CN106631848A - Method for preparing calcium lysine chelate with shell of Argopecten irradias as calcium source - Google Patents
Method for preparing calcium lysine chelate with shell of Argopecten irradias as calcium source Download PDFInfo
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- CN106631848A CN106631848A CN201710002171.1A CN201710002171A CN106631848A CN 106631848 A CN106631848 A CN 106631848A CN 201710002171 A CN201710002171 A CN 201710002171A CN 106631848 A CN106631848 A CN 106631848A
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- lysine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
Abstract
The invention discloses a method for preparing a calcium lysine chelate with the shell of Argopecten irradias as a calcium source. The method comprises the following steps: treatment of the shell of Argopecten irradias: successively subjecting the shell of Argopecten irradias to conventional cleaning, air drying, crushing, charing and ashing; ash content treatment: treating the ash content of the shell with a slightly excess HCl solution so as to obtain a CaCl2 solution; mixing reaction: heating and mixing the CaCl2 solution and lysine under stirring so as to realize chelating; centrifugation: carrying out centrifugation and retaining a supernatant; evaporative concentration: subjecting a reaction solution to slow heating for evaporative concentration; alcohol precipitation: purifying a calcium lysine chelate obtained in the previous step by using absolute ethyl alcohol; and drying: collecting a gel precipitate, repeatedly washing the gel precipitate with absolute ethyl alcohol and then carrying out drying at a constant temperature of 60 to 80 DEG C so as to obtain the calcium lysine chelate. The preparation method for the calcium lysine chelate in the invention uses processing waste of Argopecten irradias, i.e., the shell, and the essential amino acid lysine as raw materials and prepares the calcium lysine chelate through water-phase synthesis; and the method is low in cost, good in chelation yield and suitable for large-scale batch production.
Description
Technical field
The present invention relates to technical field of food biotechnology, more particularly to a kind of lysine chelating with bay scallop shell as calcium source
Calcium preparation method.
Background technology
Calcium is the important element for constituting human body, in human body content at most, can account for body weight 1,5%-2,
0%.Calcium amount 99% in adult normal's body is present in bone and tooth, and remaining 1% is present in extracellular fluid, cell membrane
In soft tissue.Status of the calcium in human body is extremely important, and on the one hand it give bone strength in the form of bone salts, becomes human body
Main support, bear the weight of body；On the other hand, calcium passes through the form of ion in various physiological functions and metabolic process,
Such as blood clotting, contraction of muscle, neuromuscular are played in terms of, stress improving the phagocytosis of microcirculation and leucocyte to bacterium
Very important effect.
The shortage of calcium is extremely universal phenomenon in China, resident's body.Obtained according to Chinese 4th national nutrition survey
Arrive《Chinese residents nutrition and Health Situation survey report》, often the daily calcium mean intake of standard people is only urban and rural residents of China
391mg, equivalent to the 41% of recommended intake.It was recognized that when calcium deficiency phenomenon, meet the tendency of on market generate it is many
Plant various calcium supplementing product.
In the evolution of calcium complement agent, the calcium preparation based on inorganic calcium salt and organic acid calcium salt is occurred in that in early days,
It is also more common in market.Inorganic calcium salt is broadly divided into calcium carbonate, calcium monohydrogen phosphate, calcium activated etc., the calcium carbonate in inorganic calcium salt
Calcium content highest, but it is water-soluble poor, must be by hydrochloric acid in gastric juice and and being dissociated into Ca into after stomach2+, there is very strong to stomach
Excitant.Because its major part cannot be neutralized completely, can be excreted in the form of indissoluble salt, so absorptivity compares
It is low, and easily easily cause kidney stone in kidney stop.But because the cheap and convenience of calcium carbonate, it has become
The most widely used calcium complement agent.Organic acid calcium salt mainly has calcium lactate, calcium acetate and calcium gluconae etc., organic acid calcium salt
Molecular weight is higher, and calcium content is relatively low, but has considerable absorptivity, and effect of supplemented calcium is better than traditional inorganic calcium salt.But
Organic acid calcium salt there is also different degrees of toxic and side effect.Calcium acetate acute toxicity is larger, be easily caused kidney stone,
Heart spasm and soft tissue calciffication's disease, therefore calcium acetate never has the certification by U.S. FDA as calcium complement agent, is only facing
Bed is used as the serum phosphate lowering medicament of hyperphospheremia.Calcium lactate can also give people body while replenishing the calcium and introduce lactic acid and make human body tired
Labor, is not suitable for long-term taking.The water solubility of calcium gluconae very well, either reduces the permeability of capillary, or maintains
The NE of nerve and muscle has very significant effect.But its calcium content is relatively low, and it is unsuitable for patient of diabetes
Person takes, and has larger limitation.
The shellfish yield of China is huge, but goes out of use the accessory substance shell of shellfish processing more, not only greatly wastes
Resource, also causes pollution to environment.Calcium content is considerable in shell, if comprehensively utilizing to waste shell, both can be with
Increase economic benefit, turn avoid the pollution to environment.At present to how to better profit from the not yet relevant report of shell, shell
Comprehensive utilization key is selection and its technical difficulty of its product form.
Lysine is the first limiting amino acids of human body, can not voluntarily be synthesized completely in human body, in cereals food
Extremely lack in product.When lysine is supplemented does not reach standard, other amino acid can also receive restriction or be not used, right
The various vital movements of human body bring many harmful effects.And R Civitelli etc. demonstrate the addition of lysine and can have
Effect increases calcium uptake, reduces calcium loss, contributes to forming the internal calcium balance of health.With perfect, the ammonia of people's health consciousness
The supplement of base acid receives increasing attention.
The content of the invention
The present invention proposes a kind of preparation method of L-Lysine Ca of Chelate for the defect of existing calcium complement agent, with bay fan
Shellfish processing waste-shell and essential amino acid lysine are raw material, and by aqueous phase synthesis method preparation product is obtained.Should
Method technique is relatively simple, and cost is than relatively low, and chelating yield is considerable, and is adapted to large-scale mass production.
To solve above-mentioned technical problem, the present invention is adopted the following technical scheme that：
A kind of L-Lysine Ca of Chelate preparation method with bay scallop shell as calcium source, comprises the steps：
A, shell process：Shell dries after routinely cleaning, crushes, and is carbonized, ashing is processed；
B, ash treatment：Shell ash content is processed with slightly excessive HCl solution, CaCl is obtained2Solution；
C, hybrid reaction：By CaCl2Solution and lysine heating stirring, are chelated；
D, centrifugation：Reactant liquor is centrifuged, is retained supernatant；
E, evaporation and concentration：Slow heating evaporation and concentration is carried out to reactant liquor；
F, alcohol precipitation：L-Lysine Ca of Chelate is purified with absolute ethyl alcohol；
G, drying：Gel precipitation is collected, absolute ethyl alcohol cyclic washing is used, the constant temperature drying at 60～80 DEG C obtains product.
Preferably, the actual conditions of step A is：Bay scallop shell is carried out into conventional cleaning, warm water soaks 1～2h,
Wash in water without clay stain, after scallop shell dries, it is crushed with pulverizer, cross 60～80 mesh sieves obtain powder
End, is put into crucible by gained powder first, is carbonized on electromagnetic heating furnace, with smokeless as the mark for carbonizing terminal, subsequently
Oyster shell whiting after charing is put in Muffle furnace, after 950～1000 DEG C of fully 2～3h of ashing shell ash content is obtained.
Preferably, the actual conditions of step B is：After processing gained shell ash content, atomic absorption spectrophotometry is used
Photometric determination its calcium content, through calculating, with slightly excessive 3～5% HCl solution shell ash content is processed, and obtains CaCl2It is molten
Liquid.
Preferably, the actual conditions of step C is：After with distilled water FE-5 is fully dissolved, with upper one
Step gained CaCl2Solution is mixed, and makes calcium ion be 1 with the amount ratio of lysine material：2～2.5 (preferably 1:2), lysine
Concentration is 4%, and it is 8～9 to adjust system pH with NaOH solution, and mixed solution is heated instead in digital display constant temperature blender with magnetic force
Should, reaction temperature is 60～70 DEG C (preferably 65 DEG C), and the reaction time is 30～40min (preferred 35min).
Preferably, the actual conditions of step D is：While hot by reactant liquor under the conditions of 5000～6000r/min normal temperature
15～20min of centrifugation, discards precipitation, retains supernatant.
Preferably, the actual conditions of step E is：By previous step gained supernatant using Rotary Evaporators at 60 DEG C
Slow heating concentration is carried out, makes supernatant volume be concentrated into the 5～8% of original volume.
Preferably, the actual conditions of step F is：It is molten in absolute ethyl alcohol using amino acids metal ion chelate complex
Xie Du is minimum, and free metal ion and amino acid can be dissolved in absolute ethyl alcohol this condition, using 8～15 times of original concentrate
The absolute ethyl alcohol of (preferably ten times) volume is purified to L-Lysine Ca of Chelate, and Conditions Temperature is set to 4 DEG C, and the time is 12～15h
(preferred 13h).
Preferably, the actual conditions of step G is：Previous step gained gel precipitation is collected by filtration, it is anti-with absolute ethyl alcohol
After backwashing is washed, suction filtration, till filtrate and ninhydrin reagent no longer show bluish violet, is dried gel under the conditions of 60～80 DEG C and is sunk
Form sediment, that is, obtain L-Lysine Ca of Chelate product.
Compared with prior art, Advantageous Effects of the invention：
(1) Jing after process above processing, pure L-Lysine Ca of Chelate product can be obtained；Through process optimization, rely ammonia
The chelated calcium chelating yield of acid and calcium content are more considerable, respectively reach 80% and more than 9%, and simplify operating procedure,
Reduce cost so that L-Lysine Ca of Chelate can industrialize large-scale production, increased yield；
(2) the L-Lysine Ca of Chelate good stability obtained by the present invention, absorptivity is high, and dissolubility has also obtained changing significantly
It is kind, lysine is supplemented while replenishing the calcium, with dual trophism；In addition, the presence of lysine not only has improving
Immunity, constitutional effect can also promote absorption of the body to calcium, contribute to being formed the calcium balance of internal health, and two
Plant trophic factors to bring out the best in each other；L-Lysine Ca of Chelate physiological-toxicity-free, the crowd for being adapted to all age group takes on demand, is future
The developing direction of calcium complement agent.
Specific embodiment
A kind of L-Lysine Ca of Chelate preparation method with bay scallop shell as calcium source, comprises the steps：
A, shell process：Shell dries after routinely cleaning, crushes, and is carbonized, ashing is processed；
B, ash treatment：Shell ash content is processed with slightly excessive HCl solution, CaCl is obtained2Solution；
C, hybrid reaction：By CaCl2Solution and lysine heating stirring, are chelated；
D, centrifugation：Reactant liquor is centrifuged, is retained supernatant；
E, evaporation and concentration：Slow heating evaporation and concentration is carried out to reactant liquor；
F, alcohol precipitation：L-Lysine Ca of Chelate is purified with absolute ethyl alcohol；
G, drying：Gel precipitation is collected, absolute ethyl alcohol cyclic washing is used, the constant temperature drying at 60～80 DEG C obtains product.
Wherein, the actual conditions of step A is：Bay scallop shell is carried out into conventional cleaning, warm water soaks 1～2h, washes
Wash in water without clay stain, after scallop shell dries, it is crushed with pulverizer, cross 60～80 mesh sieves obtain powder,
First gained powder is put into into crucible, is carbonized on electromagnetic heating furnace, with the smokeless mark as charing terminal, subsequently charcoal
Oyster shell whiting is put in Muffle furnace after change, and after 950～1000 DEG C of fully 2～3h of ashing shell ash content is obtained；Step B it is concrete
Condition is：After processing gained shell ash content, its calcium content is determined with atomic absorption spectrophotometer, through calculating, used
The HCl solution of slightly excessive 3～5% processes shell ash content, obtains CaCl2Solution；The actual conditions of step C is：With steaming
After distilled water fully dissolves FE-5, with previous step gained CaCl2Solution is mixed, and makes calcium ion and lysine thing
The amount ratio of matter is 1：2～2.5, lysine concentration is 4%, and it is 8～9 to adjust system pH with NaOH solution, and mixed solution is being counted
Heating response in aobvious constant temperature blender with magnetic force, reaction temperature is 60～70 DEG C, and the reaction time is 30～40min；Step D
Actual conditions is：While hot by reactant liquor, normal temperature is centrifuged 15～20min under the conditions of 5000～6000r/min, discards precipitation, retains
Supernatant；The actual conditions of step E is：Previous step gained supernatant is carried out slowly using Rotary Evaporators at 60 DEG C
Heating concentration, makes supernatant volume be concentrated into the 5～8% of original volume；The actual conditions of step F is：Using amino acid
Solubility of the chelate of metal ion in absolute ethyl alcohol is minimum, and free metal ion and amino acid can be dissolved in absolute ethyl alcohol
This condition, is purified using the absolute ethyl alcohol of 8～15 times of volumes of original concentrate to L-Lysine Ca of Chelate, and Conditions Temperature sets
For 4 DEG C, the time is 12～15h；The actual conditions of step G is：Previous step gained gel precipitation is collected by filtration, anhydrous second is used
Alcohol cyclic washing, suction filtration till filtrate and ninhydrin reagent no longer show bluish violet, is dried solidifying under the conditions of 60～80 DEG C
Glue is precipitated, that is, obtain L-Lysine Ca of Chelate product.
The present invention prepares pure L-Lysine Ca of Chelate product, through process optimization, the chelating of L-Lysine Ca of Chelate
Yield and calcium content are more considerable, respectively reach 80% and more than 9%, and simplify operating procedure, reduce cost so that
L-Lysine Ca of Chelate can industrialize large-scale production, increased yield；Meanwhile, the L-Lysine Ca of Chelate obtained by the present invention is steady
Qualitative good, absorptivity is high, and dissolubility is also substantially improved, and lysine is supplemented while replenishing the calcium, with dual battalion
Support effect；In addition, the presence of lysine not only has enhance immunity, constitutional effect can also promote body to calcium
Absorption, contribute to being formed the calcium balance of internal health, two kinds of trophic factors bring out the best in each other；L-Lysine Ca of Chelate is without physiology poison
Property, the crowd for being adapted to all age group takes on demand, is the developing direction of following calcium complement agent.
L-Lysine Ca of Chelate results of animal：
With cleaning grade SD female rats as research object, low calcium control group is set respectively, L-Lysine Ca of Chelate is basic, normal, high
Dosage group, positive controls, gavage continues 4 weeks, and the indexs such as Growth in Rats situation, femoral bmd are united after off-test
Meter.
Result of the test shows, calcium lysinate product is to the body weight of rat, body length increases certain promotion.Testing
Cheng Zhong, middle and high dosage chelating CAL group and positive controls rat body weight increment all apparently higher than low calcium control group,
There is significant difference (P ＜ 0.05) in the chelating CAL group of wherein middle dosage, the chelating CAL group and the positive of high dose is right
There is pole significant difference (P ＜ 0.01) according to group, compared to low calcium control group, 53.70%, 70.89% and is increased respectively
73.87%.Rat body length is being affected in test, the chelating CAL group and the rat body of positive controls of basic, normal, high dosage
Long increment all apparently higher than low calcium control group, wherein there is significant difference (P ＜ in low, middle dosage chelating CAL group
0.05), there is pole significant difference (P ＜ 0.01) in the chelating CAL group and positive controls of high dose, compared to low calcium pair
According to group, 81.82%, 71.59%, 118.18% and 117.05% is increased respectively.
The femur length of middle and high dosage group rat is significantly higher than low calcium control group (P ＜ 0.05).The stock of middle dose group rat
Bone mass is significantly higher than low calcium control group (P ＜ 0.05), and the femoral bone mass of high dose group rat has pole significant difference (P ＜
0.01), compared to low calcium control group, it increases for the chelating CAL group of middle and high dosage and the femoral bone mass of positive controls rat
Long amount is respectively 9.16%, 11.44% and 10.28%.
The calcium content of bone and bone density of middle and high dosage group rat all rises appreciably compared with low calcium control group, exists and extremely shows
Write difference (P ＜ 0.01).The femur calcium content of middle and high dosage chelating CAL group and positive controls rat is apparently higher than low calcium
Control group, compared with low calcium control group 13.19%, 35.15% and 29.16% has been respectively increased.Middle and high dosage chelating CAL group and
The femoral bmd of positive controls rat apparently higher than low calcium control group, be respectively increased 35.29% compared with low calcium control group,
63.55% and 60.59%.Show that calcium lysinate has certain improvement result to rat femur situation.
The apparent absorptivity of calcium lysinate more has advantage compared with the positive controls containing same calcium amount.Three doses water
Flat chelates the calcium in rats apparent absorptivity of CAL group and positive controls all apparently higher than low calcium control group, compares with low calcium
Group is compared, and 39.51%, 58.39%, 79.98% and 72.99% is increased respectively, is respectively provided with pole significant difference (P ＜
0.01)。
Bone tissue HE normal dyeing results show calcium lysinate dosage group also superior to low calcium control group.Low calcium control group it is big
Mouse femur bone structure is more loose, though its bone trabecula has certain amount, thinner thickness, relative volume is less, and
There are crack conditions in local, and spacing increase has the sunken phenomenon of nest.The SD rat femur bone groups of low dose group and middle dose group
Situation about knitting is closer to, and bone trabecular form has certain thickness than more complete, but the bone of wherein middle dose group is little
Occurs connection between beam, nest falls into and reduces, and bone trabecula quantity is slightly above low dose group.The SD rat femur bone structures of high dose group
More complete, bone trabecula thickness is higher, and quantity is more, and the sunken phenomenon of nest is less, and osteoblastic quantity is more, osteoclast
Negligible amounts, will be substantially better than low calcium control group for bone amount.
Embodiment described above is only that the preferred embodiment to the present invention is described, and not the scope of the present invention is carried out
Limit, on the premise of without departing from design spirit of the present invention, those of ordinary skill in the art make to technical scheme
Various modifications and improvement, all should fall into claims of the present invention determination protection domain in.
Claims (8)
1. a kind of L-Lysine Ca of Chelate preparation method with bay scallop shell as calcium source, it is characterised in that：Comprise the steps：
A. shell is processed：Shell dries after routinely cleaning, crushes, and is carbonized, ashing is processed；
B. ash treatment：Shell ash content is processed with slightly excessive HCl solution, CaCl is obtained2Solution；
C. hybrid reaction：By CaCl2Solution and lysine heating stirring, are chelated；
D. centrifugation：Reactant liquor is centrifuged, is retained supernatant；
E. it is concentrated by evaporation：Slow heating evaporation and concentration is carried out to reactant liquor；
F. alcohol precipitation：L-Lysine Ca of Chelate is purified with absolute ethyl alcohol；
G, drying：Gel precipitation is collected, absolute ethyl alcohol cyclic washing is used, the constant temperature drying at 60～80 DEG C obtains product.
2. the L-Lysine Ca of Chelate preparation method with bay scallop shell as calcium source according to claim 1, it is characterised in that：
The actual conditions of step A is：Bay scallop shell is carried out into conventional cleaning, warm water soaks 1～2h, washs into water without soil
Till spot, after scallop shell dries, it is crushed, crosses 60～80 mesh sieves and obtain powder, first carbonized in gained powder,
With the smokeless mark as charing terminal, subsequently oyster shell whiting after charing is obtained shell after 950～1000 DEG C fully 2～3h of ashing
Ash content.
3. the L-Lysine Ca of Chelate preparation method with bay scallop shell as calcium source according to claim 1, it is characterised in that：
The actual conditions of step B is：After processing gained shell ash content, with atomic absorption spectrophotometer its calcic is determined
Amount, through calculating, with slightly excessive 3～5% HCl solution shell ash content is processed, and obtains CaCl2Solution.
4. the L-Lysine Ca of Chelate preparation method with bay scallop shell as calcium source according to claim 1, it is characterised in that：
The actual conditions of step C is：After with distilled water FE-5 is fully dissolved, with previous step gained CaCl2Solution
Mixed, make calcium ion be 1 with the amount ratio of lysine material：2～2.5, lysine concentration is 4%, and with NaOH solution body is adjusted
Be pH value for 8～9, by mixed solution in digital display constant temperature blender with magnetic force heating response, reaction temperature is 60～70 DEG C, reaction
Time is 30～40min.
5. the L-Lysine Ca of Chelate preparation method with bay scallop shell as calcium source according to claim 1, it is characterised in that：
The actual conditions of step D is：While hot by reactant liquor, normal temperature is centrifuged 15～20min under the conditions of 5000～6000r/min, abandons
Precipitation is gone, retains supernatant.
6. the L-Lysine Ca of Chelate preparation method with bay scallop shell as calcium source according to claim 1, it is characterised in that：
The actual conditions of step E is：Previous step gained supernatant is carried out into slow heating concentration at 60 DEG C, supernatant volume is made
It is concentrated into the 5～8% of original volume.
7. the L-Lysine Ca of Chelate preparation method with bay scallop shell as calcium source according to claim 1, it is characterised in that：
The actual conditions of step F is：It is minimum using solubility of the amino acids metal ion chelate complex in absolute ethyl alcohol, and dissociate
Metal ion and amino acid can be dissolved in absolute ethyl alcohol this condition, using the absolute ethyl alcohol of 8～15 times of volumes of original concentrate
L-Lysine Ca of Chelate is purified, Conditions Temperature is set to 4 DEG C, and the time is 12～15h.
8. the L-Lysine Ca of Chelate preparation method with bay scallop shell as calcium source according to claim 1, it is characterised in that：
The actual conditions of step G is：Previous step gained gel precipitation is collected by filtration, absolute ethyl alcohol cyclic washing is used, suction filtration, until
Till filtrate no longer shows bluish violet with ninhydrin reagent, gel precipitation is dried under the conditions of 60～80 DEG C, that is, obtain lysine
Chelating calcium product.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108675917A (en) * | 2018-05-17 | 2018-10-19 | 青岛大学 | The chelated calcium isolation and purification method of sugar alcohol in a kind of organic fertilizer |
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| CN101058782A (en) * | 2006-04-20 | 2007-10-24 | 缪锦来 | Sports beer |
| CN101973899A (en) * | 2010-09-13 | 2011-02-16 | 三亚百泰微纳生物工程有限公司 | Novel production process of nanometer calcium amino acid chelate with high efficiency |
| CN102334676A (en) * | 2010-07-27 | 2012-02-01 | 河北农业大学 | Method for preparing collagen chelated calcium |
| CN103951575A (en) * | 2014-04-29 | 2014-07-30 | 吉林大学 | Lysine chelated calcium powder and processing method |
| WO2015195491A1 (en) * | 2014-06-18 | 2015-12-23 | Thetis Pharmaceuticals Llc | Mineral amino-acid complexes of active agents |
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- 2017-01-03 CN CN201710002171.1A patent/CN106631848B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1666978A (en) * | 2004-03-12 | 2005-09-14 | 上海福赐德营养保健品有限责任公司 | L-chelated calcium lysine |
| CN101058782A (en) * | 2006-04-20 | 2007-10-24 | 缪锦来 | Sports beer |
| CN102334676A (en) * | 2010-07-27 | 2012-02-01 | 河北农业大学 | Method for preparing collagen chelated calcium |
| CN101973899A (en) * | 2010-09-13 | 2011-02-16 | 三亚百泰微纳生物工程有限公司 | Novel production process of nanometer calcium amino acid chelate with high efficiency |
| CN103951575A (en) * | 2014-04-29 | 2014-07-30 | 吉林大学 | Lysine chelated calcium powder and processing method |
| WO2015195491A1 (en) * | 2014-06-18 | 2015-12-23 | Thetis Pharmaceuticals Llc | Mineral amino-acid complexes of active agents |
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| CN108675917A (en) * | 2018-05-17 | 2018-10-19 | 青岛大学 | The chelated calcium isolation and purification method of sugar alcohol in a kind of organic fertilizer |
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