Phospholipids, processes for their preparation and use

Abstract

The application discloses phospholipid and a preparation method and application thereof, and relates to the technical field of organic compounds. The phospholipid of the application takes lysophosphatidylcholine, p-carboxymethyl formaldehyde and a fatty amine as raw materials, and the synthesized phospholipid has a dynamic covalent bond Schiff base structure. The molecular structure of the phospholipid can realize dissociation and assembly under the action of acid or alkali. Compared with conventional natural phospholipids, the problems such as complex composition and strong odor are avoided, the phospholipid can be used for constructing active ingredient liposomes of pesticides and cosmetics, the formed liposomes have excellent stability and transdermal absorption performance, and the Schiff base dynamic covalent bond structure in the structure of the phospholipid can also realize the slow and controlled release of the pesticide raw drug, improve the half-life of the pesticide, and play a role of reducing application and increasing efficiency.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic compounds, in particular to a phospholipid and a preparation method and application thereof. BACKGROUND

[0002] Phospholipids are important components of human skin cells and important raw materials for cosmetics, and have the effects of repairing skin barrier, reducing water loss, improving skin roughness, resisting external pollutant stimulation, improving inflammation, antioxidant, etc., and also have the effects of emulsification and wrapping active ingredients, and are important carrier materials in the preparation of current daily chemical liposomes. However, natural phospholipids are extracted from soybeans or egg yolks, and have the disadvantages of complex composition, low purity, deep color, strong odor and easy oxidation. Hydrogenated lecithin obtained by further hydrogenation of natural phospholipids can improve the quality of phospholipids. However, the current imported hydrogenated lecithin products have the problems of low purity, incomplete hydrogenation leading to yellow color, single molecular structure and high price, and due to the low production process and quality of hydrogenated lecithin, the imported products cannot be effectively replaced, which greatly limits the high-quality development of the cosmetic industry.

[0003] In addition, the phospholipids synthesized in the prior art, such as phosphatidylcholine, phosphatidylethanolamine and phosphatidylinositol, also belong to the components of natural phospholipids, and these natural phospholipids have relatively simple and stable structures and do not have the effect of controlled release, so they cannot meet the multi-scene application of phospholipids in other fields, for example, the application field of phospholipids is limited. SUMMARY

[0004] The present application aims to at least solve one of the above-mentioned technical problems in the prior art. To this end, the purpose of the present application is to provide a phospholipid, which belongs to a synthetic phospholipid, avoids the defects of natural phospholipids such as complex composition, low purity, deep color and strong odor, and can realize the dissociation and assembly of molecular structure under the action of acid or base, realizing the effect of controlled release.

[0005] The second aspect of the present application provides a preparation method of a phospholipid.

[0006] The third aspect of the present application provides a liposome.

[0007] The fourth aspect of the present application provides an application of a phospholipid or a liposome.

[0008] In order to achieve the above-mentioned purposes, the technical solution adopted by the present application is:

[0009] The first aspect of the present application provides a phospholipid having the following structure shown in formula (I):

[0010]

[0011] wherein n is an odd number between 1 and 20; and m is an even number between 1 and 20.

[0012] The phospholipid shown in formula (I) is a synthetic phospholipid with special functions. The phospholipid has a dynamic covalent bond Schiff base structure in the molecule, and the dissociation and assembly of the phospholipid can be reversibly controlled by the action of acid or base. The self-assembly structure of the aqueous solution of the phospholipid can be reversibly changed from a vesicle to a micelle, so that the slow controlled release effect in a special application scenario can be achieved.

[0013] Meanwhile, the phospholipid avoids the disadvantages of natural phospholipids, such as complex composition, low purity, deep color, strong odor, etc. The liposome formed by the phospholipid has excellent stability and transdermal absorption performance.

[0014] Preferably, n is 1, 3, 5, 7, 9, 11, 13, 15 or 17; and m is 2, 4, 6, 8, 10, 12, 14, 16 or 18.

[0015] Further preferably, n is 3, 5, 7, 9, 11, 13 or 15; more preferably, n is 7, 9, 11, 13 or 15; and more preferably, n is 9, 11, 13 or 15.

[0016] Further preferably, m is 4, 6, 8, 10, 12 or 14; more preferably, m is 6, 8, 10 or 12; and more preferably, m is 6, 8 or 10.

[0017] Preferably, the raw materials for preparing the phospholipid include lyso-egg phospholipid, p-carboxybenzaldehyde and fatty amine.

[0018] The second aspect of the present application provides a method for preparing the phospholipid of the first aspect of the present application, comprising the following steps:

[0019] S1. reacting lyso-egg phospholipid and p-carboxybenzaldehyde, and purifying to obtain phospholipid molecules containing aldehyde groups;

[0020] S2. reacting the phospholipid molecules containing aldehyde groups and fatty amine to obtain the phospholipid.

[0021] Preferably, the molar ratio of lyso-egg phospholipid to p-carboxybenzaldehyde is 1:(0.5-2).

[0022] Further preferably, the molar ratio of lyso-egg phospholipid to p-carboxybenzaldehyde is 1:(0.5-1.5); and more preferably, the molar ratio of lyso-egg phospholipid to p-carboxybenzaldehyde is 1:(0.8-1.2).

[0023] Preferably, the molar ratio of the phospholipid molecules containing aldehyde groups to fatty amine is 1:(0.8-1.3).

[0024] Further preferably, the molar ratio of the aldehyde group-containing phospholipid molecule to the fatty amine is 1:(0.9-1.2).

[0025] Preferably, in the step S1, the reaction is carried out under catalysis of a catalyst; the molar ratio of the catalyst to the total amount of the lysophosphatidylcholine and the p-carboxybenzaldehyde is (1-8):1.

[0026] Further preferably, in the step S1, the molar ratio of the catalyst to the total amount of the lysophosphatidylcholine and the p-carboxybenzaldehyde is (1-4):1; further preferably (2-3):1.

[0027] Further preferably, in the step S1, the lysophosphatidylcholine, the p-carboxybenzaldehyde and the catalyst are heated and dissolved in the first organic solvent to carry out the reaction.

[0028] More preferably, in the step S1, the temperature of the heating and dissolving is 25-80℃; more preferably, the temperature of the heating and dissolving is 25-50℃.

[0029] More preferably, in the step S1, the first organic solvent comprises at least one of toluene, ethyl acetate, acetone, ethanol, methanol, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, dichloromethane and trichloromethane.

[0030] Further preferably, in the step S1, the catalyst comprises at least one of dichlorohexane and 4-dimethylaminopyridine mixture, concentrated sulfuric acid, concentrated hydrochloric acid, p-methylbenzenesulfonic acid and chlorosulfoxide.

[0031] Preferably, in the step S1, the lysophosphatidylcholine comprises at least one of caproylphosphatidylcholine, butyrylphosphatidylcholine, caprylphosphatidylcholine, caprylphosphatidylcholine, caprylphosphatidylcholine, laurylphosphatidylcholine, myristoylphosphatidylcholine, palmitoylphosphatidylcholine and stearoylphosphatidylcholine.

[0032] Preferably, in the step S1, the temperature of the reaction is 0-180℃.

[0033] Further preferably, in the step S1, the temperature of the reaction is 40-80℃.

[0034] Preferably, in the step S1, the reaction time is 3-24h; further preferably, the reaction time is 4-12h.

[0035] Preferably, in the step S1, the reaction is carried out under an inert atmosphere.

[0036] Further preferably, the inert atmosphere comprises at least one of argon, nitrogen or helium.

[0037] Preferably, in the step S1, the purifying comprises the following steps: filtering the reactants after the reaction to obtain a filtrate; removing the solvent in the filtrate to obtain a crude product; performing column chromatography separation and purification on the crude product to obtain a product solution; removing the solvent in the product solution and drying to obtain the phospholipid molecule containing aldehyde group.

[0038] Further preferably, the solvent is removed by using a rotary evaporator.

[0039] Preferably, in the step S2, the phospholipid molecule containing aldehyde group and the fatty amine are mixed in a second organic solvent to perform the reaction.

[0040] Further preferably, the second organic solvent comprises at least one of methanol, methanol, isopropanol, acetone, acetonitrile.

[0041] Preferably, in the step S2, the reaction is performed under the condition that the pH is 6-12.

[0042] Further preferably, in the step S2, the reaction is performed under the condition that the pH is 8-11.

[0043] Further preferably, in the step S2, the pH of the reaction is adjusted by using an alkaline reagent; more preferably, the alkaline reagent comprises sodium hydroxide.

[0044] Preferably, in the step S2, the temperature of the reaction is 30-120°C.

[0045] Further preferably, in the step S2, the temperature of the reaction is 50-70°C.

[0046] Preferably, in the step S2, the reaction time is 1-12h; further preferably, the reaction time is 4-8h.

[0047] Preferably, in the step S2, the fatty amine comprises at least one of butylamine, hexylamine, octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, eicosylamine.

[0048] Preferably, in the step S2, after the reaction, a step of removing the solvent is further included; further preferably, the solvent is removed by using a rotary evaporator.

[0049] Preferably, in the steps S1 and S2, the reaction is monitored by TCL to determine whether the reaction is completed.

[0050] Specifically, the reaction formula involved in the preparation method of the phospholipid is as follows:

[0051]

[0052] The third aspect of the present application provides a liposome, the preparation raw material of which comprises the phospholipid according to the first aspect of the present application or the phospholipid prepared by the preparation method according to the second aspect of the present application.

[0053] Preferably, the mass content of the phospholipid in the liposome is 0.1-15%.

[0054] Further preferably, the mass content of the phospholipid in the liposome is 1-10%; more preferably, the mass content of the phospholipid in the liposome is 3-7%.

[0055] Preferably, the preparation raw material of the liposome comprises the phospholipid, the polyhydric alcohol and the active ingredient; the active ingredient comprises a cosmetic active ingredient or a pesticide active ingredient.

[0056] Further preferably, the polyhydric alcohol comprises at least one of 1,4-butanediol, 1,3-propanediol, glycerol, sorbitol, polyethylene glycol, dipropylene glycol.

[0057] Further preferably, the cosmetic active ingredient comprises at least one of ginsenoside CK, ginsenoside Rg3, ceramide, retinol, tetrahydrocurcumin.

[0058] Further preferably, the pesticide active ingredient comprises at least one of abamectin, imidacloprid, thiamethoxam, fipronil, acetamiprid.

[0059] Further preferably, the preparation raw material of the liposome further comprises an aqueous phase.

[0060] More preferably, the preparation raw material of the liposome comprises the following components by mass percentage:

[0061] 0.1-15% of the phospholipid, 5-30% of the polyhydric alcohol, 0.5-20% of the active ingredient, and the balance of the aqueous phase.

[0062] More preferably, the preparation raw material of the liposome comprises the following components by mass percentage:

[0063] 3-7% of the phospholipid, 5-15% of the polyhydric alcohol, 5-20% of the active ingredient, and the balance of the aqueous phase.

[0064] More preferably, the preparation method of the liposome comprises the following steps:

[0065] mixing the phospholipid, the polyhydric alcohol and the active ingredient to obtain solution A; heating the aqueous phase to obtain solution B; mixing the solution A and the solution B to obtain the liposome.

[0066] Preferably, the mixing temperature of the phospholipid, the polyol and the active ingredient is 65-85 DEG C; more preferably 75-85 DEG C.

[0067] Preferably, the heating temperature of the water phase is 75-95 DEG C; more preferably 75-85 DEG C.

[0068] Preferably, the solution A and the solution B after mixing further comprise homogenization and ultrasonic treatment; the rotation speed of the homogenization is 10000-20000 rpm, more preferably 12000-15000 rpm; the time of the homogenization is 2-11 min, more preferably 3-7 min; the temperature of the homogenization is 70-90 DEG C, more preferably 75-85 DEG C; the temperature of the ultrasonic treatment is 5-20 DEG C, more preferably 10-15 DEG C; the time of the ultrasonic treatment is 10-20 min; the power of the ultrasonic treatment is 350-500 W, more preferably 400-500 W.

[0069] The fourth aspect of the present application provides a use of the phospholipid of the first aspect of the present application or the liposome of the third aspect of the present application in the preparation of cosmetics, pesticides.

[0070] Compared with the prior art, the present application has the following beneficial effects:

[0071] (1) The molecular structure of the phospholipid provided by the present application is different from that of the conventional natural phospholipid molecule, and the phospholipid has a Schiff base dynamic covalent bond structure in the structure, which can realize the dissociation and assembly of the molecular structure under the action of acid or base, thereby realizing the effect of controlled release. As a synthetic phospholipid, the phospholipid of the present application avoids the problems of complex composition, low purity, deep color, strong odor, etc. compared with natural phospholipid.

[0072] (2) The phospholipid of the present application is prepared from lyso-egg phospholipid, p-carboxybenzaldehyde and fatty amine, and has the advantages of simple preparation method and relatively mild preparation conditions, which is suitable for industrial application.

[0073] (3) The liposome formed by the phospholipid has excellent stability and transdermal absorption performance, and the Schiff base dynamic covalent bond structure in the molecule also makes it have the effect of controlled release. Therefore, the phospholipid is suitable for the construction of active ingredient liposomes in pesticides and cosmetics, and the formed liposomes have good stability in cosmetics and are beneficial to the absorption of active ingredients by the skin. When used in pesticide technical, it can realize the controlled release of pesticide technical, improve the half-life of pesticide, and play a role in reducing application and increasing efficiency. BRIEF DESCRIPTION OF DRAWINGS

[0074] Figure 1 The nuclear magnetic resonance spectrum of the phospholipid molecule containing an aldehyde group synthesized in Example 3 of the present application.

[0075] Figure 2 NMR spectrum of the phospholipid synthesized in Example 3 of the present application.

[0076] Figure 3 CMC curve of the phospholipid molecule containing an aldehyde group and the phospholipid in Example 3 of the present application.

[0077] Figure 4 CMC curve of the phospholipid synthesized in Example 3 of the present application at different pHs.

[0078] Figure 5 CMC curve of the phospholipid in Examples 1 to 3 of the present application.

[0079] Figure 6 Appearance of the abamectin liposome in Application Example 1 of the present application and its particle size distribution diagram.

[0080] Figure 7 Appearance of the ginsenoside CK liposome in Application Example 2 of the present application and its particle size distribution diagram.

[0081] Figure 8 Appearance of the abamectin liposome in Application Example 1 of the present application at different pHs. DETAILED DESCRIPTION

[0082] The content of the present application will be further explained in detail by specific examples. The raw materials, reagents or devices used in the examples and comparative examples are commercially available or can be obtained by the prior art methods unless otherwise specified. The test or test method is the conventional method in the art unless otherwise specified.

[0083] Example 1

[0084] A phospholipid, the preparation method thereof comprising the following steps:

[0085] S1. Dissolve 1 mol of already acylated phosphatidylcholine and 1 mol of p-carboxybenzaldehyde into 30 mL of dichloromethane, add 4 mol of dichlorocyclohexane and 1 mol of 4-dimethylaminopyridine, heat to dissolve at 25°C, protect with nitrogen, and react at 40°C for 4 hours; monitor the progress of the reaction after completion by TLC, filter the solution, collect the filtrate, and remove the excess solvent using a rotary evaporator to obtain a crude product; purify the crude product by column chromatography, collect the solution of the target product, remove the solvent using a rotary evaporator, and vacuum dry to obtain a phospholipid molecule containing an aldehyde group;

[0086] S2. Mix 1 mol of the phospholipid molecule containing an aldehyde group and 1 mol of butylamine in methanol and stir to dissolve, adjust the pH of the solution to 10 with NaOH, then stir at 40°C for 4 hours, monitor the reaction using TLC, and remove the solvent using a rotary evaporator after the reaction is completed to obtain a phospholipid.

[0087] The structural formula of the phospholipid is shown in the following formula (1):

[0088]

[0089] Example 2

[0090] A phospholipid, the preparation method thereof comprising the following steps:

[0091] S1. Dissolve 1 mol of octanoylphosphatidylcholine and 1 mol of p-carboxybenzaldehyde into 30 mL of chloroform, add 4 mol of p-toluenesulfonic acid, heat and dissolve at 25°C, protect with argon, react at 60°C for 8 hours; after monitoring the progress of the reaction by TLC, filter, collect the filtrate, remove the excess solvent using a rotary evaporator, and obtain a crude product; purify the crude product by column chromatography, collect the solution of the target product, remove the solvent using a rotary evaporator, and vacuum dry to obtain an aldehyde group-containing phospholipid molecule;

[0092] S2. Mix 1 mol of the aldehyde group-containing phospholipid molecule and 1 mol of eicosylamine in ethanol, stir and dissolve, adjust the pH of the solution to 9 with NaOH, then stir at 45°C for 6 hours, monitor the reaction by TLC, and after the reaction is completed, remove the solvent using a rotary evaporator to obtain a phospholipid.

[0093] The structural formula of the phospholipid is shown in the following formula (2):

[0094]

[0095] Example 3

[0096] A phospholipid, the preparation method thereof comprising the following steps:

[0097] S1. Dissolve 1 mol of octanoylphosphatidylcholine and 1 mol of p-carboxybenzaldehyde into 30 mL of chloroform, add 4 mol of p-toluenesulfonic acid, heat and dissolve at 25°C, protect with argon, react at 60°C for 8 hours; after monitoring the progress of the reaction by TLC, filter, collect the filtrate, remove the excess solvent using a rotary evaporator, and obtain a crude product; purify the crude product by column chromatography, collect the solution of the target product, remove the solvent using a rotary evaporator, and vacuum dry to obtain an aldehyde group-containing phospholipid molecule;

[0098] S3. Mix 1 mol of the aldehyde group-containing phospholipid molecule and 1 mol of dodecylamine in ethanol, stir and dissolve, adjust the pH of the solution to 9.5 with NaOH, then stir at 40°C for 8 hours, monitor the reaction by TLC, and after the reaction is completed, remove the solvent using a rotary evaporator to obtain a phospholipid.

[0099] The structural formula of the phospholipid is shown in formula (3) below:

[0100]

[0101] Taking Example 3 as an example, the phospholipid molecules containing aldehyde groups and the phospholipids synthesized in Example 3 were tested, and the results are as follows: Figures 1-4 As shown.

[0102] Figure 1 The above is the 1H NMR spectrum of the phospholipid molecule containing an aldehyde group synthesized in Example 3 of this invention. Figure 2 This is the 1H NMR spectrum of the phospholipid synthesized in Example 3 of this invention. Figure 1 and Figure 2 As can be seen, in Example 3 of the present invention, phospholipid molecules containing aldehyde groups were successfully synthesized by lysophosphatidylcholine and p-carboxybenzaldehyde, and further reacted with fatty amines to obtain phospholipids.

[0103] It should be understood that since phospholipids were prepared in Examples 1-3 using lysophospholipids, p-carboxybenzaldehyde, and fatty amines as raw materials, although the specific selection of lysophospholipids and fatty amines differed, the preparation principle, reaction process, and reaction conditions were the same. Although specific 1H NMR spectra were not provided in Examples 1-2, phospholipids were also successfully synthesized.

[0104] Figure 3 The figure shows the CMC (critical micelle concentration) curves of phospholipid molecules containing aldehyde groups and phospholipids in Example 3 of this invention. As can be seen from the figure, the CMC and surface tension of the phospholipids (i.e., synthetic phospholipids) are lower than those of phospholipid molecules containing aldehyde groups (i.e., aldehyde-containing phospholipids), indicating that the phospholipids synthesized in this invention have excellent surface activity. When the liposomes formed from these phospholipids are applied to cosmetics, they exhibit excellent transdermal absorption performance.

[0105] Figure 4 The CMC curves of the phospholipid synthesized in Example 3 of this invention are shown at different pH values. Figure 4 As can be seen, the CMC and surface tension of the phospholipid are higher at pH 5 than at pH 10. This is because at low pH, the Schiff base dynamic covalent bond structure of the phospholipid breaks, forming phospholipid molecules containing aldehyde groups and dodecammonium salts. The electrostatic interaction between these two components results in lower surface tension and CMC compared to before the breakage. Therefore, the phospholipids of this invention can dissociate and assemble under the action of acid or alkali, achieving a reversible transformation of the phospholipid aqueous solution's self-assembled structure from vesicles to micelles. Thus, a controlled-release effect can be achieved during application.

[0106] The surface activity of the phospholipids in Examples 1-3 was compared, and the results are as follows: Figure 5 As shown. Figure 5The CMC curves of the phospholipids in Examples 1-3 can be seen from the figure, and it can be seen that the CMC of the phospholipid synthesized in Example 3 is the smallest, and the surface tension is the lowest, and the phospholipid has higher surface activity than the phospholipids of Examples 1 and 2.

[0107] Application Example 1

[0108] An avermectin liposome comprises, by mass percentage, 5% of a phospholipid, 10% of 1,4-butanediol, 14% of avermectin, and 71% of water; wherein the phospholipid is the phospholipid in Example 3.

[0109] The preparation method of the avermectin liposome comprises the following steps:

[0110] S1. The phospholipid, 1,4-butanediol, and avermectin are mixed and dissolved at 75℃ to a transparent solution to obtain solution A;

[0111] S2. Water is heated to 80℃ to obtain solution B, and then solution A obtained in step S1 is slowly added to solution B at 80℃ and 12000rmp by using a high-speed homogenizer, and after the addition is completed, homogenization is continued for 5min to obtain solution C;

[0112] S3. Solution C obtained in step S2 is placed in a probe ultrasonic instrument and ultrasonically treated at 480W and 10℃ for 20min to prepare the avermectin liposome.

[0113] Application Example 2

[0114] A ginsenoside CK liposome comprises, by mass percentage, 5% of a phospholipid, 10% of 1,3-propanediol, 8% of ginsenoside CK, and 77% of water; wherein the phospholipid is the phospholipid in Example 3.

[0115] The preparation method of the ginsenoside CK liposome comprises the following steps:

[0116] S1. The synthetic phospholipid, 1,3-propanediol, and ginsenoside CK are mixed and dissolved at 85℃ to a transparent solution to obtain solution A;

[0117] S2. Water is heated to 80℃ to obtain solution B, and then solution A obtained in step S1 is slowly added to solution B at 80℃ and 15000rmp by using a high-speed homogenizer, and after the addition is completed, homogenization is continued for 5min to obtain solution C;

[0118] S3. Solution C obtained in step S2 is placed in a probe ultrasonic instrument and ultrasonically treated at 450W and 15℃ for 20min to prepare the ginsenoside CK liposome.

[0119] The physicochemical properties of the liposomes obtained in Application Examples 1 and 2 are detected, and the results are shown in Table 1. Figures 6-8 Table 1

[0120] Figure 6 The appearance of the abamectin liposome in application example 1 of the present application and the particle size distribution diagram thereof; Figure 7 The appearance of the ginsenoside CK liposome in application example 2 of the present application and the particle size distribution diagram thereof. Figure 6 and Figure 7 The particle size distribution is repeated for 3 times. The average particle size of the abamectin liposome is 78 nm, and the average particle size of the ginsenoside CK liposome is 63 nm. In addition, from the appearance pictures of the abamectin liposome and the ginsenoside CK liposome in the normal temperature for 3 months, it can be seen that the liposome still maintains stability after being placed for 3 months, indicating that the phospholipid and the liposome formed by the phospholipid of the present application have excellent stability. Figure 6 and Figure 7 From the appearance pictures of the abamectin liposome and the ginsenoside CK liposome in the normal temperature for 3 months, it can be seen that the liposome still maintains stability after being placed for 3 months, indicating that the phospholipid and the liposome formed by the phospholipid of the present application have excellent stability.

[0121] Figure 8 The appearance pictures of the abamectin liposome in application example 1 of the present application under different pH. It can be seen from the figure that the abamectin liposome is in a semi-transparent state when pH>6, indicating that the liposome is in a vesicular structure. When pH<6, the system changes from semi-transparent to transparent, indicating that the vesicular structure of the liposome is broken and changes into a spherical micelle. This change is mainly because the phospholipid constituting the liposome contains a Schiff base dynamic covalent bond structure, which can be broken under acidic conditions, so that the microstructure formed by the self-assembly of the phospholipid further changes. This change of microstructure can be used to realize the controlled release of the drug under different pH conditions.

[0122] In summary, the phospholipid synthesized in the present application has a Schiff base dynamic covalent bond structure. The molecular structure of the phospholipid can realize dissociation and assembly under the action of acid or base. Compared with conventional natural phospholipids, the problems of complex composition and strong odor are avoided. The phospholipid can be used to construct the active ingredient liposome of pesticides and cosmetics. The formed liposome has excellent stability and transdermal absorption performance. In addition, the Schiff base dynamic covalent bond structure in the structure can also realize the controlled release of the pesticide technical material, improve the half-life of the pesticide, and play a role in reducing the application and increasing the efficiency.

[0123] The above examples are the preferred embodiments of the present application, but the embodiments of the present application are not limited by the above examples. Any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present application shall be equivalent replacement modes and shall be included in the protection scope of the present application.

Claims

1. A phospholipid, characterized in that, It has the structure shown in equation (Ⅰ): Equation (I); Where n is an odd number between 1 and 20; m is an even number between 1 and 20; In this context, 'm' refers to the number of carbon atoms in the saturated straight-chain carbon chain within the parentheses.

2. The phospholipid according to claim 1, characterized in that, The n is 1, 3, 5, 7, 9, 11, 13, 15 or 17; the m is 2, 4, 6, 8, 10, 12, 14, 16 or 18.

3. A method for preparing the phospholipid according to claim 1 or 2, characterized in that, Includes the following steps: S1. Reaction of lysophosphatidylcholine and p-carboxybenzaldehyde, followed by purification, yields phospholipid molecules containing aldehyde groups; S2. The phospholipid molecule containing an aldehyde group is reacted with a fatty amine to obtain the phospholipid.

4. The preparation method according to claim 3, characterized in that, The molar ratio of the lysophosphatidylcholine to p-carboxybenzaldehyde is 1:(0.5~2); Alternatively, the molar ratio of the phospholipid molecule containing the aldehyde group to the fatty amine is 1:(0.8~1.3).

5. The preparation method according to claim 3, characterized in that, In step S1, the reaction is carried out under the catalysis of a catalyst; the molar ratio of the total amount of the catalyst to lysophosphatidylcholine and p-carboxybenzaldehyde is (1~8):

1. Alternatively, in step S1, the reaction temperature is 0~180℃; Alternatively, in step S1, the reaction is carried out in an inert atmosphere.

6. The preparation method according to claim 3, characterized in that, In step S2, the reaction is carried out under conditions where the pH is 6 to 12; Alternatively, in step S2, the reaction temperature is 30~120℃.

7. The preparation method according to claim 5, characterized in that, The lysophosphatidylcholine is selected from at least one of hexanoylphosphatidylcholine, butyroylphosphatidylcholine, hexanoylphosphatidylcholine, capryloylphosphatidylcholine, decanoylphosphatidylcholine, lauroylphosphatidylcholine, myristoylphosphatidylcholine, palmitoylphosphatidylcholine, and stearoylphosphatidylcholine. Alternatively, the fatty amine is selected from at least one of butylamine, hexylamine, octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, and eicosamine; Alternatively, the catalyst is selected from at least one of a mixture of dichlorocyclohexane and 4-dimethylaminepyridine, concentrated sulfuric acid, concentrated hydrochloric acid, p-toluenesulfonic acid, and thionyl chloride.

8. A liposome, characterized in that, The raw materials include the phospholipids described in any one of claims 1 to 2 or the phospholipids prepared by the preparation method described in any one of claims 3 to 7.

9. The liposomes according to claim 8, characterized in that, The phospholipid content in the liposomes is 0.1-15% by mass.

10. The liposomes according to claim 8 or 9, characterized in that, The raw materials for preparing the liposomes include phospholipids, polyols, and active ingredients; the active ingredients include cosmetic active ingredients or pesticide active ingredients.

11. The use of a phospholipid according to any one of claims 1 to 2 or a liposome according to any one of claims 8 to 10 in the preparation of cosmetics or pesticides.

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