Coating composition comprising c4-C28 fatty acid monoglyceride and c8-C20 fatty acid alkyl ester

Abstract

The present invention relates to compositions comprising monoglycerides of fatty acids and alkyl esters. Exemplary embodiments include from about 15% to about 99% by weight of one or more monoglycerides of a C4-C28 fatty acid and from about 1% to about 75% by weight of one or more alkyl esters of a C8-C20 fatty acid.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of priority to U.S. Application No. 63 / 408,964, filed on September 22, 2022, the entire contents of which are hereby incorporated by reference. Technical Field

[0003] The present invention relates to coatings for agricultural products. Background Art

[0004] Common agricultural products are susceptible to degradation and decomposition (i.e., corruption) when exposed to the environment. These agricultural products may include, for example, eggs, fruits, vegetables, fruits, seeds, nuts, flowers and / or whole plants (including their processed and semi-processed forms). Non-agricultural products (e.g., vitamins, candies, etc.) are also susceptible to degradation when exposed to the surrounding environment. Degradation of agricultural products can occur by non-biological means, due to evaporation loss of water from the outer surface of the agricultural product to the atmosphere, and / or oxidation caused by oxygen diffusion from the environment into the agricultural product, and / or mechanical damage to the surface, and / or light-induced degradation (i.e., photodegradation). In addition, biological stressors such as bacteria, fungi, viruses and / or pests can also parasitize and decompose agricultural products.

[0005] Conventional solutions for preventing agricultural products from degrading, maintaining quality and improving lifespan include freezing and / or special packaging. Freezing requires capital-intensive devices, requires constant energy consumption, can cause product damage or quality loss if not carefully controlled, and must be actively managed. In addition, the benefits of freezing are lost when the supply chain of the controlled temperature fails. Special packaging also may require expensive devices, consume packaging materials, increase transportation costs, and require active management. Although benefits can be provided by freezing and special packaging, the processing and transportation of agricultural products can cause surface wear or abrasion, which makes consumers feel unsightly and can become an invasion point for bacteria and fungi. In addition, the expense relevant to these solutions can increase the cost of agricultural products. Summary of the invention

[0006] The present invention provides a composition comprising: C4-C 28 One or more monoglycerides of fatty acids present in a total amount of about 15% to about 99% by weight of the composition, and C8-C 20 One or more alkyl esters of fatty acids are present in a total amount of about 1% to about 75% by weight of the composition.

[0007] The present invention also provides a composition comprising C4-C 28 One or more monoglycerides of fatty acids and C8-C 20One 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 from about 100:1 to about 1:5.

[0008] Also provided herein are mixtures of the compositions described herein and solvents.

[0009] Also provided herein is a coated agricultural product comprising an agricultural product and a layer disposed on a surface of the agricultural product, the layer comprising a composition described herein.

[0010] Also provided herein is a method for coating an agricultural product, the method comprising contacting the surface of the agricultural product 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 product. 28 One or more monoglycerides of fatty acids and C8-C 20 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 from about 100:1 to about 1:5.

[0011] Also provided herein is a method of coating an agricultural product, the method comprising contacting a surface of the agricultural product with a mixture as described herein, and removing at least a portion of the solvent to form a coating on the surface of the agricultural product.

[0012] While the disclosed inventive concepts include those defined in the appended claims, it is to be understood that the inventive concepts may also be defined in terms of the following embodiments.

[0013] In addition to the embodiments of the appended claims and the embodiments described above, the following numbered embodiments are also innovative.

[0014] Embodiment 1 is a composition comprising:

[0015] C4-C 28 one or more monoglycerides of fatty acids present in a total amount of about 15% to about 99% by weight of the composition; and

[0016] C8-C 20 One or more alkyl esters of fatty acids are present in a total amount of about 1% to about 75% by weight of the composition.

[0017] Embodiment 2 is the composition of embodiment 1, wherein:

[0018] The one or more monoglycerides are present in a total amount of about 70% to about 99% by weight of the composition; and

[0019] The one or more alkyl esters are present in a total amount of about 1% to about 15% by weight of the composition.

[0020] 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.

[0021] Embodiment 4 is the composition of embodiment 1, wherein:

[0022] The one or more monoglycerides are present in a total amount of about 15% to about 85% by weight of the composition; and

[0023] The one or more alkyl esters are present in a total amount of about 15% to about 75% by weight of the composition.

[0024] Embodiment 5 is the composition of any of embodiments 1-4, 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.

[0025] Embodiment 6 is the composition of any one of embodiments 1-5, further comprising C4-C 28 One or more salts of fatty acids are present in a total amount of 0.1% to about 30% by weight of the composition.

[0026] 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.

[0027] 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.

[0028] Embodiment 9 is a composition comprising:

[0029] C4-C 28 one or more monoglycerides of fatty acids; and

[0030] C8-C 20 one or more alkyl esters of fatty acids;

[0031] 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 100:1 to about 1:5.

[0032] Embodiment 10 is the composition of embodiment 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.

[0033] Embodiment 11 is the composition of embodiment 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.

[0034] Embodiment 12 is the composition of any of embodiments 9-11, 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.

[0035] Embodiment 13 is the composition of any one of embodiments 9-12, further comprising C4-C 28 One or more salts of fatty acids.

[0036] Embodiment 14 is the composition of embodiment 13, wherein the ratio of the total moles of the one or more monoglycerides and the one or more alkyl esters to the total moles of the one or more salts is from about 100:1 to about 4:1.

[0037] Embodiment 15 is the composition of embodiment 13, wherein the ratio of the total moles of the one or more monoglycerides and the one or more alkyl esters to the total moles of the one or more salts is from about 50:1 to about 6:1.

[0038] Embodiment 16 is the composition of any of embodiments 13-15, wherein the one or more monoglycerides, the one or more alkyl esters, and the one or more salts comprise at least 80% by weight of the composition.

[0039] Embodiment 17 is the composition of any of embodiments 1-16, wherein the one or more alkyl esters each independently comprise a C1-C5 alkyl ester.

[0040] 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 isopentyl ester.

[0041] Embodiment 19 is the composition of any of embodiments 1-16, wherein the at least one alkyl ester comprises an ethyl ester or a propyl ester.

[0042] Embodiment 20 is the composition of any one of embodiments 1-16, wherein the one or more alkyl esters each independently comprise a compound of formula III:

[0043]

[0044] in:

[0045] R B is a C1-C8 alkyl group; and

[0046] R H It is C7-C 19 Sidechain.

[0047] Embodiment 21 is the composition of embodiment 20, wherein R B It is a C1-C5 alkyl group.

[0048] Embodiment 22 is the composition of embodiment 20, wherein R B It is a C2 alkyl group or a C3 alkyl group.

[0049] Embodiment 23 is the composition of any one of embodiments 20-22, wherein R H is a saturated unsubstituted side chain.

[0050] Embodiment 24 is the composition of any one of embodiments 20-23, wherein R H It is C 11 -C 17 Sidechain.

[0051] Embodiment 25 is the composition of any of embodiments 1-16, wherein the one or more alkyl esters each independently comprise a compound of formula IIIA:

[0052]

[0053] in:

[0054] R B is a C1-C8 alkyl group;

[0055] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0056] Each occurrence of R 10A , R 10B , R 11A and R 11B Independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl and C1-C6 alkoxy;

[0057] 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 may form together with the carbon atoms to which they are attached a double bond, a 3-membered to 6-membered cycloheterocycloalkyl or a C3-C6 cycloalkyl;

[0058] o is an integer from 0 to 15;

[0059] p is an integer from 0 to 15; and

[0060] The sum of o and p is 3 to 15.

[0061] Embodiment 26 is the composition of embodiment 25, wherein R B It is a C1-C5 alkyl group.

[0062] Embodiment 27 is the composition of embodiment 25, wherein R B It is a C2 alkyl group or a C3 alkyl group.

[0063] Embodiment 28 is the composition of any one of embodiments 1-27, wherein the one or more monoglycerides each independently comprise a compound of Formula Ii or Formula I-ii:

[0064]

[0065]

[0066] in:

[0067] R A1 and R A2 Each is independently selected from H and C1-C6 alkyl; and

[0068] R H It is C3-C 27 Sidechain.

[0069] Embodiment 29 is the composition of embodiment 28, wherein R A1 and R A2 Each is H.

[0070] Embodiment 30 is the composition of embodiment 28 or embodiment 29, wherein R H is a saturated unsubstituted side chain.

[0071] Embodiment 31 is the composition of any one of embodiments 28-30, wherein R H It is C 11 -C 21 Sidechain.

[0072] Embodiment 32 is the composition of any one of embodiments 28-31, wherein the one or more monoglycerides comprises:

[0073] The first compound of formula Ii or formula I-ii, wherein R HIt is C 15 -C 27 Sidechains; and

[0074] The second compound of Formula Ii or Formula I-ii, wherein R H It is C3-C 13 Sidechain.

[0075] Embodiment 33 is the composition of any one of embodiments 1-27, wherein the one or more monoglycerides each independently comprise a compound of Formula IA-i or Formula IA-ii:

[0076]

[0077] in:

[0078] R A1 and R A2 Each is independently selected from H and C1-C6 alkyl;

[0079] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0080] Each occurrence of R 10A , R 10B , R 11A and R 11B Independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl and C1-C6 alkoxy;

[0081] 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 may form together with the carbon atoms to which they are attached a double bond, a 3-membered to 6-membered cycloheterocycloalkyl or a C3-C6 cycloalkyl;

[0082] o is an integer from 0 to 17;

[0083] p is an integer from 0 to 17; and

[0084] The sum of o and p is 0 to 17.

[0085] Embodiment 34 is the composition of embodiment 33, wherein R A1 and R A2 Each is H.

[0086] Embodiment 35 is the composition of any one of embodiments 1-34, wherein the one or more salts present in the composition each independently comprises a compound of Formula II:

[0087]

[0088] in:

[0089] R H It is C3-C 27 Sidechains; and

[0090] X n+ It is a cationic moiety having a formal charge n.

[0091] Embodiment 36 is the composition of embodiment 35, wherein

[0092] X n+ Selected from Li + 、Na + , K + , Cs + 、Ag + , Ca 2+ Mg 2+ 、Zn 2+ , Cu 2+ and (R D )4N + ;and

[0093] Each occurrence of R D is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl and heteroaryl, wherein

[0094] Each C1-C6 alkyl group is optionally substituted with 1-3 R E Replace the 1-3 R E independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl and heteroaryl; and

[0095] Optionally, R D One or more instances of together with the nitrogen atom to which they are attached form a C3-C6 heterocycloalkyl.

[0096] Embodiment 37 is a composition of embodiment 35 or embodiment 36, wherein R His a saturated unsubstituted side chain.

[0097] Embodiment 38 is the composition of any one of embodiments 1-37, wherein the one or more salts present in the composition each independently comprises a compound of Formula IIA:

[0098]

[0099] in:

[0100] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0101] Each occurrence of R 10A , R 10B , R 11A and R 11B Independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl and C1-C6 alkoxy;

[0102] 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 may form together with the carbon atoms to which they are attached a double bond, a 3-membered to 6-membered cycloheterocycloalkyl or a C3-C6 cycloalkyl;

[0103] o is an integer from 0 to 17;

[0104] p is an integer from 0 to 17;

[0105] The sum of o and p is 0 to 17; and

[0106] X n+ It is a cationic moiety having a formal charge n.

[0107] Embodiment 39 is the composition of embodiment 38, wherein

[0108] Xn+ Selected from Li + 、Na + , K + , Cs + 、Ag + , Ca 2+ Mg 2+ 、Zn 2+ , Cu 2+ and (R D )4N + ;and

[0109] Each occurrence of R D is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl and heteroaryl, wherein:

[0110] Each C1-C6 alkyl group is optionally substituted with 1-3 R E Replace the 1-3 R E independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl and heteroaryl; and

[0111] Optionally, R D One or more instances of together with the nitrogen atom to which they are attached form a C3-C6 heterocycloalkyl.

[0112] Embodiment 40 is a mixture comprising:

[0113] The composition of any one of embodiments 1-39; and

[0114] Solvent.

[0115] Embodiment 41 is the mixture of embodiment 40, wherein the mixture comprises from about 30 wt % to about 99.9 wt % solvent.

[0116] Embodiment 42 is the mixture of embodiment 40, wherein the mixture comprises from about 90 wt % to about 99.5 wt % solvent.

[0117] Embodiment 43 is a mixture of any one of embodiments 40-42, wherein the solvent comprises one or more of the following: water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether.

[0118] Embodiment 44 is a coated agricultural product comprising an agricultural product and a layer located on a surface of the agricultural product, wherein the layer comprises the composition of any one of embodiments 1-39.

[0119] Embodiment 45 is the coated agricultural product of embodiment 44, wherein the layer is located on a skin surface of the agricultural product.

[0120] Embodiment 46 is the coated agricultural product of embodiment 44 or embodiment 45, wherein the thickness of the layer is from about 0.1 μm to about 20 μm.

[0121] Embodiment 47 is the coated agricultural product of any of embodiments 44-46, wherein the thickness of the layer is from about 0.1 μm to about 10 μm.

[0122] Embodiment 48 is a method of coating agricultural products, the method comprising:

[0123] The surface of the produce is contacted with a mixture comprising a coating agent and a solvent, wherein the coating agent comprises:

[0124] C4-C 28 one or more monoglycerides of fatty acids; and

[0125] C8-C 20 one or more alkyl esters of fatty acids;

[0126] 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 100:1 to about 1:5; and

[0127] At least a portion of the solvent is removed to form a coating on the surface of the produce.

[0128] Embodiment 49 is the method of embodiment 48, wherein the surface is a skin surface of an agricultural product.

[0129] Embodiment 50 is the method of embodiment 48 or embodiment 49, wherein the contacting surface comprises:

[0130] Spray the mixture onto the surface; or

[0131] Dip produce into the mixture.

[0132] Embodiment 51 is the method of any one of embodiments 48-50, wherein removing at least a portion of the solvent comprises evaporating at least a portion of the solvent.

[0133] Embodiment 52 is the method of any one of embodiments 48-51, wherein the solvent comprises one or more of the following: water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether.

[0134] Embodiment 53 is the method of any one of embodiments 48-52, further comprising adding a coating agent to the solvent to form a mixture.

[0135] Embodiment 54 is the method of any one of embodiments 48-53, further comprising: 20One or more alkyl esters of fatty acids are added to a solvent and a C4-C 28 A premix of one or more monoglycerides of fatty acids is added to form a mixture.

[0136] Embodiment 55 is the method of any one of embodiments 48-54, wherein the concentration of the coating agent in the mixture is about 1 mg / mL to about 200 mg / mL.

[0137] Embodiment 56 is the method of any one of embodiments 48-54, wherein the concentration of the coating agent in the mixture is about 25 mg / mL to about 150 mg / mL.

[0138] Embodiment 57 is the method of any one of embodiments 48-56, wherein:

[0139] The one or more monoglycerides are present in a total amount of about 70% to about 99% by weight of the coating agent; and

[0140] The one or more alkyl esters are present in a total amount of about 1 wt % to about 15 wt % of the coating agent.

[0141] Embodiment 58 is the method of any one of embodiments 48-56, wherein:

[0142] The one or more monoglycerides are present in a total amount of about 15% to about 85% by weight of the coating agent; and

[0143] The one or more alkyl esters are present in a total amount of about 15% to about 75% by weight of the coating agent.

[0144] Embodiment 59 is the method of any one 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.

[0145] Embodiment 60 is the method of any one 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.

[0146] Embodiment 61 is the method of any one of embodiments 48-60, wherein the one or more alkyl esters each independently comprise a C1-C5 alkyl ester.

[0147] Embodiment 62 is the method of any one of embodiments 48-60, 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 isopentyl ester.

[0148] Embodiment 63 is the method of any one of embodiments 48-60, wherein the at least one alkyl ester comprises an ethyl ester or a propyl ester.

[0149] Embodiment 64 is the method of any one of embodiments 48-63, wherein the coating agent further comprises C4-C 28 One or more salts of fatty acids, wherein the ratio of the total moles of the one or more monoglycerides and the one or more alkyl esters to the total moles of the one or more salts is from about 100:1 to about 4:1.

[0150] Embodiment 65 is the method of embodiment 64, wherein the one or more monoglycerides, the one or more alkyl esters, and the one or more salts comprise at least 80 weight percent of the coating agent.

[0151] Embodiment 66 is the method of any one of embodiments 48-65, wherein the one or more monoglycerides and the one or more alkyl esters comprise from about 70% to about 98% by weight of the coating agent.

[0152] Embodiment 67 is the method of any of embodiments 48-66, wherein the coating agent and the solvent comprise at least 95 weight percent of the mixture.

[0153] Embodiment 68 is a method of coating agricultural products, the method comprising:

[0154] contacting a produce surface with the mixture of any of embodiments 40-43; and

[0155] At least a portion of the solvent is removed to form a coating on the surface of the produce.

[0156] The details of one or more embodiments of the inventive subject matter are set forth in the drawings and the specification. Other features, aspects, and advantages of the subject matter will become apparent from the specification, drawings, and claims. BRIEF DESCRIPTION OF THE DRAWINGS

[0157] Figure 1 is a graph showing small angle X-ray scattering (SAXS) / wide angle X-ray scattering (WAXS) data collected from a monoglyceride film.

[0158] Figure 2 is a graph showing SAXS / WAXS data collected from films of the compositions described herein.

[0159] Figure 3 is a graph showing SAXS / WAXS data collected from an alkyl ester film.

[0160] Figure 4 is a graph showing viscosity data collected from certain compositions herein. DETAILED DESCRIPTION

[0161] The present invention relates to compositions comprising monoglycerides and alkyl esters of fatty acids. Specifically, the compositions described herein can be applied to agricultural products to provide improved barrier properties for, for example, gas or water. Such coatings can better limit the loss of quality and / or the generation of CO2 of agricultural products compared to those lacking fatty acid alkyl esters.

[0162] Reference will now be made to details of certain embodiments of the disclosed subject matter.While the disclosed subject matter will be described in conjunction with the enumerated claims, it will be understood that the exemplary subject matter is not intended to limit the claims to the disclosed subject matter.

[0163] definition

[0164] As used herein, the terms "a", "an" and "the" include one or more than one, unless the context clearly indicates otherwise. The term "or" is used to refer to a non-exclusive "or" unless otherwise indicated. A statement "at least one of A and B" has the same meaning as "A, B or A and B". In addition, it should be understood that the words or terms used in the present invention are used for illustrative purposes only and are not intended to be limiting unless otherwise defined. Any section headings used are intended to aid reading of the document and are not to be construed as limiting; information related to the section heading may be present within or outside the specific section.

[0165] Values ​​expressed in range format should be interpreted in a flexible manner to include not only the values ​​explicitly stated as limits of the range, but also all individual values ​​or subranges included in the range, as if each 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 of "about X to Y" has the same meaning as "about X to about Y" unless otherwise indicated. Similarly, a statement of "about X, Y or about Z" has the same meaning as "about X, about Y or about Z" unless otherwise indicated.

[0166] As used herein, the term "about" allows for variability in the value or range within 10% of the stated value or limit of the stated range.

[0167] In the methods described herein, the actions may be performed in any order, except when a temporal order or order of operations is explicitly stated. In addition, the specified actions may be performed simultaneously, unless the language explicitly stated that they are performed separately. For example, a claimed action of performing X and a claimed action of performing Y may be performed simultaneously in a single operation, and the resulting method will fall within the literal scope of the claimed method.

[0168] As used herein, the term "monoglyceride" refers to the condensation product of a glycerol molecule and a fatty acid, that is, the glycerol group is connected to a fatty acid by an ester bond. Monoglycerides can, but are not necessarily derived from a condensation reaction. For example, monoglycerides can be obtained by an esterification reaction between glycerol and fatty acids, by transesterification of triglycerides with glycerol (glycerolysis), etc. Monoglycerides may also be referred to as monoalkanoic acid glycerides. In the case where the glycerol group is connected to the ester bond at position 1 (e.g., in the case of 2,3-dihydroxyprop-1-yl octadecanoate), the monoglyceride may be referred to as alkanoic acid 1-monoglyceride or 1-glycerol alkanoate (e.g., in the case of 1-glycerol octadecanoate). In the case where the glycerol group is connected to the ester bond at position 2 (e.g., in the case of 1,3-dihydroxyprop-2-yl hexadecanoate), the monoglyceride may be referred to as alkanoic acid 2-monoglyceride or 2-glycerol alkanoate (e.g., in the case of 2-glycerol hexadecanoate). The glycerol group of the monoglyceride may be unsubstituted (for example, in the case of 2,3-dihydroxyprop-1-ylalkanoate), or may be further substituted with one or more groups other than fatty acids (for example, in the case of 1,3-dialkoxyprop-2-ylalkanoate).

[0169] The term "alkyl ester" used in reference to fatty acids refers to the condensation product of an alkanol and a fatty acid, that is, an alkyl group is attached to a fatty acid via an ester bond. Alkyl esters may, but need not, be derived from a condensation reaction. For example, alkyl esters may be obtained by esterification between an alkanol and a fatty acid, by transesterification of monoglycerides, triglycerides, and the like. Alkyl esters may also be referred to as alkyl alkanoates. For example, the ethyl ester of hexadecanoic acid may also be referred to as ethyl hexadecanoate.

[0170] As used herein, the term "fatty acid" refers to a carboxylic acid with an aliphatic side chain. The fatty acid may be naturally occurring or non-naturally occurring, and may include branched or unbranched (e.g., linear), substituted or unsubstituted, and saturated or unsaturated side chains.

[0171] As used herein, the term "side chain" refers to the aliphatic portion of a fatty acid or a portion thereof. Unless otherwise indicated, the side chain of a given fatty acid includes the carbon of the carboxylic acid group. For example, dodecanoic acid can be described as including a linear, saturated C 12 side chain, and can also be represented as R H -C(O)OH, where R H It is a linear saturated C 11 Side chains. Side chains may be present in compounds other than fatty acids, such as esters or amides, and may, but need not, be derived from fatty acids. For example, lauryl amide may be described as an amide of a fatty acid, regardless of whether the compound is actually derived from dodecanoic acid.

[0172] The term "salt" used in reference to the disclosed compounds (e.g., fatty acids) refers to derivatives of compounds in which the parent compound is modified by converting the acid or base moiety into their salt form. Examples of such salts include, but are not limited to, inorganic or organic acid salts of basic residues such as amines, inorganic (e.g., alkaline) or organic salts of acidic residues such as carboxylic acids, and the like.

[0173] When certain features of the compounds described herein are disclosed as groups or ranges, such disclosure includes each and every individual subcombination of the members of such groups or 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.

[0174] As used herein, the term "n-membered" (where n is an integer) generally describes the number of ring-forming atoms in a moiety, where the number of ring-forming atoms is n. For example, piperidinyl is an example of a 6-membered heterocycloalkyl ring, and 1,2,3,4-tetralin is an example of a 10-membered cycloalkyl.

[0175] As used herein, the term "substituted" means that an atom or a group of atoms formally replaces hydrogen as a "substituent" connected to another group. Unless otherwise indicated, "substituted" refers to any substitution level, such as mono-, di-, tri-, tetra- or penta-substitution, where such substitution is allowed. Substituents are independently selected, and substitutions can be at any chemically feasible position. Substitution at a given atom is limited to valence. Substitution at a given atom produces a chemically stable molecule. The phrase "optionally substituted" means unsubstituted or substituted. A single divalent substituent such as oxygen can replace two hydrogen atoms.

[0176] As used herein, the term “C n -C m " denotes a range including the endpoints, where n and m are integers and denote the number of carbons. Examples include C1-C4, C1-C6, etc.

[0177] As used herein, the term "alkyl" refers to a saturated hydrocarbon group, which may be straight chain or branched. n -C m "Alkyl" refers to an alkyl radical having n to m carbon atoms. Alkyl radicals formally correspond to alkanes in which one CH bond is replaced by the point of attachment of the alkyl radical to the rest 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 homologues such as 2-methyl-1-butyl, n-pentyl, 3-pentyl, n-hexyl, 1,2,2-trimethylpropyl, and the like.

[0178] 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. Alkenyl formally corresponds to olefins, in which one CH bond is replaced by the point of attachment of the alkenyl group to the rest of the compound. n -C m "Alkenyl" refers to an alkenyl group having n to m carbons. Exemplary alkenyl groups include, but are not limited to, ethenyl, n-propenyl, isopropenyl, n-butenyl, sec-butenyl, and the like.

[0179] As used herein, the term "alkoxy" refers to a group of the formula -O-alkyl, wherein alkyl is as defined above. n -C m "Alkoxy" refers to an alkoxy group whose alkyl group has n to m carbons. Exemplary alkoxy groups include methoxy, ethoxy, propoxy (eg, n-propoxy and isopropoxy), tert-butoxy, and the like.

[0180] As used herein, the term "cycloalkyl" refers to a non-aromatic hydrocarbon ring system (monocyclic, bicyclic or polycyclic) including cyclized alkyl and alkenyl groups. n -C m "Cycloalkyl" refers to a cycloalkyl radical having n to m ring member carbon atoms. Cycloalkyl radicals may include fused, bridged and / or spiro bicyclic or polycyclic ring systems. Examples of cycloalkyl radicals include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cyclohexadienyl, cycloheptatrienyl, norbornyl, norpinyl, norcaryl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.2.0]hexyl, bicyclo[3.1.0]hexyl, bicyclo[3.2.0]heptyl and bicyclo[3.3.0]-octyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl and bicyclo[1.1.1]pentyl, and the like.

[0181] As used herein, the term "heterocycloalkyl" refers to a non-aromatic ring system (monocyclic, bicyclic or polycyclic), which may optionally contain one or more alkenylene groups as part of the ring structure, which has at least one heteroatom ring member, which is independently selected from nitrogen, sulfur, oxygen and phosphorus. The term "n-membered to m-membered ring heterocycloalkyl" refers to a heterocycloalkyl having n to m ring atoms. The ring-forming carbon atoms and heteroatoms of the heterocycloalkyl may be optionally oxidized to form oxo or thio groups or other oxidized bonds (e.g., C(O), S(O), C(S), S(O)2, N-oxides, etc.), or the nitrogen atom may be quaternized. The heterocycloalkyl may be connected by ring-forming carbon atoms or ring-forming heteroatoms. The heterocycloalkyl may include double bonds, such as up to 3 double bonds. Examples of heterocycloalkyl 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, tetrahydrooxazolyl, morpholinyl, oxetanyl, dioxetane 1-H-isoindolyl, 2-azabicyclo[2.2.1]heptanoyl, 3-azabicyclo[3.1.0]hexyl, 3-azabicyclo[4.1.0]heptyl, and the like. Other examples of heterocycloalkyl 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-oxazolidin-3-yl, 1,4- Oxazepan-1-yl, isothiazolidinyl, 1,3-thiazolidin-3-yl, 1,2-pyrazolidin-2-yl, 1,2-tetrahydrothiazin-2-yl, 1,3-thiazin-3-yl, 1,2-tetrahydrodiazin-2-yl, 1,3-tetrahydrodiazin-1-yl, 1,4-oxazin-4-yl, oxazolidinone, 2-oxo-piperidinyl (e.g., 2-oxo-piperidin-1-yl), and the like.

[0182] Composition

[0183] This article provides C4-C 28 One or more monoglycerides of fatty acids and C8-C 20 A composition of one or more alkyl esters of fatty acids.

[0184] In some embodiments, the one or more monoglycerides are present in a total amount from about 15% to about 99% by weight of the composition, for example, from about 15% to about 85% by weight, from about 15% to about 65% by weight, from about 25% to about 85% by weight, from about 25% to about 65% by weight, from about 35% to about 85% by weight, from about 35% to about 65% by weight, from about 70% to about 99% by weight, from about 70% to about 96% by weight, from about 80% to about 99% by weight, or from about 80% to about 96% by weight of the composition.

[0185] In some embodiments, the one or more alkyl esters are present in a total amount from about 1% to about 75% by weight of the composition, for example, from about 1% to about 15%, from about 1% to about 10%, from about 2.5% to about 15%, from about 2.5% to about 10%, from about 5% to about 15%, from about 5% to about 10%, from about 15% to about 75%, from about 15% to about 55%, from about 25% to about 75%, from about 25% to about 55%, from about 35% to about 75%, or from about 35% to about 55%.

[0186] In some embodiments, the ratio of the total moles of one or more monoglycerides to the total moles of one or more alkyl esters is from about 100:1 to about 1:5, e.g., from about 100:1 to about 5:1, from about 100:1 to about 7:1, from about 50:1 to about 5:1, from about 50:1 to about 7:1, from about 25:1 to about 5:1, from about 25:1 to about 7:1, from about 5:1 to about 1:5, from about 5:1 to about 1:2, from about 3:1 to about 1:5, from about 3:1 to about 1:2, from about 2:1 to about 1:5, or from about 2:1 to about 1:2.

[0187] In some embodiments, the one or more monoglycerides and the one or more alkyl esters comprise from about 70% to about 99% by weight of the composition, e.g., from about 70% to about 96% by weight, from about 80% to about 99% by weight, from about 80% to about 96% by weight, from about 85% to about 99% by weight, or from about 85% to about 96% by weight of the composition.

[0188] In some embodiments, the composition further comprises C4-C 28One or more salts of fatty acids. In some embodiments, the one or more salts are present in a total amount of about 0.1% to about 30% by weight of the composition, about 0.1% to about 15% by weight of the composition, about 0.1% to about 10% by weight, about 1% to about 30% by weight, about 1% to about 15% by weight, about 1% to about 10% by weight, about 2% to about 30% by weight, about 2% to about 15% by weight, or about 2% to about 10% by weight. 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 about 100:1 to about 4:1, for example, about 100:1 to about 8:1, about 75:1 to about 4:1, about 75:1 to about 4:1, about 50:1 to about 4:1, or 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% by weight of the composition, e.g., at least about 85%, at least about 90%, at least about 95%, or at least about 99% by weight of the composition.

[0189] C4-C 28 Monoglycerides of fatty acids

[0190] The compositions described herein include C4-C 28 In some embodiments, the composition includes a C4-C 28 In some embodiments, the composition includes two, three or more C4-C 28 Fatty acid monoglycerides, for example, include two C4-C 28 Fatty acid monoglycerides. In some embodiments, the monoglycerides include one or more monoglycerides of naturally occurring fatty acids.

[0191] Monoglycerides may include one or more 1-monoglycerides, one or more 2-monoglycerides, or mixtures thereof. In some embodiments, monoglycerides include one or more fatty acid 2,3-dihydroxypropan-1-yl esters, one or more fatty acid 1,3-dihydroxypropan-2-yl esters, or mixtures thereof. In some embodiments, 1-monoglycerides account for at least about 50% by weight, at least about 70% by weight, at least about 80% by weight, at least about 90% by weight, or about 100% by weight of the monoglycerides present in the composition. In some embodiments, 1-monoglycerides account for about 70% by weight to about 100% by weight, about 70% by weight to about 90% by weight, about 75% by weight to about 100% by weight, about 75% by weight to about 90% by weight, about 80% by weight to about 100% by weight, or about 80% by weight to about 90% by weight of the monoglycerides present in the composition.

[0192] In some embodiments, the monoglycerides include one or more monoglycerides of the following fatty acids: 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 monoglycerides include unsubstituted side chains, such as unsubstituted C 12 -C 22 In some embodiments, one or more monoglycerides include linear side chains, such as linear C 12 -C 22 In some embodiments, one or more monoglycerides include saturated side chains, such as saturated C 12 -C 22 Sidechain.

[0193] In some embodiments, the monoglyceride comprises one or more compounds of Formula Ii:

[0194]

[0195] in:

[0196] R A1 and R A2 Each is independently selected from H and C1-C6 alkyl; and

[0197] R H It is C3-C 27 Sidechain.

[0198] In some embodiments, the monoglyceride comprises one or more compounds of Formula I-ii:

[0199]

[0200] in:

[0201] R A1 and R A2 Each is independently selected from H and C1-C6 alkyl; and

[0202] R H It is C3-C 27 Sidechain.

[0203] In some embodiments, the one or more monoglycerides each independently comprise a compound of Formula Ii or Formula I-ii. In some embodiments of Formula Ii or Formula I-ii, R A1 and R A2 Each is 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 It is C5-C 17 In some embodiments of Formula Ii or Formula I-ii, R H It is C 11 -C 21 Sidechain.

[0204] In some embodiments, the monoglyceride comprises a first compound of Formula Ii or Formula I-ii, wherein R H It is C 15 -C 27 side chain; and a second compound of Formula Ii or Formula I-ii, wherein R H It is C3-C 13 In some embodiments, R of the first compound H It is C 15 -C 21 side chain, and R of the second compound H It is C 11 -C 13 Sidechain.

[0205] In some embodiments, the monoglyceride includes one or more compounds of Formula IA-i:

[0206]

[0207] in:

[0208] R A1 and R A2 Each is independently selected from H and C1-C6 alkyl;

[0209] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0210] Each occurrence of R 10A , R 10B , R 11A and R 11B Independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl and C1-C6 alkoxy;

[0211] 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 may form together with the carbon atoms to which they are attached a double bond, a 3-membered to 6-membered cycloheterocycloalkyl group, or a C3-C6 cycloalkyl group;

[0212] o is an integer from 0 to 17;

[0213] p is an integer from 0 to 17; and

[0214] The sum of o and p is 0 to 17.

[0215] In some embodiments, the monoglyceride includes one or more compounds of Formula IA-ii:

[0216]

[0217] in:

[0218] R A1 and R A2 Each is independently selected from H and C1-C6 alkyl;

[0219] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0220] Each occurrence of R 10A , R 10B , R11A and R 11B Independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl and C1-C6 alkoxy;

[0221] 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 may form together with the carbon atoms to which they are attached a double bond, a 3-membered to 6-membered cycloheterocycloalkyl or a C3-C6 cycloalkyl;

[0222] o is an integer from 0 to 17;

[0223] p is an integer from 0 to 17; and

[0224] The sum of o and p is 0 to 17.

[0225] In some embodiments, the one or more monoglycerides each independently comprise 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 Each is H. In some embodiments of Formula IA-i or Formula IA-ii, each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B are 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 , R11A and R 11B Any two of the R atoms, taken together with the carbon atoms to which they are attached, form ethylene oxide. In some embodiments of Formula IA-i or Formula IA-ii, two, one, or zero pairs of R atoms on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B Together with the carbon atoms to which they are attached, they form a double bond. In some embodiments of Formula IA-i or Formula IA-ii, one or zero pairs of R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B Together with the carbon atom to which they are attached, they form ethylene oxide. In some embodiments of Formula IA-i or Formula IA-ii, two, one, or zero R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B It's OH.

[0226] 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.

[0227] In some embodiments, the monoglyceride includes one or more 1-monoglycerides 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.

[0228] C4-C 28 Salts of fatty acids

[0229] The compositions described herein may include C4-C 28 In some embodiments, the composition includes C4-C 28 In some embodiments, the composition includes C4-C 28 Two, three or more salts of fatty acids, for example, including C4-C 28 Two Salts of Fatty Acids. In some embodiments, the salts include one or more salts of naturally occurring fatty acids.

[0230] In some embodiments, the salt comprises one or more salts of the following acids: 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 Fatty acids. In some embodiments, the salt comprises C 12 -C 22 Two salts of fatty acids, such as C 16 Fatty acids and C 18 In some embodiments, one or more salts include unsubstituted side chains, such as unsubstituted C 12 -C 22 In some embodiments, one or more salts include linear side chains, such as linear C 12 -C 22 In some embodiments, one or more salts include saturated side chains, such as saturated C 12 -C 22 Sidechain.

[0231] In some embodiments, the salt comprises one or more compounds of Formula II:

[0232]

[0233] in:

[0234] R H It is C3-C 27 Sidechains; and

[0235] X n+ It is a cationic moiety having a formal charge n.

[0236] In some embodiments, the one or more salts each independently comprise a compound of Formula II. In some embodiments of Formula II, X n+ Selected from Li + 、Na + , K + , Cs + 、Ag + , Ca 2+ Mg 2+ 、Zn 2+ , Cu 2+ and (R D )4N + , where each occurrence of R D is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl and heteroaryl, and each C1-C6 alkyl is optionally substituted with 1-3 R E Replace the 1-3 R E is independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl and heteroaryl. n+ Yes (R D )4N + , and R D One or more instances of together with the nitrogen atom to which they are attached form a C3-C6 heterocycloalkyl. In some embodiments of Formula II, X n+ Selected from 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 It is C5-C 17 In some embodiments of Formula II, R H It is C 11 -C 21 Sidechain.

[0237] In some embodiments, the salt includes one or more compounds of Formula IIA:

[0238]

[0239] in:

[0240] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0241] Each occurrence of R 10A , R 10B , R 11A and R 11B Independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl and C1-C6 alkoxy;

[0242] 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 may form together with the carbon atoms to which they are attached a double bond, a 3-membered to 6-membered cycloheterocycloalkyl or a C3-C6 cycloalkyl;

[0243] o is an integer from 0 to 17;

[0244] p is an integer from 0 to 17;

[0245] The sum of o and p is 0 to 17; and

[0246] X n+ It is a cationic moiety having a formal charge n.

[0247] In some embodiments, the one or more salts each independently comprise a compound of Formula IIA. In some embodiments of Formula IIA, X n+ Selected from Li + 、Na + , K + , Cs +、Ag + , Ca 2+ Mg 2+ 、Zn 2+ , Cu 2+ and (R D )4N + , where each occurrence of R D is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl and heteroaryl, and each C1-C6 alkyl is optionally substituted with 1-3 R E Replace the 1-3 R E is independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl and heteroaryl. n+ Yes (R D )4N + , and R D One or more instances of together with the nitrogen atom to which they are attached form a C3-C6 heterocycloalkyl. In some embodiments of Formula II, X n+ Selected from Na + , K + , Ca 2+ Mg 2+ and Zn 2+ .

[0248] In some embodiments of Formula IIA, each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B are 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 Any two of the R on adjacent carbon atoms, together with the carbon atoms to which they are attached, form ethylene oxide.1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B Together with the carbon atoms to which they are attached, they form a double bond. In some embodiments of Formula IIA, one or zero pairs of R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B Together with the carbon atom to which they are attached, they form ethylene oxide. In some embodiments of Formula IIA, two, one, or zero R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B It's OH.

[0249] In some embodiments of Formula IIA, 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.

[0250] In some embodiments, the salt comprises one or more salts of saturated linear unsubstituted fatty acids, such as sodium, potassium, silver, calcium, magnesium or zinc salts. In some embodiments, the salt comprises one or more salts of the following acids, such as sodium, potassium, silver, calcium, magnesium or zinc salts: 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.

[0251] Alkyl esters

[0252] The compositions described herein include C4-C 28 One or more alkyl esters of fatty acids. In some embodiments, the alkyl esters include one or more C1-C5 alkyl esters. In some embodiments, each alkyl ester is independently a C1-C5 alkyl ester. In some embodiments, the alkyl esters include methyl esters, ethyl esters, propyl esters, isopropyl esters, tert-butyl esters, isopentyl esters, or any combination thereof. In some embodiments, at least one alkyl ester includes ethyl esters or propyl esters.

[0253] In some embodiments, the alkyl ester includes one or more compounds of Formula III:

[0254]

[0255] in:

[0256] R B is a C1-C8 alkyl group; and

[0257] R H It is C7-C 19 Sidechain.

[0258] In some embodiments, the one or more alkyl esters each independently comprise 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. H is a saturated side chain. H is an unsubstituted side chain. H is a linear side chain. H It 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 Sidechain.

[0259] In some embodiments, the alkyl ester includes one or more compounds of Formula IIIA:

[0260]

[0261] in:

[0262] R B is a C1-C8 alkyl group;

[0263] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0264] Each occurrence of R 10A , R 10B , R 11A and R 11B Independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl and C1-C6 alkoxy;

[0265] 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 may form together with the carbon atoms to which they are attached a double bond, a 3-membered to 6-membered cycloheterocycloalkyl or a C3-C6 cycloalkyl;

[0266] o is an integer from 0 to 15;

[0267] p is an integer from 0 to 15; and

[0268] The sum of o and p is 3 to 15.

[0269] In some embodiments, the one or more alkyl esters each independently comprise 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, each R 1 , R2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B are 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 11B Any two of the R on adjacent carbon atoms together with the carbon atoms to which they are attached form ethylene oxide. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B Together with the carbon atoms to which they are attached, they form a double bond. In some embodiments of Formula IIIA, one or zero pairs of R on adjacent carbon atoms 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B Together with the carbon atom to which they are attached, they form ethylene oxide. In some embodiments of Formula IIIA, two, one, or zero R 1 , R 2 , R 3 , R4 , R 5 , R 6 , R 7 , R 8 and R 9 and each occurrence of R 10A , R 10B , R 11A and R 11B It's OH.

[0270] In some embodiments, the monoglyceride includes one or more alkyl esters of the following acids, such as ethyl or propyl esters: 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, 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-(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-epoxyoctadecanoic 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)-docosa-13-enoic acid, or (13E)-docosa-13-enoic acid.

[0271] Additional components

[0272] The compositions described herein may include one or more additional components, such as components that are non-toxic and safe for human and / or animal consumption. For example, the compositions may include direct or indirect food additives or food contact substances approved by the U.S. Food and Drug Administration (FDA), components that meet the FDA's regulatory requirements for use as food additives or food contact substances, or components that are generally recognized as safe (GRAS) by the FDA.

[0273] In some embodiments, the compositions described herein further include one or more fatty acids, such as C4-C 22Fatty acids. In some embodiments, the composition includes less than about 10% by weight, e.g., less than about 5% by weight, less than about 2% by weight, less than about 1% by weight, or is free of one or more of the following: triglycerides, diglycerides, acetylated monoglycerides, lactated monoglycerides, succinylated monoglycerides, sterols, bile acids, proteins, polysaccharides, phenols, lignans, aromatic acids, terpenoids, flavonoids, carotenoids, alkaloids, alcohols, alkanes, aldehydes, and any salts thereof.

[0274] mixture

[0275] Also provided herein is a mixture comprising a composition as described herein and a solvent. In some embodiments, the mixture comprises a dispersion of the composition as 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 the following substances: 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.

[0276] In some embodiments, the mixture includes about 30% to about 99.9% by weight, about 30% to about 99.5% by weight, about 30% to about 99% by weight, about 50% to about 99.9% by weight, about 50% to about 99.5% by weight, about 50% to about 99% by weight, about 90% to about 99.9% by weight, about 90% to about 99.5% by weight, or about 90% to about 99% by weight of solvent.

[0277] 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.

[0278] coating

[0279] Also provided herein is a coated agricultural product comprising a layer formed by the composition described herein on the surface of the agricultural product. In some embodiments, the agricultural product is an edible agricultural product, including, for example, fruits, vegetables, edible seeds and nuts, herbs, spices, fruits, meat, eggs, dairy products, seafood, cereals or any other consumables. In other embodiments, the agricultural product is an inedible agricultural product, including, for example, inedible flowers, seeds, seedlings, stems, leaves, whole plants, etc. In some embodiments, the layer is located on the outer surface (e.g., epidermal surface) of the agricultural product.

[0280] In some embodiments, the thickness of the layer is about 0.1 μm to about 20 μm, for example, 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.

[0281] Coating method

[0282] Also provided herein is a method for coating an agricultural product, the method comprising: contacting the surface of the agricultural product 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 product. 28 One or more monoglycerides of fatty acids and C8-C 20 In some embodiments, the coating agent is a composition as described herein. For example, 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. In some embodiments, the coating agent includes C4-C 28 One or more monoglycerides of fatty acids present in a total amount of about 15% to about 99% by weight of the coating agent, and C8-C 20 One or more alkyl esters of fatty acids are present in a total amount of 1 wt % to about 75 wt % of the coating agent.

[0283] In some embodiments of the coating method, the agricultural product is an edible agricultural product, including, for example, fruits, vegetables, edible seeds and nuts, herbs, spices, fruits, meat, eggs, dairy products, seafood, grains, or any other consumables. In other embodiments of the coating method, the agricultural product is an inedible agricultural product, including, for example, inedible flowers, seeds, seedlings, stems, leaves, whole plants, etc. In some embodiments, the method includes contacting the outer surface (e.g., epidermal surface) of the agricultural product with a mixture comprising a coating agent.

[0284] In some embodiments of the coating method, contacting the surface of the agricultural product includes spraying the mixture onto the surface of the agricultural product. The mixture can be sprayed, for example, by a commercially available sprayer. In some embodiments, the mixture is sprayed onto the surface of the agricultural product as an aerosol. In some embodiments of the coating method, contacting the surface of the agricultural product includes immersing the agricultural product in the mixture. In other embodiments of the coating method, the mixture can be brushed, dripped, drip-casted, rolled, wiped, or poured onto the surface of the agricultural product.

[0285] 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, evaporation may be passive. In other embodiments, evaporation may be active, such as convection 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 the following substances: 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.

[0286] 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.

[0287] In some embodiments of the coating method, the one or more monoglycerides are present in a total amount of about 70% to about 99% by weight of the coating agent, or about 15% to about 85% by weight, and the one or more alkyl esters are present in a total amount of about 1% to about 15% by weight, or about 15% to about 75% by weight of the coating agent. In some embodiments, the ratio of the total number of moles of the one or more monoglycerides present in the coating agent to the total number of moles of the one or more alkyl esters is about 50:1 to about 6:1, or about 3:1 to about 1:3.

[0288] In some embodiments, the monoglyceride comprises a compound of Formula Ii, Formula I-ii, Formula IA-i, or Formula IA-ii as described herein. In some embodiments, the alkyl ester comprises a compound of Formula III or Formula IIIA as described herein. In some embodiments, the coating agent further comprises a compound of Formula II or Formula IIA as described herein.

[0289] In some embodiments, the one or more monoglycerides and the one or more alkyl esters account for about 70% to about 99% by weight of the coating agent, for example, about 70% to about 98% by weight, about 70% to about 96% by weight, about 80% to about 99% by weight, about 80% to about 98% by weight, about 80% to about 96% by weight, about 85% to about 99% by weight, about 85% to about 98% by weight, or about 85% to about 96% by weight of the coating agent. In some embodiments, the coating agent further comprises C4-C 28 One or more salts of fatty acids, and the one or more monoglycerides, one or more alkyl esters and one or more salts account for at least about 80% by weight of the composition, for example, at least about 85% by weight, at least about 90% by weight, at least about 95% by weight, at least about 97.5% by weight, at least about 98% by weight or at least about 99% by weight of the coating agent.

[0290] Example

[0291] Example 1. Preparation of alkyl esters and mixtures

[0292] When available, ethyl esters of fatty acids were commercially available. Other alkyl esters were synthesized from commercially available starting materials and used without further purification.

[0293] General Procedures

[0294] Use funnel to add 300g fatty acid and 2 equivalents of alkanol in the 2000mL round-bottom flask with stirring rod of drying, then add 500mL toluene.Start stirring, and add 0.005 equivalent (relative to fatty acid) of toluenesulfonic acid monohydrate.Use toluene to wash off any material adhering to funnel or flask, and then add toluene so that volume reaches~1500mL.Dean-Stark trap and reflux condenser are connected to flask.Flask is heated to reflux, and the reaction is monitored by the change of water collected in the separator.After 24 hours, the reaction is cooled, and 80mL activated (grade 1) basic alumina is added and stirred for 5 minutes.Then the mixture is filtered by 300mL glass frit (it has added Celite 545) and 1cm other activated alumina layer, to remove acid catalyst.Most of solvent is removed by rotary evaporation, and residual solvent is removed by stirring under high vacuum (<100 microns) using liquid nitrogen trap. NMR analysis showed a single product consistent with the expected alkyl ester.

[0295] Alternatively, molecular sieves are used to dry the condensed vapor portion that is distilled off to drive the reaction. This can help avoid unfavorable azeotropes and drive the reaction forward.

[0296] Characterization

[0297] Propyl Palmitate: 1 H NMR (600MHz, CDCl3) δ3.99 (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 CNMR (151MHz, CDCl3) δ173.76, 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.

[0298] Propyl Stearate: 1 H NMR (600MHz, CDCl3) δ4.02 (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) δ173.67, 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 O2 measured 326.6; calculated 326.3.

[0299] Butyl Stearate: 1 H NMR (600MHz, CDCl3) δ4.05 (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). 13 C NMR (151MHz, CDCl3) δ173.92, 77.20, 76.99, 76.78, 64.03, 34.37, 31.91, 30.70, 29.67 ,29.62,29.57,29.57,29.45,29.34,29.24,29.14,25.00,22.66,19.12,14.06,13.66. GC-MS: [(M + )]C 22 H 44 O2 measured 340.6; calculated 340.3.

[0300] Amyl Stearate: 1 H NMR (600MHz, CDCl3) δ4.01 (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) δ173.68, 77.22, 77.01, 76.80, 64.19, 34.28, 31.89, 29.66, 29.63, 29.62 , 29.56, 29.43, 29.43, 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 O2 measured 354.6; calculated 354.3.

[0301] Hexyl Stearate: 1 H NMR (600MHz, CDCl3) δ4.02 (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). 13 C NMR (151MHz, CDCl3) δ173.67, 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 24 H 48 O2 measured 368.6; calculated 368.4.

[0302] Propyl Behenate: 1 H NMR (600MHz, CDCl3) δ4.01 (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) δ173.84, 77.21, 76.99, 76.78, 65.72, 34.33, 31.91, 29.68, 29 .66, 29.62, 29.58, 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 O2 measured 382.4; calculated 382.4.

[0303] Preparation of mixture

[0304] Deionized water heated to above 85°C was added to a Vitamix blender (model 5010). The appropriate amount of coating agent was slowly added to the blender at setting 1. The blender was capped and the mixture was blended on 'high' for 3 minutes, then poured into a 1 L Schott bottle and stored until use.

[0305] Example 2. Coated citrus

[0306] Coating agents A and B having the compositions shown in Table 1 were prepared.

[0307] Table 1. Coating agent composition

[0308]

[0309] *Mixture of 2,3-dihydroxyprop-1-yl octadecanoate and 1,3-dihydroxyprop-2-yl octadecanoate (molar ratio of about 85:15 to about 95:5)

[0310] Mixtures 1, 2, 3 and 4 were prepared in which coating agents A, B, C and D were 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 mixer for 3 minutes. For each of Mixtures 1 and 2, a group of 120 waxed limes of the same size, quality, maturity, packaging date and orchard were coated by dipping each lime in a bowl of the mixture and then drying it in a rolling translating hot tunnel at 65-70°C for 100 seconds. For each of Mixtures 3 and 4, a group of 120 unwaxed citrus of the same size, quality, maturity, packaging date and orchard were coated by dipping each citrus or lime in a bowl of the mixture and then drying it in a rolling translating hot tunnel at 65-70°C for 100 seconds. The mass loss of the coated citrus and limes and the control group of uncoated citrus and limes was then measured. The results are shown in Table 2.

[0311] Table 2. Mixture composition; mass loss of mandarin and lime

[0312]

[0313]

[0314] *Ratio of the average mass loss rate of the untreated control to the average mass loss rate of the corresponding tested fruit over a given period of time

[0315] As shown in Table 2, the coating formed from the coating agent including fatty acid alkyl esters better reduced the mass loss of the fruit than the coating lacking the alkyl esters.

[0316] Example 3. Coated Avocado

[0317] Coating agent CF having the composition shown in Table 3 was prepared.

[0318] Table 3. Coating agent composition

[0319] C D E F Glyceryl Monostearate 90% by weight 90% by weight 90% by weight 90% by weight Sodium stearate 5 wt% 5 wt% 5 wt% 5 wt% Ethyl laurate 5 wt% - - - Ethyl tetradecanoate - 5 wt% - - Ethyl palmitate - - 5 wt% - Ethyl stearate - - - 5 wt%

[0320] Mixtures 3-7 were prepared in which coating agents A and CF were dispersed in water at the concentrations shown in Table 4. For each of Mixtures 3-7, a group of 120 Mexican Hass avocados of the same size, quality, maturity, packaging date, and orchard were coated by dipping each avocado into a bowl of the mixture and then drying at 65-70° C. for 100 seconds in a rolling, translating hot tunnel. The mass loss and CO2 respiration of the coated avocados and a control group of uncoated avocados were then measured. The results are shown in Table 4.

[0321] Table 4. Mixture composition; mass loss and CO2 respiration of avocado

[0322] Coating agent concentration Quality loss factor Respiratory Factor* Mixture 3 A 30g / L 1.52 1.32 Mixture 4 C 30g / L 1.65 1.37 Mixture 5 D 30g / L 1.63 1.37 Mixture 6 E 30g / L 1.72 1.36 Mixture 7 F 30g / L 1.68 1.31 Unprocessed - - 1 1

[0323] *Ratio of the average CO2 respiration rate (peak day) of the untreated control to the average CO2 respiration rate (peak day) of the corresponding tested fruit

[0324] As shown in Table 4, the 12 -C 18 The coating formed by the fatty acid ethyl ester coating agent reduced the mass loss and respiration of the fruit.

[0325] Example 4. Coated Avocado

[0326] Coating agent GJ having the composition shown in Table 5 was prepared.

[0327] Table 5. Coating agent composition

[0328] G H I J Glyceryl Monostearate 71.25% by weight 63.33% by weight 23.75 wt% - Sodium stearate 5 wt% 5 wt% 5 wt% 5 wt% Ethyl palmitate 23.75 wt% 31.67 wt% 71.25% by weight 95% by weight

[0329] Mixtures 8-12 were prepared in which coating agents A and CF were dispersed in water at the concentrations shown in Table 6. For each of Mixtures 8-12, a group of 120 Mexican Hass avocados of the same size, quality, maturity, packaging date, and orchard were coated by dipping each avocado into a bowl of the mixture and then drying at 65-70° C. for 100 seconds in a rolling, translating hot tunnel. The mass loss and respiration of the coated avocados and a control group of uncoated avocados were then measured. The results are shown in Table 6.

[0330] Table 6. Mixture composition; mass loss and respiration of avocado

[0331] Coating agent concentration Quality loss factor Respiratory Factor Mixture 8 A 30g / L 1.20 1.06 Mixture 9 G 30g / L 1.38 1.09 Mixture 10 H 30g / L 1.43 1.12 Mixture 11 I 30g / L 1.21 1.14 Mixture 12 J 30g / L 1.11 1.11 Unprocessed - - 1 1

[0332] As shown in Table 6, the coating formed of the coating agent including the alkyl ester and the monoglyceride in a weight ratio of 1:3 to 3:1 reduced the mass loss and respiration of the fruit.

[0333] Example 5. Coated Avocado

[0334] Mixtures 13-18 were prepared in which coating agents A and G were dispersed in water at the concentrations shown in Table 7. For each of Mixtures 13-18, a group of 120 California Hass avocados of the same size, quality, maturity, packaging date, and orchard were coated by dipping each avocado into a bowl of the mixture and then drying at 65-70° C. for 100 seconds in a rolling, translating hot tunnel. The mass loss and respiration of the coated avocados and a control group of uncoated avocados were then measured. The results are shown in Table 7.

[0335] Table 7. Mass loss and respiration of avocado

[0336] Coating agent concentration Quality loss factor Respiratory Factor Mixture 13 A 10g / L 1.26 1.06 Mixture 14 G 10g / L 1.38 1.05 Mixture 15 A 30g / L 1.61 1.15 Mixture 16 G 30g / L 1.80 1.22 Mixture 17 A 50g / L 1.86 1.21 Mixture 18 G 50g / L 2.08 1.30 Unprocessed - - 1 1

[0337] As shown in Table 7, for application concentrations ranging from 10 g / L to 50 g / L, coatings formed from coating agents including alkyl esters better reduced mass loss and respiration of fruit than corresponding coatings lacking the alkyl esters.

[0338] Example 6. Morphological Characterization

[0339] Films 1-3 of coating agents A, G, and J were prepared as shown in Table 8. About 20 uL of each coating agent dispersed in water was drop cast onto a plastic substrate and dried at 70°C for about 10 minutes.

[0340] Table 8. Mixture composition

[0341] membrane Coating agent 1 A 2 G 3 J

[0342] Films 1-3 were analyzed by small angle X-ray scattering (SAXS) and wide angle X-ray scattering (WAXS); Figure 1-3 SAXS data (which provides information about long-range order) show that films 1-3 each exhibit Bragg reflections indicative of a lamellar mesophase. WAXS data (which provides information about short-range order) show that film 2 exhibits ethyl palmitate within the film. and the fatty acyl chains of monoglycerides Chain stacking properties of both components.

[0343] Example 7. Mixture Characterization, Coated Avocado

[0344] Coating agents K-AH were prepared having the compositions shown in Tables 9-14.

[0345] Table 9. Coating agent composition

[0346] K L M N Glyceryl Monostearate 71.25% by weight 47.5 wt% 23.75 wt% 0% by weight Sodium stearate 5 wt% 5 wt% 5 wt% 5 wt% Methyl stearate 23.75 wt% 47.5 wt% 71.25% by weight 100% by weight

[0347] Table 10. Coating agent composition

[0348] O P Q R Glyceryl Monostearate 71.25% by weight 47.5 wt% 23.75 wt% 0% by weight Sodium stearate 5 wt% 5 wt% 5 wt% 5 wt% Ethyl stearate 23.75 wt% 47.5 wt% 71.25% by weight 100% by weight

[0349] Table 11. Coating agent composition

[0350] S T U V Glyceryl Monostearate 71.25% by weight 47.5 wt% 23.75 wt% 0% by weight Sodium stearate 5 wt% 5 wt% 5 wt% 5 wt% Propyl Stearate 23.75 wt% 47.5 wt% 71.25% by weight 100% by weight

[0351] Table 12. Coating agent composition

[0352] W X Y Z Glyceryl Monostearate 71.25% by weight 47.5 wt% 23.75 wt% 0% by weight Sodium stearate 5 wt% 5 wt% 5 wt% 5 wt% Isopropyl stearate 23.75 wt% 47.5 wt% 71.25% by weight 100% by weight

[0353] Table 13. Coating agent composition

[0354] AA AB AC AD Glyceryl Monostearate 71.25% by weight 47.5 wt% 23.75 wt% 0% by weight Sodium stearate 5 wt% 5 wt% 5 wt% 5 wt% Butyl stearate 23.75 wt% 47.5 wt% 71.25% by weight 100% by weight

[0355] Table 14. Coating agent composition

[0356] AE AF AG AH Glyceryl Monostearate 71.25% by weight 47.5 wt% 23.75 wt% 0% by weight Sodium stearate 5 wt% 5 wt% 5 wt% 5 wt% Isoamyl stearate 23.75 wt% 47.5 wt% 71.25% by weight 100% by weight

[0357] 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 a portion of each mixture was then set aside for routine evaluation of stability.

[0358] For each of Mixes 19-48, groups of 60 Mexican Hass avocados of the same size, quality, maturity, pack date, and orchard were coated within 24 hours of preparation by dipping each avocado into a bowl of the mixture and then drying at 70°C in a rolling, translating hot tunnel with a residence time of 100 seconds. The avocados were removed from cold storage for 30 minutes prior to treatment. The coatings were evaluated before and after drying. The mass loss and respiration of the coated avocados and a control group of uncoated avocados ("UT") were then measured. The results are shown in Tables 15-20.

[0359] Table 15. Mixture properties; mass loss and respiration factor of avocado

[0360]

[0361] * Mass loss factor (MLF)

[0362] ** Respiratory Factor (RF)

[0363] MLF / RF, normalized to mixture 19

[0364] MLF 2 / RF, normalized to mixture 19

[0365] Table 16. Mixture properties; mass loss and respiration factor for avocado

[0366]

[0367]

[0368] MLF / RF, normalized to mixture 24

[0369] MLF 2 / RF, normalized to mixture 24

[0370] Table 17. Mixture properties; mass loss and respiration factor for avocado

[0371]

[0372] MLF / RF, normalized to mixture 29

[0373] MLF 2 / RF, normalized to mixture 29

[0374] Table 18. Mixture properties; mass loss and respiration factor for avocado

[0375]

[0376] MLF / RF, normalized to mixture 34

[0377] MLF 2 / RF, normalized to mixture 34

[0378] Table 19. Mixture properties; mass loss and respiration factor for avocado

[0379]

[0380]

[0381] MLF / RF, normalized to mixture 39

[0382] MLF 2 / RF, normalized to mixture 39

[0383] Table 20. Mixture properties; mass loss and respiration factor for avocado

[0384]

[0385] MLF / RF, normalized to mixture 44

[0386] MLF 2 / RF, normalized to mixture 44

[0387] As shown in Tables 15-20, stability decreases with increasing alkyl carbon number and decreases with increasing amount of alkyl ester. Increasing the amount of alkyl ester also increases opacity. For mixtures including greater than 50% by weight alkyl ester, stability becomes more difficult to determine due to increased opacity. Visual observations showed that the viscosity of the coated mixture increased with increasing amount of alkyl ester, from an apparent increase of about 1-2 cP to about 5 cP. The viscosity of mixture 30 after contact with cold fruit appeared to increase to about 100 cP.

[0388] As shown in Tables 15-20, inclusion of up to 50 wt% of the alkyl ester selectively increases the mass barrier properties relative to the respiratory barrier properties of the coating (MLF / RF>1). 2 / RF values ​​indicate particularly high performance coatings.

[0389] Example 8. Coated Lime

[0390] Coating agent AI-AM having the composition shown in Table 21 was prepared.

[0391] Table 21. Coating agent composition

[0392]

[0393] Mixtures 49-64 of coating agents A, S and AI-AM dispersed in water at the concentrations shown in Tables 22-24 were prepared. For each of mixtures 49-64, groups of 120 unwaxed Persian limes of the same size, quality, maturity, packaging date and orchard were coated by dipping each lime into a bowl of the mixture and then drying in a rolling translating hot tunnel at 70°C with a drive speed of 10 Hz (residence time of ~120 seconds). Prior to treatment, the limes were taken out of cold storage for one hour. The mass loss and respiration of the coated limes and the control group of uncoated limes were then measured. The results are shown in Tables 22-24.

[0394] Table 22. Mixture composition; mass loss of lime

[0395] Coating agent concentration Mass loss factor* Mixture 49 A 25g / L 1.35 Mixture 50 A 50g / L 1.39 Mixture 51 AI 25g / L 1.82 Mixture 52 AJ 25g / L 2.06 Mixture 53 S 25g / L 2.14 Mixture 54 AK 25g / L 2.37 Unprocessed - - 1

[0396] * Superscripts indicate statistically different groups (α = 0.05)

[0397] Table 23. Mixture composition; mass loss of lime

[0398] Coating agent concentration Quality loss factor Mixture 55 A 25g / L 1.35 Mixture 56 A 50g / L 1.39 Mixture 57 S 25g / L 2.14 Mixture 58 S 35g / L 2.56 Mixture 59 S 50g / L 2.65 Unprocessed - - 1

[0399] Table 24. Mixture composition; mass loss of lime

[0400]

[0401]

[0402] As shown in Table 22, coatings formed from coating agents including increased propyl stearate better reduced mass loss. As shown in Table 23, coatings formed from mixtures including increasing concentrations of coating agents better reduced mass loss. As shown in Table 24, coatings formed from coating agents including 5 wt % sodium stearate better reduced mass loss relative to those including 10 wt % or more sodium stearate.

[0403] Example 9. Differential Scanning Calorimetry, Viscometry

[0404] Mixtures 65-67 were prepared in which coating agents A, S and O were dispersed in water at the concentrations shown in Table 25. Samples of propyl stearate and mixtures 65 and 66 were placed in an Al sealed pan and cycled from 10°C to 90°C at a temperature ramp rate of 10°C / min on a differential scanning calorimeter. The second cycle was analyzed. -1 The viscosity of the mixture was measured in the shear range of 65-67 Pa·s. Figure 4 Shown in.

[0405] Table 25. Mixture composition; mass loss of lime

[0406] Coating agent concentration Mixture 65 A 25g / L Mixture 66 S 25g / L Mixture 67 O 25g / L

[0407] Differential scanning calorimetry (DSC) results showed a melting transition of propyl stearate at about 29.8°C, crystallization at 24.8°C and a phase transition at 18°C. A liquid crystal transition at 58.6°C (transition enthalpy 1.64 J / g) was observed for mixture 65 during the heating cycle. For mixture 66, a liquid crystal transition at 56.9°C (transition enthalpy 1.30 J / g) was observed during the heating cycle. No evidence of pure domains of propyl stearate was observed. Without wishing to be bound by theory, the results suggest that propyl stearate is incorporated into the vesicles dominated by monostearate in a disordered manner.

[0408] like Figure 4 As shown, the viscosity of mixture 65 is constant within the tested shear range, while that of mixtures 66 and 67 is about 2×10 -2 to 3×10-1 Pa·s and 2-4×10 -2 Pa·s shows shear thinning. This result indicates that propyl stearate and ethyl stearate act as viscosity modifiers, which can provide improved films in the low shear regime.

[0409] Example 10. Coated Apples

[0410] Coating agent AN-AP was prepared having the composition shown in Table 26.

[0411] Table 26. Coating agent composition

[0412]

[0413] *Mixture of 2,3-dihydroxyprop-1-yl dodecanoate and 1,3-dihydroxyprop-2-yl dodecanoate (molar ratio of about 90:10)

[0414] Mixtures 68-73 of coating agents A, O, S, and AN-AP dispersed in water at the concentrations shown in Table 27 were prepared. For each of mixtures 68-73, groups of apples of the same size, quality, maturity, packaging date, and orchard were coated by dipping each apple into a bowl of the mixture and then drying at 65-70° C. for 100 seconds in a rolling, translating hot tunnel. The mass loss of the coated apples and a control group of uncoated apples was then measured. The results are shown in Table 27.

[0415] Table 27. Mass loss of apples; coating efficiency

[0416]

[0417] Ratio of coating mass (in grams) to the product of mass loss factor and fruit mass (in kg) (lower is better)

[0418] As shown in Table 27, coatings formed from coating agents including glyceryl monolaurate exhibited better performance than those lacking glyceryl monolaurate. As shown in Table 27, coating agents including propyl stearate were more efficient than those including ethyl stearate.

[0419] Example 11. Coated Avocado

[0420] Coating agents AQ and AR were prepared having the compositions shown in Table 28.

[0421] Table 28. Coating agent composition

[0422] AQ AR Glyceryl Monostearate 80% by weight 60% by weight Sodium stearate 20% by weight 20% by weight Propyl Stearate - 20% by weight

[0423] Mixtures 74-85 of coating agents A, S, AQ and AR dispersed in water at the concentrations shown in Table 29 were prepared. For each of mixtures 74-85, a group of 60 Mexican Hass avocados of the same size, quality, maturity, packaging date and orchard were coated within 24 hours of preparation by dipping each avocado in a bowl of the mixture and then drying at 70°C in a rolling, translating hot tunnel with a residence time of 100 seconds. Before treatment, the avocados were taken out of cold storage for 30 minutes. The mass loss and respiration of the coated avocados and the uncoated avocados (UT) of the control group were then measured. The results are shown in Table 29.

[0424] Table 29. Mixture composition; mass loss and respiration factor of avocado

[0425]

[0426]

[0427] MLF / RF, normalized to mixture 74

[0428] MLF 2 / RF, normalized to mixture 74

[0429] As shown in Table 29, coatings formed from coating agents including propyl stearate performed similarly or better than coatings formed from coating agents lacking propyl stearate when applied at 10-20 g / L, and even when applied at 40 g / L.

[0430] Although the present invention includes the details of many specific embodiments, they should not be interpreted as limitations on the scope of the subject matter or the scope that may be claimed, but rather as descriptions of features that may be specific to a specific embodiment. Certain features described in the context of the present invention in separate embodiments may also be implemented in combination in a single embodiment. On the contrary, each feature described in the context of a single embodiment may also be implemented in multiple embodiments separately or in any suitable sub-combination. In addition, although the aforementioned features may be described as being implemented in certain combinations and even implemented as initially required, one or more features from the required combination may be deleted from the combination in some cases, and the required combination may be directed to a sub-combination or a variant of a sub-combination.

[0431] Specific embodiments of the subject matter have been described. Other embodiments, variations and permutations of the embodiments within the scope of the following claims will be apparent to those skilled in the art. Although operations are described in a particular order in the drawings or claims, this should not be understood as requiring that such operations be performed in the particular order shown or in a sequential order, or that all of the operations shown (some operations may be considered optional) be performed to achieve the desired results.

[0432] Therefore, the foregoing exemplary embodiments do not define or limit the present invention.Other changes, substitutions and alterations are also possible without departing from the spirit and scope of the present invention.

Claims

1. A composition comprising: C4-C 28 one or more monoglycerides of fatty acids present in a total amount of about 15% to about 99% by weight of the composition; and C8-C 20 One or more alkyl esters of fatty acids are present in a total amount of about 1% to about 75% by weight of the composition.

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

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

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

5. The composition of any one of claims 1-4, 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. The composition according to any one of claims 1 to 5, further comprising C4-C 28 One or more salts of fatty acids are present in a total amount of from 0.1% to about 30% by weight of the composition.

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

9. A composition comprising: C4-C 28 one or more monoglycerides of fatty acids; and C8-C 20 one or more alkyl esters of fatty acids; 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 100:1 to about 1:

5.

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. 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. The composition of any one of claims 9-11, 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.

13. The composition according to any one of claims 9 to 12, further comprising C4-C 28 One or more salts of fatty acids.

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

1.

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

1.

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

17. The composition of any one of claims 1-16, wherein the one or more alkyl esters each independently comprise a C1-C5 alkyl ester.

18. The composition of any one of claims 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 isopentyl ester.

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

20. The composition of any one of claims 1-16, wherein the one or more alkyl esters each independently comprise a compound of formula III: in: R B is a C1-C8 alkyl group; and R H It is C7-C 19 Sidechain.

21. The composition according to claim 20, wherein R B It is a C1-C5 alkyl group.

22. The composition according to claim 20, wherein R B It is a C2 alkyl group or a C3 alkyl group.

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

24. A composition according to any one of claims 20-23, wherein R H It is C 11 -C 17 Sidechain.

25. The composition of any one of claims 1-16, wherein the one or more alkyl esters each independently comprise a compound of Formula IIIA: in: R B is a C1-C8 alkyl group; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; Each occurrence of R 10A , R 10B , R 11A and R 11B 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 may form together with the carbon atoms to which they are attached a double bond, a 3-membered to 6-membered cycloheterocycloalkyl 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.

26. The composition according to claim 25, wherein R B It is a C1-C5 alkyl group.

27. The composition according to claim 25, wherein R B It is a C2 alkyl group or a C3 alkyl group.

28. The composition of any one of claims 1-27, wherein the one or more monoglycerides each independently comprise a compound of Formula Ii or Formula I-ii: in: R A1 and R A2 Each is independently selected from H and C1-C6 alkyl; and R H It is C3-C 27 Sidechain.

29. The composition according to claim 28, wherein R A1 and R A2 Each is H.

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

31. A composition according to any one of claims 28-30, wherein R H It is C 11 -C 21 Sidechain.

32. The composition of any one of claims 28-31, wherein the one or more monoglycerides comprise: The first compound of formula Ii or formula I-ii, wherein R H It is C 15 -C 27 Sidechains; and The second compound of Formula Ii or Formula I-ii, wherein R H It is C3-C 13 Sidechain.

33. The composition of any one of claims 1-27, wherein the one or more monoglycerides each independently comprise a compound of Formula IA-i or Formula IA-ii: in: R A1 and R A2 Each is 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 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; Each occurrence of R 10A , R 10B , R 11A and R 11B 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 may form together with the carbon atoms to which they are attached a double bond, a 3-membered to 6-membered cycloheterocycloalkyl 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.

34. The composition according to claim 33, wherein R A1 and R A2 Each is H.

35. The composition of any one of claims 1-34, wherein the one or more salts present in the composition each independently comprises a compound of formula II: in: R H It is C3-C 27 Sidechains; and X n+ It is a cationic moiety having a formal charge n.

36. The composition of claim 35, wherein: X n+ Selected from Li + 、Na + , K + , Cs + 、Ag + , Ca 2+ Mg 2+ 、Zn 2+ , Cu 2+ and (R D )4N + ;and Each occurrence of R D is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl and heteroaryl, wherein Each C1-C6 alkyl group is optionally substituted with 1-3 R E Substituted, the 1-3 R E independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl and heteroaryl; and Optionally, R D One or more instances of together with the nitrogen atom to which they are attached form a C3-C6 heterocycloalkyl.

37. A composition according to claim 35 or claim 36, wherein R H is a saturated unsubstituted side chain.

38. The composition of any one of claims 1-37, wherein the one or more salts present in the composition each independently comprises a compound of Formula IIA: in: R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; Each occurrence of R 10A , R 10B , R 11A and R 11B 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 may form together with the carbon atoms to which they are attached a double bond, a 3-membered to 6-membered cycloheterocycloalkyl 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+ It is a cationic moiety having a formal charge n.

39. The composition of claim 38, wherein: X n+ Selected from Li + 、Na + , K + , Cs + 、Ag + , Ca 2+ Mg 2+ 、Zn 2+ , Cu 2+ and (R D )4N + ;and Each occurrence of R D is selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl and heteroaryl, wherein Each C1-C6 alkyl group is optionally substituted with 1-3 R E Substituted, the 1-3 R E independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl and heteroaryl; and Optionally, R D One or more instances of together with the nitrogen atom to which they are attached form a C3-C6 heterocycloalkyl.

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

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

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

43. The mixture of any one of claims 40-42, wherein the solvent comprises one or more of the following: 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 on a surface of the agricultural product, wherein the layer comprises the composition of any one of claims 1-39.

45. The coated agricultural product of claim 44, wherein the layer is located on a skin surface of the agricultural product.

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

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

48. A method of coating an agricultural product, the method comprising: contacting the surface of the agricultural product with a mixture comprising a coating agent and a solvent, wherein the coating agent comprises: C4-C 28 one or more monoglycerides of fatty acids; and C8-C 20 one or more alkyl esters of fatty acids; 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 100:1 to about 1:5; and At least a portion of the solvent is removed to form a coating on the surface of the agricultural product.

49. The method of claim 48, wherein the surface is a skin surface of an agricultural product.

50. The method of claim 48 or claim 49, wherein contacting the surface comprises: spraying the mixture onto the surface; or The produce is dipped into the mixture.

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

52. The method of any one of claims 48-51, wherein the solvent comprises one or more of the following: water, methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, and methyl tert-butyl ether.

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

54. The method according to any one of claims 48-53, further comprising treating the C8-C 20 One or more alkyl esters of fatty acids are added to the solvent and the C4-C 28 A premix of one or more monoglycerides of fatty acids is added to form the mixture.

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

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

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

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

59. The method of any one of claims 48-58, 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.

60. The method of any one of claims 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.

61. The method of any one of claims 48-60, wherein the one or more alkyl esters each independently comprise a C1-C5 alkyl ester.

62. The method of any one of claims 48-60, 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 isopentyl ester.

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

64. The method according to any one of claims 48-63, wherein the coating agent further comprises C4-C 28 One or more salts of fatty acids, wherein the ratio of the total moles of the one or more monoglycerides and the one or more alkyl esters to the total moles of the one or more salts is from about 100:1 to about 4:

1.

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% by weight of the coating agent.

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

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

68. A method of coating an agricultural product, the method comprising: contacting the surface of the agricultural product with the mixture of any one of claims 40-43; and At least a portion of the solvent is removed to form a coating on the surface of the agricultural product.

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