CN105693583B - The method of composition is endangered in a kind of removal carotenoid - Google Patents
The method of composition is endangered in a kind of removal carotenoid Download PDFInfo
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- CN105693583B CN105693583B CN201511011475.1A CN201511011475A CN105693583B CN 105693583 B CN105693583 B CN 105693583B CN 201511011475 A CN201511011475 A CN 201511011475A CN 105693583 B CN105693583 B CN 105693583B
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- carotenoid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; DRIERS (SICCATIVES); TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/02—Purification
Abstract
Present invention relates particularly to a kind of method that composition is endangered in removal carotenoid, comprise the following steps 1）, carotenoid product cleaned with alcoholic solvent, obtain product phase and solvent phase；2）, product mutually concentrate removal solvent, the carotenoid product after being cleaned, addition n-hexane configuration solution S 1；3）, by step 2 resulting solution S1 samplings, sample introduction into silica gel chromatographic column, be used as mobile phase by the use of n-hexane and ethyl acetate, pass through gradient elution, collection eluent S2；4）, S2 removed into solvent, obtain the carotenoid product of high-purity.Whole to isolate and purify process product rate of recovery height, stability is good, and technological operation is easy, and automaticity is high, can further be amplified to industrial production.
Description
Technical field
The invention belongs to carotenoid separating and purifying technology field, and in particular to one kind remove carotenoid in harm into
The method divided.
Background technology
Capsicum red pigment is a contained Carotenoids in ripe capsicum, is the focus of natural pigment research, in food,
Health care and medicine etc. have higher application value and wide domestic and international market, particularly a High color values, high-purity it is peppery
Green pepper haematochrome, ranked the first in the foreign exchange earning of China's plant extracts, and its revenue in foreign exchange created also increases constantly.
Lutein is a kind of oxygen containing carotenoid, is widely present in the days such as marigold, banana, Kiwi berry and corn
Among right plant.It is a kind of antioxidant of excellent performance, oxygen radical can be resisted cell and organ damage are caused in human body,
Prevent the symptoms such as cardiovascula arteriosclerosis, the coronary heart disease of body aging initiation.Above all lutein is that uniquely there may be eyes
The carotenoid composition of crystalline, is the primary pigments and antioxidant content of macula retinae, and important protection is played for eyes
Effect.
Lycopene is primarily present the Carotenoids in the ripening fruits such as plant of Solanaceae tomato..It is mesh
Preceding most one of powerful antioxidant being found in the plant of nature.Science proves that the singlet oxygen and oxygen in human body are free
Base is the arch-criminal for encroaching on human body self immune system.The effect of lycopene removing free radical, outclass other carotenoids
Element and vitamin E, its singlet-oxygen quenching speed constant are 100 times of vitamin E.It can exempt from effectively preventing because of aging
Various diseases caused by the decline of epidemic disease power.Therefore, it is paid close attention to by countries in the world expert.
BaP is also known as benzo [α] pyrene, english abbreviation BaP, is a kind of common high activity indirect-acting carcinogen and Mutagen.
After 3,4- BaPs are discharged into the atmosphere, always it is combined together with all kinds particulate is formed in air aerosol,
In inhalable grit below 8 microns, it is higher to suck the ratio of lung, and lung is sucked through respiratory tract, into alveolar even blood
Liquid, cause lung cancer and angiocardiopathy.
The pollution sources of BaP mostly come from environment, and as the deterioration of ecological environment, crops pass through soil, water
Body, packing material etc. form trace contamination by BaP, and then have influence on processing industry downstream, although this contaminant capacity is still in health
In the range of can ensureing, but BaP has turned into the emphasis hazardous material of every profession and trade management and control, including using agricultural byproducts as each of raw material
Carotenoids product, and its index request is more and more tighter, has become the technical threshold of developed country.
The content of the invention
The shortcomings that in order to overcome prior art, the invention provides one kind from capsicum red pigment, lutein, lycopene oil
The method except BaP is separated in the carotenoid such as resin, using pre-wash, prepares solution, liquid chromatography process, gradient
The method of elution, the separation of target components and BaP is realized, collect the eluent containing target components, low-temperature reduced-pressure revolving is dense
After contracting, nitrogen drying, high-purity target product is obtained.
In order to solve the above technical problems, the technical solution used in the present invention is：One kind remove carotenoid in harm into
The method divided, comprises the following steps：
1）, carotenoid product cleaned with alcoholic solvent, obtain product phase and solvent phase；
2）, product mutually concentrate removal solvent, the carotenoid product after being cleaned, addition n-hexane configuration solution S 1；
3）, by step 2 resulting solution S1 samplings, sample introduction into silica gel chromatographic column, by the use of n-hexane and ethyl acetate as flowing
Dynamic phase, by gradient elution, collect eluent S2；
4）, S2 removed into solvent, obtain the carotenoid product of high-purity.
Step 1 of the present invention）Middle carotenoid product includes capsicum red pigment, lutein, lycopene oleoresin.
Step 1 of the present invention）Middle alcoholic solvent is 20-45% ethanol or methanol solvate；The specific method of alcoholic solvent cleaning
For：Carotenoid product quality is 1 with alcoholic solvent volume ratio:2-4, the mass unit are kg, and the volume unit is L, is stirred
Mix stratification after mixing；
Step 2 of the present invention）Carotenoid product design is 0.05-0.2g/mL in middle S1 solution.
Step 3 of the present invention）Silica gel chromatograph system used is low pressure, medium-pressure or high pressure preparative liquid chromatography, silica gel
Granularity is 100-300 mesh.
Step 3 of the present invention）The mass ratio of middle sample size and silica gel chromatograph column packing is 0.1：50-80, it is described enter
Sample amount, the mass unit of filler are g；
Step 3 of the present invention）From normal hexane/ethyl acetate mixed system as eluant, eluent, flowed with gradual increase
Phase order of polarity, the ratio of regulation wherein ethyl acetate are further added by 10% from 0 regulation to 5%, finally reach 100%, each section of stream
Dynamic phase volume is respectively 25,75,100 and 25mL, and elution flow rate 5-20mL/min, monitoring wavelength is 254nm and 472nm.
Step 4 of the present invention）After low-temperature reduced-pressure concentrated by rotary evaporation, nitrogen drying, high-purity target product is obtained.
It is using beneficial effect caused by above-mentioned technical proposal：1st, the technology of the present invention is with strong points, is carried using alcoholic solvent
Preceding cleaning, by the impurity of alcohol-soluble in carotenoid, it can especially be removed, be advantageous to further by the composition that low alcohol dissolves
Isolate and purify, reach more preferable effect；For different classes of carotenoid, various concentrations, different proportion, difference need to be selected
The alcoholic solvent of species, to reach more preferable effect；2nd, the adaptability of technology is wide, suitable for low pressure, pressure and high pressure prepare liquid phase
Chromatogram, using preparative liquid chromatography, have automaticity high, favorable reproducibility is simple to operate, the characteristics of efficiency high；3rd, to class
The clearance of BaP can reach more than 95% in carrotene；4th, whole to isolate and purify process product rate of recovery height, stability is good,
Technological operation is easy, and automaticity is high, can further be amplified to industrial production.
Embodiment
With reference to specific embodiment, the present invention is further detailed explanation.
Embodiment 1
The filling of silica gel chromatographic column and balance：Chromatographic column void column pipe and drying are cleaned with acetone, using dry column-packing, with burning
Cup weighs about 50g silica gel, slow along funnel, continuously pours into void column pipe, the outer wall of void column pipe is rapped with glass bar, simultaneously will
Column jecket rotates in the same direction, about 45 ° every time, until silica gel adds rear 3-5 minutes, finally loads onto sieve plate and column cap.Will dress
The chromatographic column filled in is connected on preparative liquid chromatograph, with n-hexane with 2.0mL/min flow velocitys Balance Treatment 3 hours.
Sample preparation and processing：Capsicum red pigment 2.5g, color value 100, it is mixed with 7.5 milliliter 35% of alcohol solvent
Conjunction is stirred, and stratification after cleaning, obtains solvent phase and product phase, and the solvent concentration in product phase is removed, and is obtained clear
Product after washing, add it in 25 mL volumetric flasks, with n-hexane constant volume, prepare the capsicum red pigment sample as 0.1g/mL
Product S1.Each sample size is 0.1g, by the use of normal hexane/ethyl acetate mixed system as eluant, eluent, gradually to increase mobile phase pole
Property sequential adjustment wherein ethyl acetate ratio, from 0 regulation to 5%, be further added by 10%, finally reach 100%, each section of mobile phase
Volume is respectively 25,75,100 and 25mL, and it is 90 to collect normal hexane/ethyl acetate volume ratio：10 eluent S2, elution flow rate
5mL/min, monitoring wavelength are 254nm and 472nm.After 50 DEG C of vacuum rotary steams concentrate, the sticky capsicum of dark red oil is obtained
Haematochrome, quality 0.06g, color value yield are 90.5%, detection BaP clearance 96.3%.
Embodiment 2
The filling of silica gel chromatographic column and balance：Chromatographic column void column pipe and drying are cleaned with acetone, using dry column-packing, with burning
Cup weighs about 60g silica gel, slow along funnel, continuously pours into void column pipe, the outer wall of void column pipe is rapped with glass bar, simultaneously will
Column jecket rotates in the same direction, about 45 ° every time, until silica gel adds rear 3-5 minutes, finally loads onto sieve plate and column cap.Will dress
The chromatographic column filled in is connected on preparative liquid chromatograph, with n-hexane with 2.0mL/min flow velocitys Balance Treatment 4 hours.
Sample preparation and processing：Take lutein extract 3.0g, color value 300, it is mixed with 6 milliliter 30% of alcohol solvent
Conjunction is stirred, and stratification after cleaning, obtains solvent phase and product phase, and the solvent concentration in product phase is removed, and is obtained clear
Product after washing, add it in 50 mL volumetric flasks, with n-hexane constant volume, prepare the lutein sample as 0.05g/mL
S1.Each sample size is 0.1g, by the use of normal hexane/ethyl acetate mixed system as eluant, eluent, gradually to increase mobile phase polarity
The ratio of sequential adjustment wherein ethyl acetate, from 0 regulation to 5%, it is further added by 10%, finally reaches 100%, each section of mobile phase body
Product is respectively 25,75,100 and 25mL, and it is 90 to collect normal hexane/ethyl acetate volume ratio：10 eluent S2, elution flow rate
10mL/min, monitoring wavelength are 254nm and 472nm.After 45 DEG C of vacuum rotary steams concentrate, brownish red crystal powder, quality are obtained
For 0.024g, color value yield is 91.3%, detection BaP clearance 95.8%.
Embodiment 3
The filling of silica gel chromatographic column and balance：Chromatographic column void column pipe and drying are cleaned with acetone, using dry column-packing, with burning
Cup weighs about 80g silica gel, slow along funnel, continuously pours into void column pipe, the outer wall of void column pipe is rapped with glass bar, simultaneously will
Column jecket rotates in the same direction, about 45 ° every time, until silica gel adds rear 3-5 minutes, finally loads onto sieve plate and column cap.Will dress
The chromatographic column filled in is connected on preparative liquid chromatograph, with n-hexane with 2.0mL/min flow velocitys Balance Treatment 6 hours.
Sample preparation and processing：Lycopene oleoresin 5.0g, color value 300, by its methanol solvate with 20 milliliter 45%
It is mixed evenly, stratification after cleaning, obtains solvent phase and product phase, the solvent concentration in product phase is removed, obtained
Product after cleaning, add it in 25 mL volumetric flasks, with n-hexane constant volume, prepare the lycopene sample as 0.2g/mL
Product S1.Each sample size is 0.1g, by the use of normal hexane/ethyl acetate mixed system as eluant, eluent, gradually to increase mobile phase pole
Property sequential adjustment wherein ethyl acetate ratio, from 0 regulation to 5%, be further added by 10%, finally reach 100%, each section of mobile phase
Volume is respectively 25,75,100 and 25mL, and it is 90 to collect normal hexane/ethyl acetate volume ratio：10 eluent S2, elution flow rate
20mL/min, monitoring wavelength are 254nm and 472nm.After 40 DEG C of vacuum rotary steams concentrate, peony crystal powder, quality are obtained
For 0.11g, color value yield is 91.5%, detection BaP clearance 98.1%.
Preferred embodiment of the invention described in detail above.It should be appreciated that one of ordinary skill in the art without
Creative work can is needed to make many modifications and variations according to the design of the present invention.Therefore, all technologies in the art
Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea
Technical scheme, all should be in the protection domain being defined in the patent claims.
Claims (7)
1. a kind of remove the method that composition is endangered in carotenoid, it is characterised in that comprises the following steps：
1）, carotenoid product cleaned with alcoholic solvent, obtain product phase and solvent phase；
2）, product mutually concentrate removal solvent, the carotenoid product after being cleaned, addition n-hexane configuration solution S 1；
3）, by step 2 resulting solution S1 samplings, sample introduction into silica gel chromatographic column, by the use of n-hexane and ethyl acetate as mobile phase,
By gradient elution, eluent S2 is collected；
4）, S2 removed into solvent, obtain the carotenoid product of high-purity；
The step 1）Middle alcoholic solvent is 20-45% ethanol or methanol solvate；Alcoholic solvent cleaning specific method be：Carotenoids
Plain product quality is 1 with alcoholic solvent volume ratio:2-4, the mass unit are kg, and the volume unit is L, is stirred and evenly mixed rear quiet
Put layering；
The step 3）From normal hexane/ethyl acetate mixed system as eluant, eluent, gradually to increase mobile phase order of polarity,
The ratio of regulation wherein ethyl acetate is further added by 10% from 0 regulation to 5%, finally reaches 100%, each section of mobile phase volume difference
For 25,75,100 and 25mL, elution flow rate 5-20mL/min.
2. the method for composition is endangered in a kind of removal carotenoid according to claim 1, it is characterised in that the step
Rapid 1）Middle carotenoid product includes capsicum red pigment, lutein, lycopene oleoresin.
3. the method for composition is endangered in a kind of removal carotenoid according to claim 1, it is characterised in that the step
Rapid 2）Carotenoid product design is 0.05-0.2g/mL in middle S1 solution.
4. the method for composition is endangered in a kind of removal carotenoid according to claim 1, it is characterised in that the step
Rapid 3）Silica gel chromatograph system used is low pressure, medium-pressure or high pressure preparative liquid chromatography, and silica gel granularity is 100-300 mesh.
5. the method for composition is endangered in a kind of removal carotenoid according to claim 1, it is characterised in that the step
Rapid 3）The mass ratio of middle sample size and silica gel chromatograph column packing is 0.1：50-80, the sample size, the mass unit of filler are
g。
6. the method for composition is endangered in a kind of removal carotenoid according to claim 1, it is characterised in that the step
Rapid 3）From normal hexane/ethyl acetate mixed system as eluant, eluent, monitoring wavelength is 254nm and 472nm.
7. the method for composition is endangered in a kind of removal carotenoid according to claim 1, it is characterised in that the step
Rapid 4）After low-temperature reduced-pressure concentrated by rotary evaporation, nitrogen drying, high-purity target product is obtained.
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106280542B (en) * | 2016-08-15 | 2017-11-17 | 晨光生物科技集团股份有限公司 | A kind of production method for improving lycopene oleoresin quality |
| CN110308220A (en) * | 2019-06-20 | 2019-10-08 | 厦门大学 | The orange red sufficient flesh Xi Shi Bao carotenoid identification of one kind and content assaying method |
| CN111718598B (en) * | 2020-06-22 | 2021-11-26 | 河南中大恒源生物科技股份有限公司 | Production method of capsanthin with low polycyclic aromatic hydrocarbon |
| CN113200835B (en) * | 2021-04-28 | 2022-08-05 | 晨光生物科技集团股份有限公司 | Method for removing various harmful substances in capsorubin |
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Application publication date: 20160622 Assignee: Xinjiang Chenxi Pepper Industry Co.,Ltd. Assignor: Chengguang Natural Pigment Group Co., Ltd. Contract record no.: 2019990000135 Denomination of invention: Method for removing harmful ingredients in carotenoid Granted publication date: 20180209 License type: Common License Record date: 20190430 |