CN1935789A - Method for preparing full-trans beta-carrotin - Google Patents
Method for preparing full-trans beta-carrotin Download PDFInfo
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- CN1935789A CN1935789A CN 200610053892 CN200610053892A CN1935789A CN 1935789 A CN1935789 A CN 1935789A CN 200610053892 CN200610053892 CN 200610053892 CN 200610053892 A CN200610053892 A CN 200610053892A CN 1935789 A CN1935789 A CN 1935789A
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Abstract
The invention discloses a total reversal beta-carotene preparing method, mixing beta-carotene and high-boiling point, low-toxicity polar solvent at 70-160 deg.C in the mass ratio of 1 to (1-10), reacting in protective nitrogen gas for 10-30 h, filtering and water-washing and drying to make it. And the invention has advantages of: 1) using low-toxicity solvent as reacting medium, safe and environmental-protection and applied to transposition of natural beta-carotene and synthetic beta-carotene in the courses of preparing drugs, food, feeds, and other preparation products at various levels; 2) high reaction temperature, fast transposition and basically having no by-products; 3) the selected solvent basically has no solubility to beta-carotene, and the reaction yield is high; 4) large beta-carotene processing quality of the selected solvent and less solvent utilization.
Description
Technical field
The present invention relates to a kind of preparation method of content full cis-beta-carotene.
Background technology
(β-Carotene) is the typical case's representative in the carotenoid family to β-Hu Luobusu, be not only the important source of vitamin A in the body, and itself also has the important physical function to human body, it can prevent, delays and treat some disease, especially cancer also can improve body's immunological function simultaneously.Its molecular formula is C
40H
56, molecular weight is 536.88, its molecular structural formula is as shown in the figure.
Owing to contain long conjugated double bond chromophore in the β-Hu Luobusu molecule, thereby have by the character of photoabsorption, it is crystal or the crystalloid powder of scarlet to glossiness oblique parallelepiped of garnet or plate crystal, it is orange-yellow to yellow that dilute solution is, concentration is with orange when increasing, because of the polarity of solution can be slightly redly.Water insoluble, methyl alcohol, ethanol, propylene glycol, glycerine, bronsted lowry acids and bases bronsted lowry are slightly soluble in vegetables oil, in aliphatics and aromatic hydrocarbon medium solvability are arranged, and are soluble in chlorinated hydrocarbons such as trichloromethane.
The fusing point of β-Hu Luobusu is 184 ℃, have 20 approximately surplus kind of isomer.Just because of its unsaturated structure, make it have the ability of stronger anti-oxidant activity and removing free radical, thereby have certain physiologically active.But,, make and its unstable chemcial property oxygenolysis take place when illumination and heating easily also just because of its many double bond structures.Comparatively speaking, the chemical property of alltrans isomer is stable than other isomer, and tiring in vivo is higher.Therefore in the process of various processing β-Hu Luobusus, to keep away a series of sfgd.s such as oxygen except taking lucifuge, it also is a kind of important channel that keeps its biological value that β-Hu Luobusu is prepared into the alltrans isomer as far as possible.
Few about the report of preparation content full cis-beta-carotene specially before this, mainly contain following several:
1, US2849507 mention with 100g15-suitable-β-Hu Luobusu is an initial reactant, is 80 ℃ of heating transpositions 10 hours in 80 ℃～100 ℃ the sherwood oil in the boiling range of 500ml, can obtain the content full cis-beta-carotene of 95g～97g; Or 80 ℃ of heating transpositions 10 hours in the 500ml ethyl acetate, can obtain the content full cis-beta-carotene about 90g.This method transposition is very fast, but yield is not very high, and some β-Hu Luobusu is dissolved in the organic solvent, and the organic solvent that remains in addition in the content full cis-beta-carotene will limit its application in fields such as a lot of food, medicines.
2, US3441623 introduced a kind of with 13-suitable-β-Hu Luobusu is converted into the method for content full cis-beta-carotene, this patent be with 13-suitable-β-Hu Luobusu mixes in varsol, 50 ℃～100 ℃ heating 1 hour～10 hours even longer times down.This is the method for a kind of US2849507 of being similar to, though it does not disclose concrete transposition yield, obviously still has problems such as the not high and range of application of yield is narrow.
3, US3989757 report is that 44.2% β-Hu Luobusu crude reaction 500g is mixed in 2.5 premium on currency with solid content, in its boiling point (100 ℃) transposition 20 hours down, obtains 133.9g content full cis-beta-carotene crude product through subsequent disposal.Though this method selects for use water to make the transposition solvent, also will use acetone and other organic solvent in subsequent disposal, solvent load is big in addition, and transposition yield is not high.
Summary of the invention
The objective of the invention is problem, a kind of preparation method of widely used content full cis-beta-carotene is provided at above-mentioned existence.
The preparation method of content full cis-beta-carotene: mass ratio is that 1: 1～10 β-Hu Luobusu mixes under 70 ℃～160 ℃ with the polar solvent of high boiling point low toxicity; the lucifuge reaction is 10 hours～30 hours under nitrogen protection, and filtration and washing, drying obtain content full cis-beta-carotene.
Described β-Hu Luobusu is natural beta-carotin and synthetic β-Hu Luobusu.The polar solvent of high boiling point low toxicity is glycerol, propylene glycol, a glycerol acetate, glyceryl diacetate or diglycol monotertiary ethyl ester.The polar solvent of high boiling point low toxicity is preferably glycerol or propylene glycol.The mass ratio of the polar solvent of β-Hu Luobusu and high boiling point low toxicity is preferably 1: 2～and 5.Temperature of reaction is preferably 80 ℃～140 ℃.
Advantage of the present invention is: 1) utilize low poison solvent as reaction medium, safety and environmental protection is applicable to natural beta-carotin and the transposition of synthetic β-Hu Luobusu in formulation products preparation process at different levels such as medicine, food and feed.2) temperature of reaction of this reaction is higher, and transposition speed is fast, and basic no coupling product.3) solvent selected for use of this reaction does not have solvability substantially to β-Hu Luobusu, the reaction yield height.4) solvent selected for use of this reaction is big to the β-Hu Luobusu treatment capacity, and solvent load is few.
Embodiment
The present invention utilizes various cis-trans β-Hu Luobusu mixtures to be starting raw material; it is joined in the polar solvent of high boiling point low toxicity; temperature is controlled at 70 ℃～160 ℃; the lucifuge reaction is 10 hours～30 hours under nitrogen protection; then above-mentioned mixed solution filtration and washing, drying are obtained content full cis-beta-carotene, also this mixed solution can be directly applied to formulation products at different levels such as medicine, food and feed.The present invention is described in detail below in conjunction with embodiment.
Embodiment 1
Add Dunaliella salina β-Hu Luobusu extract 100g and the glycerol 1000g that contains 48% cis-isomeride in the 1000ml there-necked flask, control reaction temperature is 130 ℃, and the lucifuge reaction is 3 hours under the nitrogen protection, is cooled to 70 ℃ then, continues reaction 12 hours.Reaction is finished this mixed solution filtered while hot, and obtains containing the β-Hu Luobusu 98g of 99% alltrans isomer after the washing, drying.
Embodiment 2
Add synthetic β-Hu Luobusu 500g and the propylene glycol 500g that contains 67% cis-isomeride in the 1000ml there-necked flask, control reaction temperature is 160 ℃, and nitrogen protection was reacted lucifuge 5 hours down, was cooled to 100 ℃ then, continues reaction 25 hours.Reaction is finished this mixed solution filtered while hot, and obtains containing the β-Hu Luobusu 492g of 98% alltrans isomer after the washing, drying.
Embodiment 3
Add a synthetic β-Hu Luobusu 200g and a glycerol acetate 800g who contains 26% cis-isomeride in the 1000ml there-necked flask, control reaction temperature is 120 ℃, and the lucifuge reaction is 6 hours under the nitrogen protection, is cooled to 80 ℃ then, continues reaction 22 hours.Reaction is finished this mixed solution filtered while hot, and obtains containing the β-Hu Luobusu 195g of 98% alltrans isomer after the washing, drying.
Embodiment 4
Add synthetic β-Hu Luobusu 300g and the glyceryl diacetate 700g that contains 35% cis-isomeride in the 1000ml there-necked flask, control reaction temperature is 140 ℃, and the lucifuge reaction is 4 hours under the nitrogen protection, is cooled to 100 ℃ then, continues reaction 25 hours.Reaction is finished this mixed solution filtered while hot, and obtains containing the β-Hu Luobusu 291g of 97% alltrans isomer after the washing, drying.
Embodiment 5
Add synthetic β-Hu Luobusu 400g and the diglycol monotertiary ethyl ester 600g that contains 10% cis-isomeride in the 1000ml there-necked flask, control reaction temperature is 90 ℃, and the lucifuge reaction is 10 hours under the nitrogen protection.Reaction is finished this mixed solution filtered while hot, and obtains containing the β-Hu Luobusu 398g of 97% alltrans isomer after the washing, drying.
Claims (6)
1. the preparation method of a content full cis-beta-carotene; it is characterized in that: mass ratio is that 1: 1～10 β-Hu Luobusu mixes under 70 ℃～160 ℃ with the polar solvent of high boiling point low toxicity; the lucifuge reaction is 10 hours～30 hours under nitrogen protection, and filtration and washing, drying obtain content full cis-beta-carotene.
2. the preparation method of a kind of content full cis-beta-carotene according to claim 1 is characterized in that, described β-Hu Luobusu is natural beta-carotin and synthetic β-Hu Luobusu.
3. the preparation method of a kind of content full cis-beta-carotene according to claim 1 is characterized in that, the polar solvent of described high boiling point low toxicity is glycerol, propylene glycol, a glycerol acetate, glyceryl diacetate or diglycol monotertiary ethyl ester.
4. according to the preparation method of claim 1 or 3 described a kind of content full cis-beta-carotenes, it is characterized in that the polar solvent of described high boiling point low toxicity is glycerol or propylene glycol.
5. the preparation method of a kind of content full cis-beta-carotene according to claim 1 is characterized in that, the mass ratio of the polar solvent of described β-Hu Luobusu and high boiling point low toxicity is 1: 2～5.
6. the preparation method of a kind of content full cis-beta-carotene according to claim 1 is characterized in that, described temperature of reaction is 80 ℃～140 ℃.
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| Application Number | Priority Date | Filing Date | Title |
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| CNB2006100538927A CN100484919C (en) | 2006-10-19 | 2006-10-19 | Method for preparing full-trans beta-carrotin |
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| Application Number | Priority Date | Filing Date | Title |
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| CNB2006100538927A CN100484919C (en) | 2006-10-19 | 2006-10-19 | Method for preparing full-trans beta-carrotin |
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|---|---|
| CN1935789A true CN1935789A (en) | 2007-03-28 |
| CN100484919C CN100484919C (en) | 2009-05-06 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101314554B (en) * | 2007-05-29 | 2011-01-12 | 中国科学院理化技术研究所 | Method for synthesizing cis-lycopene isomer from full trans lycopene with photochemistry isomerization reaction |
| CN112961089A (en) * | 2021-03-12 | 2021-06-15 | 上虞新和成生物化工有限公司 | Method for reducing viscosity of beta-carotene oil |
| CN113292468A (en) * | 2021-06-28 | 2021-08-24 | 万华化学集团股份有限公司 | Preparation method of all-trans beta-carotene |
| CN114133348A (en) * | 2021-11-09 | 2022-03-04 | 湖北广济药业股份有限公司 | Method for extracting high-purity all-trans beta-carotene |
-
2006
- 2006-10-19 CN CNB2006100538927A patent/CN100484919C/en active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101314554B (en) * | 2007-05-29 | 2011-01-12 | 中国科学院理化技术研究所 | Method for synthesizing cis-lycopene isomer from full trans lycopene with photochemistry isomerization reaction |
| CN112961089A (en) * | 2021-03-12 | 2021-06-15 | 上虞新和成生物化工有限公司 | Method for reducing viscosity of beta-carotene oil |
| CN112961089B (en) * | 2021-03-12 | 2022-09-27 | 上虞新和成生物化工有限公司 | Method for reducing viscosity of beta-carotene oil |
| CN113292468A (en) * | 2021-06-28 | 2021-08-24 | 万华化学集团股份有限公司 | Preparation method of all-trans beta-carotene |
| CN114133348A (en) * | 2021-11-09 | 2022-03-04 | 湖北广济药业股份有限公司 | Method for extracting high-purity all-trans beta-carotene |
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| Publication number | Publication date |
|---|---|
| CN100484919C (en) | 2009-05-06 |
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Owner name: ZHEJIANG XINHECHENG CO., LTD. SHANGYU XINHECHENG B Free format text: FORMER OWNER: ZHEJIANG XINHECHENG CO., LTD. Effective date: 20120301 |
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Effective date of registration: 20120301 Address after: 310027 Hangzhou, Zhejiang Province, Zhejiang Road, No. 38 Co-patentee after: Zhejiang Xinhecheng Co., Ltd. Patentee after: Zhejiang University Co-patentee after: Shangyu Xinhecheng Bio-Chemical Co., Ltd. Co-patentee after: Zhejiang NHU Pharmaceutical Co., Ltd. Address before: 310027 Hangzhou, Zhejiang Province, Zhejiang Road, No. 38 Co-patentee before: Zhejiang Xinhecheng Co., Ltd. Patentee before: Zhejiang University |