L-Valine
- Iupac Name：(2S)-2-amino-3-methylbutanoic acid
- CAS No.: 72-18-4
- Molecular Weight：117.14634
- Modify Date.: 2022-10-28 09:16
- Introduction: 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.
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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(EC#)
- 200-773-6
- 1.6 Molecular Formula
- C5H11NO2 (isomer)
- 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 InChIkey
- 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 Density
- 1.23
- 2.1 Melting point
- 315℃
- 2.1 Boiling point
- 213.6 °C at 760 mmHg
- 2.1 Refractive index
- 1.507
- 2.1 Flash Point
- 83 °C
- 2.1 Precise Quality
- 117.07900
- 2.1 PSA
- 63.32000
- 2.1 logP
- 0.75460
- 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)
- 2.11 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: The L-enantiomer of valine.
- 3.2 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.]
- 3.3 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 Hazard Codes
- Xn
- 4.1 Risk Statements
- R40
- 4.1 Safety Statements
- S24/25
- 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. - View all
- 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. - View all
- 4.4 RIDADR
- NONH for all modes of transport
- 4.4 Safety Profile
- Mutation data reported.When heated to decomposition it emitstoxic fumes of NOx.
- 4.5 WGK Germany
- 3
- 4.5 RTECS
- YV9361000
- 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.
- 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 .
- 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
7. Synthesis Route
72-18-4Total: 76 Synthesis Route
9. Other Information
- 9.0 Merck
- 14,9909
- 9.1 BRN
- 1721136
- 9.2 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. - View all
- 9.3 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).
- 9.4 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).
- 9.5 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
- 9.6 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.
- 9.7 Chemical Properties
- White or almost white, crystalline powder or colourless crystals, soluble in water, very slightly soluble in alcohol.
- 9.8 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.
- 9.9 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.
- 9.10 Definition
- ChEBI: The L-enantiomer of valine.
- 9.11 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.
- 9.12 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
- 9.13 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.
- 9.14 Safety Profile
- Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
- 9.15 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
.
- 9.16 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.]
- 9.17 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.
- 9.18 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.
10. Computational chemical data
- Molecular Weight: 117.14634g/mol
- Molecular Formula: C5H11NO2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 117.078978594
- Monoisotopic Mass: 117.078978594
- Complexity: 90.4
- Rotatable Bond Count: 2
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 63.3
- Heavy Atom Count: 8
- Defined Atom Stereocenter Count: 1
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBiMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQCAAADSjBgAQCCABAAgAIAACQCAAAAAAAAAAAAIGAAAACABAAAAAAQAAEEAAAAAAAAAAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
-
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..
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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..
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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..
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What are the chemical reactions responsible for the breakdown of valine in the body? I know oxidative deamination is part of the process but how is valine further broken down from an keto acid to iso..
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