107-43-7 Usage
Physical and Chemical Properties
Betaine is also known as trimethylamine, and is the quaternary ammonium derivatives of glycine and a class of N-methyl-compound or trimethyl inner salt after the hydrogen of the amino group being substituted by the methyl group. Common kinds include glycyl betaine, β-alanyl-betaine and prolyl-betaine. We can obtain prismatic crystals or leaf-shaped crystals from ethanol, is sweet taste, and deliquescent. Melting point: 293 °C; it will decomposed at 300 °C. It is soluble in water, methanol and ethanol, but insoluble in ether, and can be isomerized into dimethylamino methyl acetate at the melting point. We can obtain its monohydrate crystal from the aqueous solution of the free acid HO-N (CH3) 3-CH2COOH which generates betaine upon dehydration at 100 °C, and is stable in acid. It can obtain trimethylamine upon reaction with concentrated aqueous potassium hydroxide and can have Maillard reaction with sugar (browning reaction). It is presented in plant such as cottonseed and beetroot as well as in animal substance such as barbed shark meat and crab refined juice. It can be recycled from the mother liquor of beet sugar. It may also be obtained from the methylation reaction of amino acetate or the reaction between chloroacetate with trimethylamine. Clinically it is used in combination with N-amidino glycine for treatment of myasthenia gravis. In analytic chemistry, it can also be used as the reagent for identifying gold. This product is the amphoteric surfactants of betaine used as a leveling agent for vat dyes dying. Drought or salt stress, many plants can accumulate betaine inside their body and become a major organic solutes for osmotic adjustment and have a further protective effect on cell membrane and cellular proteins.
The above information is edited by the lookchem of Dai Xiongfeng.
Feed additives
Betaine is a natural compound, and belonging to a kind of quaternary ammonium alkaloids. The name of this substance is because of that it is first extracted from sugar beet. It has been over 50 years since it has been used as a feed additive. It has attracted much attention due to its important of in protein metabolism and lipid metabolism of animals, and has been widely applied. Adding to the chicken feed can increase the amount of broiler carcass quality and chest quantity and also improve the food palatability and utilization rate. Increased feed intake and daily gain is the main component of palatability of aquatic attractant. It can also improve the feed rate of piglet, and thus promoting its growth. It has another important feature as a kind of osmotic pressure regulator which can alleviate the stress of gastrointestinal and increase the viability of juvenile shrimp and fish seedlings under the variation of various stress conditions, such as: cold, heat, disease, and weaning in living conditions. Betaine has a protective effect on the stability of VA and VB and can further improve their application efficacy without having the irritation effect of betaine hydrochloride at the same time.
Efficient active methyl donor
Betaine is widely presented in plants and animals with beet containing the highest content among plants. In animal body, betaine is acted as a highly active methyl donor which plays a important role in regulating the metabolism of methyl group, and can partially substitute the methionine and choline, and thus promoting fat metabolism, improving feed palatability, alleviating heat stress, regulating the osmotic pressure of the body, and maintaining the stability of the vitamin premix for improving farming efficiency.
Inside animal bodies, betaine provide methyl group to cysteine, generating methionine which is further converted into S-adenosine methionine, and further transferring methyl group then to DNA, RNA, protein, creatine, lipids and other important methyl-containing ingredients. Methyl group is very unstable and can’t be synthesized by animals themselves but can only rely on food supply. The efficiency of betaine of providing methyl group is 1.2 times as high as choline chloride, and 3.8 times as high as methionine. Choline itself can’t act as a methyl donor which must be first transported to the mitochondria for oxidation into betaine and finally released into the cytoplasm before being able to act as a methyl donor. Studies have shown: Adding 1.25 kg of this product at per ton of pig feed has no effect on growth, development and feed efficiency, but causing 15% decrease in back fat content and increasing the tenderloin quantity in cross-sectional area, improving carcass meat; adding betaine to chicken feed can reduce the necessary amount of dietary methionine. During the initial phase of broiler feed, adding 750 g of betaine pre ton of feed can substitute 1.5 kg of methionine, and adding 450 g of betaine can substitute 1 kg of methionine during the latter phase. Betaine also has effects on prevention and treatment of fatty liver of pigs, chickens and fish.
Chemical Properties
Different sources of media describe the Chemical Properties of 107-43-7 differently. You can refer to the following data:
1. It is colorless crystals or white crystalline powder, odorless, and has a sweet taste. Melting point: 293 °C (decomposition). It is highly deliquescent. 1g of this product can be dissolved in 0.63 g of water, 1.8g of methanol, and 11.5g of ethanol. It is slightly soluble in ether. Concentrated alkaline can lead to its decomposition and release of trimethylamine. Male rats: orally LD50:11.2g/kg, female rats by oral LD50:11.15g/kg.
2. White crystalline powder; bland aroma.
3. White cryst. powder
Uses
Different sources of media describe the Uses of 107-43-7 differently. You can refer to the following data:
1. 1. Adding betaine to the feed has protective effects on the vitamins contained in the feed, also makes feed be tolerable to high temperature and can subject to long-term storage, and thus greatly improving feed utilization rate as well as reducing the costs. Adding 0.05% betaine to the chicken feed can substitute 0.1% methionine; adding betaine to the bait have palatability effect on both fishes and shrimp, thus betaine can be used as the swelling agent of aquatic product in large amount. Adding betaine to the pig feed added betaine can increase the appetite of pigs and increase the rate of lean meat. 1kg Betaine is equivalent to 3.5kg of methionine. The ability to provide methyl of betaine is 1.2 times as strong as that of choline chloride, and 3.8 times as strong as that of methionine with a very significant feed efficiency.
2. It is used as betaine type amphoteric surfactants, also used as leveling agent of dye vat dyes.
3. It can be used as feed grade anhydrous betaine for being as a feed additive. It is a natural and efficient methyl donor which can partially substitute methionine and choline chloride, lower the feed costs, reduce back-fat of pig, and increase the rate lean meat and carcass quality.
4. It can be used for lowering blood pressure, anti-fatty liver and anti-aging.
5. It can be used as a feed additive for promoting animal growth and increased disease resistance.
2. Betaine has been used to study the effects of antioxidants on regrowth from cryopreservation.
3. Betaine is an active ingredient in toothpaste to control the symptoms of dryness of the mouth. It is used to treat homocystinuria, which is a defect in the major pathway of methionine biosynthesis. It is also used for boosting the immune system and for improving athletic performance. It is helpful to prevent noncancerous tumors in the colon (colorectal adenomas).
4. betaine is a surfactant, humectant, and excellent skin conditioner. It is also used to build product viscosity and as a foam booster. It is found mostly in skin cleansers, shampoos, and bath products.
Production method
It is recycled from beet sugar mother liquor, and can also be used for synthetic production.
1. Extraction method. The mother liquor of beet sugar contains 12%-15% of the betaine, which can directly used for recycle. Heat 300 parts of the mother liquor to 50 °C, add 80 parts of calcium chloride, stir and filter while hot for a certain time. The filtrate was acidified with hydrochloric acid after cooling for crystallization at 20-30 °C, after separation, dry to obtain 30 parts of betaine.
2. Synthesis method through the quaternization between chloroacetate and trimethylamine.
Use 16% sodium hydroxide solution for neutralization of 195 parts of 48.6% aqueous solution of chloroacetate into sodium chloroacetate and then mix with 360 parts of 16.4% trimethylamine for ventilation at 50 °C for 1h, then ventilate at 80 °C for 1 h. The reaction was diluted and further adhered by ion exchange resin (Dowex-50-8) with ammonia elution to obtain the betaine solution. It further undergoes vacuum concentration and crystallization to obtain the final product.
Definition
ChEBI: The amino acid betaine derived from glycine.
General Description
Betaine also called trimethylglycine or N,N,N triethylammonium acetate, is an analog of glycine with three methyl groups. It is highly compatible with polymerase chain reaction (PCR) buffer mixture. Betaine is a PCR enhancing reagent that is widely used for improving the yield and specificity of PCR products, especially during the PCR amplification of targets rich in GC content or those that form secondary structures resulting in poor yield. Betaine facilitates DNA strand separation and manages the DNA melting temperature (Tm) difference between the GC and AT pairs in DNA. It stabilizes the ds DNA by equalizing the contribution of GC- and AT-base pairs. Betaine has been broadly used to optimize multiplex and ‘long and accurate′ polymerase chain reaction (LA-PCR). The addition of 1.0-1.7 M aqueous betaine to a PCR mixture has been reported to reduce the base pair composition dependence on DNA strand melting.
Flammability and Explosibility
Nonflammable
Biochem/physiol Actions
End-product of oxidative metabolism of choline, betaine is a general methyl donor, in particular in a minor pathway of methionine biosynthesis. It is used to treat homocystinuria, which is a defect in the major pathway of methionine biosynthesis.
Purification Methods
Crystallise betaine from aqueous EtOH or EtOH/Et2O. The monohydrate loses H2O above 100o. Betaine undergoes internal alkylation to methyl dimethylaminoacetate Purification of Biochemicals — Amino Acids and Peptides above its melting point. It is also prepared by treating the hydrochloride (below) with silver oxide and recrystallising from EtOH/Et2O. [Edsall J Am Chem Soc 66 1767 1943, Leifer & Lippincott J Am Chem Soc 79 5098 1957, for pK see Grob et al. Chem and Ind (London) 1222 1955, Beilstein 4 III 1127, 4 IV 2369.]
Check Digit Verification of cas no
The CAS Registry Mumber 107-43-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 7 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 107-43:
(5*1)+(4*0)+(3*7)+(2*4)+(1*3)=37
37 % 10 = 7
So 107-43-7 is a valid CAS Registry Number.
InChI:InChI:1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
107-43-7Relevant articles and documents
A New Microbial Pathway for Organophosphonate Degradation Catalyzed by Two Previously Misannotated Non-Heme-Iron Oxygenases
Rajakovich, Lauren J.,Pandelia, Maria-Eirini,Mitchell, Andrew J.,Chang, Wei-Chen,Zhang, Bo,Boal, Amie K.,Krebs, Carsten,Bollinger, J. Martin
, p. 1627 - 1647 (2019)
The assignment of biochemical functions to hypothetical proteins is challenged by functional diversification within many protein structural superfamilies. This diversification, which is particularly common for metalloenzymes, renders functional annotations that are founded solely on sequence and domain similarities unreliable and often erroneous. Definitive biochemical characterization to delineate functional subgroups within these superfamilies will aid in improving bioinformatic approaches for functional annotation. We describe here the structural and functional characterization of two non-heme-iron oxygenases, TmpA and TmpB, which are encoded by a genomically clustered pair of genes found in more than 350 species of bacteria. TmpA and TmpB are functional homologues of a pair of enzymes (PhnY and PhnZ) that degrade 2-aminoethylphosphonate but instead act on its naturally occurring, quaternary ammonium analogue, 2-(trimethylammonio)ethylphosphonate (TMAEP). TmpA, an iron(II)- and 2-(oxo)glutarate-dependent oxygenase misannotated as a γ-butyrobetaine (γbb) hydroxylase, shows no activity toward γbb but efficiently hydroxylates TMAEP. The product, (R)-1-hydroxy-2-(trimethylammonio)ethylphosphonate [(R)-OH-TMAEP], then serves as the substrate for the second enzyme, TmpB. By contrast to its purported phosphohydrolytic activity, TmpB is an HD-domain oxygenase that uses a mixed-valent diiron cofactor to enact oxidative cleavage of the C-P bond of its substrate, yielding glycine betaine and phosphate. The high specificities of TmpA and TmpB for their N-trimethylated substrates suggest that they have evolved specifically to degrade TMAEP, which was not previously known to be subject to microbial catabolism. This study thus adds to the growing list of known pathways through which microbes break down organophosphonates to harvest phosphorus, carbon, and nitrogen in nutrient-limited niches.
Purification and characterization of an alkaliphilic choline oxidase of fusarium oxysporum
Enokibara, Shogo
, p. 2219 - 2224 (2012)
A novel choline oxidase found in a fungus, Fusarium oxysporum strain V2, was purified to homogeneity as determined by sodium dodecyl sulfate polyacrylamide gel electrophoresis. The enzyme has a molecular mass of 128 kDa and consists of two identical subunits. The purified enzyme showed adsorption peaks at 340nm and 450 nm. It showed alkaliphilic pH characteristics: its optimum pH was 9.0-10.0, and it was stable at pH 8.0- 10.2. The Michaelis constant (Km) values for choline and betaine aldehyde were 0.28mM and 0.39mM respectively. Trimethylamino-alcohols, dimethylaminoalcohols, and diethylaminoethanol were substrates for the enzyme, but the Km values for them increased with decreasing numbers of methyl groups on the ammonium headgroup. A marked decrease in the maximum velocity (Vmax) and Vmax/Km values was observed when Nreplaced choline analogs were used as substrate instead of choline. The enzyme had a remarkably higher affinity for choline and betaine aldehyde than do previously reported enzymes. The enzyme oxidized these two substrates more quickly than a choline oxidase from Arthrobacter globiformis, and oxidation by the V2 enzyme was accompanied by an increase in the stoichometric amount of hydrogen peroxide.
Oxygen- and temperature-dependent kinetic isotope effects in choline oxidase: Correlating reversible hydride transfer with environmentally enhanced tunneling
Fant, Fan,Gadda, Giovanni
, p. 17954 - 17961 (2005)
Choline oxidase catalyzes the flavin-linked oxidation of choline to glycine betaine, with betaine aldehyde as intermediate and oxygen as electron acceptor. Here, the effects of oxygen concentration and temperature on the kinetic isotope effects with deuterated choline have been investigated. The D(kcat/Km) and D/kcat values with 1,2-[2H4]-choline were pH-independent at saturating oxygen concentrations, whereas they decreased at high pH to limiting values that depended on oxygen concentration at ≤0.97 mM oxygen. The k cat/Km and kcat pH profiles had similar patterns reaching plateaus at high pH. Both the limiting kcat/K m at high pH and the pKa values were perturbed to lower values with choline and ≤0.25 mM oxygen. These data suggest that oxygen availability modulates whether the reduced enzyme-betaine aldehyde complex partitions forward to catalysis rather then reverting to the oxidized enzyme-choline alkoxide species. At saturating oxygen concentrations, the D(kcat/Km) was 10.6 ± 0.6 and temperature independent, and the isotope effect on the preexponential factors (AH′/AD′) was 14 ± 3, ruling out a classical over-the-barrier behavior for hydride transfer. Similar enthalpies of activation (ΔH?) with values of 18 ± 2 and 18 ± 5 kJ mol-1 were determined with choline and 1,2-[2H 4]-choline. These data suggest that the hydride transfer reaction in which choline is oxidized by choline oxidase occurs quantum mechanically within a preorganized active site, with the reactive configuration for hydride tunneling being minimally affected by environmental vibrations of the reaction coordinate other than those affecting the distance between the donor and acceptor of the hydride.
Micellar Effects upon the Reaction of Betaine Esters with Hydroxide Ion
Al-Lohedan, Hamad,Bunton, Clifford A.,Romsted, Laurence S.
, p. 2123 - 2129 (1981)
The reaction of hydroxide ion with methyl N,N,N-trimethylglycinate (1a) is inhibited by cationic micelles of C14H29NMe3Cl and C16H33NMe3Cl (MTACl and CTACl) besause the substrate is largely in the aqueous pseudophase which is depleted in OH- by the cationic micelles.Added Cl- displaces OH- from the micelles and decreases micellar inhibition.The corresponding reaction of methyl N-dodecyl-N,N-dimethylglycinate (1b) is catalyzed by both MTACl and CTACl which bind both reactants, but this catalysis is reduced by NaCl.Self-micellization of methyl N-hexadecyl-N,N-dimethylglycinate (1c) speeds reaction with OH-, and the rate constants reach plateau values with increasing substrate concentration and are independent of OH-.But addition of either CTACl or NaCl slows reaction because Cl- displaces OH- from the micelle.These diverse rate effents can be accounted for quantitatively in terms of the pseudophase ion-exchange model, which considers reactions in both the aqueous and micellar pseudophases and the distribution of both reactants between the pseudophases.
Chapman,D. et al.
, p. 3645 - 3658 (1963)
A label-free silicon quantum dots-based photoluminescence sensor for ultrasensitive detection of pesticides
Yi, Yinhui,Zhu, Gangbing,Liu, Chang,Huang, Yan,Zhang, Youyu,Li, Haitao,Zhao, Jiangna,Yao, Shouzhuo
, p. 11464 - 11470 (2013)
Sensitive, rapid, and simple detection methods for the screening of extensively used organophosphorus pesticides and highly toxic nerve agents are in urgent demand. A novel label-free silicon quantum dots (SiQDs)-based sensor was designed for ultrasensitive detection of pesticides. This sensing strategy involves the reaction of acetylcholine chloride (ACh) with acetylcholinesterase (AChE) to form choline that is in turn catalytically oxidized by choline oxidase (ChOx) to produce betaine and H2O2 which can quench the photoluminescence (PL) of SiQDs. Upon the addition of pesticides, the activity of AChE is inhibited, leading to the decrease of the generated H 2O2, and hence the PL of SiQDs increases. By measuring the increase in SiQDs PL, the inhibition efficiency of pesticide to AChE activity was evaluated. It was found that the inhibition efficiency was linearly dependent on the logarithm of the pesticides concentration. Consequently, pesticides, such as carbaryl, parathion, diazinon, and phorate, were determined with the SiQDs PL sensing method. The lowest detectable concentrations for carbaryl, parathion, diazinon, and phorate reached 7.25 × 10-9, 3.25 × 10-8, 6.76 × 10-8, and 1.9 × 10-7 g/L, respectively, which were much lower than those previously reported. The detecting results of pesticide residues in food samples via this method agree well with those from high-performance liquid chromatography. The simple strategy reported here should be suitable for on-site pesticides detection, especially in combination with other portable platforms.
The preparation of free betaines by use of ion exchange resins
Utsunomiya
, p. 1422 - 1424 (1967)
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Tissue metabolomic profiling to reveal the therapeutic mechanism of reduning injection on LPS-induced acute lung injury rats
Xiong, Zhili,Weng, Yanmin,Lang, Lang,Ma, Shuping,Zhao, Longshan,Xiao, Wei,Wang, Yanjuan
, p. 10023 - 10031 (2018/03/23)
Acute lung injury (ALI) is a severe respiratory disease. To date, no medical interventions have been proven effective in improving the outcome. Reduning injection (RDN) showed a potential effect in the therapy of ALI. However, seldom does research concern the holistic pharmacological mechanisms of RDN on ALI. A metabolomic strategy, based on two consecutive extractions of the lung tissue, has been developed to investigate therapeutic mechanisms of RDN on ALI model rat. The extraction procedure was an aqueous extraction with methanol-water followed by organic extraction with dichloromethane-methanol. According to the lipophilicity of extracts, aqueous extracts were analyzed on the T3 column and organic extracts on the C18 column. Partial least-squares discriminant analysis was utilized to identify differences in metabolic profiles of rats. A total of 14 potential biomarkers in lung tissue were identified, which mainly related to phospholipid metabolism, sphingolipid metabolism, nucleotide metabolism and energy metabolism. The combined analytical method provides complementary metabolomics information for exploring the action mechanism of RDN against ALI. And the obtained results indicate metabolomics is a promising tool for understanding the holism and synergism of traditional Chinese medicine.
