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| L-Valine Basic information |
| Amino acids The main effect of feed additives Content Analysis Toxicity Maximum level Chemical propertyApplications Synthetic method |
| Product Name: | L-Valine |
| Synonyms: | (S)-(+)-VALINE;(S)-ALPHA-AMINOISOVALERIC ACID;VALINE, L-;VALINE;2-AMINO-3-METHYLBUTANOIC ACID;2-AMINOISOVALERIC ACID;H-VAL-OH;H-L-VAL-OH |
| CAS: | 72-18-4 |
| MF: | C5H11NO2 |
| MW: | 117.15 |
| EINECS: | 200-773-6 |
| Product Categories: | Amino Acids;Amino Acid Derivatives;Valine [Val, V];Amino Acids and Derivatives;alpha-Amino Acids;Biochemistry;Nutritional Supplements;Amino Acids;amino |
| Mol File: | 72-18-4.mol |
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| L-Valine Chemical Properties |
| mp | 295-300 °C (subl.)(lit.) |
| alpha | 28 º (c=8, 6N HCl) |
| density | 1.23 |
| refractive index | 28 ° (C=8, HCl) |
| storage temp. | Store at RT. |
| solubility | H2O: 25 mg/mL |
| form | powder |
| Water Solubility | 85 g/L (20 ºC) |
| Merck | 14,9909 |
| BRN | 1721136 |
| CAS DataBase Reference | 72-18-4(CAS DataBase Reference) |
| NIST Chemistry Reference | Valine(72-18-4) |
| Safety Information |
| Hazard Codes | Xn |
| Risk Statements | 40 |
| Safety Statements | 24/25-36-22 |
| WGK Germany | 3 |
| RTECS | YV9361000 |
| HS Code | 29224995 |
| MSDS Information |
| Provider | Language |
|---|---|
| 2-Aminoisovaleric acid | English |
| SigmaAldrich | English |
| ACROS | English |
| ALFA | English |
| L-Valine Usage And Synthesis |
| Amino acids |
L-Valine is a kind of branched-chain amino acids (BCAA). Animal cannot synthesize it by itself. It must be obtained from the diet to meet their nutritional needs. Therefore L-valine belongs to the essential amino acids. Amino acids are the basic structural unit of protein synthesis, and the predecessor of other amines that metabolism needs. They are indispensable materials in our life. At present, it is known that there are 20 to 30 amino acids. Some of them can be synthesized in the human body, which are known as non-essential amino acids. And some, called essential amino acids, cannot be synthesized in the human body that should be supplemented from the outside. Mammal cells need twelve essential amino acids: L-arginine, L-cystine, L-histidine, L-leucine, L-isoleucine, L-lysine, L-methionine, L-phenylalanine, L-threonine, L-tryptophan, L-tyrosine, L-valine. These amino acids are all laevoisomer, and some non-essential amino acids of dextroisomer may have inhibitory effect on cultured cells. L-amino acids can easier to be absorbed than D-amino acids. And the absorption of D, L-methionine has no difference. There is competition between the body transport of amino acids. The transporting of an amino acid can be suppressed by the presence of another amino acid. For example, L-valine and L-methionine can inhibit the absorption of L-leucine. Excessive lysine in dietary can inhibit the absorption of arginine. High concentration (100mM) of L-valine has no effect on the absorption of L-methionine. Because it can be transported through another route. |
| The main effect of feed additives |
1. L- Valine added in lactating sows diets can increase milk yield. Its mechanism is that valine can affect the synthesis of alanine and release of muscle. Valine added in lactating sows diets can elevate the content of alanine in the plasma to accommodate breast tissue demand for glucose raw materials. Then milk yield can be improved. Valine is very important for the production and development of breast. And valine is limiting amino acid of lactating sows protein diets. Valine deficiency can reduce the effect of lysine. Although that adding lysine into lactation pig feed can improve the quality of dietary protein. But it can also result in the lack of valine, thereby affect sow milk yield and piglet weight gain. When the concentration of lysine is at higher level, valine will be the first limiting amino acid. 2. L-Valine can improve animals’ immune function. Valine can promote animal bone cells into mature T cells. Valine deficiency can lower levels of complement C3 and transferrin. It can hinder the growth of the thymus and peripheral lymphoid tissues, and inhibit the growth of acidic and neutral cell. When weaned lack valine, it will cause a decline in the ability of synthesis of specific antibody. If chicks lack valine, the antibody response for newcastle disease virus reduce antibody response. 3. L-Valine can affect animal endocrine levels. Studies have shown that valine that is added in lactating sows and lactating rats diets can increase the concentration of prolactin and growth hormone in plasma. The above information is edited by the Chemicalbook of Ge Qian. |
| Content Analysis | About 200mg sample is accurately weighed, dissolved in 3ml formic acid and 50ml glacial acetic acid. Add 2 drops of crystal violet test solution (TS-74), then use 0.1mol/L perchloric acid to titrate the solution to green or blue disappear entirely. Each Ml0.1mol/L perchloric acid is equivalent to 11.72mg L-valine (C5H11NO2). |
| Toxicity |
LD50 5390mg/kg (rats, intraperitoneal injection). Safe for food (FDA, §172. 320, 2000). |
| Maximum level | Account for 7.4% of total protein in the food (FDA, §172. 320, 2000). |
| Chemical property | White crystal or crystalline powder, odorless, bitter taste. Soluble in water, solubility in water of 8.85% at 25℃. Almost insoluble in ethanol, ether, acetone. melting point(decomposition point) 315℃, isoelectric point 5.96, [α]25D+28.3 (C = 1-2g/ml, in 5mol/L HCl). |
| Applications |
1. Amino acids drugs, nutritional supplements. It can be used as the main component of aminophenol transfusion and synthesize aminophenol. L-Valine is one of the three branched-chain amino acids. It is essential amino acid. It can be used to treat liver failure and central nervous system dysfunction. 2. L-Valine is essential amino acid. The requirement for men is 10mg/(kg·d). Physiological effects of the L-form is 2 times of the D-type. L-Valine deficiency can cause neurological disorders, blastocolysis, loss of weight, anemia and the like. As nutritional supplements, it can be used to prepare aminophenol transfusion and synthesize aminophenol with other essential amino acid infusion. Valine added to metric pastry (1g/kg) can make the products aroma of sesame. L-Valine used in bread can also improve the flavor. 3. L-Valine is the essential amino acid. It can be used as one of pharmaceutical composition of amino acid infusion to synthesize drugs. It also can be used as food additives. 4. Nutritional supplements. It can be used to prepare aminophenol transfusion and synthesize aminophenol with other essential amino acid infusion.Valine added to metric pastry (1g/kg) can make the products aroma of sesame. L-Valine used in bread can also improve the flavor. 5. L-Valine can be used for biochemical research, the preparation of tissue culture media. It also used as amino acids nutritional drugs in medicine. |
| Synthetic method |
1. Using acetyl-DL-valine as raw materials refined by acylating enzyme in alkaline conditions. 2. There are many synthesis methods. One is that isobutyraldehyde reacts with ammonia to generate isobutanol amino. Then isobutanol amino reacts with hydrogen to form amino-isobutyronitrile. And then it hydrolyze L-valine. One is that isobutyraldehyde reacts with hydrogen cyanide to form hydroxy- isobutyronitrile. Then it reacts with ammonia to form amino-isobutyronitrile. Finally it hydrolyze L-valin. And the synthetic method also can be that isobutyraldehyde reacts with sodium cyanide and ammonium chloride directly synthesize amino-isobutyronitrile. And then it hydrolyze L-valin. The yield of the above three methods is 36% to 40%. The synthetic method also can be that isobutyraldehyde reacts with sodium cyanide and ammonium carbonate to form caprolactam urea. And L-valin can be obtained by hydrolysis. The yield of this method is about 49%. L-Valin obtained by the synthesis methods is racemate. It should be separated by racemic. Optical resolution has many ways, such as using enzyme of acyl -DL-amino acid to hydrolyze, and then using the solubility difference of free amino acids and acylate to separate. Fermentation. Strains are micrococcus glutamicus (Paracolabacterum coliforme), brevibacterium ammoniagenes, escherichia coli, aerobacter aerogenes. Using glucose, urea, salts and other medium to generate valine (1~1.5g/100m1). The products are all L-type, and need no optical resolution. 3. There are several ways to synthesize racemic valine when using isobutyraldehyde as raw materials. For example, isobutyraldehyde reacts with ammonia to form amino-butanol, and then with hydrogen cyanide to form amino-isobutyronitrile. Finally it hydrolyze to valine. There are many ways of resolution of raceme. such as using enzyme of acyl -DL-amino acid to hydrolyze, and then using the solubility difference of free amino acids and acylate to separate. Valine produced by fermentation are all L-type, and need no optical resolution. Strains of fermentation are micrococcus glutamicus (Paracolabacterum coliforme), brevibacterium ammoniagenes, escherichia coli, aerobacter aerogenes. Medium can be glucose, urea, inorganic salts and the like. 4. First method: chemical synthesis Isobutyraldehyde as raw material, and reacts with ammonia and hydrocyanic acid to produce α-amino-isobutyronitrile through Steck Reaction (Styecker) and then hydrolyzes to DL- valine. Finally split to L- valine. Second method: fermentation method Glucose, urea, salts [produce glycine micrococcus or brevibacterium ammoniagenes, etc.]→[fermentation] L- Valine |
| Chemical Properties | White crystalline powder |
| Usage | L-Valine is an essential amino acid and one of 20 proteinogenic amino acids. L-Valine cannot be manufactured by the body and must be acquired through diet or supplementation. L-valine is found in grai ns, dairy products, mushrooms, meats, peanuts and soy proteins. L-Valine has been used in studies to attenuate arrhythmias and induce hypotensive effects. |
| L-Valine Preparation Products And Raw materials |
| Preparation Products | (S)-(+)-2-HYDROXY-3-METHYLBUTYRIC ACID-->(S)-2-(Boc-amino)-3-methylbutyric acid |
| Raw materials | Urea-->D(+)-Glucose-->2-Methyl-1-propanol-->Isobutyraldehyde-->HYDROGEN CYANIDE-->L-Glutamic acid-->Ammonium carbonate-->Isobutyronitrile-->Hydantoin-->DL-Valine-->Valine |