CN101172956A - Monomer zincium lysine, preparation and use of zincium lysine complex compound - Google Patents
Monomer zincium lysine, preparation and use of zincium lysine complex compound Download PDFInfo
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- CN101172956A CN101172956A CNA200710050373XA CN200710050373A CN101172956A CN 101172956 A CN101172956 A CN 101172956A CN A200710050373X A CNA200710050373X A CN A200710050373XA CN 200710050373 A CN200710050373 A CN 200710050373A CN 101172956 A CN101172956 A CN 101172956A
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Abstract
The invention discloses a preparation method for preparing monomer lysine zinc and transferring to lysine zinc complex compound, and the usage thereof. The preparation method comprises the steps as follows: muriatic acid L-lysine is taken as the raw material, zinc butter and sodium hydroxide are added for reaction, PH value is adjusted to neutral, ethanol is added in after concentration, thereby acquiring supersaturated solution which is heated to 60 DEG C, laid in stillness, washed and filtered to get crystal powder of the lysine zinc. When using the lysine zinc as preparing agent, relative muriatic acid L-lysine or L-lysine is required to be added to form the complex compounds. The weight ratio between the lysine zinc and the L-lysine is 1:0.78. The lysine zinc complex compounds are used for making clinical medicine or zinc reinforcer. The invention with mature technique and simple producing equipment can produce crystal monomer with the purity of higher than 99 percent according to the test. The lysine zinc in the type of complex zinc can be easily absorbed by a human body. The lysine zinc is significant for supplying zinc and lysine to the human body to promote the physical growth and the intelligence development of the children.
Description
Technical field
The present invention relates to the medicine of a kind of medicine, foodstuff additive or treatment digestive tube, digestive system, especially a kind of preparation of lysine-zn complex compound and purposes.
Background technology
1958, The 2nd Army Medical College hole auspicious sign professor in Shanghai led his oral in person zinc sulfate of several students, explored the reasonable dosage of human body tolerance zinc sulfate, had started the beginning of China with zinc preparation treatment disease.1987, GuangDong Pharmaceutical Factory was succeeded in developing Zinc Gluconate, had become Guangdong Province's first new drug since carrying out the national drug administrative law, from then on treated zinc deficiency clinically and had replaced zinc sulfate gradually.Zinc sulfate and Zinc Gluconate are all still adopted in existing zinc supplementation agent, and its zinc carrier (being sulfate radical and glucose acid group) there is no use to human body.And existing zinc supplementation agent is to enter human body with ionic state zinc, and gi tract are had hormesis, and patient has taken the gastrointestinal upset sense, and toxic side effect such as serious having is nauseating, vomiting so that have to reduce dosage or drug withdrawal in advance, have influenced the specific absorption to zinc.
International research proves that zinc has important physical function and pharmacological action widely.Zinc can be grown in accelerating growth, improves a poor appetite, and promotes wound healing, helps brain development and improves intelligence, improves immunologic function etc.Methionin with different mechanism, produces the result of treatment similar in appearance to element zinc in human body.The development lysine-zn integrates these two kinds to the useful material of human body exactly, becomes the novel zinc supplementation agent that has the two biochemical function concurrently, human body is produced the therapeuticing and health effect of collaborative and addition.
Summary of the invention
It is uncomplicated to the purpose of this invention is to provide a kind of production technique, and does not have the three wastes to produce, and human body easily absorbs, novel zinc supplementation agent---the lysine-zn that bioavailability is high.
The lysine-zn brief introduction
This product is separated out from ethanolic soln with little pin cluster crystal body, collects the back and becomes white crystalline powder, contains two molecular crystal water.
The formal name of an article: L-lysine-zn (abbreviation lysine-zn)
Chemical name: two (hydrochloric acid L-2,6-diaminocaproic acid) zinc
This product is done element determination through chemistry institute of Chinese Academy of Sciences ultimate analysis chamber, determines molecular formula:
C
12H
32CL
2N
4O
6Z
n
Molecular weight: 464.69 (containing zinc 14.07%)
This product through infrared spectra, nuclear-magnetism and mass spectroscopy, is determined structural formula again:
Fusing point: 235 ℃～237.5 ℃
Specific optical rotation: [α]
20 D+ 16 °～+ 20 °
Basicity: PH7.5～9.5
This product is soluble in water, is insoluble to ethanol.
The technical solution adopted in the present invention is:
With the L-Lysine mono Hydrochloride is raw material, adds zinc chloride, sodium hydroxide reaction, and to transfer pH value be neutral, concentrates the back and adds ethanol, obtains supersaturated solution, is heated to 60 ℃, leaves standstill, and the washing suction filtration gets the lysine-zn crystalline powder.The part by weight of L-Lysine mono Hydrochloride and sodium hydroxide, zinc chloride is 2: 2: 1.PH value transfers to 6.5～7.5.Amount of alcohol added is 1.5～2 times of material cumulative volume, and alcohol concn should be between 72 °～74 °.
When making preparation with lysine-zn, need to add corresponding L-Lysine mono Hydrochloride or L-Methionin formation complex compound, the part by weight of lysine-zn and L-Lysine mono Hydrochloride is 1: 0.78.
The lysine-zn complex compound is in order to preparation clinical application or zinc enhancer.
A, monomer lysine-zn
1, preparation route and foundation:
The alpha-amino group of L-Lysine mono Hydrochloride and carboxyl are the inner salt structure, and omega-amino-and hydrochloric acid are the amine salt structure.In lysine hydrochloride solution, add zinc chloride and sodium hydroxide, zine ion and sodium ion are equably near carboxylic ions, the hydrogen ion that hydroxide ion is seized on the alpha-amino group simultaneously forms water, thereby obtain the aqueous solution of lysine-zn and Sodium lysinate coexistence, to add ethanol after this solution concentration, lysine-zn at first reaches supersaturation in the ethanol mother liquor, puts just crystallization to separate out after cold.
Chemical equation
According to above-listed chemical equation, draw up the technical scheme (Production Flow Chart) of preparation lysine-zn.
Material is prepared (in molar ratio metering):
2 (mol) L-Lysine mono Hydrochloride (with 10 times of water gaging dissolvings).
2 (mol) sodium hydroxide (being made into the 1 normal concentration aqueous solution).
1 (mol) zinc chloride (with sodium hydroxide solution equal volume water dissolution).
2, operating procedure step:
(1) preparation concentrated solution: Methionin, zinc chloride are mixed, add sodium hydroxide in the stirring, get troubled liquor, dropwise add with concentrated hydrochloric acid, stirring disappears until muddiness, and the PH test paper checks that the restriction potential of hydrogen is 6.5～7.5, get clarified liq, heating is concentrated into material cumulative volume 1/3～1/2 in water-bath.
(2) lysine-zn supersaturated solution: add concentrated solution with ethanol in the stirring, do not disappear to muddiness occurring, promptly get supersaturated solution, its volume should be slightly less than 2 times of material cumulative volume, with 2 times be the upper limit, can be less than 1.5 times of cumulative volumes under the lower limit.Measuring alcohol concn with Ebullioscope should be between 72 °～74 °.
(3) separate out crystallization: supersaturated solution is heated to 60 ℃ in water-bath, disappears to muddy, gets the clarified liq placement and is no less than 12 hours, promptly separates out bunch shape crystallization of little pin, and the washing with alcohol suction filtration is used in leaching, and promptly getting product is crystalline powder.
The lysine-zn and the Sodium lysinate that have the crystallization of failing to separate out in the reaction mother liquor, sodium-chlor etc.Mother liquor can be acidified after reclaiming ethanol, and the spent ion exchange resin column chromatography reclaims Methionin, perhaps further concentrates as fodder additives again.
Used chemical reagent must be an analytical pure, and zinc chloride must be below 10PPM through Atomic Absorption Spectrometry leaded (pb).Ethanol can heavily steam with industrial alcohol, and technological process reclaims ethanol and also can use again.
The operation water must purify through ion exchange resin, or uses distilled water.
B, lysine-zn complex compound
1, reaction principle and foundation:
Element zinc is the transition metal with four-coordination number.Zinc salt is general facile hydrolysis in the aqueous solution, and lysine-zn is no exception.Prepare lysine-zn with L-Lysine mono Hydrochloride and zinc chloride, can only obtain by two Methionins and the molecule that zinc combines, two Methionin carboxyls and zinc only form very weak ionic linkage on it, and the four-coordination number that zinc itself is had is not met, so hydrolysis easily in the aqueous solution.But hydrolysis is halfway, learns according to experiment, no matter the concentration of lysine-zn in the aqueous solution what, the limit of hydrolysis all is 50%, that is to say, when hydrolysis to a half, just stop voluntarily.This is because the Methionin that hydrolysis generates manifests the lone-pair electron on the alpha-amino nitrogen atom, this be with solution in zinc form the strong prerequisite of coordination, so the four-coordination number of zinc is met, it is the quadridentate complex compound at center that Methionin just forms with zinc with unhydrolysed lysine-zn:
Lysine-zn is met water meeting hydrolysis, is produced the zinc hydroxide precipitation, and this obviously influences its application in medical treatment.According to research to the lysine-zn hydrolysising property, known the no thoroughness of its hydrolysis, the theory that has the four-coordination number again according to zinc, zine ion trends towards forming complex compound to satisfy the needs of its four-coordination number in the aqueous solution, like this, when making preparation, add corresponding L-Lysine mono Hydrochloride in addition, not only suppressed the hydrolysis of lysine-zn but also in solution, form stable complex compound with lysine-zn.This step has broken through the obstacle of lysine-zn in practical application, has constituted the uniqueness of lysine-zn practical application, has also given the novelty of lysine-zn practical application.
2, the preparation of lysine-zn complex compound preparation and dosage control
During preparation lysine-zn complex compound, adopt L-Lysine mono Hydrochloride or L-Methionin.
According to above principle, prepare clinical application or zinc enhancer with lysine-zn, zinc content by the preparation permission accurately takes by weighing lysine-zn earlier, take by weighing in addition again with this sampling in the suitable L-Lysine mono Hydrochloride consumption of contained Methionin or take by weighing suitable L-Methionin, mix two samplings then, be equipped with other auxiliary materials again, can be pressed into tablet or be made into oral liquid.
Now following routine description operation process:
Clinically use the zinc supplementation agent, every in tablet contains 10 milligrams on zinc.Now prepare 1000 calculating with a batch, lysine-zn contains zinc 14.07%, then should take by weighing lysine-zn 10 * 1000 ÷ 14.07%=71073 (milligram)=71.073 (gram).
L-Lysine mono Hydrochloride content in lysine-zn is 78.61%, then should take by weighing L-Lysine mono Hydrochloride 71.073 gram * 78.61%=55.86 gram.
This two sampling is mixed, be equipped with correctives and other auxiliary materials again and promptly can be made into 1000 in tablet.If every oral liquid that contains 10 milligrams on zinc of preparation also can so be operated.
Attention: (1) because a-amino acid and reducing sugar place for a long time can react with together, so with lysine-zn and L-Lysine mono Hydrochloride preparaton, correctives can not be used monose, can only use disaccharide.For example sucrose can be used, glucose can not be used.
(2) Methionin is subjected to temperatures involved meeting sex change.So preparation lysine-zn preparation, when technological process need be heated, must wait for that material cools to 60 ℃ after, could add lysine-zn and L-Lysine mono Hydrochloride.
The dosage explanation:
Zinc is content 14.07% in lysine-zn, generally needs 15 milligrams of calculating of zinc supplementation every day by the adult, and then taking lysine-zn 100 milligrams just can be satisfied substantially.So, after having taken the lysine-zn preparation, enter intravital Methionin simultaneously and exceed daily needs? no, daily requirement Methionin is 800 milligrams because the male sex is grown up, take 100 milligrams of lysine-zns, 78.6 milligrams of Methionins (L-Lysine mono Hydrochloride accounts for 78.61% in lysine-zn) have been replenished simultaneously, this quantity not sufficient male sex 1/10th of daily requirement amount of being grown up, add the salt that adds one times of amount in addition for preparation complex compound preparation and join L-Methionin, replenish 157 milligrams altogether, the also not enough male sex 1/4th of the daily requirement of being grown up, also not enough women 1/2nd of 400 milliliters of the daily requirement Methionins of being grown up.So replenish zinc according to reasonable dosage, the Methionin of taking simultaneously can paranormal requirement, 10 milligrams of children's daily requirement zinc supplementations, and the Methionin of taking simultaneously can not surpass normal needs yet.
For scarce zinc patient, take the lysine-zn preparation that every dosage contains 10 milligrams on zinc, take every day what and should follow the doctor's advice the course of treatment.
Advantage of the present invention and positively effect:
1, technical maturity of the present invention does not require complicated production unit, and unique organic reagent of using is an ethanol, can heavily steam with industrial alcohol to obtain.The mother liquor of Chan Shenging can reclaim ethanol and reclaim Methionin at last, does not have the three wastes to produce.
Product of the present invention is a crystalline monomer, purity through assay all more than 99%.
No matter 2 developing countries or industrially developed country all exist very general zinc deficiency, then be the ZD performance of child and children with appetite stimulator in the world at present.Lysine-zn of the present invention is novel zinc supplementation agent.When making preparation, in the middle of four Methionins are enclosed in zinc, just there has not been hormesis to stomach and intestine." lysine-zn is at the intravital bioavailability study of rabbit " pharmacological evaluation of doing according to Guangxi Chinese materia medica research institute proves, lysine-zn doubles many in intravital bioavailability of rabbit and zinc sulfate standard control, also high more about 50% than Zinc Gluconate, illustrate that this product closes attitude zinc with chromium and absorb easily in human body.And the Methionin in the lysine-zn be human body itself can not the synthetic indispensable amino acid, the lysine content in the daily meals does not also apply normal people's daily requirement, so lysine-zn not only replenishes zinc to human body, and additional Methionin, kills two birds with one stone.
3, the curative effect along with lysine-zn gets the nod and widespread use clinically, will produce positive profound significance for health growth and the intelligence growth of promoting Chinese children.Lysine-zn will become the innovative product that China has independent intellectual property right at least in zinc supplementation agent field.Make a lysine-zn and make the complex compound preparation at last in addition, use four L-Lysine mono Hydrochlorides, this will be with the increasing of several times amount for the production that promotes China's Methionin, and its economic benefit is considerable.
Embodiment
Embodiment 1:
With 36.5 gram L-Lysine mono Hydrochloride (Guangxi Nanning Yijiang Pharmaceutical Factories, pharmaceutical grade) is dissolved in 365 ml waters in beaker, in addition with 200 ml waters dissolving, 13.6 gram zinc chloride, producing muddiness needn't filter, also pour beaker into, add 200 milliliters of 1N sodium hydroxide solutions in the stirring, in stirring, dropwise add concentrated hydrochloric acid, disappear up to muddiness, obtain settled solution.The inspection of PH test paper should be neutral (PH=7).Change reaction mother liquor over to furnace pot, heating concentrates in water-bath, and liquid level engenders suspended impurity, filter the back and continue to concentrate, get about 300 milliliters of concentrated solution, put cold, 900 milliliters of 90% ethanol that adding is earlier reclaimed add and heavily steam (95%) 200 milliliter of ethanol, measure alcohol concn with Ebullioscope, should be in 73% (if not this concentration, regulate with dehydrated alcohol again, to reach till 73 °), about 1500 milliliters of overall solution volume, change the glass conical flask over to, be heated to 60 ℃ in water-bath, the muddy disappearance gets settled solution, room temperature was placed 12 hours, the leaching crystallization with washing with alcohol suction filtration secondary, is dried, get product 30 grams, productive rate 64%.
Embodiment 2:
146 gram L-Lysine mono Hydrochlorides are dissolved in 1400 ml waters in porcelain enamel barrel, add 800 milliliters of zinc chloride (54.4 gram) aqueous solution, stir, add 800 milliliters of 1N sodium hydroxide solutions (32 gram) again, present muddiness, drip with concentrated hydrochloric acid, stir, until obtaining settled solution, the inspection of pH value test paper is neutral, 3000 milliliters of overall solution volume, place furnace pot, heating concentrates in water-bath in batches, along with solution temperature rises, a small amount of suspended impurity appears in liquid level, filter the back and continue to concentrate, merge concentrated solution and get 1200 milliliters, put cold, pour porcelain enamel barrel into, add and reclaim (90%) 3600 milliliter of ethanol, by totally 950 milliliters of part adding 95% ethanol, solution occurs muddy again, Ebullioscope is measured 73 °, get about 5700 milliliters of cumulative volume, in water-bath, be heated to 60 ℃, disappear to muddy.Get settled solution and placed 12 hours, the leaching crystallization, washing with alcohol suction filtration secondary dries, and gets product 110 grams, productive rate 59%.
Claims (6)
1. the preparation method of a monomer lysine-zn is characterized in that: be raw material with the L-Lysine mono Hydrochloride, add zinc chloride, sodium hydroxide reaction, and the accent pH value be neutral, concentrate the back and add ethanol, obtain supersaturated solution, be heated to 60 ℃, leave standstill, the washing suction filtration gets the lysine-zn crystalline powder.
2. the preparation method of monomer lysine-zn according to claim 1 is characterized in that: the part by weight of L-Lysine mono Hydrochloride and sodium hydroxide, zinc chloride is 2: 2: 1.
3. the preparation method of monomer lysine-zn according to claim 1 is characterized in that: pH value transfers to 6.5～7.5.
4. the preparation method of monomer lysine-zn according to claim 1 is characterized in that: amount of alcohol added is 1.5～2 times of material cumulative volume, and alcohol concn should be between 72 °～74 °.
5. monomer lysine-zn according to claim 1 reaches the preparation method who transfers the lysine-zn complex compound again to, it is characterized in that: when making preparation with lysine-zn, need to add corresponding L-Lysine mono Hydrochloride or L-Methionin formation complex compound, the part by weight of lysine-zn and L-Lysine mono Hydrochloride is 1: 0.78.
6. monomer lysine-zn according to claim 1 reaches the purposes that transfers the lysine-zn complex compound again to, it is characterized in that: the lysine-zn complex compound is in order to preparation clinical application or zinc enhancer.
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| CNA200710050373XA CN101172956A (en) | 2007-10-26 | 2007-10-26 | Monomer zincium lysine, preparation and use of zincium lysine complex compound |
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