(S)-(+)-2-Amino-3-methylbutyric acid
L-Valine
CAS: 72-18-4;7004-03-7
Molecular Formula: C5H11NO2
(S)-(+)-2-Amino-3-methylbutyric acid - Names and Identifiers
| Name | L-Valine |
| Synonyms | Lvaline L-Valine H-Val-OH CB4875617 DL-Aminovaleic Acid L-2-Aminoisovaleric acid 2-Amino-3-methylbutanoic acid L-2-Amino-3-methylbutyric acid (S)-(+)-2-Amino-3-methylbutyric acid L-Valine, FCC Grade L-2-Amino-3-methylbutyric acid, FCC Grade |
| CAS | 72-18-4 7004-03-7 |
| EINECS | 200-773-6 |
| InChI | InChI:1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8) |
(S)-(+)-2-Amino-3-methylbutyric acid - Physico-chemical Properties
| Molecular Formula | C5H11NO2 |
| Molar Mass | 117.147 |
| Melting Point | 315℃ |
| Boling Point | 213.6ºC at 760 mmHg |
| Specific Rotation(α) | 28 º (c=8, 6N HCl) |
| Water Solubility | 85 g/L (20℃) |
| Solubility | The solubility of 25°C in water is 8.85%, and it is almost insoluble in ethanol, ether and acetone. |
| Appearance | White crystal or crystalline powder |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.507 |
| MDL | MFCD00064220 |
| Physical and Chemical Properties | Chemical properties White crystal or crystalline powder; odorless, slightly sweet and then bitter. Easily soluble in water, almost insoluble in ethanol. The specific rotation is 26.5 ° to 29.0 °. |
| Use | It is an essential amino acid for human body. It is used as one of the amino acid infusion components in medicine, synthesizes new drugs, and can also be used as a food additive. |
(S)-(+)-2-Amino-3-methylbutyric acid - Risk and Safety
| Safety Description | S24/25 - Avoid contact with skin and eyes. |
(S)-(+)-2-Amino-3-methylbutyric acid - Upstream Downstream Industry
| Raw Materials | Dextrose Anhydrate |
| Downstream Products | L-Valine D-Valine (2S)-2-[[2-chloro-4-(trifluoromethyl)phenyl]amino]-3-methyl-butanoate |
(S)-(+)-2-Amino-3-methylbutyric acid - Nature
Open Data Verified Data
- This product is white crystal or crystalline powder; Odorless, slightly sweet and then bitter. Decomposition temperature of 315 deg C, can sublimation. Dissolved in water (8.85%,25 °c), almost insoluble in ethanol.
- L-valine is one of the three branched chain amino acids and is an essential amino acid. The first step of catabolism in the body is to convert the amino group into a-ketoisovaleric acid, and then to generate methacryloyl CoA by decarboxylation, and finally to generate succinyl CoA. It can be seen that valine is a sugar-generating amino acid. The oxidative decomposition of valine produces 32mol of ATP per mol. And leucine, isoleucine between competitive inhibition. The lack of valine in the human body will affect the growth and development of the body, causing neurological disorders, movement disorders, anemia and so on. The minimum daily requirement is 0.8G, preferably 1.6g.
Last Update：2024-01-02 23:10:35
(S)-(+)-2-Amino-3-methylbutyric acid - Preparation Method
Open Data Verified Data
- synthesis method.
- fermentation method.
Last Update：2022-01-01 11:10:17
(S)-(+)-2-Amino-3-methylbutyric acid - Use
Open Data Verified Data
amino acid drugs. Nutritional supplements can be used as the main components of amino acid infusion and comprehensive amino acid preparation.
Last Update：2022-01-01 11:10:18
(S)-(+)-2-Amino-3-methylbutyric acid - Safety
Open Data Verified Data
light shielding, closed storage.
Last Update：2022-01-01 11:10:18
(S)-(+)-2-Amino-3-methylbutyric acid - Use
- is an essential amino acid. Adult men need 10mg/(kg d). The physiological effect of the L-form is twice that of the D-form. Such as the lack can cause neurological disorders, stop development, weight loss, anemia and so on. As a nutritional supplement, amino acid infusion and comprehensive amino acid preparation can be formulated together with other essential amino acids. Rice cake added valine (1 g/kg), the product has sesame flavor, used in bread can also improve the flavor.
- amino acid drugs. Nutritional supplements can be used as the main components of amino acid infusion and comprehensive amino acid preparation.
L-valine is one of the branched chain amino acids (BCAA), which cannot be synthesized by the animal body itself and must be ingested from the diet to meet its nutritional needs. Therefore, it is an essential amino acid.
Amino acid is the basic structural unit of protein synthesis, the precursor of other amines required for metabolism, and is an indispensable substance for life. At present, there are 20 to 30 kinds of amino acids, some of which can be synthesized in the human body, called non-essential amino acids, and some cannot be synthesized in the human body, and must be supplemented from the outside, called essential amino acids, mammalian cells require 12 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 levorotatory isomers, while the dextrorotatory isomers of some non-essential amino acids may have an inhibitory effect on cultured cells.
L-type amino acids are easier to absorb than D-type amino acids, while there is no difference in the absorption of D and L-methionine. The body competes for the delivery of amino acids, and the delivery of one amino acid can be inhibited by the presence of another amino acid. For example, L-valine and L-methionine inhibit the absorption of L-leucine. Excessive lysine in the feed inhibits the absorption of arginine. A high concentration (100mm) of L-valine has no effect on the absorption of L-methionine, since it can be transported by another route.
Last Update：2024-04-10 22:29:15
(S)-(+)-2-Amino-3-methylbutyric acid - Synthetic Methods
- can be obtained by condensation of 2-aminothiazole with P-nitrobenzenesulfonyl chloride followed by reduction.
- The racemic valine can be synthesized by a variety of methods using isobutyraldehyde as a starting material. For example, isobutyraldehyde and ammonia produce amino isobutanol, and then with hydrogen cyanide synthesis of amino isobutyronitrile, and then hydrolysis to obtain valine, racemic resolution of this also has a variety of methods, such as using acyl-DL-amino acid enzyme hydrolysis, the free amino acid and the difference in the solubility of the acylate are used for separation. The valine produced by fermentation is L-form without optical rotation. The strains of fermentation method were Micrococcus glutamicum, short ammonia producing bacteria, Escherichia coli and Aerobacter aerogenes. With glucose, urea, inorganic salts and other media.
- fermentation method
- Tobacco: BU,22;FC,21; Synthesis: it can be obtained by hydrolysis and purification of fish protein and the like, and can also be synthesized by chemical methods.
Last Update：2024-04-10 22:29:15
(S)-(+)-2-Amino-3-methylbutyric acid - Preparation method
The chemical synthesis method is characterized by high production cost, complicated reaction, many steps, and many by-products. Using isobutyraldehyde as raw material, there are many methods to synthesize racemic valine. For example, isobutyraldehyde and ammonia form amino isobutanol, and then synthesize amino isobutanitrile with hydrogen cyanide, and then hydrolyze to obtain valine. There are also many methods for the resolution of racemic materials, such as acyl-DL-amino acid The enzyme is hydrolyzed, and then separated by the poor solubility of free amino acids and acylates.
Microbial fermentation production has the advantages of low raw material cost, mild reaction conditions and large-scale production. It is a very economical production method. Valine produced by fermentation method is L-type and does not require optical splitting. The strains of the fermentation method are Micrococcus glutamate, Brevibacterium ammonia, Escherichia coli, and Aerobacillus. Use glucose, urea, inorganic salt and other media.
Last Update：2024-04-10 22:29:15
(S)-(+)-2-Amino-3-methylbutyric acid - Essential amino acids
Valine is one of the 20 amino acids that make up proteins. Its chemical name is 2-amino-3-methylbutyric acid. It belongs to branched-chain amino acids and is also an essential 8 amino acids and sugar-producing amino acids for the human body. It works with other two high-concentration amino acids (isoleucine and leucine) to promote normal growth of the body, repair tissues, regulate blood sugar, and provide needed energy. When participating in intense physical activity, valine can provide extra energy to muscles to produce glucose to prevent muscle weakness. It also helps remove excess nitrogen (a potential toxin) from the liver and transports the nitrogen the body needs to various parts.
Valine is an essential amino acid, which means that the body itself cannot produce it and must be supplemented by dietary sources. Its natural food sources include cereals, dairy products, shiitake mushrooms, mushrooms, peanuts, soy protein and meat. In addition, D-valine is also present in some actinomycin (such as valicin). Although most people can get enough from their diet, cases of valine deficiency are also common. When valine is insufficient, the central nervous system of rats will be disturbed, ataxia and limb tremor will occur. By dissecting the brain tissue, it is found that there is red nucleus cell degeneration. Patients with advanced liver cirrhosis are prone to hyperinsulinemia due to liver function damage, resulting in a decrease in branched-chain amino acids in the blood, and the ratio of branched-chain amino acids to aromatic amino acids is changed from normal 3.0~3.5 to 1.0~1.5, so valine and other branched-chain amino acid injections are commonly used to treat liver failure and the damage.
Last Update：2024-04-10 22:29:15
(S)-(+)-2-Amino-3-methylbutyric acid - Toxicity and use limits
toxicity
LD50 5390mg/kg (rat, intraperitoneal injection).
It can be safely used in food (FDA,& sect;172.320,2000).
usage limit
7.4% by weight of the total protein in the food product (FDA,& sect;172.320,2000).
Last Update：2024-04-09 20:45:29
(S)-(+)-2-Amino-3-methylbutyric acid - Production method supplement
| the product is purified by treatment with an acylase under weak alkaline conditions using acetyl-DL-valine as a raw material. |
| There are many synthetic methods. One is from isobutyraldehyde and ammonia to produce amino isobutanol, and then with hydrogen cyanide synthesis of amino isobutyronitrile, and then hydrolyzed. One is from isobutyraldehyde and hydrogen cyanide synthesis of hydroxy isobutyronitrile, and ammonia to produce amino isobutyronitrile after hydrolysis. It can also be directly synthesized from isobutyraldehyde, sodium cyanide and ammonium chloride, and then hydrolyzed. The yield of the above three methods is 36% ~ 40%. Caprolactam can also be synthesized from isobutyraldehyde, sodium cyanide and ammonium carbonate, and then obtained by hydrolysis. The yield of this method is about 49%. The compound obtained by the synthesis method is a racemate, which must be disassembled by racemization. There are many methods for optical rotation separation, such as hydrolysis with an acyl-DL-amino acid enzyme, and separation by using the difference in solubility between the free amino acid and the acylate. Fermentation Method for the production of glutamic acid bacteria (Micrococcus glutamicus.Paracolabacterum coliforms, ammonia-producing brevibacteria, Escherichia coli, Aerobacter aerogenes, using glucose, urea, inorganic salts and other media, produced valine (1-1.5g/100 m1) is L-form, without optical rotation. |
| racemic valine can be synthesized by a variety of methods using isobutyraldehyde as a starting material. For example, isobutyraldehyde and ammonia produce amino isobutanol, and then with hydrogen cyanide synthesis of amino isobutyronitrile, and then hydrolysis to obtain valine, racemic resolution of this also has a variety of methods, such as using acyl-DL-amino acid enzyme hydrolysis, the free amino acid and the difference in the solubility of the acylate are used for separation. The valine produced by fermentation is L-form without optical rotation. The strains of fermentation method were Micrococcus glutamicum, short ammonia producing bacteria, Escherichia coli and Aerobacter aerogenes. With glucose, urea, inorganic salts and other media. |
| method I. Chemical synthesis Using isobutyraldehyde as raw material, it reacts with ammonia and hydrocyanic acid to form α-aminoisobutyronitrile, then hydrolyzes to obtain DL-valine, and then separates to obtain L-valine. Method 2. Fermentation method Glucose, urea, inorganic salt [producing amino acid Micrococcus or short ammonia producing bacteria, etc.] & rarr;[fermentation] L-valine |
Last Update：2024-04-09 21:11:58
(S)-(+)-2-Amino-3-methylbutyric acid - Use Supplement
| amino acid drugs. Nutritional supplements can be used as the main components of amino acid infusion and comprehensive amino acid preparation. L-valine is one of the three branched chain amino acids, which is an essential amino acid. It can treat liver failure and central nervous system dysfunction. |
| is an essential amino acid. Adult men need 10mg/(kg d). The physiological effect of the L-form is twice that of the D-form. Such as the lack can cause neurological disorders, stop development, weight loss, anemia and so on. As a nutritional supplement, amino acid infusion and comprehensive amino acid preparation can be formulated together with other essential amino acids. Rice cake added valine (1 g/kg), the product has sesame flavor, used in bread can also improve the flavor. |
| is an essential amino acid for human body. It is used as one of the amino acid infusion components in medicine, synthesizes new drugs, and can also be used as a food additive |
| nutritional supplements. Amino acid infusion and comprehensive amino acid preparation can be prepared together with other essential amino acids. Valine (1G,/kg) was added to the rice cake, and the product had Sesame flavor. For bread can also improve the flavor. |
Last Update：2024-04-09 21:31:46
(S)-(+)-2-Amino-3-methylbutyric acid - As a feed additive
- supplementation of L-valine in the diets of lactating sows can increase the amount of lactation. The mechanism of action is that valine can affect the synthesis of alanine and the release of muscle. Adding valine in sow diet can increase alanine in plasma to meet the demand of mammary gland tissue for glucose raw material, thereby increasing the amount of lactation. Valine is of great significance to the production and development of mammary gland, and valine is the limiting amino acid in the protein diet of lactating sows. Valine deficiency can reduce the effect of lysine, adding lysine to feed of lactating pigs can improve the quality of dietary protein, but it also causes the lack of valine, which affects the milk yield of sows and the weight gain of piglets. At higher levels of lysine, valine becomes the first limiting amino acid.
- improves the immune function of animals. Valine can promote the conversion of animal bone cells into mature T cells. Valine deficiency can reduce the levels of complement C3 and transferrin, significantly hinder the growth of thymus and peripheral lymphoid tissue, and inhibit the growth of acidic and neutral cells. The lack of valine in weaned piglets leads to a decrease in the ability to synthesize specific antibodies. The lack of valine in chicks reduced the antibody response to Newcastle disease Virus.
- affects the endocrine level of animals. Studies have shown that the addition of valine to the diets of lactating sows and lactating rats can increase the concentration of prolactin and growth hormone in plasma.
Last Update：2024-04-09 20:52:54
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Raw Materials for (S)-(+)-2-Amino-3-methylbutyric acid
Downstream Products for (S)-(+)-2-Amino-3-methylbutyric acid