CN105693583A - Method for removing harmful ingredients in carotenoid - Google Patents
Method for removing harmful ingredients in carotenoid Download PDFInfo
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- CN105693583A CN105693583A CN201511011475.1A CN201511011475A CN105693583A CN 105693583 A CN105693583 A CN 105693583A CN 201511011475 A CN201511011475 A CN 201511011475A CN 105693583 A CN105693583 A CN 105693583A
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- 150000001747 carotenoids Chemical class 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 25
- 239000004615 ingredient Substances 0.000 title abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 48
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Classifications
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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
-
- 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; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/02—Purification
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention particularly relates to a method for removing harmful ingredients in carotenoid. The method comprises the following steps that 1, a carotenoid product is cleaned with alcohol solvent to obtain a product phase and a solvent phase; 2, the product phase is concentrated to remove the solvent to obtain a cleaned carotenoid product, and n-hexane is added to prepare a solution S1; 3, the solution S1 obtained in the step 2 is sampled and introduced into a silicagel column, n-hexane and ethyl acetate serve as mobile phases, gradient elution is performed, and eluant S2 is collected; 4, the solvent in the S2 is removed, and the high-purity carotenoid product is obtained. In the whole separation and purification process, the product recycling rate is high, the stability is good, technological operation is easy and convenient, the automation degree is high, and the method can be further widely applied to industrial production.
Description
Technical field
The invention belongs to carotenoid separating and purifying technology field, be specifically related to a kind of method removed and endanger composition in carotenoid。
Background technology
Capsicum red pigment is a contained Carotenoids in ripe Fructus Capsici, it it is the focus of natural pigment research, at food, the aspects such as health care and medicine have higher using value and wide domestic and international market, particularly High color values, highly purified capsicum red pigment, ranks the first in China's plant extract foreign exchange earning, and its revenue in foreign exchange created also increases constantly。
Phylloxanthin is a kind of oxygen containing carotenoid, is widely present in the middle of the natural plants such as Flos Tagetis Erectae, Fructus Musae, Fructus actinidiae chinensis and Semen Maydis。It is the antioxidant of a kind of excellent performance, oxygen-derived free radicals can be resisted in human body, cause the symptoms such as cell and organ injury, the cardiovascula sclerosis of prevention body aging initiation, coronary heart disease。The most important thing is that phylloxanthin is the carotenoid composition that uniquely can there is eyes crystalline lens, be primary pigments and the antioxidant content of macula retinae, important protective effect is played for eyes。
Lycopene is primarily present the Carotenoids in the mature fruits such as plant of Solanaceae Fructus Lycopersici esculenti。。It is one of most powerful antioxidant of being found in the plant of nature at present。Science proves, singlet oxygen and oxygen-derived free radicals in human body are the arch-criminals encroaching on human body self immune system。Effect of lycopene scavenging free radicals outclass other carotenoid and vitamin E, and its singlet-oxygen quenching speed constant is 100 times of vitamin E。It can effectively preventing because of aging, the various diseases that immunity degradation causes。Therefore, it receives the concern of countries in the world expert。
Benzopyrene, also known as benzo [α] pyrene, english abbreviation BaP, is a kind of common high activity indirect acting carcinogens and Mutagen。After 3,4-benzopyrene are discharged into the atmosphere, the aerosol always formed with all kinds microgranule in air combines, in inhalable particulates grain below 8 microns, the ratio sucking pulmonary is higher, sucks pulmonary through respiratory tract, enter alveolar even blood, cause pulmonary carcinoma and cardiovascular disease。
The polluter of benzopyrene mostlys come from environment, and along with the deterioration of ecological environment, crops are formed trace contamination by soil, water body, packing material etc. by benzopyrene, and then have influence on processing industry downstream, although this contaminant capacity is still in the scope that health can ensure, but benzopyrene has become the emphasis hazardous material of every profession and trade management and control, including the various types of carotene product being raw material with agricultural byproducts, and its index request is increasingly tighter, has become as the technical threshold of developed country。
Summary of the invention
For the shortcoming overcoming prior art, the invention provides a kind of method separating from the carotenoid such as capsicum red pigment, phylloxanthin, lycopene oleo-resinous and removing benzopyrene, utilization is cleaned in advance, is prepared solution, liquid chromatography process, gradient elution method, realize separating of target components and benzopyrene, collect the eluent containing target components, after low-temperature reduced-pressure concentrated by rotary evaporation, nitrogen dries up, and obtains high-purity target product。
For solving above-mentioned technical problem, the technical solution used in the present invention is: a kind of remove the method endangering composition in carotenoid, comprises the following steps:
1), carotenoid product alcoholic solvent is cleaned, obtain product phase and solvent phase；
2), product concentrate removal solvent mutually, the carotenoid product after being cleaned, add normal hexane configuration solution S 1；
3), step 2 gained solution S 1 is sampled, sample introduction in silica gel chromatographic column, by normal hexane and ethyl acetate as mobile phase, by gradient elution, collect eluent S2；
4), S2 is removed solvent, obtain highly purified carotenoid product。
In step 1) of the present invention, carotenoid product includes capsicum red pigment, phylloxanthin, lycopene oleo-resinous。
In step 1) of the present invention, alcoholic solvent is ethanol or the methanol solvate of 20-45%；Alcoholic solvent cleans method particularly includes: carotenoid product quality and alcoholic solvent volume ratio are 1:2-4, and described mass unit is kg, and described volume unit is L, stratification after stirring and evenly mixing；
Step 2 of the present invention) in S1 solution carotenoid product design be 0.05-0.2g/mL。
Silica gel chromatography system used by step 3) of the present invention is low pressure, medium-pressure or high pressure preparative liquid chromatography, and silica gel granularity is 100-300 order。
In step 3) of the present invention, the mass ratio of sample size and silica gel chromatography column packing is 0.1:50-80, described sample size, filler mass unit be g；
Step 3) of the present invention selects n-hexane/ethyl acetate mixed system as eluant, to be gradually increased mobile phase order of polarity, the ratio regulating wherein ethyl acetate regulates to 5% from 0, it is further added by 10%, finally reach 100%, each section of mobile phase volume respectively 25,75,100 and 25mL, elution flow rate 5-20mL/min, monitoring wavelength is 254nm and 472nm。
Step 4) of the present invention is after low-temperature reduced-pressure concentrated by rotary evaporation, and nitrogen dries up, and obtains high-purity target product。
Adopt having the beneficial effects that of technique scheme generation: 1, the technology of the present invention is with strong points, using alcoholic solvent to clean in advance, by the impurity of alcohol-soluble in carotenoid, the composition that especially can be dissolved by low alcohol is removed, be conducive to separating further purification, reach better effect；For different classes of carotenoid, variable concentrations, different proportion, different types of alcoholic solvent need to be selected, in order to reach better effect；2, the adaptability of technology is wide, it is adaptable to low pressure, middle pressure and high pressure preparative liquid chromatography, utilizes preparative liquid chromatography, has an automaticity height, and favorable reproducibility is simple to operate, the feature that efficiency is high；3, the clearance of benzopyrene in carotenoid can be reached more than 95%；4, whole separation purge process product recovery rate is high, good stability, and technological operation is easy, and automaticity is high, can be amplified to commercial production further。
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is further detailed explanation。
Embodiment 1
The filling of silica gel chromatographic column and balance: clean chromatographic column void column pipe with acetone and dry, adopt dry column-packing, about 50g silica gel is weighed with beaker, slow along funnel, continuous print is poured in void column pipe, raps the outer wall of void column pipe with Glass rod, column jecket is rotated in the same direction simultaneously, about 45 ° every time, until silica gel adds latter 3-5 minute, finally load onto sieve plate and stigma。The chromatographic column filled is connected on preparative liquid chromatograph, with normal hexane with 2.0mL/min flow velocity Balance Treatment 3 hours。
Sample preparation and process: capsicum red pigment 2.5g, color valency is 100, by its alcohol solvent mixing and stirring with 7.5 milliliter 35%, stratification after cleaning, obtains solvent phase and product phase, by product mutually in solvent concentration elimination, product after being cleaned, adding it in 25mL volumetric flask, use normal hexane constant volume, preparation becomes the capsicum red pigment sample S1 of 0.1g/mL。Each sample size is 0.1g, with n-hexane/ethyl acetate mixed system as eluant, regulate the ratio of wherein ethyl acetate being gradually increased mobile phase order of polarity, regulate to 5% from 0, be further added by 10%, finally reach 100%, each section of mobile phase volume respectively 25,75,100 and 25mL, collecting eluent S2, elution flow rate 5mL/min that n-hexane/ethyl acetate volume ratio is 90:10, monitoring wavelength is 254nm and 472nm。After 50 DEG C of vacuum rotary steam concentrations, obtaining the capsicum red pigment of dark red oil thickness, quality is 0.06g, and color valency yield is 90.5%, detects benzopyrene clearance 96.3%。
Embodiment 2
The filling of silica gel chromatographic column and balance: clean chromatographic column void column pipe with acetone and dry, adopt dry column-packing, about 60g silica gel is weighed with beaker, slow along funnel, continuous print is poured in void column pipe, raps the outer wall of void column pipe with Glass rod, column jecket is rotated in the same direction simultaneously, about 45 ° every time, until silica gel adds latter 3-5 minute, finally load onto sieve plate and stigma。The chromatographic column filled is connected on preparative liquid chromatograph, with normal hexane with 2.0mL/min flow velocity Balance Treatment 4 hours。
Sample preparation and process: take lutein extract 3.0g, color valency is 300, by its alcohol solvent mixing and stirring with 6 milliliter 30%, stratification after cleaning, obtains solvent phase and product phase, by product mutually in solvent concentration elimination, product after being cleaned, adding it in 50mL volumetric flask, use normal hexane constant volume, preparation becomes the phylloxanthin sample S1 of 0.05g/mL。Each sample size is 0.1g, with n-hexane/ethyl acetate mixed system as eluant, regulate the ratio of wherein ethyl acetate being gradually increased mobile phase order of polarity, regulate to 5% from 0, be further added by 10%, finally reach 100%, each section of mobile phase volume respectively 25,75,100 and 25mL, collecting eluent S2, elution flow rate 10mL/min that n-hexane/ethyl acetate volume ratio is 90:10, monitoring wavelength is 254nm and 472nm。After 45 DEG C of vacuum rotary steam concentrations, obtaining brownish red crystal powder, quality is 0.024g, and color valency yield is 91.3%, detects benzopyrene clearance 95.8%。
Embodiment 3
The filling of silica gel chromatographic column and balance: clean chromatographic column void column pipe with acetone and dry, adopt dry column-packing, about 80g silica gel is weighed with beaker, slow along funnel, continuous print is poured in void column pipe, raps the outer wall of void column pipe with Glass rod, column jecket is rotated in the same direction simultaneously, about 45 ° every time, until silica gel adds latter 3-5 minute, finally load onto sieve plate and stigma。The chromatographic column filled is connected on preparative liquid chromatograph, with normal hexane with 2.0mL/min flow velocity Balance Treatment 6 hours。
Sample preparation and process: lycopene oleo-resinous 5.0g, color valency is 300, by its methanol solvate mixing and stirring with 20 milliliter 45%, stratification after cleaning, obtains solvent phase and product phase, by product mutually in solvent concentration elimination, product after being cleaned, adding it in 25mL volumetric flask, use normal hexane constant volume, preparation becomes the lycopene sample S1 of 0.2g/mL。Each sample size is 0.1g, with n-hexane/ethyl acetate mixed system as eluant, regulate the ratio of wherein ethyl acetate being gradually increased mobile phase order of polarity, regulate to 5% from 0, be further added by 10%, finally reach 100%, each section of mobile phase volume respectively 25,75,100 and 25mL, collecting eluent S2, elution flow rate 20mL/min that n-hexane/ethyl acetate volume ratio is 90:10, monitoring wavelength is 254nm and 472nm。After 40 DEG C of vacuum rotary steam concentrations, obtaining peony crystal powder, quality is 0.11g, and color valency yield is 91.5%, detects benzopyrene clearance 98.1%。
The preferred embodiment of the present invention described in detail above。Should be appreciated that those of ordinary skill in the art just can make many modifications and variations according to the design of the present invention without creative work。Therefore, all technical staff in the art, all should in the protection domain being defined in the patent claims under this invention's idea on the basis of existing technology by the available technical scheme of logical analysis, reasoning, or a limited experiment。
Claims (8)
1. remove the method endangering composition in carotenoid for one kind, it is characterised in that comprise the following steps:
1), carotenoid product alcoholic solvent is cleaned, obtain product phase and solvent phase；
2), product concentrate removal solvent mutually, the carotenoid product after being cleaned, add normal hexane configuration solution S 1；
3), step 2 gained solution S 1 is sampled, sample introduction in silica gel chromatographic column, by normal hexane and ethyl acetate as mobile phase, by gradient elution, collect eluent S2；
4), S2 is removed solvent, obtain highly purified carotenoid product。
2. according to claim 1 a kind of remove the method endangering composition in carotenoid, it is characterised in that in described step 1), carotenoid product includes capsicum red pigment, phylloxanthin, lycopene oleo-resinous。
3. according to claim 1 a kind of remove the method endangering composition in carotenoid, it is characterised in that in described step 1), alcoholic solvent is ethanol or the methanol solvate of 20-45%；Alcoholic solvent cleans method particularly includes: carotenoid product quality and alcoholic solvent volume ratio are 1:2-4, and described mass unit is kg, and described volume unit is L, stratification after stirring and evenly mixing。
4. according to claim 1 a kind of remove the method endangering composition in carotenoid, it is characterised in that described step 2) in S1 solution carotenoid product design be 0.05-0.2g/mL。
5. according to claim 1 a kind of remove the method endangering composition in carotenoid, it is characterised in that the silica gel chromatography system used by described step 3) is low pressure, medium-pressure or high pressure preparative liquid chromatography, and silica gel granularity is 100-300 order。
6. according to claim 1 a kind of remove the method endangering composition in carotenoid, it is characterised in that in described step 3), sample size is 0.1:50-80 with the mass ratio of silica gel chromatography column packing, described sample size, filler mass unit be g。
7. according to claim 1 a kind of remove the method endangering composition in carotenoid, it is characterized in that, described step 3) selects n-hexane/ethyl acetate mixed system as eluant, to be gradually increased mobile phase order of polarity, the ratio regulating wherein ethyl acetate regulates to 5% from 0, is further added by 10%, finally reach 100%, each section of mobile phase volume respectively 25,75,100 and 25mL, elution flow rate 5-20mL/min, monitoring wavelength is 254nm and 472nm。
8. according to claim 1 a kind of remove the method endangering composition in carotenoid, it is characterised in that described step 4) is after low-temperature reduced-pressure concentrated by rotary evaporation, and nitrogen dries up, and obtains high-purity target product。
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