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L-Valine structure

L-Valine
  • CAS：72-18-4
  • MW:117.14634
  • MF：C5H11NO2
Valine (abbreviated as Val or V) is an α-amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. L-Valine is one of 20 proteinogenic amino acids. Its codons are GUU, GUC, GUA, and GUG. This essential amino acid is classified as nonpolar. Human dietary sources are any proteinaceous foods such as meats, dairy products, soy products, beans and legumes. Along with leucine and isoleucine, valine is a branched-chain amino acid. It is named after the plant valerian. In sickle-cell disease, valine substitutes for the hydrophilic amino acid glutamic acid in hemoglobin. Because valine is hydrophobic, the hemoglobin is prone to abnormal aggregation. View more+
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1. Names and Identifiers
1.1 Name
L-Valine
1.2 Synonyms
(+)-2-Amino-3-methylbutyric acid; (2S)-2-Amino-3-methylbutanoic acid; (2S)-2-Azaniumyl-3-methylbutanoate; (S)-(+)-2-Amino-3-methylbutyric acid; (S)-2-Amino-3-methylbutanoic acid; (s)-2-amino-3-methylbutanoicacid; (S)-2-Amino-3-methylbutansαure; (S)-2-Amino-3-methylbutyric acid; (s)-2-amino-3-methylbutyricacid; (s)-alpha-amino-beta-methylbutyricacid; (S)-alpha-Aminoisovaleric acid, (L)-2-Amino-3-methylbutanoic acid; (S)-Valine; (S)-α-Amino-β-methylbutyric acid; 2-Amino-3-methylbutanoic acid; 2-aminoisovaleric acid; Butanoic acid, 2-amino-3-methyl-, (S)-; EINECS 200-773-6; H-L-Val-OH; H-Val-OH; L-(+)-α-Aminoisovaleric acid; L-(S)-valine; L-2-Aminoisovaleric Acid; L-Val; L-Val-OH; L-VLA; L-α-Amino-β-methylbutyric acid; MFCD00064220; NSC 76038; Valin; Valine; Valine (V) Solution, 100ppm; Valine, L-; VALINE,L;
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1.3 CAS No.
72-18-4
1.4 CID
6287
1.5 EINECS
200-773-6
1.6 Molecular Formula
C5H11NO2
1.7 Inchi
InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1
1.8 InChkey
KZSNJWFQEVHDMF-BYPYZUCNSA-N
1.9 Canonical Smiles
CC(C)C(C(=O)O)N
1.10 Isomers Smiles
CC(C)[C@@H](C(=O)O)N
2. Properties
2.1 Solubility
H2O: 25?mg/mL
2.2 Appearance
White crystalline powder
2.3 Storage
Ambient temperatures.
2.4 Chemical Properties
White or almost white, crystalline powder or colourless crystals, soluble in water, very slightly soluble in alcohol.
2.5 Color/Form
Powder
2.6 Decomposition
When heated to decomposition, it emits toxic fumes of /nitric oxides/.
2.7 PH
5.5-6.5 (100g/l, H2O, 20℃)
2.8 pKa
2.29(at 25℃)
2.9 Water Solubility
85 g/L (20 oC)
2.10 Spectral Properties
Specific optical rotation: +22.9 deg at 23 deg C/D (c = 0.8 in 20% HCl). Molecular rotation: + 33.1 deg at at sodium line (5N HCl); + 72.6 deg at sodium line (glacial acetic acid)
MASS: 26146 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
IR: 5139 (Coblentz Society Spectral Collection)
1H NMR: 15096 (Sadtler Research Laboratories spectral collection)
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2.11 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 Definition
ChEBI: The L-enantiomer of valine.
3.2 Description
L-Valine (CAS 72-18-4) is a non-polar, aliphatic, essential amino acid that is commonly found in proteins. It is one of the 20 amino acids that make up proteins in the human body. L-Valine has a molecular formula of C5H11NO2 and a molecular weight of 117.15 g/mol. It appears as a white, crystalline powder with a sweet taste. It is sparingly soluble in water, but soluble in hot water and ethanol. L-Valine is stable under normal conditions and does not undergo any significant decomposition or degradation.

Applicable Fields
L-Valine is widely used in various fields due to its important role in protein synthesis and metabolism. Some of its main applications include:

Pharmaceutical Industry: L-Valine is commonly used as a nutritional supplement in the pharmaceutical industry. It is an essential amino acid that cannot be synthesized by the human body and must be obtained through diet or supplementation. L-Valine plays a crucial role in muscle growth and repair, and it is often included in sports nutrition products and dietary supplements.

Food Industry: L-Valine is also used as a food additive in the food industry. It is classified as a flavor enhancer and is commonly added to various processed foods, such as soups, sauces, and snacks. L-Valine can enhance the taste and aroma of food products, improving their overall flavor profile.

Animal Feed: L-Valine is an important component of animal feed formulations. It is added to animal feed to ensure proper nutrition and promote healthy growth in livestock and poultry. L-Valine is essential for the synthesis of proteins and plays a vital role in the metabolism of animals.

Storage Conditions
L-Valine should be stored in a cool, dry place, away from direct sunlight. It should be kept in a tightly sealed container to prevent moisture absorption and degradation. Proper storage conditions will help maintain the quality and stability of L-Valine over time.
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3.3 Purification Methods
Crystallise L-valine from water by addition of EtOH. It sublimes at 178-188o/0.03mm with 99.3% recovery and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Perrin J Chm Soc 3125 1958, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2368-23771961, Beilstein 4 IV 2659.]
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3.4 Usage
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.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.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.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.L-Valine can be used for biochemical research, the preparation of tissue culture media. It also used as amino acids nutritional drugs in medicine.
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4. Safety and Handling
4.1 Exposure Standards and Regulations
L-Valine is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: valine is included in weight control drug products.
Valine used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.
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4.2 Octanol/Water Partition Coefficient
log Kow = -2.26
4.3 DisposalMethods
SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
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4.4 Safety Profile
Mutation data reported.When heated to decomposition it emitstoxic fumes of NOx.
4.5 Report

Reported in EPA TSCA Inventory.

4.6 Safety

Hazard Codes:?Xn
Risk Statements: 40?
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 24/25-36-22?
S24/25:Avoid contact with skin and eyes.?
S36:Wear suitable protective clothing.?
S22:Do not breathe dust.
WGK Germany: 3
RTECS: YV9361000
HS Code: 29224995
Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

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4.7 Specification

?L-Valine,?its cas register number is 72-18-4. It also can be called?(S)-2-Amino-3-methylbutanoic acid ; (S)-2-Amino-3-methylbutyric acid ; (S)-Valine ; (S)-alpha-Amino-beta-methylbutyric acid ; 2-Amino-3-methylbutanoic acid ; 2-Amino-3-methylbutanoic acid, (S)- ; Butanoic acid, 2-amino-3-methyl- ; Butanoic acid, 2-amino-3-methyl-, (S)- ; L(+)-alpha-Aminoisovaleric acid ; L-alpha-Amino-beta-methylbutyric acid ; Valina ; Valine ; Valinum .

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4.8 Toxicity
Organic Compound; Amine; Drug; Food Toxin; Dietary Supplement; Micronutrient; Metabolite; Nutraceutical; Animal Toxin; Natural Compound; Amino Acid, Essential
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none
Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
ESR : COPPER(II) COMPLEX, IN H2O/CH3OH(1:1), 77K  
13C NMR : in D2O (PH 1.34)  
13C NMR : in D2O (PH 6.73)  
13C NMR : in D2O (PH 9.58)  
IR : KBr disc  
IR : nujol mull  
Raman : 4880 A,200 M,powder  
Mass  
Mass spectrum (electron ionization)  
7. Synthesis Route
72-18-4Total: 144 Synthesis Route
 
96-81-1
96-81-1 94 Suppliers
 
72-18-4
72-18-4 645 Suppliers
 
52-67-5
52-67-5 121 Suppliers
 
640-68-6
640-68-6 320 Suppliers
 
72-18-4
72-18-4 645 Suppliers
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8. Precursor and Product
precursor:
96-81-1
96-81-1
349-00-8
349-00-8
52-67-5
52-67-5
516-06-3
516-06-3
484-42-4
484-42-4
759-05-7
759-05-7
67-56-1
67-56-1
product:
96-81-1
96-81-1
79-83-4
79-83-4
2026-48-4
2026-48-4
349-00-8
349-00-8
6306-52-1
6306-52-1
78-84-2
78-84-2
686-43-1
686-43-1
640-68-6
640-68-6
516-06-3
516-06-3
759-05-7
759-05-7
9. Computed Properties
10.Other Information
Usage
L-Valine is used in the enhancement of muscle growth and energy. It is utilized in tissue repair. It is also involved in the studies to attenuate arrhythmias and induce hypotensive effects. It acts as a precursor for the preparation of penicillin through biosynthetic pathway. It also employed as nutritional supplements in food and beverage industries. Further, it plays an important role in maintaining mental vigor, muscle coordination and emotional calm.
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Merck
14,9909
BRN
1721136
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.
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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).
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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).
Uses
  • 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.
  • 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.
  • 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.
  • 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.
  • L-Valine can be used for biochemical research, the preparation of tissue culture media. It also used as amino acids nutritional drugs in medicine.
View all
Description
Valine (abbreviated as Val or V) is an α-amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. L-Valine is one of 20 proteinogenic amino acids. Its codons are GUU, GUC, GUA, and GUG. This essential amino acid is classified as nonpolar. Human dietary sources are any proteinaceous foods such as meats, dairy products, soy products, beans and legumes.
Along with leucine and isoleucine, valine is a branched-chain amino acid. It is named after the plant valerian. In sickle-cell disease, valine substitutes for the hydrophilic amino acid glutamic acid in hemoglobin. Because valine is hydrophobic, the hemoglobin is prone to abnormal aggregation.
View all
Chemical Properties
White or almost white, crystalline powder or colourless crystals, soluble in water, very slightly soluble in alcohol.
Uses
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.
View all
Uses
valine is an amino acid used as a skin-conditioning and odor-masking agent. It is more commonly used in hair care preparations than in skin care.
Definition
ChEBI: The L-enantiomer of valine.
Biosynthesis
Valine is an essential amino acid, hence it must be ingested, usually as a component of proteins. It is synthesized in plants via several steps starting from pyruvic acid. The initial part of the pathway also leads to leucine. The intermediate α-ketoisovalerate undergoes reductive amination with glutamate. Enzymes involved in this biosynthesis include :
Acetolactate synthase
Acetohydroxy acid isomeroreductase
Dihydroxyacid dehydratase
Valine aminotransferase.
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Synthesis Reference(s)
Tetrahedron Letters, 22, p. 2411, 1981 DOI: 10.1016/S0040-4039(01)82922-1
Chemical and Pharmaceutical Bulletin, 23, p. 167, 1975 DOI: 10.1248/cpb.23.167
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General Description
Valine is an essential amino acid, involved in the biosynthesis of glutamine and alanine. Valine being a branched-chain amino acid (BCAA), maintains a balance among the BCAAs. L-Valine serves as an energy fuel.
Safety Profile
Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Chemical Synthesis
Racemic valine can be synthesized by bromination of isovaleric acid followed by amination of the α-bromo derivative
HO2CCH2CH(CH3)2 + Br2 → HO2CCHBrCH(CH3)2 + HBr
HO2CCHBrCH(CH3)2 + 2 NH3 → HO2CCH(NH2)CH(CH3)2 + NH4Br
.
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Purification Methods
Crystallise L-valine from water by addition of EtOH. It sublimes at 178-188o/0.03mm with 99.3% recovery and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Perrin J Chm Soc 3125 1958, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2368-23771961, Beilstein 4 IV 2659.]
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Nomenclature
According to IUPAC, carbon atoms forming valine are numbered sequentially starting from 1 denoting the carboxyl carbon, whereas 4 and 4' denote the two terminal methyl carbons.
11. Toltal 585 Suppliers View more
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12. Related Questions
What is L-Valine and its Applications in the Body? What is L-Valine and its Applications in the Body? L-Valine (symbol Val or V) is an α-amino acid that plays a crucial role in protein biosynthesis. It is a non-polar aliphatic amino acid, containing..
What are the medical benefits of high-purity L-Valine?High-purity L-Valine is a natural amino acid and one of the essential components of human protein. It has various biological effects and can be applied in the field of medicine. Below, we will explore..
Why is L-Valine Important and How is it Produced?L-Valine is a branched-chain amino acid and one of the essential amino acids in the human body. In recent years, amino acids have been widely used in various industries such as food, medicine, feed, a..
Does Biotin impact L-Valine fermentation? L-Valine is one of the 8 essential amino acids required by the human body. It has special physiological functions in the human body and is an important substance for maintaining human life activities..
13. Realated Product Infomation
 
1. Names and Identifiers
2. Properties
3. Use and Manufacturing
4. Safety and Handling
5. Msds
6. NMR Spectrum
7. Synthesis Route
8. Precursor and Product
9. Computational chemical data
10. Other Information
11. Toltal 585 Suppliers
12. Related Questions
13. Realated Product Infomation
 
 
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