CN116102609A - Preparation method of oryzanol - Google Patents
Preparation method of oryzanol Download PDFInfo
- Publication number
- CN116102609A CN116102609A CN202111327105.4A CN202111327105A CN116102609A CN 116102609 A CN116102609 A CN 116102609A CN 202111327105 A CN202111327105 A CN 202111327105A CN 116102609 A CN116102609 A CN 116102609A
- Authority
- CN
- China
- Prior art keywords
- oryzanol
- preparation
- rice bran
- bran oil
- solvent
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- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 235000019774 Rice Bran oil Nutrition 0.000 claims abstract description 18
- 239000008165 rice bran oil Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 17
- 238000005406 washing Methods 0.000 claims abstract description 15
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000001914 filtration Methods 0.000 claims abstract description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000002425 crystallisation Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 230000008025 crystallization Effects 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 239000000706 filtrate Substances 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 16
- 230000001105 regulatory effect Effects 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 12
- 159000000000 sodium salts Chemical class 0.000 abstract description 5
- 238000002844 melting Methods 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 210000000467 autonomic pathway Anatomy 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000009874 alkali refining Methods 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 1
- 229940114124 ferulic acid Drugs 0.000 description 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 1
- 235000001785 ferulic acid Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000007661 gastrointestinal function Effects 0.000 description 1
- 239000003163 gonadal steroid hormone Substances 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention discloses a preparation method of oryzanol, which belongs to the field of oryzanol preparation and mainly solves the problems of low yield and poor purity of products in the prior art, and the method comprises the following steps: dissolving rice bran oil nigre with ester solvent, adjusting pH, filtering, collecting filtrate, adding lower solvent, heating to dissolve, cooling for crystallization, washing, and drying. According to the preparation method of oryzanol, provided by the invention, dilute hydrochloric acid is added into an ester solvent, so that oryzanol sodium salt in rice bran oil soapstock is converted into oryzanol, the oryzanol is extracted by the ester solvent, the yield of a product is improved by 83.0%, the oryzanol which is concentrated and nearly dried is further purified by a low-polarity solvent hot-melting cold-separating method, the purity of oryzanol is improved, the content of the obtained oryzanol finished product is more than or equal to 99.4%, and the problems of low yield and poor purity of the product in the prior art can be solved.
Description
Technical Field
The invention relates to the field of oryzanol preparation, in particular to a oryzanol preparation method.
Background
The oryzanol is the combined fat of ferulic acid and phytosterol, and can be extracted from cereal oil such as rice bran oil, germ oil and the like. The product has white to white crystal powder, no smell, special fragrance, and is soluble in various oils and water-insoluble. Oryzanol is often used clinically to improve the functions of autonomic nerves and endocrine regulation, and has various physiological effects of antioxidation, aging resistance and the like. The physiological functions are as follows: regulating autonomic nerves and promoting animal growth; regulating and improving gastrointestinal function, preventing autologous synthesis of cholesterol, reducing serum cholesterol, promoting skin microvascular circulation, protecting skin, and has weak sex hormone effect. Oryzanol also has the effects of resisting hyperlipidemia and inhibiting endogenous cholesterol synthesis in vivo.
Currently, oryzanol is extracted by weak acid substitution method, solution extraction method, low temperature crystallization method, adsorption method, etc. The most adopted weak acid substitution method at present has the advantages of less working procedures, simple equipment and low cost, but the methanol loss is more and the yield is low. In order to make oryzanol yield higher, two alkaline refineries are usually adopted in rice bran oil refining, wherein the first primary purpose is to neutralize a part of free fatty acid and reduce a part of acid value, and the second primary purpose is to change oryzanol into oryzanol sodium salt and concentrate the oryzanol into nigre. By utilizing the characteristic that oryzanol is dissolved in alkaline methanol and is insoluble in acidic methanol, oryzanol sodium salt is dissolved in alkaline aqueous methanol, impurities are removed by filtration, about 80% of oryzanol in rice bran oil is enriched in methanol solution at the moment, the pH of the solution is regulated to be acidic, so that oryzanol sodium salt is reduced to oryzanol and then separated out, and crude oryzanol is obtained by filtration. The crude rice bran oil is directly used for alkali refining, so that the consumption is excessive, and the refining yield of the rice bran oil is too low, so that a novel method is needed for preparing oryzanol, and the problems of low product yield and poor purity are solved.
Disclosure of Invention
The invention aims to provide a preparation method of oryzanol. Can solve the problems of low product yield and poor purity in the oryzanol preparation method.
The technical scheme of the invention is as follows: a oryzanol preparation method comprises dissolving rice bran oil nigre in ester solvent, adjusting pH, filtering, collecting filtrate, adding lower solvent, heating to dissolve, cooling for crystallization, washing, and drying.
Preferably, the ester solvent is one of ethyl formate, ethyl acetate and butyl acetate.
Preferably, the mass volume ratio of the rice bran oil soapstock to the ester solvent is 1:2-6 in g/mL.
Preferably, the dissolution temperature is 40-60 ℃.
Preferably, the pH is adjusted to a pH of 5-7 with dilute hydrochloric acid.
Preferably, the low-grade solution is one of n-hexane, petroleum ether and n-heptane.
Preferably, the mass-volume ratio of the rice bran oil soapstock to the low-grade solution is 1:1-3.
Preferably, the crystallization temperature is 5-20 ℃ and the crystallization time is 4-8h.
Preferably, the washing is sequentially a low-grade solvent washing and a hot water washing.
Advantageous effects
Compared with the prior art, the invention has the advantages that:
1. according to the preparation method of oryzanol, provided by the invention, dilute hydrochloric acid is added into an ester solvent, so that oryzanol sodium salt in rice bran oil nigre is converted into oryzanol, and the oryzanol is extracted by the ester solvent, thereby improving the yield of the product by 83.0%.
2. According to the preparation method of oryzanol, disclosed by the invention, the rice bran oil soapstock is cooled in an ester solution, most of oil soap impurities are separated out, oryzanol is still dissolved in the ester solvent, and the oryzanol is filtered, and is primarily separated and purified, so that the production process method is simple.
3. The invention provides a preparation method of oryzanol, which further purifies the oryzanol which is concentrated and nearly dried by a low-polarity solvent hot-melting cold-separating method, improves the purity of oryzanol, and obtains the oryzanol finished product content
≥99.4％。
Detailed Description
The invention will be further illustrated with reference to specific examples.
Example 1
200g of rice bran oil nigre (oryzanol content 20%) is taken and placed in a beaker, 800ml of ethyl acetate is added, the mixture is heated to 40 ℃, the mixture is stirred and dissolved, dilute hydrochloric acid solution is added, the pH of the solution is regulated to be less than 5, the solution is cooled to be less than 5 ℃, and the solution is filtered and is collected. Concentrating and recovering ethyl acetate, adding 200ml of n-hexane into the residue, heating and dissolving, cooling, preserving heat and crystallizing at 5 ℃ for 4 hours, filtering to obtain crude oryzanol, taking n-hexane as a washing material, taking hot water as a washing material, and drying to obtain 33.3g of oryzanol finished product, wherein the recovery rate is 83.25%, and the content is 99.4%.
Example 2
200g of rice bran oil nigre (oryzanol content 20%) is taken and placed in a beaker, 600ml of ethyl acetate is added, the mixture is heated to 50 ℃, stirred and dissolved, dilute hydrochloric acid solution is added, the pH of the solution is regulated to be less than 5, the solution is cooled to 10 ℃, and then filtered, and ethyl acetate solution is collected. Concentrating and recovering ethyl acetate, adding 400ml of n-hexane into the residue, heating and dissolving, cooling, preserving heat and crystallizing at 5 ℃ for 5 hours, filtering to obtain crude oryzanol, taking n-hexane as a washing material, taking hot water as a washing material, and drying to obtain 33.8g of oryzanol finished product, wherein the recovery rate is 84.5%, and the content is 99.6%.
Example 3
200g of rice bran oil nigre (oryzanol content 20%) is taken and placed in a beaker, 400ml of ethyl acetate is added, the mixture is heated to 60 ℃, the mixture is stirred and dissolved, dilute hydrochloric acid solution is added, the pH of the solution is regulated to be 6, the mixture is cooled to 15 ℃, and then the mixture is filtered, and ethyl acetate solution is collected. Concentrating and recovering ethyl acetate, adding 600ml of n-hexane into the residue, heating and dissolving, cooling, preserving heat and crystallizing at 10 ℃ for 7h, filtering to obtain crude oryzanol, taking n-hexane as a washing material, taking hot water as a washing material, and drying to obtain 33.2g of oryzanol finished product, wherein the recovery rate is 83.0%, and the content is 99.4%.
The foregoing is merely a preferred embodiment of the present invention, and it should be noted that modifications and improvements can be made by those skilled in the art without departing from the structure of the present invention, and these do not affect the effect and practicality of the implementation of the present invention.
Claims (9)
1. A process for preparing oryzanol includes such steps as dissolving the soapstock of rice bran oil in ester solvent, regulating pH value, filtering, collecting filtrate, adding lower-class solvent, heating to dissolve, cooling for crystallizing, washing and drying.
2. The method for preparing oryzanol according to claim 1, wherein the ester solvent is one of ethyl formate, ethyl acetate and butyl acetate.
3. The method for preparing oryzanol according to claim 1 or 2, wherein the mass-to-volume ratio of the rice bran oil soapstock to the ester solvent is 1:2-6 in terms of g/mL.
4. The process for the preparation of oryzanol according to claim 1, characterized in that the dissolution temperature is 40-60 ℃.
5. The process for the preparation of oryzanol according to claim 1, characterized in that the PH is adjusted to 5-7 with dilute hydrochloric acid.
6. The method for preparing oryzanol according to claim 1, wherein the low-grade solution is one of n-hexane, petroleum ether and n-heptane.
7. The method according to claim 6, wherein the mass-to-volume ratio of the rice bran oil soapstock to the low-grade solution is 1:1-3.
8. The method for preparing oryzanol according to claim 1, wherein the crystallization temperature is 5-20 ℃ and the crystallization time is 4-8h.
9. The method for preparing oryzanol according to claim 1, wherein the washing is sequentially a low-grade solvent washing and a hot water washing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111327105.4A CN116102609A (en) | 2021-11-10 | 2021-11-10 | Preparation method of oryzanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111327105.4A CN116102609A (en) | 2021-11-10 | 2021-11-10 | Preparation method of oryzanol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116102609A true CN116102609A (en) | 2023-05-12 |
Family
ID=86256667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111327105.4A Pending CN116102609A (en) | 2021-11-10 | 2021-11-10 | Preparation method of oryzanol |
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| Country | Link |
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| CN (1) | CN116102609A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112552368A (en) * | 2020-12-11 | 2021-03-26 | 桂林莱茵生物科技股份有限公司 | Method for refining oryzanol by using mixed solvent |
| CN112625081A (en) * | 2020-12-11 | 2021-04-09 | 桂林莱茵生物科技股份有限公司 | Method for producing oryzanol by using rice bran oil soapstock as raw material |
-
2021
- 2021-11-10 CN CN202111327105.4A patent/CN116102609A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112552368A (en) * | 2020-12-11 | 2021-03-26 | 桂林莱茵生物科技股份有限公司 | Method for refining oryzanol by using mixed solvent |
| CN112625081A (en) * | 2020-12-11 | 2021-04-09 | 桂林莱茵生物科技股份有限公司 | Method for producing oryzanol by using rice bran oil soapstock as raw material |
Non-Patent Citations (1)
| Title |
|---|
| 沈鸿 等: "响应面法优化柱层析工艺提取米糠油皂脚中的谷维素", 粮食与油脂, vol. 29, no. 7, 31 December 2016 (2016-12-31), pages 55 - 61 * |
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