CN101386622A - Method for preparing sodium copper chlorophyllin in red-purple pitaya sterm - Google Patents
Method for preparing sodium copper chlorophyllin in red-purple pitaya sterm Download PDFInfo
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- CN101386622A CN101386622A CNA2008101397338A CN200810139733A CN101386622A CN 101386622 A CN101386622 A CN 101386622A CN A2008101397338 A CNA2008101397338 A CN A2008101397338A CN 200810139733 A CN200810139733 A CN 200810139733A CN 101386622 A CN101386622 A CN 101386622A
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Abstract
The invention discloses a method for preparing sodium copper chlorophyll from a pitaya fruit stem. The method uses a fresh pitaya fruit stem as a raw material to extract chlorophyll and prepare the sodium copper chlorophyll through the steps of pre-processing the material, reflux extracting, saponifying, concentrating, extracting, regulating acid and putting copper in, salifying and drying. The invention also researches the stability of the sodium copper chlorophyll, and the color agent produced has fresh color, stable performance, and strong coloring power and is safe and nontoxic. Therefore the color agent can be widely applied for food coloration and as cosmetics and pharmaceutical colorant.
Description
Technical field
The present invention relates to the preparation method of chlorophyll copper sodium extracting in a kind of celestial mamoncillo stem.
Background technology
Along with deepening continuously of toxicology and biological study, people find most of synthetic food colors such as azo class pigment, phenyl amines pigment gradually, in human body, can form carcinogenic substance p-aniline and amino-phenol, long-term edible meeting serious harm human beings'health.Along with the raising of people to self health requirements, synthetic colour will be replaced by natural pigment.Therefore, develop natural food colour and its stability studied an important topic that becomes foodstuffs industry energetically.
Chlorophyll is a kind of green pigment of early developing, and it is one of the widest natural pigment that distributes on the earth, extensively is present in the leaf and some other organ of green plants.Chlorophyll is nontoxic, and edible is a kind of good natural food colour, but because chlorophyll stability extreme difference is met effect instant color-changings such as light, heat, bronsted lowry acids and bases bronsted lowry, and water insoluble, its application is restricted.Because CHLOROPHYLLINE salt has kept the original porphyrin ring structure of chlorophyll and to the complexing of magnesium ion, and keeps green, easy to use, often be made into chlorophyll copper sodium and use.Through acidifying, de-magging, copper generation and change into final chlorophyll copper sodium again, its stability significantly increases with CHLOROPHYLLINE salt.Sodium copper chlorophyllin is a kind of natural food colour of water-soluble safety non-toxic, LD
5010000mg/kg (mouse bore), ADI is 0-15mg/kg (a FAO/WHO1980 regulation).1% pH value of aqueous solution is 9.5-10.2, and cupric ion is no more than 50PPM.Can be used for fruity water, carbonated drink, assembled alcoholic drinks, candy, can, cake etc.; In addition, also be widely used as the basic pigment of makeup and the tinting material of toothpaste.The world of medicine is consistent to be thought, is necessary to increase that some toxicity are low, stability pigment new variety preferably.Sodium copper chlorophyllin just meets this requirement.Carry out dressing on the tablet that with the green is keynote, light green bright-coloured, the good stability of color and luster, effect are comparatively desirable.Make ginseng stilbene shizandra berry dressing tinting material with sodium copper chlorophyllin, the every 50Kg substrate of consumption is 1.5-2g.Keep sample and observed in 1 year, do not fade, become phenomenons such as dirt, piebald, contrast with the tablet of firm dressing, outward appearance is in full accord.Compare with other pigment, consumption greatly reduces, and cost is lower.Therefore, developing natural food colour energetically and its stability is studied an important topic that becomes foodstuffs industry, particularly is the natural harmless pigment of raw material with the agriculture and forestry by-product.
Celestial mamoncillo (pitaya) claims Hylocereus undatus again, for the fruit of Cactaceae (Cactaceae) hylocereus platymiscium hylocereus (Hylocereus undatus) is used Cultivar, originate in Central America torrid zone desert area such as Brazil, Mexico, in tropical America, all there is distribution the West Indies and other torrid areas.Early 1990s begins to introduce China Taiwan plants experimentally, and introduces a fine variety provinces and regions plantations such as Guangxi, Guangdong, Hainan, Fujian in recent years successively, and its reproductivity and adaptive capacity to environment are all very strong.China is from the seventies, doing a lot of work in aspects such as biological characteristics, ecological suitability, plantation resource, chemical ingredients, pharmacological toxicology, cultivation and product development at celestial mamoncillo, does not see the report of relevant celestial mamoncillo chlorophyll research and development aspect at present.
Summary of the invention
It is raw material that purpose of the present invention is exactly with celestial mamoncillo stem, extracts its chlorophyll, preparation sodium copper chlorophyllin, and its stability is studied, for the development and application of natural pigment provides the science reference.
The present invention is achieved through the following technical solutions:
In a kind of celestial mamoncillo stem sodium copper chlorophyllin the preparation method, its main points are: with the bright stem of celestial mamoncillo is raw material, through raw materials pretreatment, refluxing extraction, saponification, concentrate, extraction, acid adjustment put copper, salify, baking step, extracts its chlorophyll, preparation sodium copper chlorophyllin;
The step preparation method of concrete order is:
A. raw materials pretreatment
Get celestial mamoncillo stem, clean drying will not contain chlorophyllous part and other impurity is removed, and smash standby;
B. the optimization of extraction conditions
Serve as to extract solvent with the mixing solutions of sherwood oil, chloroform, acetone, methyl alcohol, ethanol, acetone and the different proportionings of ethanol respectively, solid-liquid ratio (W/V) is 1:4, and 60 ℃ of refluxing extraction 2h carry out the optimization experiment of extraction conditions, and test design sees Table 1.Wherein the chlorophyll total amount be chlorophyll a and chlorophyll b and, calculation formula is: total chlorophyll=8.02A
663+ 20.2A
645
The optimization Test design of table 1 chlorophyll extraction conditions
Tab 1 Design of the extract conditions of chlorophyll
| Extraction agent Extract solution | Sherwood oil Petrole um ether | Chloroform Chloro form | Acetone Aceto ne | Acetone: ethanol (4:1) Aceto ne:ethano 1 (4:1) | Acetone: ethanol (3:2) Aceto ne:ethano 1 (3:2) | Acetone: ethanol (1:1) Aceto ne:ethano 1 (1:1) | Acetone: ethanol (2:3) Aceto ne:ethano 1 (2:3) | Acetone: ethanol (1:4) Aceton e:ethanol (1:4) | Ethanol Ethano 1 | Methyl alcohol Metha nol |
| The total chlorophyll of A663 A645 | 0 0.004 0.0808 | 0.049 0.036 1.1202 | 0.089 0.353 7.844 4 | 0.926 0.384 15.183 3 | 0.811 0.344 13.453 0 | 0.784 0.350 13.357 7 | 0.848 0.361 14.093 2 | 0.749 0.331 12.693 2 | 0.744 0.331 12.653 1 | 0.360 0.176 6.4424 |
Extract optimization experiment result (seeing Table 1) and find that use acetone: the mixing solutions of ethanol (4:1) is cooked extraction agent, solid-liquid ratio (W/V) is 1:4,60 ℃ of refluxing extraction 2h, and it is the highest to extract chlorophyllous amount, extraction effect the best.
When the selective extraction agent, to extracting solvent following requirement is arranged generally: 1. solvent wants big to the solubleness of required composition, and is little to impurity solubleness, otherwise or; 2. solvent can not produce chemical reaction with plant constituent, should belong to reversible as if responding; 3. solvent economy is easy to get, and has certain security; 4. boiling point should be moderate, is convenient to reclaim repeatedly use.Consider these requirements, do not use sherwood oil, chloroform, acetone and methyl alcohol to cook extraction agent during extraction; Ethanol is the most frequently used extraction agent simultaneously, have, moderate boiling point strong, safe, nontoxic, be convenient to reclaim characteristics such as use repeatedly tissue permeability, so when the selective extraction agent, except selecting acetone: the mixing solutions of ethanol (4:1) is cooked extraction agent, also selected for use ethanol to cook extraction agent, but extracted amount is a little less than acetone: the mixing solutions of ethanol (4:1).
C. saponification
With chlorophyll extracting solution suction filtration, filtrate adds 5%NaOH solution, adjusts 11～12,70 ℃ of water-baths of pH value, and saponification is 1 hour under the normal pressure;
The judgement of saponification effect is very important in the saponification process, directly influences the product yield, and the saponification effect can be by judging with the partly-hydrolysed liquid of petroleum ether extraction: after the extraction, green if petroleum ether layer is, the expression saponification is incomplete; Be yellow and represent that then saponification is complete.
D. concentrate
With the saponification liquor concentrating under reduced pressure, reclaim solution circulated and use.Vacuum tightness is 0.06-0.1MPa when concentrating, and temperature is concentrated into 1/10 of original volume at 50-80 ℃; This experiment is selected in 69 ℃, both can prevent that chlorophyll sodium salt from decomposing, and can accelerate steaming of solvent again;
Saponification liquor must concentrate when concentrating thoroughly, and judging criterion is to be concentrated into basic absence of liquid under 69 ℃ the temperature condition to steam, otherwise the chlorophyll cupric acid that generates in the operating process afterwards can be dissolved in the acetone that does not steam, thereby can reduce the yield of sodium copper chlorophyllin.
E. extraction
The sherwood oil that concentrated solution is added equivalent vibrates, standing demix, and it is yellow that the upper strata is, and is oil-soluble impuritieses such as xenthophylls, carotene, wax, pohytol, and lower floor's water is cyan chlorophyllide saponification liquor.Extract 4 times, each 2min merges petroleum ether extraction liquid, reclaims solvent behind the decompression rotary evaporation and utilizes;
Contain lipid-soluble substances such as xenthophylls, pohytol, wax, carotenoid in the celestial mamoncillo, its solvability and chlorophyll are close, and therefore will to remove these impurity quality producies ability up to standard as far as possible, so it is very important with petroleum ether extraction the material of saponification reaction not to take place.
F. copper is put in acid adjustment
To use hydrochloric acid adjust pH to 1.5～2.0 of 6mol/L through the saponification liquor of extraction, add 20%CuSO
4Solution, reaction 60min will constantly at the uniform velocity stir in the reaction process under 60-80 ℃; Consumption is by copper sulfate: alkali lye amount=1:6 (V/V), the chlorophyll cupric acid of generation is the black dope.Suction filtration then, filter residue with 40% ethanolic soln washing repeatedly to remove excessive soluble impurities such as copper sulfate, improves the quality of chlorophyll cupric acid.
G. salify
Be dissolved in the acetone after the gained chlorophyll cupric acid drying, the NaOH-ethanolic soln of adding 5% (must be used the ethanolic soln of sodium hydroxide, existing if any water can be with the sodium copper chlorophyllin dissolving that generates, reduce productive rate), transfer pH to 10～12, have this moment a large amount of blackish green precipitations to generate, placement is volatilized acetone naturally, precipitation is transferred when dry, with acetone wash repeatedly up to washing lotion be light yellow till.The gained sodium copper chlorophyllin is deposited in 70～80 ℃ of dryings down, pulverizes, and porphyrize gets product.
Preparation principle of the present invention:
Nitrogen-atoms on magnesium atom in the chlorophyll molecule structure and four pyrrole rings combines, and is the ester of two carboxyls on the ring, and one by the esterification of methyl alcohol institute, and another is generated sodium salt (is example with the chlorophyll a) by the esterification of leaf-alcohol base institute so saponification reaction can take place.
C
35H
72O
5Mg+2NaOH→C
34H
30O
5N
4MgNa
2+CH
3OH+C
20H
39OH
In under acidic conditions, the magnesium in the chlorophyll sodium molecules of salt is very easily replaced the chlorophyllin that generates brown by hydrogen atom.
C
34H
30N
4MgNa
2+4H
+→C
34H
34O
5N
4+Mg
2++2Na
+
Chlorophyllin can generate chlorophyll cupric acid with mantoquita and separate out under heating condition, chlorophyll cupric acid is molten
In acetone,, promptly generate sodium copper chlorophyllin again with alkali reaction.
C
34H
34O
5N
4+Cu
2+→C
34H
32O
5N
4Cu+2H
+
C
34H
32O
5N
4Cu+2NaOH→C
34H
30O
5N
4CuNa
2+2H
2O
Physical properties of the present invention
The sodium copper chlorophyllin that makes with present method is blackish green powdery substance, metalluster slightly, and it is the mixture of chlorophyll copper sodium a and b, do not have and to smell or have special odor slightly, soluble in water, be slightly soluble in ethanol, methyl alcohol, chloroform, be insoluble to sherwood oil, acetone, hexane.
The invention effect
Adopting the present invention is raw material with celestial mamoncillo stem, extracts its chlorophyll, preparation sodium copper chlorophyllin, and its stability is studied, and the color and luster that makes pigment is vivid, and performance is relatively stable, strong coloring force, safety non-toxic.Can be widely used in food color and makeup, medicine work tinting material.
Description of drawings
Accompanying drawing is sodium copper chlorophyllin uv-visible absorption spectra figure of the present invention.
The qualitative analysis of contrast accompanying drawing: prepare 0.01% chlorophyll copper sodium salting liquid, scan its absorption spectrum with the S54 ultraviolet-uisible spectrophotometer at 400-800nm, the product sodium copper chlorophyllin that is prepared as can be known by accompanying drawing has maximum absorption band at 408nm and 634nm place. Be blackish green powdered substance by the prepared sodium copper chlorophyllin of process of the present invention, slightly metallic luster is soluble in water, dissolves in the low concentration hydrous ethanol, is slightly soluble in ethanol, methyl alcohol, chloroform, is insoluble to benzinum, acetone, n-hexane. Under greater than 80 ℃ high temperature, its stability reduces; This compound is stable unstable to acid, especially unstable under strong acid condition to alkali; Basicly stable under room temperature, indoor illumination strength condition; Copper, aluminium ion are large to its stability influence, and carbohydrate (except soluble starch) and parabens anticorrisive agent do not affect its stability substantially.
Embodiment
The raw materials used celestial mamoncillo stem of the present invention is provided by Cao County, Shandong China immortal attitude Technology Park.
Embodiment 1: preparation sodium copper chlorophyllin optimised process
Get celestial mamoncillo stem 5kg, clean drying will not contain chlorophyllous part and other impurity is removed, and smash standby; Use acetone: the mixing solutions of ethanol (4:1) is cooked extraction agent, and solid-liquid ratio (W/V) is 1:4, and 60 ℃ of refluxing extraction 2h use 5%NaOH in 70 ℃ of water-bath saponification 60min (pH=11～12), 20%CuSO
460 ℃ of copper of solution are for 60min, and consumption is used acetone solution at last by copper sulfate: alkali lye amount=1:6 (V/V), 5%NaOH ethanolic soln salify, sodium copper chlorophyllin yield 1.73%.
Embodiment 2: extract the influence of solvent to yield
Get celestial mamoncillo stem 5kg, clean drying will not contain chlorophyllous part and other impurity is removed, and smash standby; Cook extraction agent with ethanol, solid-liquid ratio (W/V) is 1:4, and 60 ℃ of refluxing extraction 2h use 5%NaOH in 70 ℃ of water-bath saponification 60min (pH=11～12), 20%CuSO
460 ℃ of copper of solution are for 60min, and consumption is used acetone solution at last by copper sulfate: alkali lye amount=1:6 (V/V), 5%NaOH ethanolic soln salify, sodium copper chlorophyllin yield 1.45%.
Embodiment 3: temperature is to the influence of yield
Get celestial mamoncillo stem 5kg, clean drying will not contain chlorophyllous part and other impurity is removed, and smash standby; Use acetone: the mixing solutions of ethanol (4:1) is cooked extraction agent, and solid-liquid ratio (W/V) is 1:4, and 60 ℃ of refluxing extraction 2h use 5%NaOH in 70 ℃ of water-bath saponification 60min (pH=11～12), 20%CuSO
480 ℃ of copper of solution are for 60min, and consumption is used acetone solution at last by copper sulfate: alkali lye amount=1:6 (V/V), 5%NaOH ethanolic soln salify, sodium copper chlorophyllin yield 1.53%.
The sodium copper chlorophyllin that makes with the sweet stem of celestial being is lower than 80 ℃ temperature at neutrality and basic solution, and most metal ion stability is good; Glucose, sucrose are little to the influence of chlorophyll copper sodium salt-stable, and long-time outdoor solar light irradiation and high temperature are bigger to its stability influence; Cu
2+, Fe
3+, Al
3+Three kinds of its stability of ion pair have considerable influence, and especially cupric ion has the greatest impact.
In a word, the color and luster that makes pigment is vivid, and performance is relatively stable, strong coloring force, safety non-toxic.
Claims (1)
1, in a kind of celestial mamoncillo stem sodium copper chlorophyllin the preparation method, it is characterized in that: with the bright stem of celestial mamoncillo is raw material, through raw materials pretreatment, refluxing extraction, saponification, concentrate, extraction, acid adjustment put copper, salify, baking step, extracts its chlorophyll, preparation sodium copper chlorophyllin;
Concrete sequential steps preparation method is:
A. raw materials pretreatment
Get the bright stem of celestial mamoncillo, clean drying will not contain chlorophyllous part and other impurity is removed, and smash standby;
B. the optimization of extraction conditions
Respectively with the different proportionings of sherwood oil, chloroform, acetone, methyl alcohol, ethanol, acetone and ethanol (4:1,3:2,1:1,2:3, mixing solutions 1:4) is for extracting solvent, solid-liquid ratio (W/V) is 1:4,60 ℃ of refluxing extraction 2h extract total chlorophyll;
C. saponification
With chlorophyll extracting solution suction filtration, filtrate adds 5%NaOH solution, adjusts 11～12,70 ℃ of water-baths of pH value, and saponification is 1 hour under the normal pressure;
D. concentrate
With the saponification liquor concentrating under reduced pressure, to reclaim solution circulated and use, vacuum tightness is 0.06-0.1MPa when concentrating, temperature is concentrated into 1/10 of original volume at 50-80 ℃;
E. extraction
The sherwood oil that concentrated solution is added equivalent vibrates, standing demix, and it is yellow that the upper strata is, and is oil-soluble impuritieses such as xenthophylls, carotene, wax, pohytol, and lower floor's water is cyan chlorophyllide saponification liquor; Extract 4 times, each 2min merges petroleum ether extraction liquid, reclaims solvent behind the decompression rotary evaporation and utilizes;
F. copper is put in acid adjustment
To use hydrochloric acid adjust pH to 1.5～2.0 of 6mol/L through the saponification liquor of extraction, add 20%CuSO
4Solution, reaction 60min will constantly stir in the reaction process under 60-80 ℃; Consumption is by copper sulfate: alkali lye amount=1:6 (V/V), and the chlorophyll cupric acid of generation is the black dope; Suction filtration then, filter residue are with 40% ethanolic soln washing repeatedly;
G. salify
Be dissolved in the acetone after the gained chlorophyll cupric acid drying, the NaOH-ethanolic soln of adding 5%, transfer pH to 10～12, have at this moment a large amount of blackish green precipitations to generate, placement is volatilized acetone naturally, transfers when precipitating near drying, with acetone wash repeatedly up to washing lotion be light yellow till, the gained sodium copper chlorophyllin is deposited in 70～80 ℃ of dryings down, pulverizes, and porphyrize gets product.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102491978A (en) * | 2011-12-02 | 2012-06-13 | 中国科学院过程工程研究所 | Method for preparing natural pigments, polysaccharide and saponin by utilizing disused asparagus resources |
| CN102775414A (en) * | 2012-06-12 | 2012-11-14 | 宁波立华植物提取技术有限公司 | Process for preparing sodium copper chlorophyllin from ginkgo leaf leftovers |
| CN103145718A (en) * | 2013-03-22 | 2013-06-12 | 重庆理工大学 | Method for extracting sodium copper chlorophyllin from chlorella |
| CN104557953A (en) * | 2015-01-29 | 2015-04-29 | 陕西科技大学 | One-step method for separating pectin, chlorophyll and tigogenin in sisal hemp pressed liquor |
| CN104926915A (en) * | 2015-05-06 | 2015-09-23 | 陕西科技大学 | One-step method for separating pectin, chlorophyll and tigogenin in sisal pressed liquid |
| CN113754671A (en) * | 2021-10-14 | 2021-12-07 | 云南博瑞生物科技有限公司 | Preparation method of sodium copper chlorophyllin |
-
2008
- 2008-09-03 CN CNA2008101397338A patent/CN101386622A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102491978A (en) * | 2011-12-02 | 2012-06-13 | 中国科学院过程工程研究所 | Method for preparing natural pigments, polysaccharide and saponin by utilizing disused asparagus resources |
| CN102491978B (en) * | 2011-12-02 | 2014-07-02 | 中国科学院过程工程研究所 | Method for preparing natural pigments, polysaccharide and saponin by utilizing disused asparagus resources |
| CN102775414A (en) * | 2012-06-12 | 2012-11-14 | 宁波立华植物提取技术有限公司 | Process for preparing sodium copper chlorophyllin from ginkgo leaf leftovers |
| CN102775414B (en) * | 2012-06-12 | 2014-07-09 | 宁波立华植物提取技术有限公司 | Process for preparing sodium copper chlorophyllin from ginkgo leaf leftovers |
| CN103145718A (en) * | 2013-03-22 | 2013-06-12 | 重庆理工大学 | Method for extracting sodium copper chlorophyllin from chlorella |
| CN103145718B (en) * | 2013-03-22 | 2015-07-29 | 重庆理工大学 | The method of chlorophyll copper sodium extracting from chlorella |
| CN104557953A (en) * | 2015-01-29 | 2015-04-29 | 陕西科技大学 | One-step method for separating pectin, chlorophyll and tigogenin in sisal hemp pressed liquor |
| CN104557953B (en) * | 2015-01-29 | 2016-08-24 | 陕西科技大学 | One-step method is used to separate pectin, chlorophyll and the method for tigogenin in sisal hemp pressed liquor |
| CN104926915A (en) * | 2015-05-06 | 2015-09-23 | 陕西科技大学 | One-step method for separating pectin, chlorophyll and tigogenin in sisal pressed liquid |
| CN113754671A (en) * | 2021-10-14 | 2021-12-07 | 云南博瑞生物科技有限公司 | Preparation method of sodium copper chlorophyllin |
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