Silanized phytosphingosine, process for its preparation and use thereof

Abstract

The application belongs to the technical field of chemical synthesis, and particularly relates to a kind of silylated phytosphingosine and its preparation method and application. The preparation method comprises the following steps: S1, dissolving phytosphingosine in a solvent to obtain a mixed solution; S2, warming the mixed solution, adding double-end epoxy silicone oil for incubation reaction; S3, after the incubation reaction is completed, the reaction mixture is taken out for rotary evaporation, and after the solvent is completely volatilized, silylated phytosphingosine is obtained; the molar ratio of phytosphingosine and double-end epoxy silicone oil is 1:0.5-0.6. The preparation method provided by the application has the advantages of simplicity, industrialization batch production, high utilization rate of phytosphingosine, high yield of silylated phytosphingosine, and the obtained silylated phytosphingosine can be dissolved in various oils at room temperature.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of chemical synthesis, and particularly relates to a silanized phytosphingosine as well as a preparation method and application thereof. BACKGROUND

[0002] Phytosphingosine, also known as 2-amino-1,3,4-octadecanetriol, belongs to sphingolipids. As one of the components of cell membranes, phytosphingosine is a precursor of naturally occurring ceramides in the skin surface layer, and as a signal lipid molecule, it is involved in the regulation of cell growth, differentiation, aging and cell programmed death and other signal transduction processes.

[0003] Phytosphingosine is a natural bacteriostatic lipid derived from the skin, which has a significant inhibitory effect on human harmful bacteria such as propionibacterium acnes, malassezia and candida albicans. At the same time, phytosphingosine is the core contribution value to maintain the stability of the skin barrier. It can promote the expression of TGase1 (transglutaminase 1), promote the formation of keratin envelope, make keratinocytes mature, and promote the expression of Caspase-14 (caspase-14) and BLMH (bleomycin hydrolase), and then promote the degradation of filaggrin into natural moisturizing factor, which has high application value in the field of cosmetics.

[0004] However, phytosphingosine is not soluble in water or in absolute part of cosmetic oils (such as vegetable oils, animal oils, mineral oils and silicone oils, etc.), which greatly limits its application in cosmetics. In order to overcome the solubility problem of phytosphingosine in oil, it is prepared into nano-liposomes in the prior art. For example, a phytosphingosine skin lotion is disclosed in Chinese Patent No. CN105496886B. The technical solution prepares nano-liposomes by adding cholesterols and hydrogenated lecithin, which improves the affinity of phytosphingosine and ceramide to oil phase, and the absorption effect is better. However, the preparation of nano-liposomes usually requires complex process and technology, resulting in relatively high production cost. SUMMARY

[0005] In order to solve the above problems, the application provides a silanized phytosphingosine as well as a preparation method and application thereof. The preparation method of the silanized phytosphingosine has the advantages of simplicity, industrialized batch production, high utilization rate of phytosphingosine and high yield of silanized phytosphingosine. The obtained silanized phytosphingosine can be dissolved in various oils at room temperature.

[0006] To achieve the above object, the technical scheme adopted by the application is as follows:

[0007] The application provides a preparation method of silanized phytosphingosine, which comprises the following steps:

[0008] S1, dissolving phytosphingosine in a solvent to obtain a mixed solution;

[0009] S2, warming the mixed solution and adding double-end epoxy silicone oil to perform a heat preservation reaction;

[0010] S3, after the heat preservation reaction is completed, removing the reaction mixture and performing rotary evaporation to completely volatilize the solvent to obtain silanized phytosphingosine; the molar ratio of the phytosphingosine to the double-end epoxy silicone oil is 1:0.5-0.6.

[0011] In some preferred embodiments, the molar ratio of the phytosphingosine to the double-end epoxy silicone oil is 1:0.55-0.6.

[0012] Most preferably, the molar ratio of the phytosphingosine to the double-end epoxy silicone oil is 1:0.6.

[0013] In some preferred embodiments, the solvent is at least one selected from the group consisting of methanol, ethanol, chloroform, and dimethyl sulfoxide, and is preferably ethanol.

[0014] In some preferred embodiments, the phytosphingosine can be dissolved in the solvent by heating.

[0015] In some preferred embodiments, the mass ratio of the phytosphingosine to the solvent is 1:8-12, and is preferably 1:10.

[0016] In some preferred embodiments, the reaction temperature of the heat preservation reaction is 65-100℃, and the reaction time is 6-12h.

[0017] In some preferred embodiments, the reaction temperature of the heat preservation reaction is 85-100℃, and the reaction time is 9-12h.

[0018] Most preferably, the reaction temperature of the heat preservation reaction is 100℃, and the reaction time is 12h.

[0019] The second aspect of the present application provides silanized phytosphingosine obtained by the preparation method of the above silanized phytosphingosine.

[0020] The third aspect of the present application provides the use of silanized phytosphingosine obtained by the preparation method of the above silanized phytosphingosine in cosmetics or skin care products.

[0021] Compared with the prior art, the present application has the following beneficial effects:

[0022] The preparation method of the silanized phytosphingosine provided by the application has the advantages of simplicity, industrialized batch production, high utilization rate of phytosphingosine, and high yield of silanized phytosphingosine; the obtained silanized phytosphingosine can be dissolved in various oils at room temperature, expanding the application of phytosphingosine in cosmetics, and the silanized phytosphingosine can increase the sliding feeling and improve the skin feeling of the cosmetic due to the introduction of silicone oil. BRIEF DESCRIPTION OF DRAWINGS

[0023] Figure 1 The nuclear magnetic hydrogen spectrum of the silanized phytosphingosine of Example 1 is shown in the figure;

[0024] Figure 2 The nuclear magnetic hydrogen spectrum of the silanized phytosphingosine of Example 2 is shown in the figure;

[0025] Figure 3 The nuclear magnetic hydrogen spectrum of the silanized phytosphingosine of Example 3 is shown in the figure;

[0026] Figure 4 The nuclear magnetic hydrogen spectrum of the silanized phytosphingosine of Example 4 is shown in the figure;

[0027] Figure 5 The nuclear magnetic hydrogen spectrum of the silanized phytosphingosine of Example 5 is shown in the figure;

[0028] Figure 6 The nuclear magnetic hydrogen spectrum of the silanized phytosphingosine of Example 6 is shown in the figure;

[0029] Figure 7 The nuclear magnetic hydrogen spectrum of the silanized phytosphingosine of Example 7 is shown in the figure;

[0030] Figure 8 The solubility figures of the silanized phytosphingosine of Example 3, Comparative Examples 1-2, and phytosphingosine in caprylic / capric triglyceride are shown in the figures;

[0031] Figure 9 The solubility figures of the silanized phytosphingosine of Example 3, Comparative Examples 1-2, and phytosphingosine in white oil are shown in the figures;

[0032] Figure 10 The solubility figures of the silanized phytosphingosine of Example 3, Comparative Examples 1-2, and phytosphingosine in dimethicone are shown in the figures;

[0033] Figure 11 The solubility figures of the silanized phytosphingosine of Example 3, Comparative Examples 1-2, and phytosphingosine in sunflower seed oil are shown in the figures;

[0034] Figures 8-11 In the figures, a is Example 3, b is Comparative Example 1, c is Comparative Example 2, and d is phytosphingosine. DETAILED DESCRIPTION

[0035] Various exemplary embodiments of the present application will now be described in detail, which should be considered to be non-limiting examples of the present application, and are understood to be illustrative of certain aspects, features and embodiments of the present application.

[0036] It is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the present application. Additionally, for a range of values of a parameter, unless otherwise stated, each intervening value of the parameter is also specifically included within the scope of the present application. The intervening values of the parameter are combined with a stated value of the parameter in range form. These are only examples of the various embodiments of the present application. Other embodiments can be employed without departing from the scope of the application. Accordingly, the phraseology or terminology employed herein, and not otherwise expressly set forth in this specification, is taken to be mere example and not limiting in scope.

[0037] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present application, the preferred methods and materials are described. All patents, patent applications, publications, and descriptions mentioned herein are incorporated by reference in their entirety for the disclosure and

[0038] Many modifications and variations of the present application described in the specification are possible without departing from the scope or spirit of the application. Other embodiments of the application will be apparent to those skilled in the art from consideration of the specification and practice of the application disclosed herein. The specification and examples given are exemplary only. It is to be understood that the application is not limited in scope by the described embodiments.

[0039] As used herein, the terms "comprises", "comprising", "includes", "including", "has", "having", "contains", "containing", or variations thereof, are intended to be open-ended terms that mean inclusion, but not limited to, the listed materials and methods.

[0040] In the following examples and comparative examples, the raw materials used are commercially available or prepared by conventional methods in the art, unless otherwise specified.

[0041] The bidentate epoxy silicone oil has a molecular weight of 2200 and is commercially available from Guangzhou Slocow New Material Co., Ltd. under the trade designation 3592F2 with an epoxy equivalent weight of 900.

[0042] Phytosphingosine is commercially available from Guangzhou Xufan Trading Co., Ltd. under the trade designation P0101-S2308001.

[0043] The other silicone oils in the comparative examples are commercially available from Aldrich. The bidentate amino silicone oil has an average molecular weight of 2500 and the bidentate hydroxyl silicone oil has an average molecular weight of 2000.

[0044] Example 1

[0045] The preparation method of the silanized phytosphingosine is as follows:

[0046] S1, 1.5875 g of phytosphingosine powder was added into 15.875 g of ethanol, and the mixture was stirred and mixed at 60°C, and a mixed solution was obtained after sufficient dissolution;

[0047] S2, the mixed solution was heated to 85°C, and 5.5 g of double-end epoxy silicone oil was added for heat preservation reaction for 9 h;

[0048] S3, after the completion of the heat preservation reaction, the reaction mixture was taken out, and rotary evaporation was performed for 2 h to completely volatilize the ethanol, and silanized phytosphingosine was obtained.

[0049] Example 2

[0050] The preparation method of the silanized phytosphingosine is as follows:

[0051] S1, 1.5875 g of phytosphingosine powder was added into 15.875 g of ethanol, and the mixture was stirred and mixed at 60°C, and a mixed solution was obtained after sufficient dissolution;

[0052] S2, the mixed solution was heated to 85°C, and 6.05 g of double-end epoxy silicone oil was added for heat preservation reaction for 9 h;

[0053] S3, after the completion of the heat preservation reaction, the reaction mixture was taken out, and rotary evaporation was performed for 2 h to completely volatilize the ethanol, and silanized phytosphingosine was obtained.

[0054] Example 3

[0055] The preparation method of the silanized phytosphingosine is as follows:

[0056] S1, 1.5875 g of phytosphingosine powder was added into 15.875 g of ethanol, and the mixture was stirred and mixed at 60°C, and a mixed solution was obtained after sufficient dissolution;

[0057] S2, the mixed solution was heated to 100°C, and 6.6 g of double-end epoxy silicone oil was added for heat preservation reaction for 12 h;

[0058] S3, after the completion of the heat preservation reaction, the reaction mixture was taken out, and rotary evaporation was performed for 2 h to completely volatilize the ethanol, and silanized phytosphingosine was obtained.

[0059] Example 4

[0060] The preparation method of the silanized phytosphingosine is as follows:

[0061] S1, 1.5875 g of phytosphingosine powder was added into 15.875 g of ethanol, and the mixture was stirred and mixed at 60°C, and a mixed solution was obtained after sufficient dissolution;

[0062] S2, the mixed solution is heated to 65°C, 6.05g of double-end epoxy silicone oil is added, and the reaction is maintained for 9h;

[0063] S3, after the completion of the reaction, the reaction mixture is taken out, rotary evaporation is performed for 2h to completely volatilize ethanol, and silanized phytosphingosine is obtained.

[0064] Example 5

[0065] The preparation method of silanized phytosphingosine is as follows:

[0066] S1, 1.5875g of phytosphingosine powder is added into 15.875g of ethanol, the mixture is heated to 60°C and stirred, and after being fully dissolved, a mixed solution is obtained;

[0067] S2, the mixed solution is heated to 100°C, 6.05g of double-end epoxy silicone oil is added, and the reaction is maintained for 9h;

[0068] S3, after the completion of the reaction, the reaction mixture is taken out, rotary evaporation is performed for 2h to completely volatilize ethanol, and silanized phytosphingosine is obtained.

[0069] Example 6

[0070] The preparation method of silanized phytosphingosine is as follows:

[0071] S1, 1.5875g of phytosphingosine powder is added into 15.875g of ethanol, the mixture is heated to 60°C and stirred, and after being fully dissolved, a mixed solution is obtained;

[0072] S2, the mixed solution is heated to 85°C, 6.05g of double-end epoxy silicone oil is added, and the reaction is maintained for 6h;

[0073] S3, after the completion of the reaction, the reaction mixture is taken out, rotary evaporation is performed for 2h to completely volatilize ethanol, and silanized phytosphingosine is obtained.

[0074] Example 7

[0075] The preparation method of silanized phytosphingosine is as follows:

[0076] S1, 1.5875g of phytosphingosine powder is added into 15.875g of ethanol, the mixture is heated to 60°C and stirred, and after being fully dissolved, a mixed solution is obtained;

[0077] S2, the mixed solution is heated to 85°C, 6.05g of double-end epoxy silicone oil is added, and the reaction is maintained for 12h;

[0078] S3, after the completion of the reaction, the reaction mixture is taken out, rotary evaporation is performed for 2h to completely volatilize ethanol, and silanized phytosphingosine is obtained.

[0079] The silanized phytosphingosine prepared in Examples 1-7 was detected by nuclear magnetic resonance hydrogen spectrum, and the spectrum is shown in Figures 1-7 The amount of each characteristic group in the product was analyzed, and the residual rate of the double-end epoxy silicone oil and the yield of the silanized phytosphingosine were calculated:

[0080] 1. The calculation formula of the residual rate of the double-end epoxy silicone oil: Residual rate of the double-end epoxy silicone oil (%) = peak area of the epoxy group after reaction / total nuclear magnetic peak area. The results are shown in Table 1.

[0081] 2. The calculation formula of the yield of the silanized phytosphingosine: Yield of the silanized phytosphingosine (%) = (1-residual content of the double-end epoxy silicone oil + theoretical amount of the excess epoxy silicone oil in reaction) * 100%. The results are shown in Table 2.

[0082] Table 1

[0083] Sample Residual rate of double-end epoxy silicone oil (%) Example 1 39.39 Example 2 39.39 Example 3 21.21 Example 4 36.63 Example 5 30.30 Example 6 45.45 Example 7 30.30

[0084] Table 2

[0085] Sample Yield of silanized phytosphingosine (%) Example 1 60.61 Example 2 70.61 Example 3 98.79 Example 4 73.37 Example 5 79.70 Example 6 64.55 Example 7 79.70

[0086] As can be seen from Tables 1 and 2, the silanized phytosphingosine prepared from phytosphingosine as raw material, ethanol as solvent and double-end epoxy silicone oil has high utilization rate of the phytosphingosine raw material and high yield.

[0087] Comparative Example 1

[0088] The preparation method of the silanized phytosphingosine is the same as that of Example 3, except that the double-end epoxy silicone oil is replaced by double-end amino silicone oil.

[0089] Comparative Example 2

[0090] The preparation method of the silanized phytosphingosine is the same as that of Example 3, except that the double-end epoxy silicone oil is replaced by double-end hydroxyl silicone oil.

[0091] Effect Example 1

[0092] The silanized phytosphingosine of Example 3 and Comparative Examples 1-2 and phytosphingosine were respectively added to caprylic acid / capric acid triglyceride at 60°C, and the addition amount was 20wt% of the caprylic acid / capric acid triglyceride. The results are shown in Figure 8 .

[0093] Effect Example 2

[0094] The silanized phytosphingosine of Example 3 and Comparative Examples 1-2 and phytosphingosine were respectively added to white oil at 60°C, and the addition amount was 20wt% of the white oil. The results are shown in Figure 9 .

[0095] Example 3

[0096] The silanized phytosphingosine of Example 3 and Comparative Examples 1-2, and phytosphingosine were added to polydimethylsiloxane at 60°C, with the addition amount being 20 wt% of polydimethylsiloxane. The results are shown in […]. Figure 10 .

[0097] Example of effect 4

[0098] The silanized phytosphingosine of Example 3 and Comparative Examples 1-2, and phytosphingosine were added to sunflower seed oil at 60°C, with an addition amount of 20 wt% of the sunflower seed oil. The results are shown in […]. Figure 11 .

[0099] Depend on Figures 8-11 It can be seen that the silanized phytosphingosine prepared by using double-ended epoxy silicone oil has good solubility in various oils at 60℃, while the silanized phytosphingosine and phytosphingosine of Comparative Examples 1-2 are not easily soluble in various oils at 60℃.

[0100] Finally, it should be noted that the above content is only used to illustrate the technical solution of the present invention, and is not intended to limit the scope of protection of the present invention. Simple modifications or equivalent substitutions made by those skilled in the art to the technical solution of the present invention do not depart from the essence and scope of the technical solution of the present invention.

Claims

1. A method for preparing silanized phytosphingosine, characterized in that, Includes the following steps: S1. Dissolve phytosphingosine in a solvent to obtain a mixed solution; S2. Heat the mixed solution and add double-ended epoxy silicone oil to carry out the heat preservation reaction. S3. After the heat preservation reaction is completed, the reaction mixture is taken out and rotary evaporated to completely evaporate the solvent to obtain silanized phytosphingosine; the molar ratio of the phytosphingosine and the double-ended epoxy silicone oil is 1:0.5-0.

6.

2. The preparation method according to claim 1, characterized in that, The molar ratio of the plant sphingosine and the double-ended epoxy silicone oil is 1:0.55-0.

6.

3. The preparation method according to claim 2, characterized in that, The molar ratio of the plant sphingosine and the double-ended epoxy silicone oil is 1:0.

6.

4. The preparation method according to claim 1, characterized in that, The solvent is selected from at least one of methanol, ethanol, chloroform, and dimethyl sulfoxide.

5. The preparation method according to claim 1, characterized in that, The mass ratio of the plant sphingosine to the solvent is 1:8-12.

6. The preparation method according to claim 1, characterized in that, The heat preservation reaction is carried out at a temperature of 65-100℃ for 6-12 hours.

7. The preparation method according to claim 6, characterized in that, The heat preservation reaction is carried out at a temperature of 85-100℃ for 9-12 hours.

8. The preparation method according to claim 7, characterized in that, The heat preservation reaction was carried out at a temperature of 100°C for 12 hours.

9. The silanized phytosphingosine obtained by the method for preparing silanized phytosphingosine according to any one of claims 1-8.

10. The application of silanized phytosphingosine obtained by the method for preparing silanized phytosphingosine according to any one of claims 1-8 in cosmetics or skin care products.

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