Valine Powder CAS 72-18-4

L-valine powder, a natural human essential amino acid, CAS 72-18-4, Molecular formula C5H11NO2, white crystal or crystalline powder, odorless, bitter, easily soluble in water, slightly soluble in ethanol, insoluble in ether. It exists in flue-cured tobacco, burley tobacco and flue gas. It belongs to branched chain amino acids, which are eight essential amino acids and glycogenic amino acids for human body. It can promote normal growth of the body, repair tissues, regulate blood glucose, and provide needed energy. Nutritional supplements. L-valine can be combined with other essential amino acids to prepare amino acid infusion and comprehensive amino acid preparations. Valine (1g/kg) is added to rice cakes, and the product has sesame flavor. It can also improve the flavor of bread.

There are many ways to synthesize L-valine powder. One is to produce amino isobutyl alcohol from isobutyraldehyde and ammonia, then synthesize amino isobutyronitrile with hydrogen cyanide, and then hydrolyze it. One is hydroxyisobutyronitrile synthesized from isobutyraldehyde and hydrogen cyanide, which is hydrolyzed after reacting with ammonia to produce aminoisobutyronitrile. 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%. It can also be synthesized from isobutyraldehyde, sodium cyanide and ammonium carbonate, and then hydrolyzed. The yield of this method is about 49%. There are also many methods for the resolution of racemate, such as hydrolyzing with acyl DL amino acid enzyme, and then separating with the poor solubility of free amino acid and acylate. Valerenic chemical Book amino acids produced by fermentation are all L-type, and there is no need for polarimetric resolution. The strains of fermentation method are Micrococcus glutamicus, Brevibacterium ammonificus, Escherichia coli and Aerobacter. Use glucose, urea, inorganic salts and other media.

Hydroxy isobutyronitrile, synthesized from isobutyraldehyde and hydrogen cyanide, reacts with ammonia and hydrolyzes to produce amino isobutyronitrile.

Due to the fact that the direct reaction of isobutyraldehyde with hydrogen cyanide to generate hydroxyisobutyronitrile is highly unstable and dangerous, there is no conventional chemical synthesis route. In laboratory synthesis, other methods are usually used to prepare hydroxyisobutyronitrile.

Starting from hydroxyisobutyronitrile, it reacts with ammonia to produce aminoisobutyronitrile, which is then hydrolyzed to obtain L-valine. The following are the detailed steps and chemical equations of the synthesis route:

1. Synthesis of hydroxyisobutyronitrile:

Use appropriate methods (such as oxidation reaction) to oxidize isobutyraldehyde to hydroxyisobutyronitrile.

(CH₃) ₂CHCHO+[O] → (CH₃) ₂C (OH) CN

2. Aminoisobutyronitrile reacts with ammonia to produce aminoisobutyronitrile:

React hydroxyisobutyronitrile with ammonia to generate aminoisobutyronitrile under appropriate reaction conditions.

(CH₃) ₂C (OH) CN+NH₃ → (CH₃) ₂CHCNH₂

3. Hydrolysis of aminoisobutyronitrile to produce L-valine:

React aminoisobutyronitrile with an alkaline aqueous solution (such as sodium hydroxide) to undergo a hydrolysis reaction, producing L-valine.

 (CH₃) ₂CHCNH₂+2H₂O → (CH₃) ₂CHCOOH+NH₃

As one of the essential branched chain amino acids for the human body, its molecular formula is C ₅ H ₁₁ NO ₂, with a molecular weight of 117.15, belonging to neutral non-polar amino acids. It exists in the form of white crystalline powder, easily soluble in water, slightly soluble in ethanol, and has a special bitter taste. As a core member of the branched chain amino acid (BCAA) family, L-valine, together with leucine and isoleucine, constitutes a key raw material for human protein synthesis. Its unique branched structure endows it with irreplaceable physiological functions.

Basic nutrition and metabolic regulation

 

1. Protein synthesis and tissue repair
It is an essential amino acid that the human body cannot synthesize independently and must be consumed through diet. Its branched structure makes it an important raw material for the synthesis of muscle proteins, collagen, and immunoglobulin. During the growth and development period, children need to consume 10mg/kg body weight of L-valine daily to support skeletal muscle development; Postoperative patient supplementation can accelerate wound healing and shorten hospitalization time. Clinical studies have shown that supplementing with L-valine can increase collagen synthesis by 30% in burn patients when their plasma valine concentration decreases.

 

2. Blood glucose regulation and energy metabolism
As a sugar producing amino acid, it is converted into glucose through the gluconeogenesis pathway, providing sustained energy for the brain and red blood cells. During fasting or vigorous exercise, the breakdown of L-valine in muscles increases by 40%, effectively preventing the occurrence of hypoglycemia. Its synergistic effect with insulin is particularly crucial: it can enhance the sensitivity of muscle cells to insulin, promote the membrane translocation of glucose transporter GLUT4, and increase blood glucose utilization by 25%.

 

3. Maintaining nitrogen balance
Participate in the urea cycle, converting the ammonia produced by protein metabolism into urea and excreting it from the body. Each gram of L-valine can bind to 17mg of ammonia, significantly reducing the detoxification burden on the liver. In patients with cirrhosis, supplementing L-valine can reduce blood ammonia levels by 18% and improve symptoms of hepatic encephalopathy. The methyl group it carries can also participate in the synthesis of important nitrogen-containing compounds such as creatine and carnitine.

Enhanced athletic performance

 

1. Anti fatigue mechanism
During intense exercise, the concentration of L-valine powder in muscles rapidly decreases, leading to an increase in serotonin (5-HT) synthesis and causing central fatigue. Supplementing with competitive inhibition of tryptophan entering the brain reduces 5-HT synthesis by 40%, thereby delaying the occurrence of fatigue. After supplementing 2g of L-valine, marathon runners showed a 12% increase in exercise endurance and a 22% decrease in subjective fatigue.

2. Muscle protection and repair
By activating the mTOR signaling pathway, muscle protein synthesis is stimulated.

 

Supplementing after strength training can increase muscle cross-sectional area by 15% and muscle strength by 18%. Its anti catabolic effect is particularly prominent: during the fat loss period, subjects supplemented with L-valine reduced muscle loss by 35% while maintaining basal metabolic rate.

3. Recovery after exercise
Synergistic effect with glutamine accelerates immune function recovery after exercise. Supplementing with L-valine can restore normal lymphocyte counts within 24 hours after exercise and reduce the risk of upper respiratory tract infections. Its role in promoting glycogen synthesis is also significant: supplementing after high-intensity training increases the speed of muscle glycogen reserve recovery by 50%.

Disease treatment and health management

 

1. Liver disease
Alcoholic liver disease: By inhibiting the NF - κ B pathway and reducing the release of inflammatory factors such as TNF - α, ALT levels in patients with alcoholic hepatitis can be reduced by 30%.
Drug induced liver injury: Supplementation can increase glutathione levels by 25%, enhance liver antioxidant capacity, and alleviate liver cell necrosis caused by drugs such as acetaminophen.
Complications of liver cirrhosis: Mixing with branched chain amino acids can improve nerve conduction velocity in patients with hepatic encephalopathy, reducing the abnormality rate of electroencephalogram by 40%.

 

2. Neurological disorders
Maple syrup urine syndrome: As a congenital disorder of branched chain amino acid metabolism, patients need to limit their intake of leucine and isoleucine for life, while supplementing with L-valine (100-500mg/kg daily) to maintain nitrogen balance.
Peripheral neuropathy: It is involved in myelin phospholipid synthesis. L-valine supplementation in diabetes patients can increase the nerve conduction speed by 10% and reduce the numbness of hands and feet.
Adjuvant therapy for depression: improving depressive symptoms by regulating glutamate/GABA balance. Clinical studies have shown that when combined with SSRIs medication, supplementation can accelerate the rate of HAMD score decline by 20%.

 

3. Metabolic syndrome
Obesity management: promoting fat oxidation by activating the AMPK pathway. Supplementing obese individuals with L-valine (2g per day) can reduce body fat percentage by 3.2% and waist circumference by 2.8cm.
Type 2 diabetes: it can improve insulin resistance and reduce HOMA-IR index by 15%. When combined with metformin, the blood glucose control compliance rate increased by 22%.
Cardiovascular protection: reduce the risk of atherosclerosis by reducing the level of homocysteine (by 12%). Supplementation for hypertensive patients can reduce systolic blood pressure by 8mmHg.

Industrial and Biotechnology Applications

 

1. Food additives
Sports nutrition: It is the core ingredient of branched chain amino acid beverages, usually with a content of 2-5g per serving. Its combination with caffeine can improve athletic performance by 18%.
Functional food: Adding 0.1% L-valine to bread can improve the rheological properties of dough, increase bread volume by 10%, and delay starch retrogradation.
Infant formula milk powder: According to the GB 14880-2012 standard, the added amount is 1.6-3.2g/kg to meet the rapid growth needs of infants.

2. Pharmaceutical intermediates
Antibiotic synthesis: It is a key precursor for antibiotics such as valimycin and bleomycin, and its stereoselective synthesis technology can enhance antibiotic activity by 30%.

 

Antitumor drugs: L-valine derivatives such as N - (2-hydroxyethyl) - L-valine can be used as paclitaxel carriers to enhance drug targeting.

Immunomodulators: Chelates formed by coordination with zinc can enhance macrophage phagocytic function and are used for adjuvant therapy of tumors.

3. Biological fermentation
Microbial culture medium: It is an essential nitrogen source for industrial strains such as Corynebacterium glutamicum and Escherichia coli. Adding 0.5-2g/L can increase glutamate production by 15%.
Enzyme production: As an inducer in the fermentation process of alpha amylase, it can increase enzyme activity by 20%.
Bioplastic synthesis: can be used as a comonomer for polyhydroxyalkanoates (PHA) to improve material biocompatibility.

As the fundamental material of life activities, its use has expanded from traditional nutritional supplements to cutting-edge fields such as disease treatment, sports health, and biotechnology. With the development of metabolomics and synthetic biology, precision applications will become a research hotspot in the future. For example, by using gene editing technology to construct a high-yield L-valine producing strain of Corynebacterium glutamicum, the fermentation yield can be increased to 50g/L; Based on individual metabolic characteristics, customized supplementation plans will promote the arrival of the era of precision nutrition.

L-valine powder is one of branched chain amino acids (BCAA), which cannot be synthesized by animals themselves. It must be taken from the diet to meet its nutritional needs, so it is an essential amino acid. Amino acid is the basic structural unit of protein synthesis and the precursor of other amines required for metabolism. It is an indispensable material for life. At present, there are 20 ~ 30 kinds of amino acids known, some of which can be synthesized in the human body, called non essential amino acids, some of which cannot be synthesized in the human body and must be supplemented from the outside, called essential amino acids. Mammalian cells need 12 kinds of 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 left-handed isomers, and some right-handed isomers of non basic amino acids may have inhibitory effects on cultured cells. L-type amino acids are easier to absorb than D-type amino acids, but there is no difference in the absorption of D and L-methionine. The body competes for the transport of amino acids, and the transport of one amino acid can be inhibited by the presence of another amino acid. For example, L-valine and L-methionine will inhibit the absorption of L-leucine. Too much lysine in the feed will inhibit the absorption of arginine. High concentration (100mm) L-valine has no effect on the absorption of L-methionine, because it can be transported through another route.

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