A method for preparing a suspension of lutein oil

Abstract

The present application relates to natural product separation and extraction technical field, propose a kind of preparation lutein oil suspension method, comprising the following steps: S1, marigold is added in dichloromethane extraction, filtration, and the filtrate is evaporated and concentrated to obtain concentrate;S2, the concentrate is added in ethanol, then add potassium hydroxide solution to carry out saponification reaction, obtain saponification liquid;S3, saponification liquid is washed with water respectively, washed with n-hexane, crystallization, filter drying and obtain lutein crystal;S4, lutein crystal is crushed, added in vegetable oil, add dispersing agent, stir, carry out shear emulsification, obtain lutein oil suspension;Dispersing agent is the composition of alkyl naphthalene sulfonate and fatty amine salt mass ratio 6:4~9:1.By the above technical scheme, the problem that lutein oil suspension prepared by supercritical extraction process in the prior art has poor stability and poor flowability is solved.

Description

Technical Field

[0001] This invention relates to the field of natural product separation and extraction technology, specifically to a method for preparing lutein oil suspension. Background Technology

[0002] Lutein is a natural carotenoid widely found in plants such as marigolds, cabbage, and spinach. Its structure contains two ionone rings, each with a hydroxyl group and multiple conjugated double bonds. It can undergo esterification with fatty acids to produce monoesters and diesters. Studies have shown that lutein is not only an excellent antioxidant and a non-toxic natural yellow pigment, but it can also improve human vision to some extent. Lutein crystals are insoluble in water and slightly soluble in oil. It is easily degraded by light, oxygen, moisture, heavy metals, oxidants, or reducing agents, resulting in very low bioavailability. Therefore, lutein is often formulated into different dosage forms, such as oil suspensions and water-dispersible dry powders, to improve its stability and bioavailability. Currently, the main methods for preparing lutein oil suspensions involve solvent extraction, ultrasonic extraction, and enzyme-assisted extraction to extract lutein, followed by saponification of the lutein with alkali to obtain lutein crystals. These crystals are then mixed with vegetable oil and subjected to supercritical fluid extraction to prepare the lutein oil suspension. However, these methods suffer from poor stability and poor flowability of the lutein oil suspension. Therefore, developing a method for preparing lutein oil suspensions that improves stability and meets food safety requirements is crucial. Summary of the Invention

[0003] This invention proposes a method for preparing lutein oil suspension, which solves the problems of poor stability and poor flowability of lutein oil suspension prepared by supercritical extraction in related technologies.

[0004] The technical solution of the present invention is as follows:

[0005] This invention proposes a method for preparing lutein oil suspension, comprising the following steps:

[0006] S1. Add calendula flowers to dichloromethane for extraction, filter, and evaporate and concentrate the filtrate to obtain a concentrate.

[0007] S2. Add the concentrate to ethanol, then add potassium hydroxide solution to carry out the saponification reaction to obtain the saponified solution.

[0008] S3. Wash the saponified liquid with water and n-hexane respectively, crystallize, filter and dry to obtain lutein crystals;

[0009] S4. Crush lutein crystals, add them to vegetable oil, add a dispersant, stir, and perform shear emulsification to obtain a lutein oil suspension.

[0010] The dispersant is a composition of alkyl naphthalene sulfonate and fatty amine salt in a mass ratio of 6:4 to 9:1.

[0011] As a further technical solution, the mass-to-volume ratio of lutein crystals to vegetable oil is 1:6 to 1:10 g / mL, the mass-to-volume ratio of dispersant to vegetable oil is 0.1:10 to 0.3:10 g / mL, and the vegetable oil is epoxidized soybean oil or epoxidized linseed oil.

[0012] As a further technical solution, the alkylnaphthalene sulfonate is sodium dodecylnaphthalene sulfonate or ammonium dodecylnaphthalene sulfonate, and the fatty amine salt is dodecylamine acetate or dodecylamine hydrochloride.

[0013] As a further technical solution, in step S4, after adding the dispersant, a suspending agent is also added, wherein the suspending agent is one or more of sodium alginate, sodium carboxymethyl cellulose, and Tween 80.

[0014] As a further technical solution, the mass-to-volume ratio of the suspending agent to the vegetable oil is 0.05:10~0.1:10 g / mL.

[0015] As a further technical solution, in step S4, after adding the dispersant, an emulsifier and an antioxidant are also added. The emulsifier is one or more of lecithin, soybean lecithin, and ethylene propylene glycol polymer, and the antioxidant is one or more of natural vitamin E, tocopherol, and tea polyphenols.

[0016] As a further technical solution, the mass-to-volume ratio of the emulsifier to the vegetable oil is 0.5:10~1:10 g / mL, and the mass-to-volume ratio of the antioxidant to the vegetable oil is 0.001:10~0.003:10 g / mL.

[0017] As a further technical solution, the extraction temperature is 50~70℃, the extraction time is 3~5h, the saponification reaction temperature is 40~60℃, the reaction time is 3~6h, and the crystallization temperature is 0~10℃.

[0018] As a further technical solution, the volume ratio of ethanol to potassium hydroxide solution is 1:0.5 to 1:2.

[0019] As a further technical solution, the shear emulsification is a staged shear emulsification, wherein the first stage shear rate is 15000 rpm and the shearing time is 3~5 min, the second stage shear rate is 8000 rpm and the shearing time is 10~15 min.

[0020] The working principle and beneficial effects of this invention are as follows:

[0021] 1. In this invention, calendula is extracted with dichloromethane, and the concentrate obtained by filtrate concentration is subjected to saponification reaction. The resulting saponified liquid is washed with water and n-hexane, and the lutein crystals obtained by crystallization are pulverized and added to vegetable oil. Then, by adding a dispersant, which is a combination of alkyl naphthalene sulfonate and fatty amine salt, the viscosity of the dispersion medium vegetable oil can be effectively increased, the density difference between lutein crystals and vegetable oil can be reduced, thereby reducing the sedimentation rate of lutein crystals, improving the dispersibility of lutein crystals in vegetable oil, and ultimately improving the stability of lutein crystals in vegetable oil.

[0022] 2. In this invention, after adding the dispersant, a suspending agent is also added, which further improves the dispersibility of lutein crystals in the oil suspension, thereby improving the stability of lutein crystals in the oil suspension. Detailed Implementation

[0023] The technical solutions of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative effort are within the scope of protection of the present invention.

[0024] In the following examples and comparative examples, the mass concentration of potassium hydroxide solution is 50%.

[0025] Example 1

[0026] S1. Add 100g of calendula flowers to 300mL of dichloromethane, heat to 50℃, extract for 5h, filter, and evaporate and concentrate the filtrate to obtain the concentrate.

[0027] S2. Add the concentrate to 200 mL of ethanol, then add 100 mL of potassium hydroxide solution, heat to 40 °C, and saponify for 6 h to obtain the saponified solution.

[0028] S3. Wash the saponification solution with water and n-hexane respectively, cool it to 0℃, crystallize it, filter and dry it to obtain lutein crystals;

[0029] S4. Crush 50g of lutein crystals and add them to 300mL of epoxidized soybean oil. Add 1.8g of sodium dodecyl naphthalene sulfonate and 1.2g of dodecylamine acetate, stir, and shear at 15000rpm for 13min to obtain a lutein oil suspension.

[0030] Example 2

[0031] S1. Add 100g of calendula flowers to 300mL of dichloromethane, heat to 60℃, extract for 4 hours, filter, and evaporate and concentrate the filtrate to obtain the concentrate.

[0032] S2. Add the concentrate to 200 mL of ethanol, then add 200 mL of potassium hydroxide solution, heat to 50 °C, and saponify for 5 h to obtain the saponified solution.

[0033] S3. Wash the saponification solution with water and n-hexane respectively, cool it to 5°C, crystallize it, filter and dry it to obtain lutein crystals;

[0034] S4. Crush 50g of lutein crystals and add them to 400mL of epoxidized soybean oil. Add 5.6g of ammonium dodecylnaphthalenesulfonate and 2.4g of dodecylamine hydrochloride, stir, and shear at 8000rpm for 20min to obtain a lutein oil suspension.

[0035] Example 3

[0036] S1. Add 100g of calendula flowers to 300mL of dichloromethane, heat to 70℃, extract for 3h, filter, and evaporate and concentrate the filtrate to obtain the concentrate.

[0037] S2. Add the concentrate to 200 mL of ethanol, then add 400 mL of potassium hydroxide solution, heat to 60 °C, and saponify for 3 h to obtain the saponified solution.

[0038] S3. Wash the saponification solution with water and n-hexane respectively, cool it to 10°C, crystallize it, filter and dry it to obtain lutein crystals;

[0039] S4. Crush 50g of lutein crystals and add them to 500mL of epoxidized linseed oil. Add 13.5g of sodium dodecyl naphthalene sulfonate and 1.5g of dodecylamine acetate, stir, and shear at 10000rpm for 17min to obtain a lutein oil suspension.

[0040] Example 4

[0041] S1. Add 100g of calendula flowers to 300mL of dichloromethane, heat to 50℃, extract for 5h, filter, and evaporate and concentrate the filtrate to obtain the concentrate.

[0042] S2. Add the concentrate to 200 mL of ethanol, then add 100 mL of potassium hydroxide solution, heat to 40 °C, and saponify for 6 h to obtain the saponified solution.

[0043] S3. Wash the saponification solution with water and n-hexane respectively, cool it to 0℃, crystallize it, filter and dry it to obtain lutein crystals;

[0044] S4. Crush 50g of lutein crystals and add them to 300mL of epoxidized soybean oil. Add 1.8g of sodium dodecyl naphthalene sulfonate and 1.2g of dodecylamine acetate, and 1.5g of sodium alginate. Stir and shear at 8000rpm for 5min, then shear at 10000rpm for 15min to obtain a lutein oil suspension.

[0045] Example 5

[0046] S1. Add 100g of calendula flowers to 300mL of dichloromethane, heat to 50℃, extract for 5h, filter, and evaporate and concentrate the filtrate to obtain the concentrate.

[0047] S2. Add the concentrate to 200 mL of ethanol, then add 100 mL of potassium hydroxide solution, heat to 40 °C, and saponify for 6 h to obtain the saponified solution.

[0048] S3. Wash the saponification solution with water and n-hexane respectively, cool it to 0℃, crystallize it, filter and dry it to obtain lutein crystals;

[0049] S4. Crush 50g of lutein crystals and add them to 300mL of epoxidized soybean oil. Add 1.8g of sodium dodecyl naphthalene sulfonate and 1.2g of dodecylamine acetate, and 2.4g of sodium carboxymethyl cellulose. Stir and shear at 8000rpm for 5min, then shear at 10000rpm for 15min to obtain a lutein oil suspension.

[0050] Example 6

[0051] S1. Add 100g of calendula flowers to 300mL of dichloromethane, heat to 50℃, extract for 5h, filter, and evaporate and concentrate the filtrate to obtain the concentrate.

[0052] S2. Add the concentrate to 200 mL of ethanol, then add 100 mL of potassium hydroxide solution, heat to 40 °C, and saponify for 6 h to obtain the saponified solution.

[0053] S3. Wash the saponification solution with water and n-hexane respectively, cool it to 0℃, crystallize it, filter and dry it to obtain lutein crystals;

[0054] S4. Crush 50g of lutein crystals and add them to 300mL of epoxidized soybean oil. Add 1.8g of sodium dodecyl naphthalene sulfonate and 1.2g of dodecylamine acetate, 15g of lecithin and 0.03g of natural vitamin E, stir, and shear at 8000rpm for 5min to obtain a lutein oil suspension.

[0055] Example 7

[0056] S1. Add 100g of calendula flowers to 300mL of dichloromethane, heat to 50℃, extract for 5h, filter, and evaporate and concentrate the filtrate to obtain the concentrate.

[0057] S2. Add the concentrate to 200 mL of ethanol, then add 100 mL of potassium hydroxide solution, heat to 40 °C, and saponify for 6 h to obtain the saponified solution.

[0058] S3. Wash the saponification solution with water and n-hexane respectively, cool it to 0℃, crystallize it, filter and dry it to obtain lutein crystals;

[0059] S4. Crush 50g of lutein crystals and add them to 300mL of epoxidized soybean oil. Add 1.8g of sodium dodecyl naphthalene sulfonate and 1.2g of dodecylamine acetate, 30g of ethylene oxide propylene polymer and 0.09g of tocopherol, stir, and shear at 15000rpm for 13min to obtain a lutein oil suspension.

[0060] Example 8

[0061] S1. Add 100g of calendula flowers to 300mL of dichloromethane, heat to 50℃, extract for 5h, filter, and evaporate and concentrate the filtrate to obtain the concentrate.

[0062] S2. Add the concentrate to 200 mL of ethanol, then add 100 mL of potassium hydroxide solution, heat to 40 °C, and saponify for 6 h to obtain the saponified solution.

[0063] S3. Wash the saponification solution with water and n-hexane respectively, cool it to 0℃, crystallize it, filter and dry it to obtain lutein crystals;

[0064] S4. Crush 50g of lutein crystals and add them to 300mL of epoxidized soybean oil. Add 1.8g of sodium dodecyl naphthalene sulfonate and 1.2g of dodecylamine acetate, stir, and shear at 15000rpm for 3min and at 8000rpm for 15min to obtain a lutein oil suspension.

[0065] Example 9

[0066] S1. Add 100g of calendula flowers to 300mL of dichloromethane, heat to 50℃, extract for 5h, filter, and evaporate and concentrate the filtrate to obtain the concentrate.

[0067] S2. Add the concentrate to 200 mL of ethanol, then add 100 mL of potassium hydroxide solution, heat to 40 °C, and saponify for 6 h to obtain the saponified solution.

[0068] S3. Wash the saponification solution with water and n-hexane respectively, cool it to 0℃, crystallize it, filter and dry it to obtain lutein crystals;

[0069] S4. Crush 50g of lutein crystals and add them to 300mL of epoxidized soybean oil. Add 1.8g of sodium dodecyl naphthalene sulfonate and 1.2g of dodecylamine acetate, stir, and shear at 8000rpm for 10min, then shear at 15000rpm for 3min to obtain a lutein oil suspension.

[0070] Comparative Example 1

[0071] The only difference between this comparative example and Example 1 is that no dispersant is added in step S4, and a lutein oil suspension is finally obtained.

[0072] Comparative Example 2

[0073] The only difference between this comparative example and Example 1 is the addition of 1.5g sodium dodecyl naphthalene sulfonate and 1.5g dodecylamine acetate, which ultimately yielded a lutein oil suspension.

[0074] Comparative Example 3

[0075] The only difference between this comparative example and Example 1 is the addition of 2.85g sodium dodecylnaphthalene sulfonate and 0.15g dodecylamine acetate, which ultimately yielded a lutein oil suspension.

[0076] Comparative Example 4

[0077] The only difference between this comparative example and Example 1 is that in step S4, sodium dodecyl naphthalene sulfonate is replaced with sodium dodecyl phosphate, ultimately yielding a lutein oil suspension.

[0078] Comparative Example 5

[0079] The only difference between this comparative example and Example 1 is that in step S4, dodecylamine acetate is replaced with sodium dodecyl sulfate, ultimately yielding a lutein oil suspension.

[0080] The stability of the lutein oil suspensions prepared in Examples 1-9 and Comparative Examples 1-5 was tested using the following methods:

[0081] Method for determining the stability of lutein oil suspension: Weigh 10g of lutein oil suspension product and centrifuge in a centrifuge tube for 15min at a speed of 5000r / min. Take the upper oil layer and dilute it with n-hexane. Using n-hexane as a blank, measure the absorbance A1 at a wavelength of 474nm using a UV spectrophotometer. The ratio of the absorbance A1 to the absorbance A0 before centrifugation is a stability coefficient of the lutein oil suspension product. Stability coefficient (F) = A1 / A0.

[0082] The test results are shown in the table below:

[0083] Table 1. Stability test results of lutein oil suspensions prepared in Examples 1-9 and Comparative Examples 1-5

[0084]

[0085] Based on the data from Examples 1-3 and Example 6, it can be seen that the present invention, after adding a dispersant, also adds an emulsifier and an antioxidant, which improves the stability coefficient of the lutein oil suspension, thereby improving the stability of the lutein oil suspension. Based on the data from Examples 1-3 and Examples 4-5, it can be seen that the present invention, after adding a dispersant, also adds a suspending agent, further improving the stability of the lutein oil suspension.

[0086] According to the data from Examples 4 and 7, the present invention further improves the stability of lutein oil suspension by adding a dispersant, a suspending agent, an emulsifier, and an antioxidant after adding a dispersant.

[0087] Based on the data from Examples 1-3 and Examples 8-9, it can be seen that the present invention first shears the lutein oil suspension at a high speed of 15000 rpm, and then shears it at a low speed of 8000 rpm, which further improves the stability of the lutein oil suspension.

[0088] Based on the data from Examples 1-9 and Comparative Examples 1-5, it can be seen that the present invention improves the stability of lutein oil suspension by adding a composition of dispersant alkyl naphthalene sulfonate and fatty amine salt in a mass ratio of 6:4 to 9:1 during the preparation of lutein oil suspension.

[0089] The above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A method for preparing lutein oil suspension, characterized in that, Includes the following steps: S1. Add calendula flowers to dichloromethane for extraction, filter, and evaporate and concentrate the filtrate to obtain a concentrate. S2. Add the concentrate to ethanol, then add potassium hydroxide solution to carry out the saponification reaction to obtain the saponified solution. S3. Wash the saponified liquid with water and n-hexane respectively, crystallize, filter and dry to obtain lutein crystals; S4. Crush lutein crystals, add them to vegetable oil, add a dispersant, stir, and perform shear emulsification to obtain a lutein oil suspension. The dispersant is a composition of alkyl naphthalene sulfonate and fatty amine salt in a mass ratio of 6:4 to 9:1; In step S4, after adding the dispersant, a suspending agent is also added. The suspending agent is one or more of sodium alginate, sodium carboxymethyl cellulose, and Tween 80. The alkylnaphthalene sulfonate is sodium dodecylnaphthalene sulfonate or ammonium dodecylnaphthalene sulfonate, and the fatty amine salt is dodecylamine acetate or dodecylamine hydrochloride.

2. The method for preparing lutein oil suspension according to claim 1, characterized in that, The mass-to-volume ratio of lutein crystals to vegetable oil is 1:6 to 1:10 g / mL, and the mass-to-volume ratio of dispersant to vegetable oil is 0.1:10 to 0.3:10 g / mL. The vegetable oil is epoxidized soybean oil or epoxidized linseed oil.

3. The method for preparing lutein oil suspension according to claim 1, characterized in that, The mass-to-volume ratio of the suspending agent to the vegetable oil is 0.05:10~0.1:10 g / mL.

4. The method for preparing lutein oil suspension according to claim 1, characterized in that, In step S4, after adding the dispersant, an emulsifier and an antioxidant are also added. The emulsifier is one or more of lecithin, soybean lecithin, and ethylene propylene copolymer, and the antioxidant is one or more of natural vitamin E, tocopherol, and tea polyphenols.

5. The method for preparing lutein oil suspension according to claim 4, characterized in that, The mass-to-volume ratio of the emulsifier to the vegetable oil is 0.5:10 to 1:10 g / mL, and the mass-to-volume ratio of the antioxidant to the vegetable oil is 0.001:10 to 0.003:10 g / mL.

6. The method for preparing lutein oil suspension according to claim 1, characterized in that, The extraction temperature is 50~70℃, the extraction time is 3~5h, the saponification reaction temperature is 40~60℃, the saponification reaction time is 3~6h, and the crystallization temperature is 0~10℃.

7. The method for preparing lutein oil suspension according to claim 1, characterized in that, The volume ratio of ethanol to potassium hydroxide solution is 1:0.5 to 1:

2.

8. The method for preparing lutein oil suspension according to claim 1, characterized in that, The shear emulsification is a staged shear emulsification, with the first stage having a shear rate of 15,000 rpm and a shearing time of 3 to 5 minutes, and the second stage having a shear rate of 8,000 rpm and a shearing time of 10 to 15 minutes.

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