CN100357358C - Preparation method of lycopene - Google Patents
Preparation method of lycopene Download PDFInfo
- Publication number
- CN100357358C CN100357358C CNB2005101265922A CN200510126592A CN100357358C CN 100357358 C CN100357358 C CN 100357358C CN B2005101265922 A CNB2005101265922 A CN B2005101265922A CN 200510126592 A CN200510126592 A CN 200510126592A CN 100357358 C CN100357358 C CN 100357358C
- Authority
- CN
- China
- Prior art keywords
- lycopene
- lyeopene
- resinous
- low
- mixed solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of lycopene, which adopts an extraction crystallization method to prepare lycopene, wherein lycopene oleoresin is added into low-molecular alcohol solvent under stirring, the lycopene is obtained by filtering and drying after being uniformly stirred, and the obtained filtrate is used for recovering the solvent by using a conventional method. Dissolving fatty acid and its esters in oleoresin with low molecular alcohol, promoting crystallization and aggregation of lycopene, filtering, and drying to obtain refined lycopene product. The purity of the refined lycopene product obtained by the method can be controlled between 19-65%, and the refined lycopene can be conveniently used in medicines, health products and cosmetics; the lycopene yield in the whole process is high, the process flow is simple and feasible, the energy consumption is low, and the method is suitable for industrial production.
Description
Technical field
The present invention relates to the manufacture field of food, promptly relate to a kind of low molecular alcoholic solvents of using by the method for lycopene oleo-resinous through the extractive crystallization purifying lycopene.
Background technology
Lyeopene (Lycopene) molecular formula is C
40H
56, molecular weight is 536.9, its structure is the polyunsaturated fat hydrocarbon that contains 11 conjugated double bonds and two unconjugated double bonds, is a kind of important carotenoid.Recent study finds that the ability of Lyeopene cancellation singlet oxygen is 100 times of vitamin-E, (the Mascio D more than 2 times of β-Hu Luobusu, Arch BiochemBiophys, 1989,274:532-538), content of lycopene and many chronic diseases such as prostate cancer in the human body are found in epidemiological study, lung cancer, relevant (Giovannucci E, J Natl Cancer Inst, 1999 such as cancer of the stomach and mammary cancer, 91 (4), 317-331), and Lyeopene can radioprotective, preventing cardiovascular disease, regulate the human body function of immune system, (Francesco Visioli, Patrizia Riso, Simona Grande delay senility, EurJ Nutr, 2003,42 (4), 201-206).
As a kind of functional natural pigment, Lyeopene can be widely used in food, healthcare products, makeup, medicine and other fields.Abundant because of content in tomato, Lyeopene mainly extracts from tomato and goods thereof at present, comprises that with an organic solvent (as sherwood oil, normal hexane, tetrahydrofuran (THF), ether, ethyl acetate, benzene, methylene dichloride etc.) extract, or adopts supercritical CO
2Extraction process, but what generally obtain is the crude extract of Lyeopene, is called lycopene oleo-resinous, needs further refining if will obtain more high-load Lyeopene.Wang Qiang etc. pressure be 25Mpa, temperature be 50 ℃, after extracting in 3 hours, obtain content of lycopene be 12.58% product (Agricultural Sciences in China, 2003,2 (6), 670-676); CN1431257A has described and has a kind ofly used trichloromethane and acetone to make extraction agent to extract Lyeopene from fresh tomato and obtain the method for concentration greater than 5% lycopene oleo-resinous; CN1316468A has announced that a kind of employing high-speed countercurrent chromatography separates preparation high purity lycopene method from the Lyeopene crude product, the product purity that this method obtains can reach more than 95%, but used multiple organic solvent, include hypertoxic second cyanogen, chloroform etc., production efficiency is low simultaneously, the cost height, the separation scale is limited, is not suitable for suitability for industrialized production; CN1493622A uses the lycopene oleo-resinous that extracts acquisition 6-8% nonpolar or the tomato-sauce of weakly polar organic solvent (acetone, normal hexane, sherwood oil, ethyl acetate) after handling through enzymolysis, washing, freezing and pulverizing, use 75% washing with alcohol oleo-resinous then, again with ethyl acetate dissolving oil resin again, and adding diatomite removal of impurities in solution, filtering back gained filtrate decompression distillation acquisition content is the lycopene oleo-resinous of 10-15%, perhaps the gained oleo-resinous is directly used supercritical CO
2Extracting and refining obtains the Lyeopene of 16-30%, and whole process is comparatively loaded down with trivial details, and refining purity is on the low side.US5858700A has announced and has a kind ofly separated the purification lycopene method by saponification reaction from lycopene oleo-resinous, but saponification makes the tiny crystallization of the Lyeopene that dissociates out by a large amount of glyceryl ester parcels, is difficult to separate; CN1472183A has announced a kind of preparation method of high purity Lyeopene; be to be raw material with the lycopene oleo-resinous; under comparatively high temps and protection of inert gas, make it to be dissolved in and form saturated solution in the hydrocarbon organic solvent; behind the solution filtering and impurity removing at low temperature crystallization; finally obtain highly purified lycopene crystal; it is low that but the weak point of this method is a yield, the highest by only 40.1%.
Extractive crystallization has developed into the effective ways of separation of organic substances in recent years, be applicable to isomers, the separation and purification of close system of boiling point and heat-sensitive substance, as be used for separation (the I Dewa Gede Arsa Putrawan of dimethylnaphthalene isomer, Tatang HernasSoerawidjaja, Separation and Purification Technology, 2004,39,79-88), and boiling point close compound 2-methylphenol and 1, the separation of 2-anisole (Ming-Jer Lee, Yu-Hsing Chou, Ho-Mu Lin, Ind.Eng.Chem.Res.2003,42 (14), 3434-3440).
Extractive crystallization process that the present invention adopts prepares Lyeopene, yield height not only, and obtained the Lyeopene of high level, and significantly reduced the consumption of solvent, and having reduced energy consumption, this method is simple.Employed solvent adopts conventional method to carry out recycling in the whole process.
Summary of the invention
The object of the invention is, a kind of preparation method of Lyeopene is provided, and this method under agitation adds low molecular alcoholic solvents with lycopene oleo-resinous, the after-filtration that stirs, is drying to obtain Lyeopene, and remaining filtrate uses conventional method to reclaim solvent.Use compositions such as lipid acid in the low mass molecule alcohol dissolving oil resin and ester class thereof, and promote crystal of lycopene to assemble, get final product behind the filtration drying the purified lycopene product.Utilize this method the purifying lycopene product purity can be controlled between the 19-65%, can be advantageously used in medicine, healthcare products, makeup; Lyeopene yield height in the whole process, technical process is simple, and energy consumption is low, is fit to suitability for industrialized production.
The preparation method of a kind of Lyeopene of the present invention, this method adopts extractive crystallization process to prepare Lyeopene, lycopene oleo-resinous is under agitation added low molecular alcoholic solvents, solid-liquid ratio W/V is 1: 5-50, temperature is controlled at 20-60 ℃, the back mixed solution that stirs left standstill 30 minutes, then the mixed solution filtration drying was promptly got Lyeopene, and residual filtrate uses conventional method to reclaim solvent.
The content of lycopene of employed lycopene oleo-resinous is 1-12%.
Employed low mass molecule alcohol is methyl alcohol or ethanol or Virahol.
In order to obtain the purified Lyeopene with high yield, the present invention has adopted the method for extractive crystallization.Composition such as other components such as a large amount of lipid acid and ester class thereof can be dissolved in low mass molecule alcohol in the lycopene oleo-resinous, and Lyeopene is insoluble.Low mass molecule alcohol lipid acid and other polar components such as ester class thereof in not only can the dissolving oil resin, and can promote crystal of lycopene to assemble, thus reach the purified purpose.And extractive crystallization can carry out at a lower temperature, thereby helps the stable yield that improves of Lyeopene.
Gained purified Lyeopene of the present invention can be advantageously used in fields such as medicine, healthcare products, makeup.
Description of drawings
Referring to accompanying drawing
Fig. 1 is a process flow sheet of the present invention
Embodiment
The present invention will be further described below by embodiment.
Embodiment 1
Take by weighing 10g content and be 6% lycopene oleo-resinous and under agitation add the 25ml Virahol, temperature is controlled at 30 ℃, after the back mixed solution that stirs leaves standstill 30 minutes, with the mixed solution filtration drying, promptly get content and be 50.6% lycopene product, the yield of Lyeopene is 87.04%, and residual filtrate uses ordinary method to reclaim solvent.
Embodiment 2
Take by weighing 10g content and be 1% lycopene oleo-resinous and under agitation add 50ml methyl alcohol, temperature is controlled at 20 ℃, after the back mixed solution that stirs leaves standstill 30 minutes, with the mixed solution filtration drying, promptly get content and be 19.15% lycopene product, the yield of Lyeopene is 75.97%, and residual filtrate uses ordinary method to reclaim solvent.
Embodiment 3
Take by weighing 10g content and be 12% lycopene oleo-resinous and under agitation add the 5ml dehydrated alcohol, temperature is controlled at 40 ℃, after the back mixed solution that stirs leaves standstill 30 minutes, with the mixed solution filtration drying, promptly get content and be 23.5% lycopene product, the yield of Lyeopene is 88%, and residual filtrate uses ordinary method to reclaim solvent.
Embodiment 4
Take by weighing 10g content and be 6% lycopene oleo-resinous and under agitation add the 30ml Virahol, temperature is controlled at 60 ℃, after the back mixed solution that stirs leaves standstill 30 minutes, with the mixed solution filtration drying, promptly get content and be 62.05% lycopene product, the yield of Lyeopene is 76.49%, and residual filtrate uses ordinary method to reclaim solvent.
Claims (2)
1, a kind of preparation method of Lyeopene, it is characterized in that adopting extractive crystallization process to prepare Lyeopene, lycopene oleo-resinous is under agitation added low mass molecule alcohol methyl alcohol or ethanol or isopropanol solvent, solid-liquid ratio W/V is 1: 5-50, temperature is controlled at 20-60 ℃, the back mixed solution that stirs left standstill 30 minutes, then the mixed solution filtration drying was promptly got Lyeopene, and residual filtrate uses conventional method to reclaim solvent.
2, method according to claim 1, the content of lycopene that it is characterized in that employed lycopene oleo-resinous is 1-12%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005101265922A CN100357358C (en) | 2005-11-30 | 2005-11-30 | Preparation method of lycopene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005101265922A CN100357358C (en) | 2005-11-30 | 2005-11-30 | Preparation method of lycopene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1775867A CN1775867A (en) | 2006-05-24 |
| CN100357358C true CN100357358C (en) | 2007-12-26 |
Family
ID=36765592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005101265922A Expired - Fee Related CN100357358C (en) | 2005-11-30 | 2005-11-30 | Preparation method of lycopene |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100357358C (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1965693B (en) * | 2006-06-13 | 2012-12-05 | 新疆屯河投资股份有限公司 | Method for purifying natural lycopene |
| CN102924967B (en) * | 2012-11-09 | 2015-01-07 | 晨光生物科技集团股份有限公司 | Industrialization method for improving purity of lycopene oil resin |
| CN103012230A (en) * | 2013-01-06 | 2013-04-03 | 大连医诺生物有限公司 | Novel process for high-effective extraction of carotenoid in Blakeslea trispora |
| IL274216B2 (en) * | 2017-10-25 | 2024-10-01 | Chenguang Biotech Group Co Ltd | A method for preparing lycopene crystals with a high degree of purity and low damage |
| CN111373047A (en) | 2017-10-25 | 2020-07-03 | 晨光生物科技集团股份有限公司 | Pretreatment method of raw material for producing lycopene |
| CN114920642B (en) * | 2022-06-02 | 2024-03-12 | 浙江工业大学 | A separation process for obtaining high-purity fatty acid monoglycerides and fatty acid diglycerides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1545914A (en) * | 2003-12-12 | 2004-11-17 | 新疆生命红红花开发有限责任公司 | Production method of natural lycopene oleoresin and natural lycopene crystallisate |
-
2005
- 2005-11-30 CN CNB2005101265922A patent/CN100357358C/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1545914A (en) * | 2003-12-12 | 2004-11-17 | 新疆生命红红花开发有限责任公司 | Production method of natural lycopene oleoresin and natural lycopene crystallisate |
Non-Patent Citations (1)
| Title |
|---|
| 功能性番茄红素的提取生产技术 刘慧，闫树刚，仝其根.农产品加工，第6期 2003 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1775867A (en) | 2006-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2016153347A1 (en) | Cannabidiol isolate from industrial-hemp and use thereof in pharmaceutical and/or cosmetic preparations | |
| KR102025056B1 (en) | Solid/liquid extraction | |
| CN113773184B (en) | Method for extracting curcumin compounds | |
| EP4208274B1 (en) | Method of obtaining thc-free cannabinoid concentrate | |
| US8735615B2 (en) | Method for extracting unsaponifiables from renewable raw materials | |
| JP5628135B2 (en) | Method for producing hydroxysanshool-containing material | |
| CN105481711A (en) | Hydroxy-beta-sanshool monomer preparation method | |
| CN100357358C (en) | Preparation method of lycopene | |
| KR20120139690A (en) | Liquid/liquid extraction | |
| CN102320953A (en) | Method for preparing natural alpha-linolenic acid from crude oil of idesia polycarpa var.vestita diels | |
| CN1880327A (en) | Method for preparing open loop secoisolariciresinol diglucoside from flax seed | |
| CN101654398A (en) | Method for extracting high purity polyprenol from plant needle leaf raw material | |
| CN101709030B (en) | Method for extracting and separating ginkgo leaf polyprenol acetic ester from ginkgo leaf by supercritical carbon oxide | |
| Pajot et al. | Improving the extraction and the purification of fucoxanthin from Tisochrysis lutea using centrifugal partition chromatography | |
| US20080306141A1 (en) | Method of Extraction of Catechin Type-A Proanthocyanidins | |
| JP6468745B2 (en) | Functional agent having Maillard reaction inhibitory function or antioxidant function | |
| CN102134247B (en) | Xanthotoxol derivative and new composite method thereof | |
| CN104292201B (en) | Method for preparing 3-ester group catechin | |
| CN102190689A (en) | Purification method for ceramide in amorphophalms konjac | |
| EP3555057B1 (en) | Process for the preparation of tocols and squalene | |
| CN113801003A (en) | Industrial extraction method of cannabidiol | |
| JP5441433B2 (en) | Liver function improving agent containing fruit juice | |
| CN104628546A (en) | 4-hydroxyl-3-(1, 2-dimethyl-2-propylene) benzaldehyde and use | |
| CN102532211B (en) | Lignan triglycoside compound and preparation method and application thereof | |
| CN101654447B (en) | Extraction method of natural vitamin E |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20071226 Termination date: 20151130 |
|
| EXPY | Termination of patent right or utility model |