadecanoic acid, 18-hydroxyoctadecanoic acid, 9,18-dihydroxyoctadecanoic acid, 10,18-dihydroxyoctadecanoic acid, 9,10,18-trihydroxyoctadecanoic acid, 9,10-epo and ethyl or propyl esters of 18-hydroxy-9,10-dihydroxyoctadecanoic acid, (9Z)-octadec-9-enoic acid, (9E)-octadec-9-enoic acid, 18-hydroxy-9,10-dihydroxyoctadecanoic acid, 18-hydroxy-(9Z)-octadec-9-enoic acid, 18-hydroxy-(9E)-octadec-9-enoic acid, (13Z)-docos-13-enoic acid, or (13E)-docos-13-enoic acid.

[0136]

[0144] Additional ingredients

[0145] The compositions described herein can include one or more additional ingredients, e.g., ingredients 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), an ingredient that meets FDA regulatory requirements for use as a food additive or food contact substance, or an ingredient that is Generally Recognized As Safe (GRAS) by the FDA.

[0137]

[0146] In some embodiments, the compositions described herein further comprise one or more fatty acids, e.g., C4 to C22 fatty acids. In some embodiments, the compositions comprise or do not comprise less than about 10 wt%, e.g., less than about 5 wt%, less than about 2 wt%, or less than about 1 wt%, of one or more of: triglycerides, diglycerides, acetylated monoglycerides, lactylated monoglycerides, succinylated monoglycerides, sterols, bile acids, proteins, polysaccharides, phenols, lignans, aromatic acids, terpenoids, flavonoids, carotenoids, alkaloids, alcohols, alkanes, aldehydes, and salts of any thereof.

[0138]

[0147] mixture

[0148] Also provided herein are mixtures comprising a composition described herein and a solvent. In some embodiments, the mixture comprises a dispersion of a composition described herein in a 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.

[0139]

[0149] In some embodiments, the mixture comprises between about 30 wt% and about 99.9 wt%, between about 30 wt% and about 99.5 wt%, between about 30 wt% and about 99 wt%, between about 50 wt% and about 99.9 wt%, between about 50 wt% and about 99.5 wt%, between about 50 wt% and about 99 wt%, between about 90 wt% and about 99.9 wt%, between about 90 wt% and about 99.5 wt%, or between about 90 wt% and about 99 wt% of the solvent.

[0140]

[0150] 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.

[0141]

[0151] coating

[0152] Also provided herein are coated produce comprising a layer formed from a composition described herein disposed on a surface of the produce. In some embodiments, the produce is edible produce, including, for example, fruits, vegetables, edible seeds and nuts, herbs, spices, green vegetables, meat, eggs, dairy products, seafood, grains, or any other ingestible item. In other embodiments, the produce is non-edible produce, including, for example, inedible flowers, seeds, shoots, stems, leaves, whole plants, etc. In some embodiments, the layer is disposed on an outer surface (e.g., cuticle surface) of the produce.

[0142]

[0153] 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.

[0143]

[0154] Coating method

[0155] Also provided herein is a method of coating 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. 28 One or more monoglycerides of fatty acids C8 to C 20 and one or more alkyl esters of fatty acids. In some embodiments, the coating agent is a composition described herein. For example, in some embodiments, the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more alkyl esters is about 100:1 to about 1:5. In some embodiments, the coating agent comprises a C4-C glyceride present in a total amount of about 15 wt% to about 99 wt% of the coating agent. 28 One or more monoglycerides of fatty acids, C8 to C6, present in a total amount of 1 wt% to about 75 wt% of the coating. 20 and one or more alkyl esters of fatty acids.

[0144]

[0156] In some embodiments of the coating method, the produce is edible produce, including, for example, fruits, vegetables, edible seeds and nuts, herbs, spices, produce, meat, eggs, dairy, seafood, grains, or any other ingestible item. In other embodiments of the coating method, the produce is non-edible produce, including, for example, inedible flowers, seeds, shoots, stems, leaves, whole plants, etc. In some embodiments, the method includes contacting an outer surface (e.g., cuticle surface) of the produce with a mixture containing a coating agent.

[0145]

[0157] In some embodiments of the coating method, contacting the surface of the produce comprises spraying the mixture onto the surface of the 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 produce. In some embodiments of the coating method, contacting the surface of the produce comprises immersing the produce in the mixture. In other embodiments of the coating method, the mixture can be brushed, dripped, drop-cast, rolled, dabbed, or poured onto the surface of the produce.

[0146]

[0158] 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 can be passive. In other embodiments, the evaporation can be active, such as in the case of convective drying. 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.

[0147]

[0159] 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.

[0148]

[0160] In some embodiments of the coating method, the one or more monoglycerides are present in a total amount of about 70% to about 99% or about 15% to about 85% by weight of the coating, and the one or more alkyl esters are present in a total amount of about 1% to about 15% or about 15% to about 75% by weight of the coating. In some embodiments, the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more alkyl esters present in the coating is about 50:1 to about 6:1, or about 3:1 to about 1:3.

[0149]

[0161] In some embodiments, the monoglyceride comprises a compound of Formula Ii, Formula I-ii, Formula IA-i, or Formula IA-ii described herein. In some embodiments, the alkyl ester comprises a compound of Formula III or Formula IIIA described herein. In some embodiments, the coating agent further comprises a compound of Formula II or Formula IIA described herein.

[0150]

[0162] In some embodiments, the one or more monoglycerides and one or more alkyl esters comprise about 70 wt% to about 99 wt% of the coating agent, e.g., about 70 wt% to about 98 wt%, about 70 wt% to about 96 wt%, about 80 wt% to about 99 wt%, about 80 wt% to about 98 wt%, about 80 wt% to about 96 wt%, about 85 wt% to about 99 wt%, about 85 wt% to about 98 wt%, or about 85 wt% to about 96 wt% of the coating agent. 28 Further comprising one or more salts of fatty acids, and wherein the one or more monoglycerides, one or more alkyl esters, and one or more salts comprise at least about 80 wt% of the composition, e.g., at least about 85 wt%, at least about 90 wt%, at least about 95 wt%, at least about 97.5 wt%, at least about 98 wt%, or at least about 99 wt% of the coating. [Example]

[0151]

[0163] Example

[0164] Example 1. Preparation of alkyl esters and mixtures

[0165] Ethyl esters of fatty acids were purchased commercially when available. Other alkyl esters were synthesized from commercially available starting materials and used without further purification.

[0152]

[0166] General Procedure

[0167] To a dry 2000 mL round-bottom flask equipped with a stir bar, 300 g of fatty acid and 2 equivalents of alkanol were added using a funnel, followed by 500 mL of toluene. Stirring was started, and 0.005 equivalents (based on fatty acid) of p-toluenesulfonic acid monohydrate was added. Toluene was used to rinse any material adhering to the funnel or flask, and then toluene was added to bring the volume to approximately 1500 mL. A Dean-Stark trap with a reflux condenser was fitted to the flask. The flask was heated to reflux, and the reaction was monitored by the evolution of water collected in the trap. After 24 h, the reaction was cooled, and 80 mL of activated (grade 1) basic alumina was added and stirred for 5 min. The mixture was then filtered through a 300 mL frit packed with Celite 545 and an additional 1 cm layer of activated alumina to remove the acid catalyst. The bulk of the solvent was removed by rotary evaporation, and residual solvent was removed in a liquid nitrogen trap by stirring under high vacuum (<100 microns). NMR analysis suggested a single product matching the intended alkyl ester.

[0153]

[0168] Alternatively, the distillate condensed vapor fraction was dried using molecular sieves to drive the reaction, which could help avoid unfavorable azeotropes and drive the reaction forward.

[0154]

[0169] Characterization

[0155]

[0170] Propyl palmitate: 1H NMR(600MHz, CDCl3)δ 3.99(t,J=6.6Hz,2H),2.25(t,J=7.6Hz,2H),1.65-1.54(m,4H),1.31-1.17(m,26H),0.90(t,J=7.4Hz,3H),0.84(t,J=6.8Hz,3H). 13 C NMR(151MHz,CDCl3)δ 173.76,77.22,77.01,76.79,65.67,34.28,31.88,29.65,29.63,29.61,29 .60,29.55,29.42,29.32,29.22,29.12,24.97,22.63,21.97,14.00,10.29.

[0156]

[0171] プロピルステアレート: 1 H NMR(600MHz, CDCl3)δ 4.02(t,J=6.7Hz,2H),2.29(t,J=7.6Hz,2H),1.63(tq,J=14.5,7.2Hz,4H),1.33-1.19(m,30H),0.94(t,J=7.4Hz,3H),0.87(t,J=7.0Hz,3H). 13 C NMR(151MHz,CDCl3)δ 173.67,65.63,34.26,31.88,29.66,29.62,29.60,29.55,29.42,29.32,29.23,29.12,24.96,22.63,21.96,13.99,10.27.GC-MS:[((M + ))]C 21 H 42 The measured value of O2 is 326.6 and the calculated value is 326.3.

[0157]

[0172] ブチルステアレート: 1 H NMR(600MHz, CDCl3)δ 4.05(t,J=6.7Hz,2H),2.27(t,J=7.5Hz,2H),1.64-1.56(m,4H),1.37(dt,J=15. 0,7.5Hz,2H),1.32-1.20(m,30H),0.92(t,J=7.4Hz,3H),0.87(t,J=7.0Hz,3H). 13C NMR(151MHz,CDCl3)δ 173.92,77.20,76.99,76.78,64.03,34.37,31.91,30.70,29.67,29.62,29.57,2 9.57,29.45,29.34,29.24,29.14,25.00,22.66,19.12,14.06,13.66.GC-MS:[((M + ))]C 22 H 44 The measured value of O2 is 340.6 and the calculated value is 340.3.

[0158]

[0173] ペンチルステアレート: 1 H NMR(600MHz, CDCl3)δ 4.01(t,J=6.7Hz,2H),2.24(t,J=7.5Hz,2H),1.57(qt,J=7.8,4.7Hz,4H),1.35-1.18(m,33H),0.89-0.85(m,3H),0.84(t,J=6.9Hz,3H). 13 C NMR(151MHz,CDCl3)δ 173.68,77.22,77.01,76.80,64.19,34.28,31.89,29.66,29.63,29.62,29.56,29.43,2 9.43,29.33,29.24,29.12,28.33,28.05,24.96,22.63,22.26,13.99,13.84.GC-MS:[((M + ))]C 23 H 46 The measured value of O2 is 354.6 and the calculated value is 354.3.

[0159]

[0174] ヘキシルステアレート: 1 H NMR(600MHz, CDCl3)δ 4.02(t,J=6.7Hz,2H),2.24(t,J=7.6Hz,2H),1.58(p,J=6.9Hz,4H),1.36-1.17(m,35H),0.85(q,J=7.0Hz,6H). 13C NMR(151MHz,CDCl3)δ GC-MS:[(M + ))]C 24 H 48 Actual O2 value 368.6, calculated value 368.4.

[0160]

[0175] Propyl Behenate: 1 H NMR(600MHz,CDCl3)δ 4.01(t,J=6.7Hz,2H),2.27(t,J=7.6Hz,2H),1.67-1.56(m,4H),1.35-1.17(m,39H),0.92(t,J=7.5Hz,3H),0.86(t,J=6.8Hz,3H). 13 C NMR(151MHz,CDCl3)δ 173.84,77.21,76.99,76.78,65.72,34.33,31.91,29.68,29.66,29.62,29.5 8,29.45,29.35,29.25,29.14,24.99,22.66,21.99,14.05,10.33.GC-MS:[((M + ))]C 25 H 50 Actual O2 value 382.4, calculated value 382.4.

[0161]

[0176] Preparation of the mixture

[0177] Deionized water heated to over 85°C was added to a Vitamix blender (Model 5010). The appropriate amount of coating material was slowly added to the blender on setting 1. The blender was capped and the mixture was blended on "high" for 3 minutes, then poured into 1 L Schott bottles and stored until use.

[0162]

[0178] Example 2. Coat Citrus

[0179] Coating agents A and B having the compositions shown in Table 1 were prepared.

[0163]

[0180] [Table 1]

[0164]

[0181] Mixtures 1, 2, 3, and 4 were prepared with coating agents A, B, C, and D dispersed in water at the concentrations shown in Table 2. Each mixture was prepared by adding 40 g of coating agent to 1 L of water at 80°C and then homogenizing in a blender for 3 minutes. For each of Mixtures 1 and 2, groups of 120 waxed limes of the same size, quality, maturity, packing date, and orchard were coated by dipping each lime into a bowl containing the mixture and then drying for 100 seconds in a rolling, translating heat tunnel at 65-70°C. For each of Mixtures 3 and 4, groups of 120 unwaxed mandarins of the same size, quality, maturity, packing date, and orchard were coated by dipping each mandarin or lime into a bowl containing the mixture and then drying for 100 seconds in a rolling, translating heat tunnel at 65-70°C. The mass loss of the coated mandarins and limes and the comparison groups of uncoated mandarins and limes was then measured, and the results are shown in Table 2.

[0165]

[0182] [Table 2]

[0166]

[0183] As shown in Table 2, coatings formed from coating agents containing alkyl esters of fatty acids reduced mass loss from produce better than coatings lacking alkyl esters.

[0167]

[0184] Example 3. Coated avocado

[0185] Coating agents C to F having the compositions shown in Table 3 were prepared.

[0168]

[0186] [Table 3]

[0169]

[0187] Mixtures 3 through 7 were prepared of coating agents A and C through F dispersed in water at the concentrations shown in Table 4. With each of Mixtures 3 through 7, groups of 120 Mexican Hass avocados of identical size, quality, maturity, pack date, and orchard were coated by dipping each avocado into a bowl of the mixture and then drying for 100 seconds in a rolling translational heat tunnel at 65-70°C. Mass loss and CO2 respiration were then measured for the coated and uncoated avocados. The results are shown in Table 4.

[0170]

[0188] [Table 4]

[0171]

[0189] As shown in Table 4, C 12 ~C 18 Coatings formed from coatings containing ethyl esters of fatty acids reduced mass loss and respiration from produce.

[0172]

[0190] Example 4. Coated avocado

[0191] Coating agents (G to J) having the compositions shown in Table 5 were prepared.

[0173]

[0192] [Table 5]

[0174]

[0193] Mixtures 8-12 were prepared of coating agents A and C-F dispersed in water at the concentrations shown in Table 6. With each of Mixtures 8-12, groups of 120 Mexican Hass avocados of identical size, quality, maturity, pack date, and orchard were coated by dipping each avocado into a bowl of the mixture and then drying for 100 seconds in a rolling translational heat tunnel at 65-70°C. Mass loss and respiration of the coated and uncoated avocados were then measured. The results are shown in Table 6.

[0175]

[0194] [Table 6]

[0176]

[0195] As shown in Table 6, coatings formed from coating agents containing alkyl esters and monoglycerides in weight ratios of 1:3 to 3:1 reduced mass loss and respiration from produce.

[0177]

[0196] Example 5. Coated avocado

[0197] Mixtures 13-18 were prepared of coating agents A and G dispersed in water at the concentrations shown in Table 7. With each of Mixtures 13-18, groups of 120 Californian Hass avocados of identical size, quality, maturity, pack date, and orchard were coated by dipping each avocado into a bowl of the mixture and then drying for 100 seconds in a rolling translational heat tunnel at 65-70°C. Mass loss and respiration of the coated and uncoated avocados were then measured. The results are shown in Table 7.

[0178]

[0198] [Table 7]

[0179]

[0199] As shown in Table 7, at concentrations ranging from 10 g / L to 50 g / L, coatings formed from coatings containing alkyl esters reduced mass loss and respiration from produce better than corresponding coatings lacking alkyl esters.

[0180]

[0200] Example 6. Morphological characterization

[0201] Films 1 to 3 were prepared for coatings A, G, and J shown in Table 8. Approximately 20 μL of each coating dispersed in water was drop-cast onto a plastic substrate and dried at 70° C. for approximately 10 minutes.

[0181]

[0202] [Table 8]

[0182]

[0203] Films 1-3 were analyzed via small-angle X-ray scattering (SAXS) and wide-angle X-ray scattering (WAXS), and the results are shown in Figures 1-3. SAXS data, which provide information on long-range order, showed that each of films 1-3 exhibited Bragg reflections indicative of a lamellar mesophase. WAXS data, which provide information on short-range order, showed that film 2 exhibited Bragg reflections indicative of ethyl palmitate (q = 1.37 Å) within the film. -1 ) component and monoglyceride (q = 1.60Å -1 It was shown that the fatty acyl chains of both components exhibit chain packing characteristics.

[0183]

[0204] Example 7. Characterization of the mixture, coated avocado

[0205] Coating agents K to AH having the compositions shown in Tables 9 to 14 were prepared.

[0184]

[0206] [Table 9]

[0185]

[0207] [Table 10]

[0186]

[0208] [Table 11]

[0187]

[0209] [Table 12]

[0188]

[0210] [Table 13]

[0189]

[0211] [Table 14]

[0190]

[0212] Mixtures 19-48 of Coating Agents A and K-AH dispersed in water (25 g / L) were prepared as shown in Tables 15-20. The mixtures were evaluated for foaming upon mixing, and then a portion of each mixture was reserved for daily evaluation of stability.

[0191]

[0213] With each of Mixtures 19-48, within 24 hours of preparation, groups of 60 Mexican Hass avocados of identical size, quality, maturity, pack date, and orchard were coated by dipping each avocado into a bowl of the mixture and then drying for 100 seconds in a rolling, translating heat tunnel at 70°C. The avocados were removed from cold storage 30 minutes before treatment. The coatings were evaluated before and after drying. Mass loss and respiration were then measured for the coated and uncoated ("UT") comparison groups. The results are shown in Tables 15-20.

[0192]

[0214] [Table 15]

[0193]

[0215] [Table 16]

[0194]

[0216] [Table 17]

[0195]

[0217] [Table 18]

[0196]

[0218] [Table 19]

[0197]

[0219] [Table 20]

[0198]

[0220] As shown in Tables 15-20, stability decreased with increasing alkyl carbon number and with increasing alkyl ester amount. Increasing alkyl ester amount also increased opacity. For mixtures containing more than 50 wt% alkyl ester, stability became more difficult to determine due to increased opacity. The viscosity of the coating mixture was visually observed to increase significantly from about 1-2 cP to about 5 cP with increasing alkyl ester amount. The viscosity of Mix 30 was found to increase to about 100 cP upon contact with the cold fruit.

[0199]

[0221] As shown in Tables 15-20, the inclusion of up to 50 wt% alkyl esters selectively increased the mass barrier performance (MLF / RF>1) relative to the respiration barrier performance of the coating. 2 An increase in the / RF value indicated a particularly high performance coating.

[0200]

[0222] Example 8. Coat lime

[0223] Coating agents AI to AM having the compositions shown in Table 21 were prepared.

[0201]

[0224] [Table 21]

[0202]

[0225] Mixtures 49-64 were prepared of coating agents A, S, and AI-AM dispersed in water at the concentrations shown in Tables 22-24. With each of Mixtures 49-64, groups of 120 unwaxed limes of identical size, quality, maturity, pack date, and orchard were coated by dipping each lime into a bowl containing the mixture and then drying in a rolling translational heat tunnel at 70°C with a 10 Hz drive speed (approximately 120 seconds of residence time). The limes were removed from cold storage one hour before treatment. Mass loss and respiration were then measured for the coated and uncoated control groups. The results are shown in Tables 22-24.

[0203]

[0226] [Table 22]

[0204]

[0227] [Table 23]

[0205]

[0228] [Table 24]

[0206]

[0229] As shown in Table 22, coatings formed from coating agents containing increasing amounts of propyl stearate reduced mass loss better. As shown in Table 23, coatings formed from mixtures containing increasing concentrations of coating agent reduced mass loss better. As shown in Table 24, coatings formed from coating agents containing 5 wt% sodium stearate reduced mass loss better than those containing 10 wt% or more sodium stearate.

[0207]

[0230] Example 9. Differential scanning calorimetry, viscosity measurement

[0231] Mixtures 65-67 were prepared of coating agents A, S, and O dispersed in water at the concentrations shown in Table 25. Samples of propyl stearate and Mixtures 65 and 66 were loaded into Al hermetic sealing pans and cycled from 10°C to 90°C at a 10°C / min ramp rate in a differential scanning calorimeter. The second cycle was analyzed. The viscosities of Mixtures 65-67 were also measured at 2 x 10 -1 The shear strength was determined over a range of 100 Pa·s. The results are shown in Figure 4.

[0208]

[0232] [Table 25]

[0209]

[0233] Differential scanning calorimetry (DSC) results showed a melting transition for propyl stearate at approximately 29.8°C, crystallization at 24.8°C, and a phase transition at 18°C. For Mixture 65, a liquid crystalline transition was observed at 58.6°C upon heating (transition enthalpy 1.64 J / g). For Mixture 66, a liquid crystalline transition was observed at 56.9°C upon heating (transition enthalpy 1.30 J / g). No evidence of pure domains of propyl stearate was observed. Without wishing to be bound by theory, the results suggest that propyl stearate is randomly incorporated into glyceryl monostearate-dominated vesicles.

[0210]

[0234] As shown in FIG. 4, the viscosity of Mix 65 was constant over the shear range tested, while Mixes 66 and 67 each had a viscosity of about 2×10 -2 ~3×10 -1 Pa·s and 2–4×10 -2 The films exhibited shear thinning in Pa·s. The results suggest that propyl stearate and ethyl stearate act as viscosity modifiers that can provide improved films in the low shear regime.

[0211]

[0235] Example 10. Coated apples

[0236] Coating agents AN to AP having the compositions shown in Table 26 were prepared.

[0212]

[0237] [Table 26]

[0213]

[0238] Mixtures 68-73 were prepared of coating agents A, O, S, and AN-AP dispersed in water at the concentrations shown in Table 27. With each of Mixtures 68-73, groups of apples of the same size, quality, maturity, pack date, and orchard were coated by dipping each apple into a bowl of the mixture and then drying for 100 seconds in a rolling translational heat tunnel at 65-70° C. The mass loss of the coated and uncoated comparison groups was then measured. The results are shown in Table 27.

[0214]

[0239] [Table 27]

[0215]

[0240] As shown in Table 27, coatings formed from coatings containing glyceryl monolaurate demonstrated better performance compared to those lacking glyceryl monolaurate. As shown in Table 27, efficiency was better for coatings containing propyl stearate compared to those containing ethyl stearate.

[0216]

[0241] Example 11. Coated avocado

[0242] Coating agents AQ and AR having the compositions shown in Table 28 were prepared.

[0217]

[0243] [Table 28]

[0218]

[0244] Mixtures 74-85 were prepared of coating agents A, S, AQ, and AR dispersed in water at the concentrations shown in Table 29. With each of Mixtures 74-85, within 24 hours of preparation, groups of 60 Mexican Hass avocados of identical size, quality, maturity, pack date, and orchard were coated by dipping each avocado into a bowl of the mixture and then drying for 100 seconds in a rolling, translating heat tunnel at 70°C. The avocados were removed from cold storage 30 minutes before treatment. Mass loss and respiration were then measured for the coated avocados and a control group of uncoated avocados (UT). The results are shown in Table 29.

[0219]

[0245] [Table 29]

[0220]

[0246] As shown in Table 29, coatings formed from coatings containing propyl stearate and applied at 10-20 g / L performed similarly to or better than coatings formed from coatings lacking propyl stearate, even when applied at 40 g / L.

[0221]

[0247] While the present disclosure contains details of many specific embodiments, these should not be construed as limitations on the scope of the subject matter or on the scope that may be claimed, but rather as descriptions of possible specific features for particular embodiments. Certain features described herein in the context of separate embodiments may also be implemented in combination in a single embodiment. Conversely, various features described in the context of a single embodiment may also be implemented in multiple embodiments separately or in any suitable subcombination. Moreover, while previously described features may be described as working in a particular combination and may even initially be claimed as such, in some cases one or more features from a claimed combination may be deleted from that combination, and the claimed combination may relate to a subcombination or a variation of a subcombination.

[0222]

[0248] Specific embodiments of the subject matter have been described. As will be apparent to those skilled in the art, other embodiments, modifications, and permutations of the described embodiments are within the scope of the following claims. Although operations may be depicted in a particular order in the drawings or claims, this should not be understood as requiring such operations to be performed in a particular order or sequential order, nor as requiring that all illustrated operations be performed (although some operations may be considered optional) to achieve desirable results.

[0223]

[0249] Therefore, the example embodiments set forth above do not define or constrain the present disclosure. Other changes, substitutions, and alterations are also possible without departing from the spirit and scope of the present disclosure.

Claims

1. 1. A composition comprising: C, present in a total amount of about 15 wt% to about 99 wt% of the composition; ４ ~C ２８ one or more monoglycerides of fatty acids; C, present in a total amount of about 1 wt % to about 75 wt % of the composition; ８ ~C ２０ one or more alkyl esters of fatty acids; A composition comprising:

2. the one or more monoglycerides are present in a total amount of from about 70% to about 99% by weight of the composition; The composition of claim 1 , wherein the one or more alkyl esters are present in a total amount of from about 1 wt % to about 15 wt % of the composition.

3. The composition of claim 2, wherein the one or more alkyl esters are present in a total amount of from about 1 wt % to about 10 wt % of the composition.

4. the one or more monoglycerides are present in a total amount of from about 15% to about 85% by weight of the composition; The composition of claim 1 , wherein the one or more alkyl esters are present in a total amount of from about 15% to about 75% by weight of the composition.

5. 5. The composition of claim 1, wherein the one or more monoglycerides and the one or more alkyl esters comprise from about 70% to about 98% by weight of the composition.

6. C, present in a total amount of 0.1 wt % to about 30 wt % of the composition; ４ ~C ２８ The composition of any one of claims 1 to 5, further comprising one or more salts of fatty acids.

7. The composition of claim 6, wherein the one or more salts are present in a total amount of from about 1% to about 20% by weight of the composition.

8. The composition of claim 6, wherein the one or more salts are present in a total amount of from about 1% to about 10% by weight of the composition.

9. C ４ ~C ２８ one or more monoglycerides of fatty acids; C ８ ~C ２０ one or more alkyl esters of fatty acids; A composition comprising: The composition, wherein the ratio of the total number of moles of said one or more monoglycerides to the total number of moles of said one or more alkyl esters is from about 100:1 to about 1:

5.

10. 10. The composition of claim 9, wherein the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more alkyl esters is from about 50:1 to about 6:

1.

11. 10. The composition of claim 9, wherein the ratio of the total moles of the one or more monoglycerides to the total moles of the one or more alkyl esters is from about 3:1 to about 1:

3.

12. 12. The composition of any one of claims 9 to 11, wherein the one or more monoglycerides and the one or more alkyl esters comprise from about 70 wt% to about 98 wt% of the composition.

13. C ４ ~C ２８ The composition of any one of claims 9 to 12, further comprising one or more salts of fatty acids.

14. 14. The composition of claim 13, wherein the ratio of the total number of moles of the one or more monoglycerides and the one or more alkyl esters to the total number of moles of the one or more salts is from about 100:1 to about 4:

1.

15. 14. The composition of claim 13, wherein the ratio of the total number of moles of the one or more monoglycerides and the one or more alkyl esters to the total number of moles of the one or more salts is from about 50:1 to about 6:

1.

16. 16. The composition of any one of claims 13 to 15, wherein the one or more monoglycerides, the one or more alkyl esters, and the one or more salts comprise at least 80 wt% of the composition.

17. the one or more alkyl esters are each independently selected from C １ ~C ５ The composition of any one of claims 1 to 16, comprising an alkyl ester.

18. 17. The composition of any one of claims 1 to 16, 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.

19. The composition of any one of claims 1 to 16, wherein at least one of the alkyl esters comprises an ethyl ester or a propyl ester.

20. Each of the one or more alkyl esters independently has the formula III: 【Chemical 1】 (In the formula, R Ｂ is C １ ~C ８ is alkyl, R Ｈ is C ７ ~C １９ side chain) The composition of any one of claims 1 to 16, comprising a compound of formula:

21. R Ｂ is C １ ~C ５ 21. The composition of claim 20, wherein the alkyl is alkyl.

22. R Ｂ is C ２ Alkyl or C ３ 21. The composition of claim 20, wherein the alkyl is alkyl.

23. R Ｈ The composition of any one of claims 20 to 22, wherein is a saturated unsubstituted side chain.

24. R Ｈ is C １１ ~C １７ The composition according to any one of claims 20 to 23, which is a side chain.

25. Each of the one or more alkyl esters independently has the formula IIIA: 【Chemistry 2】 (In the formula, R Ｂ is C １ ~C ８ is 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; Each existing R １０Ａ , R １０Ｂ , R １１Ａ , and R １１Ｂ are 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 these 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 capable of forming a 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. The composition of any one of claims 1 to 16, comprising a compound of formula:

26. R Ｂ is C １ ~C ５ 26. The composition of claim 25, wherein the alkyl is alkyl.

27. R Ｂ is C ２ Alkyl or C ３ 26. The composition of claim 25, wherein the alkyl is alkyl.

28. Each of the one or more monoglycerides independently has the formula I-i or I-ii: 【Chemistry 3】 (In the formula, R Ａ１ and R Ａ２ are each independently H and C １ ~C ６ alkyl, R Ｈ is C ３ ~C ２７ side chain) 28. The composition of any one of claims 1 to 27, comprising a compound of formula:

29. R Ａ１ and R Ａ２ 30. The composition of claim 28, wherein each is H.

30. R Ｈ 30. The composition of claim 28 or claim 29, wherein is a saturated unsubstituted side chain.

31. R Ｈ is C １１ ~C ２１ The composition according to any one of claims 28 to 30, which is a side chain.

32. the one or more monoglycerides a first compound of formula I-i or I-ii, wherein R Ｈ is C １５ ~C ２７ side chain) and a second compound of formula I-i or I-ii, wherein R Ｈ is C ３ ~C １３ side chain) and The composition of any one of claims 28 to 31, comprising:

33. Each of the one or more monoglycerides independently has formula IA-i or formula IA-ii: 【Chemistry 4】 (In the formula, 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; Each existing R １０Ａ , R １０Ｂ , R １１Ａ , and R １１Ｂ are 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 these 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 capable of forming 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.

28. The composition of any one of claims 1 to 27, comprising a compound of formula:

34. R Ａ１ and R Ａ２ 34. The composition of claim 33, wherein each is H.

35. Each of the one or more salts present in the composition independently has the formula II: 【Chemistry 5】 (In the formula, R Ｈ is C ３ ~C ２７ is a side chain, X ｎ＋ is a cationic moiety having a formal charge n 35. The composition of any one of claims 1 to 34, comprising a compound of formula:

36. X ｎ＋ But Li ＋ , Na ＋ , K. ＋ , Cs ＋ , Ag ＋ , Ca ２＋ , Mg ２＋ , Zn ２＋ , Cu ２＋ , and (R Ｄ ) ４ N ＋ is selected from Each existing R Ｄ But H, C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ selected from heterocycloalkyl, aryl, and heteroaryl; Each C １ ~C ６ The alkyl is C ３ ~C ６ Cycloalkyl, C ３ ~C ６ 1 to 3 R independently selected from heterocycloalkyl, aryl, and heteroaryl Ｅ optionally substituted with Optionally, R Ｄ together with the nitrogen atom to which they are attached, ３ ~C ６ 36. The composition of claim 35, which forms a heterocycloalkyl.

37. R Ｈ 37. The composition of claim 35 or claim 36, wherein is a saturated unsubstituted side chain.

38. Each of the one or more salts present in the composition independently has the formula IIA: 【Chemistry 6】 (In the formula, 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; Each existing R １０Ａ , R １０Ｂ , R １１Ａ , and R １１Ｂ are 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 these 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 capable of forming 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, X ｎ＋ is a cationic moiety having a formal charge n 38. The composition of any one of claims 1 to 37, comprising a compound of formula:

39. X ｎ＋ But Li ＋ , Na ＋ , K. ＋ , Cs ＋ , Ag ＋ , Ca ２＋ , Mg ２＋ , Zn ２＋ , Cu ２＋ , and (R Ｄ ) ４ N ＋ is selected from Each existing R Ｄ But H, C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ selected from heterocycloalkyl, aryl, and heteroaryl; Each C １ ~C ６ The alkyl is C ３ ~C ６ Cycloalkyl, C ３ ~C ６ 1 to 3 R independently selected from heterocycloalkyl, aryl, and heteroaryl Ｅ optionally substituted with Optionally, R Ｄ together with the nitrogen atom to which they are attached, ３ ~C ６ 39. The composition of claim 38, which forms a heterocycloalkyl.

40. A composition according to any one of claims 1 to 39; A solvent; A mixture comprising:

41. 41. The mixture of claim 40, wherein the mixture comprises from about 30 wt% to about 99.9 wt% of the solvent.

42. 41. The mixture of claim 40, wherein the mixture comprises from about 90 wt% to about 99.5 wt% of the solvent.

43. 43. The mixture of any one of claims 40 to 42, 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.

44. 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 one of claims 1 to 39.

45. 45. The coated produce of claim 44, wherein the layer is disposed on a cuticular surface of the produce.

46. 46. ​​The coated agricultural product according to claim 44 or claim 45, wherein the layer has a thickness of from about 0.1 μm to about 20 μm.

47. The coated agricultural product according to any one of claims 44 to 46, wherein the layer has a thickness of from about 0.1 µm to about 10 µm.

48. 1. A method of coating produce, said method comprising: contacting a surface of the agricultural product with a mixture comprising a coating agent and a solvent, wherein the coating agent comprises: C ４ ~C ２８ one or more monoglycerides of fatty acids; C ８ ~C ２０ one or more alkyl esters of fatty acids; Including, the ratio of the total number of moles of the one or more monoglycerides to the total number of moles of the one or more alkyl esters is from about 100:1 to about 1:5; removing at least a portion of the solvent to form a coating on the surface of the produce; A method comprising:

49. 49. The method of claim 48, wherein the surface is a cuticular surface of the produce.

50. contacting the surfaces spraying the mixture onto the surface; or Immersing the produce in the mixture; 50. The method of claim 48 or claim 49, comprising:

51. 51. The method of any one of claims 48 to 50, wherein removing at least a portion of the solvent comprises evaporating at least a portion of the solvent.

52. 52. The method of any one of claims 48 to 51, 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.

53. 53. The method of any one of claims 48 to 52, further comprising adding the coating agent to the solvent to form the mixture.

54. The solvent and C ４ ~C ２８ and the one or more monoglycerides of fatty acids. ８ ~C ２０ 54. The method of any one of claims 48 to 53, further comprising adding said one or more alkyl esters of fatty acids to form said mixture.

55. 55. The method of any one of claims 48 to 54, wherein the concentration of the coating agent in the mixture is from about 1 mg / mL to about 200 mg / mL.

56. 55. The method of any one of claims 48 to 54, wherein the concentration of the coating agent in the mixture is from about 25 mg / mL to about 150 mg / mL.

57. the one or more monoglycerides are present in a total amount of about 70 wt % to about 99 wt % of the coating; 57. The method of any one of claims 48 to 56, wherein the one or more alkyl esters are present in a total amount of from about 1 wt % to about 15 wt % of the coating.

58. the one or more monoglycerides are present in a total amount of about 15% to about 85% by weight of the coating; 57. The method of any one of claims 48 to 56, wherein the one or more alkyl esters are present in a total amount of from about 15 wt% to about 75 wt% of the coating.

59. 59. The method of any one of claims 48-58, wherein the ratio of the total number of moles of the one or more monoglycerides to the total number of moles of the one or more alkyl esters is from about 50:1 to about 6:

1.

60. 60. The method of any one of claims 48-59, wherein the ratio of the total number of moles of the one or more monoglycerides to the total number of moles of the one or more alkyl esters is from about 3:1 to about 1:

3.

61. the one or more alkyl esters are each independently selected from C １ ~C ５ 61. The method of any one of claims 48 to 60, comprising an alkyl ester.

62. 61. The method of any one of claims 48-60, wherein each of the one or more alkyl esters independently comprises a methyl ester, an ethyl ester, a propyl ester, an isopropyl ester, a tert-butyl ester, or an iso-amyl ester.

63. 61. The method of any one of claims 48 to 60, wherein at least one of the alkyl esters comprises an ethyl ester or a propyl ester.

64. The coating agent is C ４ ~C ２８ 64. The method of any one of claims 48 to 63, further comprising one or more salts of fatty acids, wherein the ratio of the total number of moles of the one or more monoglycerides and the one or more alkyl esters to the total number of moles of the one or more salts is from about 100:1 to about 4:

1.

65. 65. The method of claim 64, wherein the one or more monoglycerides, the one or more alkyl esters, and the one or more salts comprise at least 80 wt% of the coating agent.

66. 66. The method of any one of claims 48-65, wherein the one or more monoglycerides and the one or more alkyl esters comprise from about 70 wt% to about 98 wt% of the coating agent.

67. 67. The method of any one of claims 48 to 66, wherein the coating agent and the solvent comprise at least 95 wt% of the mixture.

68. 1. A method for coating produce, comprising: contacting the surface of the agricultural product with the mixture according to any one of claims 40 to 43; removing at least a portion of the solvent to form a coating on the surface of the produce; A method comprising:

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