67-48-1 Usage
Chemical Description
Choline chloride is a quaternary ammonium salt used as a dietary supplement and in the synthesis of other chemicals.
Chemical Description
Choline chloride is a quaternary ammonium salt that is used as a dietary supplement and a food additive.
Description
Choline chloride, a quaternary ammonium salt with choline cation and chloride anion, is a white crystalline powder that is practically neutral in its aqueous solution. It is a basic constituent of lecithin, found in many plants and animal organs, and plays a crucial role as a precursor of acetylcholine, a methyl donor in various metabolic processes, and in lipid metabolism. Choline chloride is also an animal feed additive and a water-soluble B-vitamin that increases animal growth.
Uses
Used in Animal Feed Industry:
Choline chloride is used as an animal feed additive for promoting growth, enhancing physical fitness and disease resistance, and improving the laying rate of poultry. It is effective in preventing fat deposition and tissue degeneration in the organs of livestock and poultry, and it promotes the absorption and synthesis of amino acids, particularly methionine.
Used in Clinical Applications:
Choline chloride is used as a clinical anti-fatty liver agent for treating fatty liver, cirrhosis, hepatitis, liver function degradation, and pernicious anemia. It acts as a choleretic, lipotropic, and hepatoprotectant.
Used in Tissue Culture and Research:
Choline chloride is used in tissue culture media and as a component of various buffers and solutions for research purposes, such as choline acetyltransferase (ChAT) buffer, choline uptake in cultured human neuroblastoma (SK-N-SH) cells, choline standard curve generation for quantifying phospholipase D (PLD) activity, and as a component of slice solution for the dissection of entorhinal-hippocampal brain slices.
Used in Pig and Poultry Feed Industry:
Choline chloride is used in pig and poultry feed as a nourishment provider and a food flavor enhancer. It also acts as a precursor of acetylcholine and is a methyl donor in various metabolic processes and lipid metabolism.
Chemical Properties:
Choline chloride is a white, odorless, hygroscopic crystal with a fish stench. It has a melting point of 240°C and a pH of 5-6 in its 10% aqueous solution. It is unstable in alkaline solutions but easily soluble in water and ethanol, while being insoluble in ether, petroleum ether, benzene, and carbon disulfide. Choline chloride has low toxicity, with an LD50 (rat, oral) of 3400 mg/kg.
B vitamins
Choline is an indispensible fundamental component in humans and animal body, often referred to as B vitamins or vitamin B4, and is a necessary low-molecule organic compound for maintaining physiological function off animal body. It can be synthesized inside animal body but still often need to be supplied to dietary and is a kind of vitamin in maximal usage amount. Inside animal cells, it can be used to adjust the in vivo metabolism and conversion of fats, preventing the fat deposition and tissue degeneration of liver and kidney, and then promote the regeneration of amino acids, enhance utilization of amino acids as well as save some part of methionine.
Choline chloride is the most commonly used as well as most economical form of synthetic choline and is a water soluble vitamin, and is the component for constituting of acetylcholine, lecithin, and nerve phospholipids of biological tissue. Moreover, it can save methionine and is an important material required for livestock, poultry, and fish. Inside animal body, it can be used for adjusting in vivo metabolism and conversion of fats and can prevent the deposition in liver and related tissue degeneration. As a methyl donor, it can promote the re-formation of amino acids and improve the utilization of amino acids. It is mainly used as an additive for being mixing into the animal feed. During the exact usage process, in addition to prevent moisture deliquescence, you should also note that all kind of feeds usually take the addition of choline chloride as the last step. Because of its destruction effects on other vitamins, especially its rapid destruction on vitamin A, D, K in the presence of metal elements, multi-dimensional formulation should not include choline. Daily feed supplied with it should be used as soon as possible after the addition. Tests have showed that choline chloride is especially important for chicken poultry. Its synthetic amino acids and lecithin can be delivered to various locations inside chicken bodies, being able to prevent the fat deposition in the liver and kidney and accelerate the growth of chickens and increase egg production and hatchability.
The above information is edited by the lookchem of Dai Xiongfeng.
Content Analysis
Accurately weigh sample of about 300 mg and put it into 250 ml Erlenmeyer flask; add 50 ml of glacial acetic acid and heated on a steam bath until complete dissolving. After cooling, add 10 ml of mercury acetic acid mercury test solution (TS-137) and 2 drops of gentian violet reagent; use the acetic acid solution of 0.1 mol/L perchloric acid for titration to green endpoint. At the same time carry out a blank test and make necessary calibration. Each Ml of 0.1mol/L perchloric acid is equivalent to 13.96 mg of choline chloride (C5 H14ClNO).
Toxicity
ADI does not make restrictive regulations (FAO/WHO, 2001).
GRAS (FDA, §182.5252, §182.8252, 2000);
LD50: 9000mg/kg (rat, oral).
Limited use
GMP limit (FDA§182.5252.2000);
Production method
(1) Continuous method for preparation of choline chloride solution: continuously send the trimethylamine hydrochloride and a certain amount of ethylene oxide separately through pump into the reactor; the reactants had a residence time at the reactor of 1-1.5h; the reaction was carried out under stirring and has its resulting product being continuously withdrawn so that the liquid level within the reactor remained stable. The withdrawn choline chloride extraction crude product entered into the stripper to obtain 60-80% choline chloride liquid product from the bottom.
(2) Trimethylamine hydrochloride was reacted with ethylene oxide, and then added with an organic acid for neutralization and further concentration to obtain the choline chloride (3) Chloro-ethanol was reacted with trimethylamine to generate choline chloride.
(3)Ethylene oxide method. It can be made from the reaction between ethylene oxide and trimethylamine.
Add the trimethylamine ethanol solution into the reactor, send through ethylene oxide at about 30 ℃ and stirring reaction of 4 hour and further obtain it through neutralization with hydrochloric acid (control PH at 6.5-7.0). The yield of the crude product can be as high as 98%. The crude product can further be subject to activated carbon decolorizing and vacuum concentration to obtain 70% aqueous solution. The aqueous solution was added with ground corn cobs, rice hull flour, wheat bran or diatomaceous earth and some other kinds of excipients and can give 50% of the powder.
(4) Chlorohydrin method. Use chlorohydrin to substitute ethylene oxide and hydrochloric acid; have it reacted with trimethylamine in the presence of a small amount of ethylene oxide or alkaline substance;
First add 100 parts of chlorohydrin into the reaction vessel, further add 130 parts of trimethylamine from the liquid surface, while supplying 1.7 parts of ethylene oxide to trigger the reaction. After the addition, stir at 32-38 ℃ for 4h with the yield being 84% (calculated from chlorohydrin). For example, if catalyzed with an alkaline substance (such as quaternary ammonium salts), the one-way conversion rate can reach over 97%.
Trimethylamine methanol solution and chlorohydrin is subject to heating reaction, concentration under reduced pressure, and re-crystallization to generate it.
Reactivity Profile
An acidic organic salt. Materials in this group are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible. Many of these compounds catalyze organic reactions.
Fire Hazard
Choline chloride is relatively nonflammable.
Biochem/physiol Actions
The enzymatic activities of butyrylcholinesterase (BChE) and paraoxonase 1 (PON1), two serum enzymes synthesized by the liver and related with inflammation, were decreased in a sepsis animal model injected with LPS. Choline chloride administered intravenously at 20 mg/kg body weight prevents the LPS-mediated decreases in the activities of these two enzymes .
Safety Profile
Poison by
intraperitoneal and intravenous routes.
Moderately toxic experimentally by ingestion
and subcutaneous routes. Mutation data
reported. A lipotropic agent which induces
the reduction in fats contained in the liver.
When heated to decomposition it emits
toxic fumes of Cl-, SOx and NOx. See also
CHOLINE.
Purification Methods
Extremely deliquescent. Check purity by AgNO3 titration or by titration of OH-base after passage through an anion-exchange column. Crystallise it from absolute EtOH, or EtOH/Et2O, dry it under vacuum and store it in a vacuum desiccator over P2O5 or Mg(ClO4)2. [Beilstein 4 IV 1443.]
Check Digit Verification of cas no
The CAS Registry Mumber 67-48-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 7 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 67-48:
(4*6)+(3*7)+(2*4)+(1*8)=61
61 % 10 = 1
So 67-48-1 is a valid CAS Registry Number.
InChI:InChI=1/C5H14NO.2ClH/c1-6(2,3)4-5-7;;/h7H,4-5H2,1-3H3;2*1H/q+1;;/p-1
67-48-1Relevant articles and documents
Preparation and Characterization of Cleavable Surfactants Based on a Silicon-Oxygen Bond
Jaeger, David A.,Ward, Mary Darlene,Dutta, Aloke K.
, p. 1577 - 1580 (1988)
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Cleaner enzymatic production of biodiesel with easy separation procedures triggered by a biocompatible hydrophilic ionic liquid
Chen, Qianhan,Cheng, Shuang,Fan, Dongshuang,Feng, Wanlu,Guo, Yuanyang,Li, Lingjun,Li, Zhiyong,Wang, Jianji,Zhu, Anlian
, p. 1944 - 1951 (2020/04/09)
The great challenges of modern industry and the environment make it important to develop sustainable energy resources with low cost. In this work, a cleaner enzymatic procedure for biodiesel production was developed through the utilization of a biocompatible and hydrophilic ionic liquid [Choline][H2PO4]. This ionic liquid can be synthesized from cheap raw materials through simple neutralization procedures, and it has been proved to be well biocompatible. The utilization of this ionic liquid in Novozym 435 catalyzed biodiesel production makes the reaction and work-up procedures very simple, because its hydrophilicity can lead to the implementation of a pseudo homogeneous reaction and then heterogeneous separation. Various oil resources such as triolein, sunflower oil and castor oil can all be converted to biodiesels with high yields. After the completion of reaction, both the ionic liquid and Novozym 435 can be recycled and reutilized for at least five cycles without a significant activity decrease. In addition, this reaction system can be conveniently scaled up to the multi-gram level with high efficiency and feasible separation. Overall, the above mentioned benefits make this ionic liquid based enzymatic system cleaner for the production of biodiesel and promising for further industrial applications.
Highly luminescent and multi-sensing aggregates co-assembled from Eu-containing polyoxometalate and an enzyme-responsive surfactant in water
Lei, Nana,Shen, Dazhong,Chen, Xiao
, p. 399 - 407 (2019/01/24)
Hybrid co-assembly of polyoxometalates (POMs) with cationic organic matrices offers a preferable way to greatly enhance POM functionality as well as processability. Thus, multi-stimulus responsive supramolecular materials based on lanthanide-containing POMs with improved luminescence may be fabricated from appropriate components through this convenient strategy. Herein, we reported that the co-assembly of Na9(EuW10O36)·32H2O (EuW10) and a commercially available cationic surfactant, myristoylcholine chloride (Myr), in water could produce enhanced red-emitting luminescent aggregates, with their photophysical properties highly dependent on the molar ratio (R) between Myr and EuW10. The R of 36 was finally selected owing to the displayed superior luminescence intensity and good aggregate stability. The Myr/EuW10 hybrids induced by electrostatic and hydrophobic forces presented practically as multilamellar spheres with diameters varying from 80 to 300 nm. Compared to an aqueous solution of EuW10 nanoclusters, a 12-fold increase in absolute luminescence quantum yield (～23.3%) was observed for the hybrid spheres, which was ascribed to the efficient shielding of water molecules. An unusual aggregation arrangement mechanism and the excellent photophysical properties of these aggregates were thoroughly investigated. Both the enzyme substrate character of Myr and the sensitive coordination structure of EuW10 to the surrounding environment made Myr/EuW10 aggregates exhibit multi-stimulus responsiveness to enzymes, pH, and transition metal ions, thus providing potential applications in fluorescence sensing, targeted-release, and optoelectronics.
