CN105777534B - Calcium citrate salts and preparation method thereof and purposes - Google Patents
Calcium citrate salts and preparation method thereof and purposes Download PDFInfo
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- CN105777534B CN105777534B CN201410821366.5A CN201410821366A CN105777534B CN 105777534 B CN105777534 B CN 105777534B CN 201410821366 A CN201410821366 A CN 201410821366A CN 105777534 B CN105777534 B CN 105777534B
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Abstract
A kind of calcium citrate salts and preparation method thereof and purposes, the calcium citrate salts have stronger nutrition and therapeutic effect than simple calcium citrate.Preparation method is:Citric acid is soluble in water, add in calcium oxide or calcium hydroxide or calcium carbonate, sundries is filtered to remove after solution dissolving is transparent, L arginine or L lysines or acetyl L carnitines or propionyl L carnitines are added in filtrate, is reacted 28 hours in 0 100 DEG C, is concentrated under reduced pressure, cooling, add absolute ethyl alcohol crystallization, filtration drying, qualified after testing is product.Composition containing the calcium citrate salts can be made into one or more pharmacologically acceptable excipient, particularly solid-liquid oral preparation, such as pulvis, granule, tablet, capsule, oral liquid are directly prepared into beverage, available for people's diet/nutritional supplement or food supplement for animals, including supplement L arginine, L lysines, acetyl L carnitines, propionyl L carnitine nutritional supplements.
Description
Technical field
The present invention relates to a kind of acceptable salt of stabilization, non-hygroscopic extra-nutrition substance, more particularly to one kind
Calcium citrate salts and preparation method thereof and purposes belong to the technology of preparing of food additives, suitable for preparing people's use or food for animals
Product additive and nutritional supplement, including supplement L-arginine, L-lysine, acetyl L-carnitine, L-PROPIONYLCARNITINE nutritional supplement
Agent composition.
Background technology
Natural lemon acid is distributed very extensively in nature, and natural citric acid is present in plant such as lemon, citrus, pineapple etc.
In fruit and the bone of animal, muscle, blood.Artificial synthesized citric acid is containing sugared object with granulated sugar, molasses, starch, grape etc.
Prepared by matter is fermented can be divided into anhydrous and two kinds of hydrate.Sterling citric acid is crystallized for water white transparency or white powder, nothing
It is smelly, there is a kind of tempting tart flavour.All contain more citric acid in the fruit of a variety of fruits and vegetables, especially Citrus,
Particularly lemon --- they contain a large amount of citric acids for lemon and blueness.
The effect of citric acid, has many reports, has multiple functions：Because citric acid has the tart flavour of mild frankness, generally
For the manufacture of the food such as various beverages, carbonated drink, grape wine, candy, dessert, biscuit, canned fruit juice, dairy products.Have all
In the market of machine acid, more than 70% citric acid occupation rate of market, citric acid also is used as the antioxidant of flavoring agent and edible oil.
Improve the sensory properties of food simultaneously, whet the appetite and internal calcium, phosphorus substance is promoted to digest and assimilate.Anhydrous citric acid is largely used
In solid beverage.The salt such as calcium citrate and ironic citrate of citric acid are to need to add calcium ion and iron ion in certain food
Hardening agent.The esters of citric acid such as triethyl citrate can make nontoxic plasticizer, manufacture food packaging plastic film, be drink
The acid of material and food service industry, preservative.Citric acid also has the function of to prevent and eliminate cutaneous pigmentation.
L-arginine is a kind of nutritional supplement, it be ornithine cycle in a constituent have it is extremely important
Physiological function eats arginine more, can increase the activity of arginine in liver (arginase), helps to turn the ammonia in blood
Become urea and excrete out.So arginine, to hyperammonemia, hepatic dysfunction is helpful.L-arginine is also sperm
The main component of albumen plays the role of promoting the quality of sperm, improves sperm motility energy.L-arginine can effectively improve immune
Power promotes immune system secretion constant killer cell, phagocyte, the endogenys such as alkene plain (interleukin-1) in white blood cell
Substance is conducive to inhibiting tumor cell and pre- preventing virus infection.In addition, L-arginine is ornithine (L-ornithine) and dried meat ammonia
The precursors of sour (L-proline), proline are the important elements for forming collagen, supplement arginine for severe trauma,
The needs such as burn largely organize the health of maintenance protect, have apparent help, while have the effect for reducing infection and inflammation.
L-lysine is to aid in other nutriments by the key substance that human body fully absorbs and utilizes, and human body only supplements
Enough L-lysines could improve the absorption and utilization of food protein, reach balanced nutritious, enhancing development.It is made
With having：Intelligence is improved, promotes growth, builds up health；It improves a poor appetite, improves malnutritive situation；Improve insomnia, improve memory
Power；Help generates antibody, hormone and enzyme, improves immunity, increases hemochrome；The absorption of calcium is helped, treatment prevents osteoporosis
Disease；The level of triglycerides in blood is reduced, prevents the generation of cardiovascular and cerebrovascular disease.
, also there are many reports in the effect of l-carnitine, and l-carnitine is a kind of important food enrichment, is had been widely used
In food industry, such as baby milk, diet food, in nutrition of athlete's product and person in middle and old age's nutritional supplement and feed processing industry,
The effect of in addition in terms of medicine, angiocardiopathy, liver diseases, kidney trouble, hyperlipidemia, diabetes, neuromuscular
Disease etc. can be improved illness by taking l-carnitine and its series of products.
Acetyl L-carnitine is a kind of natural material being present in human body, and content is special especially in muscle, brain and sperm
Not Feng Fu, a series of important metabolic processes are participated in human body, it takes away acetyl group from cell and assists energy transfer, has
Report that acetyl L-carnitine can also improve fecundity.
L-PROPIONYLCARNITINE improves the generation of energy substrate, improves the oxygen of glucose by stimulating pyruvate dehydrogenase activity
Change Utilization ability, cardiac muscle cell can be protected from oxidative damage, treat the heart as free radical scavenger and the protective agent of active oxygen
Vascular diseases, such as congestive heart failure, cardiac arrhythmia, peripheral vascular disease and acute ischemia.In addition, L-PROPIONYLCARNITINE can compare l-carnitine
Quickly enter the generation that cardiac muscle cell inhibits free radical.The substance and energetic supersession for improving damaged myocardium are L-PROPIONYLCARNITINEs
Primary pharmacological activity shows, and L-PROPIONYLCARNITINE can directly expand skeletal muscle vescular bed in high dose, and it is horizontal to improve tissue metabolism.Third
Acyl-L-carnitine has anti-inflammatory activity in certain rodent vascular inflammation models.Having neutrophil cell and blood platelet tissue lacks
There is protective effect in blood and other inflammation diseases.Compared with l-carnitine, there are three potential advantages for L-PROPIONYLCARNITINE tool：Have
The ability of medium is supplemented for tricarboxylic acid cycle；There is the affinity of bigger to sarcolemma carrier；It is locally being lacked in complete heart
The influence muscle stress of energy bigger after blood.
Calcium to tooth and bone other than having vital effect, moreover it is possible to existence and the function of cell is maintained, to nerve
Conduction maintains immune system, blood clotting, metabolism, contraction of muscle and heart cell is helped to have important help.
Calcium is to maintaining internal acid-base balance, and it is required to maintain and adjust many biochemical processes in vivo, it can promote internal a variety of enzymes
Activity plays catalytic action for fibrin ferment.Calcium deficiency easily cause chondroma matter, osteoporosis, rickets, sciatica,
Saprodontia, white hair；Muscle cramp is easily caused, myocardial function declines, and heart disease, fecundity declines, dysmenorrhoea；Nerve can be caused emerging
Putting forth energy property enhances, psychataxia, decrease of memory, is easy to tired, allergic reaction, increase intestinal cancer illness rate, hypertension, and bone is abnormal
Shape, spasm etc..Therefore, calcium is the indispensable element of human body, is the Source of life of human body, becomes normal in various nutritional supplements
See element.
Calcium citrate is combined with L-arginine, L-lysine, acetyl L-carnitine, L-PROPIONYLCARNITINE, being formed has profit
In the calcium citrate salts for the diversified forms for preserving, transporting and being easily absorbed by the body, the nutrition of single calcium citrate had both been enhanced
Effect, and enrich the type of calcium citrate.
L-carnitine calcium citrate prepared by Publication No. CN102911069A is calcium citrate with l-carnitine into salt, only
A kind of single calcium citrate salts, do not provide can with a variety of basic amino acids, a variety of alkanyl L-carnitines into salt technology
Enlightenment, such as L-arginine, L-lysine, acetyl L-carnitine, L-PROPIONYLCARNITINE etc. are into salt.
Invention content
It is an object of the invention to overcome deficiencies of the prior art, after repetition test and research, provide
A series of acceptable calcium citrate salts and preparation method thereof and purposes.Calcium citrate salts prepared by the present invention contain citric acid
A variety of alkaline nutriments such as calcium and L-arginine, L-lysine, acetyl L-carnitine, L-PROPIONYLCARNITINE form a system into salt
Arrange colourful calcium citrate salts.Both increase the function of enhancing single L-carnitine calcium citrate, and be also convenient for preparation system
The selection application of piece, while also expanded application of the calcium citrate in the fields such as amino acid and alkanyl L-carnitine.The present invention provides
These calcium citrate salts have the characteristics that stablize, be not easy to moisture absorption, and there are stronger and more work(than simple calcium citrate
The trophism of energy.
The technical solution that the present invention provides is:The general structure of these calcium citrate salts is：
Wherein R represents the basic amino acids such as L-arginine, L-lysine, acetyl L-carnitine, L-PROPIONYLCARNITINE or alkyl L-
Carnitine.Such as：
Ith, it is L-arginine calcium citrate salts when R represents L-arginine, molar ratio 1: 1: 1.Its structural formula is as follows：
IIth, it is L-lysine calcium citrate salts when R represents L-lysine, molar ratio 1: 1: 1.Its structural formula is as follows：
IIIth, it is acetyl L-carnitine calcium citrate salts when R represents acetyl L-carnitine, molar ratio 1: 1: 1.Its structural formula is as follows：
IVth, it is L-PROPIONYLCARNITINE calcium citrate salts when R represents L-PROPIONYLCARNITINE, molar ratio 1: 1: 1.Its structural formula is as follows：
Calcium citrate salts provided by the invention substantially improve the physicochemical property of single calcium citrate, increase L- essence ammonia
Acid, L-lysine, acetyl L-carnitine, L-PROPIONYLCARNITINE function, thus expanded its application range significantly.Calcium citrate salts
A solid-state noval chemical compound, non-hygroscopic, can make consumer needs various dosage forms, while can also be applied to food,
The every field such as beverage, medicine, prospect are very broad.
The calcium citrate salt production process that the present invention provides is:
Citric acid (0.1mol) is soluble in water, calcium oxide or calcium hydroxide or calcium carbonate (0.1mol) are added in, treats solution
Dissolve it is transparent after be filtered to remove sundries, L-arginine or L-lysine or acetyl L-carnitine or L-PROPIONYLCARNITINE are added in filtrate
(0.1mol).It reacts 2-8 hours, is concentrated under reduced pressure in 0-100 DEG C, cooling adds absolute ethyl alcohol crystallization, and filtration drying obtains required
Calcium citrate salts.
In the above-mentioned technical proposal that provides of the present invention, due to using water and absolute ethyl alcohol as solvent, not only environmental protection but also be conducive to
The recycling of ethyl alcohol can more save cost.
The scope of protection of present invention should also be related to a series of application of this calcium citrate salts, i.e., with composition forms
As people's diet/nutritional supplement or as nutritional supplement for animals, wherein the composition is included described in structural formula I-IV
Any one calcium citrate salts is as active ingredient.Comprising suitable for the pharmaceutically acceptable calcium citrate salts that take orally, drink, stablize
Composition and the optional one or more pharmacologically acceptable excipient of the composition and pharmacy and Food technology
Active constituent known to expert.
Particularly preferably solid or liquid oral medicine, such as tablet, capsule, granule, pulvis, oral liquid, the group
It closes object and includes the calcium citrate salts shown in structural formula I-IV.
Example 1 is a kind of composition for preparing tablet below：
Example 2 is to prepare a kind of formula of beverage below：
Above-mentioned beverage can not only supplement calcium, and can also supplement amino acid or alkanyl L-carnitine, make various substances in body fluid
Balance is rapidly reached, and with constitutional effect.
The composition of the present invention can be used for people's diet/nutritional supplement or food supplement for animals, including supplement L- essences
Propylhomoserin, L-lysine, acetyl L-carnitine, L-PROPIONYLCARNITINE enriching substance.
Compared with prior art, beneficial effects of the present invention are:This calcium citrate salts provided have suitable for oral, steady
The characteristics of fixed, not easy to moisture absorption, convenient for storing and transporting and prepare solid pharmaceutical preparation；And have more than corresponding calcium citrate
Strong and more multi-functional nutrition and therapeutic effect are especially the increase in supplement L-arginine, L-lysine, acetyl L-carnitine, third
The effect of acyl-L-carnitine.It is exposed 24 hours during 25 DEG C of relative humidity 60 ± 5%, no tacky phenomenon of conglomeration, resistance to water soak is good.
Specific embodiment
The following examples are intended to further illustrate this stabilization, the non-hygroscopic calcium citrate salts that the present invention provides
And its preparation method and application：
Embodiment 1：The preparation of L-arginine calcium citrate salts.
Citric Acid Mono 21 grams (0.1mol) is dissolved in 200ml water, adds in calcium hydroxide 7.4 grams (0.1mol), room temperature
Dissolving filters after solution is transparent, removes the SiO in calcium hydroxide2Impurity are waited, L-arginine 17.4 is added in clean filtrate
Gram (0.1mol), is stirred to react 4 hours in 70-80 DEG C, then concentrates, cooling plus absolute ethyl alcohol crystallization, filtration drying, gained
38.8 grams of L-arginine calcium citrate salts have good mobility and resistance to water soak, yield 96.0%.
[α]D 20=+10.8 ° (C=1,0.5N HCl), L-arginine HPLC contents 42.4%, citric acid HPLC contents
47.0%, calcium content 9.7%.
Embodiment 2：The preparation of L-lysine calcium citrate salts.
Citric Acid Mono 21 grams (0.1mol) is dissolved in 200ml water, adds in calcium oxide 5.6 grams (0.1mol), room temperature is molten
Solution filters after solution is transparent, removes the SiO in calcium oxide2Impurity are waited, 14.6 grams of L-lysine is added in clean filtrate
(0.1mol) is stirred to react 4 hours in 70-80 DEG C, then concentrates, cooling plus absolute ethyl alcohol crystallization, filtration drying, the L- of gained
36.5 grams of lysine calcium citrate salts have good mobility and resistance to water soak, yield 97.1%.
[α]D 20=+8.8 ° (C=1,0.5N HCl), L-lysine HPLC contents 39.4%, citric acid HPLC contents
50.2%, calcium content 10.0%.
Embodiment 3：The preparation of acetyl L-carnitine calcium citrate salts.
Citric Acid Mono 21 grams (0.1mol) is dissolved in 200ml water, adds in calcium carbonate 10.0 grams (0.1mol), room temperature is molten
Solution filters after solution is transparent, removes the SiO in calcium carbonate2Impurity are waited, 20.3 grams of acetyl L-carnitine is added in clean filtrate
(0.1mol) is stirred to react 4 hours in 70-80 DEG C, then concentrates, cooling plus absolute ethyl alcohol crystallization, filtration drying, the second of gained
41.5 grams of acyl-L-carnitine calcium citrate salts have good mobility and resistance to water soak, yield 95.8%.
[α]D 20=-12.2 ° (C=1,0.5N HCl), acetyl L-carnitine HPLC contents 45.9%, citric acid HPLC contents
45.2%, calcium content 8.5%.
Embodiment 4：The preparation of L-PROPIONYLCARNITINE calcium citrate salts.
Citric Acid Mono 21 grams (0.1mol) is dissolved in 200ml water, adds in calcium hydroxide 7.4 grams (0.1mol), room temperature
Dissolving filters after solution is transparent, removes the SiO in calcium carbonate2Impurity are waited, L-PROPIONYLCARNITINE 21.7 is added in clean filtrate
Gram (0.1mol), is stirred to react 4 hours in 70-80 DEG C, then concentrates, cooling plus absolute ethyl alcohol crystallization, filtration drying, gained
42.6 grams of L-PROPIONYLCARNITINE calcium citrate salts have good mobility and resistance to water soak, yield 95.3%.
[α]D 20=-10.5 ° (C=1,0.5N HCl), L-PROPIONYLCARNITINE HPLC contents 47.5%, citric acid HPLC contents
43.2%, calcium content 8.4%.
HPLC：
Column：HYPERSIL C8(5μm)250×4.6mm
Temperature：25℃
Mobile phase：0.02M KH2PO4
pH：6.0H3PO4
Detection wavelength：254nm
Flow velocity：0.6 ml/min
L-arginine：Rt=6.2 minutes
L-lysine：Rt=7.3 minutes
Acetyl L-carnitine：Rt=6.4 minutes
L-PROPIONYLCARNITINE：Rt=5.8 minutes
The present invention is using composition forms as people by the use of diet/nutritional supplement or as nutritional supplement for animals, wherein institute
Comprising any one calcium citrate salts described in structural formula I-IV as active ingredient in the composition stated.The composition can be made into one
Kind or the pulvis in a variety of pharmacologically acceptable excipient, such as solid, liquid body oral preparation, granule, tablet, capsule,
Oral liquid is directly prepared into beverage.The composition includes any one calcium citrate salts described in structural formula I-IV.
The component of one of which tablet is：
The formula of one of which beverage is：
Claims (1)
1. a kind of preparation method of calcium citrate salts, which is characterized in that 0.1mol citric acids is soluble in water, add in 0.1mol oxygen
Change calcium or 0.1mol calcium hydroxides or 0.1mol calcium carbonate, be filtered to remove sundries after solution dissolving is transparent, added in filtrate
0.1mol L-arginines or 0.1mol L-lysines or 0.1mol acetyl L-carnitines or 0.1mol L-PROPIONYLCARNITINEs, in 0-100
DEG C reaction 2-8 hour, be concentrated under reduced pressure, cool down, add absolute ethyl alcohol crystallization, filtration drying obtains required calcium citrate salts.
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| CN109280005A (en) * | 2017-07-20 | 2019-01-29 | 辽宁科硕营养科技股份有限公司 | A kind of compound lemon acid zinc salt, includes its composition and application thereof at preparation method |
| CN107573253B (en) | 2017-10-25 | 2020-03-27 | 广州英赛特生物技术有限公司 | N, N-dimethyl glycine organic acid conjugate acid salt, composition and application thereof |
| US20190175533A1 (en) * | 2017-12-12 | 2019-06-13 | Pharmco International Inc. | Nutritional supplement for improved calcium absorption |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928506A (en) * | 1973-01-02 | 1975-12-23 | Ucb Sa | Lysino-calcium chloride and pharmaceutically acceptable acid salts thereof |
| CN1356976A (en) * | 1999-05-28 | 2002-07-03 | 比奥萨尔茨有限责任公司 | Therapeutically and/or nutritionaly enhanced derivatives of active ingredients and orally administrable compsns. contg. same |
| CN1972899A (en) * | 2004-06-25 | 2007-05-30 | 协和发酵工业株式会社 | L-ornithine-citric acid salt crystal |
| CN102911069A (en) * | 2011-08-04 | 2013-02-06 | 广州市奥海生物科技有限公司 | L-carnitine calcium citrate and preparation method and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1291134B1 (en) * | 1997-04-08 | 1998-12-29 | Sigma Tau Ind Farmaceuti | SOLID COMPOSITIONS SUITABLE FOR ORAL ADMINISTRATION INCLUDING AN ALCANOYL L-CARNITINE MAGNESIUM CITRATE |
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2014
- 2014-12-24 CN CN201410821366.5A patent/CN105777534B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928506A (en) * | 1973-01-02 | 1975-12-23 | Ucb Sa | Lysino-calcium chloride and pharmaceutically acceptable acid salts thereof |
| CN1356976A (en) * | 1999-05-28 | 2002-07-03 | 比奥萨尔茨有限责任公司 | Therapeutically and/or nutritionaly enhanced derivatives of active ingredients and orally administrable compsns. contg. same |
| CN1972899A (en) * | 2004-06-25 | 2007-05-30 | 协和发酵工业株式会社 | L-ornithine-citric acid salt crystal |
| CN102911069A (en) * | 2011-08-04 | 2013-02-06 | 广州市奥海生物科技有限公司 | L-carnitine calcium citrate and preparation method and application thereof |
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