WO2003028481A1 - Procede de preparation de lycopene - Google Patents

Procede de preparation de lycopene Download PDF

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Publication number
WO2003028481A1
WO2003028481A1 PCT/CN2002/000080 CN0200080W WO03028481A1 WO 2003028481 A1 WO2003028481 A1 WO 2003028481A1 CN 0200080 W CN0200080 W CN 0200080W WO 03028481 A1 WO03028481 A1 WO 03028481A1
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WO
WIPO (PCT)
Prior art keywords
lycopene
solvent
organic solvent
raw material
crystals
Prior art date
Application number
PCT/CN2002/000080
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English (en)
Chinese (zh)
Inventor
Huanzhong Chen
Original Assignee
Xinjiang Jinqi Industry Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Xinjiang Jinqi Industry Limited filed Critical Xinjiang Jinqi Industry Limited
Publication of WO2003028481A1 publication Critical patent/WO2003028481A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources

Definitions

  • the invention relates to a method for preparing lycopene, and in particular to a method for preparing a high-purity natural lycopene with lycopene crystals of 80-90% by using a ketchup product as a raw material, a simple method, and a high yield. method. Background technique
  • Lycopene belongs to the class of carotenoids and is widely found in nature. Its most important natural source is tomato. It has been used as a food, feed, cosmetic and pharmaceutical additive a lot.
  • lycopene crystals can be used as an important raw material for the production of natural anti-cancer drug preparations such as prostate cancer and breast cancer; they can be used as natural health foods (such as soft gelatin, water-soluble microcystin, Oral liquids, lozenges, etc.) additives; can also be used as food, color cosmetics for advanced cosmetics (such as lipstick, rouge, etc.).
  • lycopene Because of the wide use of lycopene, there have been many research reports on the preparation of natural lycopene.
  • the raw materials for its production are mainly fresh tomatoes (lycopene content greater than 1QGppm) or tomato products (such as tomato sauce, tomato powder, etc.) and Scraps from tomato products (tomato peel, dregs).
  • lycopene Compared with other carotenoids, lycopene has the antioxidant properties and color stability of its coarse-crystalline products. Therefore, the production of lycopene requires a purification process to achieve high stability with high purity. Nature.
  • there are publicly disclosed methods for producing natural lycopene Generally, at least twice the organic solvent is used to heat the tomato or ketchup raw material (50-6 (TC)) extraction.
  • the lycopene containing 2-5% Oleoresin and then select an appropriate solvent to extract the oleoresin, the crude lycopene crystals obtained are then washed with the solvent multiple times, the whole process is long, and the number of operation steps is not only high energy consumption, but also leads to The rate is low, for example, the method described in PCT application PCT / US95 / 14475, it takes 4-6 hours from feeding to crystallization, and the yield is only 64.72% (Example 1), that is, the tomato in the raw material after the process The total loss of lycopene is as high as 35. 28%.
  • CN1298904A can only obtain 24% lycopene-containing crystals from 6-10 hours from feeding to crystallization, and the total yield is only 19.5%. 80. 5% or more (Example 1). Similar conclusions can be obtained by studying the technical descriptions and examples in other public documents, such as Gu 44831, EP-A-382067, EP-000140, PCT / W097 / 48287, etc. Summary of invention
  • the purpose of the present invention is to provide an innovative process for the disadvantages of long production processes and low product yields in the prior art.
  • the tomato or tomato product is used as a raw material to prepare crystallinity of more than 80%, especially 90%.
  • the whole process is simple and easy to operate, and the energy consumption is low, but the yield is significantly higher than that of the prior art method, thereby achieving the purpose of high efficiency and energy saving.
  • lycopene is used to dissolve a variety of fat-soluble solvents and oils, but is only slightly soluble in low-carbon alcohols such as ethanol (heated) and hardly soluble in cold ethanol.
  • low-molecular alcohol solvents are used. Remove the moisture in tomatoes or tomato products, and some resins, volatile oils, sugars, viscose and certain alkaloids, pigments (yellow pigments) and glycosides, increase the lycopene content in the raw materials, and then use Organic solvents extract it from the raw materials, and the lycopene crystals can be directly precipitated during the solvent recovery process.
  • the process of the present invention is obviously tubular, and can be directly precipitated in the process of recovering the extraction solution without undergoing the oleoresin preparation process, and has a high crystallinity of lycopene, and the yield is greatly improved.
  • the preparation method of the lycopene proposed by the present invention uses tomato ketchup with a water-soluble solid content of 28-38% as a raw material.
  • the preparation method includes the following steps:
  • the tomato sauce raw material is extracted at room temperature with an alcohol solvent having less than 4 carbons and a concentration of more than 70%.
  • the amount of the alcohol solvent is 5 to 10 times the weight of the tomato sauce raw material.
  • the insoluble matter separated is at 30-36 ° C. Dry under vacuum to make fibrous 4-fragment material with water content of 1-5%;
  • step 2) Extract the powdery material in step 1) at room temperature with an organic solvent that can dissolve lycopene and has a boiling point below 80 ° C, and recover the solvent in the extract at 26-52 ° C to precipitate crystals.
  • the present invention selects tomato sauce as a raw material, wherein the content of water-soluble solids is 28-38%, including various specifications of tomato sauce prepared from different tomato varieties, such as lycopene Content of the feedstock in the tomato sauce 45- 70mg / 100g or more, orange-red tomato powder or lycopene in the lycopene content of the red pigment Ru 2 00mg / 100g of tomato pomace powder 30- 40mg / 100g of fresh tomatoes may be used However, it should first be thermally broken to separate the skin and seeds, and centrifuged to dehydrate to a wet slag containing less than 70% water.
  • a low-carbon alcohol solvent preferably ethanol
  • ethanol preferably ethanol
  • the extraction process preferably uses different concentrations of alcohol solvents to sequentially extract and separate various types of miscellaneous shields, for example, first use 70-95% ethanol , Generally, it is extracted by stirring for 5-15 minutes, and the insoluble matter is separated.
  • the preparation method provided by the present invention since components that affect the lycopene extraction rate are removed in advance, the lycopene content in the raw material is significantly increased, and resins, pigments and viscous components no longer exist, as long as organic solvents are used under normal conditions The extraction of lycopene can be realized, and the extraction process can be completed quickly as long as it is fully stirred. From the perspective of extracting lycopene, all organic solvents that can dissolve lycopene and have a boiling point lower than 8 ° C can be used, but from the perspective of the application of the product, the present invention preferably uses a food-grade non-toxic product that can be used for food production.
  • Solvents such as carbon disulfide, toluene, benzene, chloroform, dichloromethane, etc., although lycopene can also be dissolved, in order to avoid toxic solvent residues in crystalline products, it is generally not selected.
  • the present invention preferably uses methyl acetate ( Boiling point 55-58 ° C), ethyl acetate (boiling point 77.ire) or a mixture thereof.
  • a low-boiling point organic solvent with a weight of 3 to 8 times the weight of the powdery material for two or three extractions.
  • the filter residue after the first extraction is added to the solvent extraction again, and the extraction solution is extracted. merge.
  • the solvent recovery temperature is preferably controlled at 26-38 ° C. When the solvent evaporates 60-70%, it can be seen that a large number of fine flake lycopene begins to crystallize out. Until 90-95% of the solvent is recovered, lycopene Also about 90-95% has crystallized out.
  • the equipment for solvent recovery and precipitation crystallization process can be selected from centrifugal falling film vacuum evaporator, direct heat pump evaporator, falling film vacuum evaporator, rising film vacuum evaporator, DTB high-efficiency vacuum crystallizer, rotary thin film evaporator, etc.
  • a centrifugal falling film vacuum evaporator and a DTB high-efficiency vacuum crystallizer are preferably used.
  • the precipitated crystals are added to, for example, washed with absolute ethanol (usually in an enamel or stainless steel reaction tank with a stirrer) to remove residual yellow pigment or other impurities, and the crystals are filtered and dried again.
  • the preparation method of the present invention further includes The purification process of the crystals precipitated in step 2) and the dried crystals is washed with absolute ethanol or anhydrous methanol.
  • the solvent is filtered off with a 500-mesh filter cloth, and dried to form a dark copper fine powder (particle size 10-180 ⁇ m) lycopene crystals, wherein the lycopene content is between Above 80%, it can be as high as 90%.
  • the method for drying and washing the crystals includes: blast drying at room temperature for 20-40 minutes, for example, placing in a blast drying box for 20-40 minutes at room temperature at 20-36 ° C; controlling 30-36 ⁇ Dry under vacuum (-0. 08-0. 098MPa) for 15-30 minutes, or dry naturally at room temperature for 4-6 hours.
  • the lycopene crystal of the present invention can be packed in a pressure-resistant glass bottle or an aluminum-plastic composite bag under vacuum (-0. 09Mpa) or filled with nitrogen (purity 99.9%). Stable for a long time without deterioration (the discoloration process is the deterioration process, the crystal changes from dark copper with metallic luster to red, orange, dark yellow, yellow, and finally milky white, indicating that the lycopene content has gradually degraded to zero).
  • the present invention provides a method for preparing lycopene that is different from the prior art.
  • the unnecessary components in the tomato raw material are first separated and removed, and the oleoresin is not first extracted, and then the oleoresin is removed.
  • the low-temperature concentration of the normal temperature leaching solution of the organic solvent is used to precipitate the target product lycopene crystals during the solvent recovery process. It is no longer necessary to cool to -15 ° C for crystallization, which facilitates purification. .
  • the method of the present invention removes other components of the tomato sauce raw material to the greatest extent (effectively retains lycopene in the raw material), greatly improves the lycopene content in the raw material, and improves the extraction of lycopene while simplifying the process.
  • the measurement shows that the lycopene extraction rate of the present invention can reach more than 85%.
  • the temperatures of raw material treatment, solvent recovery and crystal dissolution are not more than 50 ° C, preferably not more than 36 ° C. Compared with the prior art method, the energy consumption can be significantly reduced.
  • the method of the present invention can prepare lycopene crystals with a crystallinity higher than 80%, especially higher than 90%. Its high purity provides relatively high stability, and can be stable for a long time without degradation under appropriate conditions. With its application in antitumor drug preparations and health foods, biological and enzyme pollution can be effectively prevented without the use of antioxidants, preservatives, and the like. detailed description
  • Lycopene yield lycopene crystal weight (g) x lycopene content (3 ⁇ 4) x 100%

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de préparation de lycopène naturel présentant un degré de cristallinité ne dépassant pas 80 %, à partir d'une purée de tomates servant de matière première. Ledit procédé comprend les étapes suivantes: tout d'abord, extraction de la matière au moyen de solvants alcoolisés de faible poids moléculaire; séparation afin d'enlever l'eau, les résines, les huiles volatiles, les saccharides, les barégines et autres substances analogues; extraction du lycopène avec des solvants organiques; et séparation du lycopène cristallin pendant la récupération des solvants. Le procédé présenté est simple, pratique, très efficace, tout en permettant d'économiser de l'énergie.
PCT/CN2002/000080 2001-09-28 2002-02-09 Procede de preparation de lycopene WO2003028481A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN01131359.5 2001-09-28
CN01131359A CN1118521C (zh) 2001-09-28 2001-09-28 番茄红素的制备方法

Publications (1)

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WO2003028481A1 true WO2003028481A1 (fr) 2003-04-10

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CN (1) CN1118521C (fr)
WO (1) WO2003028481A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114259051A (zh) * 2021-12-31 2022-04-01 新疆中基天然植物纯化高新技术研究院有限公司 一种快速制备番茄红素的方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105669350A (zh) * 2014-11-20 2016-06-15 五邑大学 一种应用高速剪切技术协同提取番茄红素的方法
JP2016119898A (ja) * 2014-12-16 2016-07-07 ライコード・リミテツド 着色剤特性が改善されたリコピン組成物
CN104479401B (zh) * 2014-12-29 2016-05-11 鲁东大学 一种高浓度番茄红素油树脂的制备方法
CN112120225B (zh) * 2020-09-29 2023-03-10 江南大学 一种未完全成熟番茄的资源化利用的方法
CN113200810B (zh) * 2021-04-30 2022-10-14 晨光生物科技集团股份有限公司 一种番茄红素晶体及番茄红素结晶工艺
CN114213867A (zh) * 2021-12-30 2022-03-22 新疆中基天然植物纯化高新技术研究院有限公司 一种高纯度番茄红素的生产方法

Citations (5)

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Publication number Priority date Publication date Assignee Title
CN1176577A (zh) * 1994-10-31 1998-03-18 马克特辛姆化学工厂有限公司 稳定的番茄红素浓缩物及其制备方法
CN1198661A (zh) * 1996-06-20 1998-11-11 利库德天然产品工业有限公司 蕃茄的工业加工
CN1252238A (zh) * 1998-09-14 2000-05-10 Basf公司 稳定的、含有结晶度大于20%的番茄红素的粉状番茄红素制剂
CN1297699A (zh) * 2000-12-01 2001-06-06 傅敏恭 一种提取番茄多种有效成分的综合利用工艺
CN1298904A (zh) * 2000-12-18 2001-06-13 新疆生命红科技投资开发有限责任公司 番茄酱制取结晶番茄红素及/或番茄红素油树脂的方法

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CN1112410C (zh) * 2000-10-20 2003-06-25 北京市农林科学院蔬菜研究中心 茄红素的提取方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1176577A (zh) * 1994-10-31 1998-03-18 马克特辛姆化学工厂有限公司 稳定的番茄红素浓缩物及其制备方法
CN1198661A (zh) * 1996-06-20 1998-11-11 利库德天然产品工业有限公司 蕃茄的工业加工
CN1252238A (zh) * 1998-09-14 2000-05-10 Basf公司 稳定的、含有结晶度大于20%的番茄红素的粉状番茄红素制剂
CN1297699A (zh) * 2000-12-01 2001-06-06 傅敏恭 一种提取番茄多种有效成分的综合利用工艺
CN1298904A (zh) * 2000-12-18 2001-06-13 新疆生命红科技投资开发有限责任公司 番茄酱制取结晶番茄红素及/或番茄红素油树脂的方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114259051A (zh) * 2021-12-31 2022-04-01 新疆中基天然植物纯化高新技术研究院有限公司 一种快速制备番茄红素的方法

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CN1341686A (zh) 2002-03-27

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