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L-Leucine
- Iupac Name：(2S)-2-amino-4-methylpentanoic acid
- CAS No.: 61-90-5
- Molecular Weight：131.17292
- Modify Date.: 2022-11-12 07:09
- Introduction: L-leucine is one of the eight essential amino acids, and belonging to the aliphatic amino acids within twenty kinds of proteins. L-leucine and L-isoleucine and L-valine are called three branched chain amino acids. L-leucineLeucine and D-leucine are enantiomers . It is a white shiny hexahedral crystal or white crystalline powder at room temperature , Odorless, slightly bitter . In the presence of hydrocarbons ,it is stable in the aqueous mineral acid. Per gram is dissolved in 40ml water and about 100ml acetic acid. Very slightly soluble in ethanol or ether, dissolved in formic acid, dilute hydrochloric acid, a solution of alkali hydroxides and a solution of carbonates. L-leucine can promote insulin secretion, can lower blood sugar; promote sleep, reduce sensitivity to pain, migraine headaches, anxiety and ease tension, reduce symptoms of chemical reactions disorder in the body caused by alcohol , and helps control alcoholism; it has a role in the treatment of dizziness , also can promote skin wound and bone healing, so doctors usually advise patients to take leucine supplements after surgery. amino acid infusion and comprehensive amino acid preparations are often formulated to be used in the treatment or health care; also be used as food, cosmetics and feed additives and plant growth promoter. The best food sources of leucine include brown rice, beans, meat, nuts, soy flour, and whole wheat. Excessive intake can also cause side effects, high intake can cause pellagra, vitamin A deficiency, dermatitis, diarrhea, mental disorders and other issues,which needs to be paid attention to . Diet containing too much leucine will increase the number of ammonia in the body and destroy the liver and kidney function. Therefore, patients with impaired liver or kidney function should not be excessive intake, otherwise it will exacerbate the condition.
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1. Names and Identifiers
- 1.1 Name
- L-Leucine
- 1.2 Synonyms
(2S)-α-Leucine (l)-leucine (S)-(+)-Leucine (S)-2-amino-4-methyl-pentanoic acid (s)-2-amino-4-methylvalericacid (S)-leucine [14C]-L-(+)-Leucine [14C]-L-Glutamic acid [3H]-L-Glutamic acid 1-Leucine 2-Amino-4-methylpentanoic acid 2-Amino-4-methylpentanoic acid, (S)- 2-amino-4-methylpentanoicacid 2-amino-4-methyl-valericaci 4-methyl-l-norvalin 4-Methyl-L-norvaline 4-methyl-norvalin Aciglut alpha-Amino-gamma-methylvaleric acid EINECS 200-522-0 GLU Glusate GLUTACID glutamic Glutaton H-GLU-OH H-Leu-OH H-L-GLU-OH L-(-)-2-Amino-4-methylpentanoic acid L-(+)-glutamic acid L-2-Amino-4-methylpentanoic acid LEU Leucine (USP) LEUCINE, L- Leucinum L-GLU l-Leu MFCD00002617 QVYZ1Y1&1 &&L or S Form S-leucine
- 1.3 CAS No.
- 61-90-5
- 1.4 CID
- 6106
- 1.5 EINECS(EC#)
- 200-522-0
- 1.6 Molecular Formula
- C6H13NO2 (isomer)
- 1.7 Inchi
- InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1
- 1.8 InChkey
- ROHFNLRQFUQHCH-YFKPBYRVSA-N
- 1.9 Canonical Smiles
- CC(C)CC(C(=O)O)N
- 1.10 Isomers Smiles
- CC(C)C[C@@H](C(=O)O)N
2. Properties
- 2.1 Density
- 1.035
- 2.1 Melting point
- 286-288℃
- 2.1 Boiling point
- 225.8 °C at 760 mmHg
- 2.1 Refractive index
- 1.4630 (estimate)
- 2.1 Flash Point
- 90.3 °C
- 2.1 Precise Quality
- 131.09500
- 2.1 PSA
- 63.32000
- 2.1 logP
- 1.14470
- 2.1 Solubility
- 1 M HCl: 50?mg/mL
- 2.2 Appearance
- Small white lustrous plates or crystalline powder; odourless
- 2.3 Storage
- Leucine is sensitive to light and moisture, and should be stored in anairtight container in a cool, dark, dry place.
- 2.4 Color/Form
- Powder
- 2.5 Decomposition
- When heated to decomposition it emits toxic fumes of /nitric oxide/.
- 2.6 PH
- 5.5-6.5 (20g/l, H2O, 20℃)
- 2.7 pKa
- 2.328(at 25℃)
- 2.8 Water Solubility
- 22.4 g/L (20 C)
- 2.9 Spectral Properties
- Specific optical rotation: -10.8 at 25 deg C/D (c = 2.2); +15.1 deg at 26 deg C/D in 6N HCl (38 mols HCl per mol leucine); +7.6 deg at 20 deg C/D in 3N NaOH (30 mols NaOH per mol leucine). Molecular rotation: +21.0 deg at /D (5NHCl); +29.5 deg /D (glacial acetic acid)
MASS: 27147 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
UV: 1-113 (Phillip et al., Organic Electronic Spectral Data, John Wiley & Sons, New York))
Raman: 427 (Sadtler Research Laboratories spectral collection)
- 2.10 Stability
- Moisture and light sensitive. Incompatible with strong oxidising agents.
- 2.11 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: The L-enantiomer of leucine.
- 3.2 Produe Method
- Leucine is produced microbially by incubating an amino-acidproducingmicroorganism including but not exclusive to Pseudomonas,Escherichia, Bacillus, or Staphylococcus in the presence ofoxygen and a hydrocarbon. The nutrient medium should contain aninhibitory amount of a growth inhibitor that is a chemically similarderivative of leucine (e.g. methylallylglycine, a-hydrozinoisocaproicacid, or b-cyclopentanealanine) to inhibit the growth of theorganism except for at least one mutant that is resistant to theinhibitory effect. The resistant mutant is then isolated and grown inthe presence of oxygen and the hydrocarbon in the absence of theinhibitor. The mutant cells are then harvested and a nutrientmedium is formed that includes a hydrocarbon as the sole source ofcarbon. Finally, the harvested cells are incubated in the medium inthe presence of oxygen.
- 3.3 Purification Methods
- Likely impurities are isoleucine, valine, and methionine. Crystallise L-leucine from water by adding 4 volumes of EtOH. It sublimes at 180-188o/0.3mm with 99.1% recovery, and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 p 2075-2094 1961, Kameda et al. J Pharm Soc Jpn 78 763 1958, Beilstein 4 IV 2738.]
- 3.4 Usage
- Amino acid drugs. Used as amino acid infusion and comprehensive amino acid preparations. For the diagnosis and treatment of children with idiopathic high blood sugar and glucose metabolism disorders,bile liver disease associated with reduced secretion , anemia, poisoning, muscular dystrophy, poliomyelitis, neuritis and mental illness. Diabetes, cerebral vascular sclerosis and kidney disease associated with proteinuria and hematuria is contraindicated. Gastric and duodenal ulcer patients should not be served. The product is used as a nutritional supplement,an amino acid infusion preparation and a comprehensive amino acid preparation,a hypoglycemic agent, a plant growth promoter.The product can be used as a spice according to GB 2760-8 .
4. Safety and Handling
- 4.1 Risk Statements
- S24/25
- 4.1 Safety Statements
- S24/25
- 4.1 Exposure Standards and Regulations
- L-Leucine 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: leucine is included in weight control drug products.
Leucine 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.
- 4.2 Octanol/Water Partition Coefficient
- log Kow = -1.52
- 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.
- 4.4 RIDADR
- NONH for all modes of transport
- 4.4 Incompatibilities
- Leucine is incompatible with strong oxidizing agents.
- 4.5 WGK Germany
- 3
- 4.5 RTECS
- OH2850000
- 4.5 Report
-
Reported in EPA TSCA Inventory.
- 4.6 Safety
-
Safety Statements of?L-Leucine (CAS NO.61-90-5): 24/25?
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: OH2850000
HS Code: 29224995
Moderately toxic by subcutaneous route. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
- 4.7 Specification
-
White crystalline powder
Safety Statements:24/25
24/25:Avoid contact with skin and eyes
- 4.8 Toxicity
- IPR-RAT LD50 5379 mg kg-1
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
61-90-5Total: 64 Synthesis Route
8. Other Information
- 8.0 Merck
- 14,5451
- 8.1 BRN
- 1721722
- 8.2 description
- L-leucine is one of the eight essential amino acids, and belonging to the aliphatic amino acids within twenty kinds of proteins. L-leucine and L-isoleucine and L-valine are called three branched chain amino acids. L-leucineLeucine and D-leucine are enantiomers . It is a white shiny hexahedral crystal or white crystalline powder at room temperature , Odorless, slightly bitter . In the presence of hydrocarbons ,it is stable in the aqueous mineral acid. Per gram is dissolved in 40ml water and about 100ml acetic acid. Very slightly soluble in ethanol or ether, dissolved in formic acid, dilute hydrochloric acid, a solution of alkali hydroxides and a solution of carbonates.
L-leucine can promote insulin secretion, can lower blood sugar; promote sleep, reduce sensitivity to pain, migraine headaches, anxiety and ease tension, reduce symptoms of chemical reactions disorder in the body caused by alcohol , and helps control alcoholism; it has a role in the treatment of dizziness , also can promote skin wound and bone healing, so doctors usually advise patients to take leucine supplements after surgery. amino acid infusion and comprehensive amino acid preparations are often formulated to be used in the treatment or health care; also be used as food, cosmetics and feed additives and plant growth promoter.
The best food sources of leucine include brown rice, beans, meat, nuts, soy flour, and whole wheat. Excessive intake can also cause side effects, high intake can cause pellagra, vitamin A deficiency, dermatitis, diarrhea, mental disorders and other issues,which needs to be paid attention to . Diet containing too much leucine will increase the number of ammonia in the body and destroy the liver and kidney function. Therefore, patients with impaired liver or kidney function should not be excessive intake, otherwise it will exacerbate the condition.
- 8.3 Chemical Properties
- White shiny hexahedral crystals or white crystalline powder. Slightly bitter (DL-leucine is sweet). Sublimation at 145~148 ℃. Melting point 293~295 ℃ (decomposition). It belongs to the essential amino acids,and adult men requirement is 2.2g/d (151 version). It is necessary in normal growth for infants and maintaining normal nitrogen balance for adults.
Natural products are found in the spleen, heart, etc., and are present in a variety of plant and animal tissues in the form of the proteins, free out after decomposition and corruption.
- 8.4 Uses
- Amino acid drugs. Used as amino acid infusion and comprehensive amino acid preparations. For the diagnosis and treatment of children with idiopathic high blood sugar and glucose metabolism disorders,bile liver disease associated with reduced secretion , anemia, poisoning, muscular dystrophy, poliomyelitis, neuritis and mental illness. Diabetes, cerebral vascular sclerosis and kidney disease associated with proteinuria and hematuria is contraindicated. Gastric and duodenal ulcer patients should not be served.
The product is used as a nutritional supplement,an amino acid infusion preparation and a comprehensive amino acid preparation,a hypoglycemic agent, a plant growth promoter.The product can be used as a spice according to GB 2760-8 .
- 8.5 toxicity
- Safe for food (FDA, §172.3202000).
LD505379mg/kg (rat, subcutaneously).
- 8.6 Description
- Small, white, lustrous plates, or a white, crystalline powder, with a slightly bitter taste. One g dissolves in about 40 mL of water and in about 100 mL of acetic acid. It is sparingly soluble in alcohol, but is soluble in dilute hydrochloric acid and in solutions of alkali hydroxides and carbonates. ι-Leucine may be synthesized by bromination, followed by amination of isocaproic acid; via the acetamidomalonic ester; by isolation from gluten, casein, keratin; from hydantoin.
- 8.7 Chemical Properties
- L-Leucine is odorless and has a slightly bitter taste. L-Leucine is a branched-chain, essential amino acid that stimulates muscle protein synthesis.
- 8.8 Chemical Properties
- White crystalline powder
- 8.9 Chemical Properties
- Leucine occurs as a white or almost off-white crystalline powder or shiny flakes.
- 8.10 Occurrence
- Reported found as a constituent in proteins; also present in the free state in the human body
- 8.11 Uses
-
L-Leucine is an essential amino acid. It is also considered to be a branched chain amino acid, along with L-Isoleucine and L-Valine. It is used as a cell culture media component in the commercial biomanufacture of therapeutic recombinant proteins and monoclonal antibodies.
- 8.12 Usage
- L-Leucine plays a vital role in hemoglobin formation, protein synthesis and metabolic functions. It assists the growth and repair of muscle and bone tissue. It is used in the treatment of amyotrophic lateral sclerosis - Lou Gehrig's disease. It prevents the breakdown of muscle proteins after trauma or severe stress and may be beneficial for individuals with phenylketonuria. It is also used as a food additive and flavor enhancer. Further, it is used to preserve muscle glycogen.
- 8.13 Usage
- In cosmetics industry it is used as antistatic agent, hair conditioning and skin conditioning. L-Leucine acts as a nutrient signal to stimulate protein synthesis. It has also activates the mammalian target of rapamycin kinase that regulates cell growth. Leucine has been used as a molecular marker in the recovery of DNA from paleontological samples for PCR analysis.
9. Computational chemical data
- Molecular Weight: 131.17292g/mol
- Molecular Formula: C6H13NO2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 131.094628657
- Monoisotopic Mass: 131.094628657
- Complexity: 101
- Rotatable Bond Count: 3
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 63.3
- Heavy Atom Count: 9
- 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: AAADccBiMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQCAAADSjBgAQCCABAAgAIAACQCAAAAAAAAAAAAIGAAAACABIAgAAAQAAEEAAAAACIAAAMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10. Question & Answer
-
When you eat protein, it triggers muscle protein synthesis in the body. A lot of this has to do with the amino acid leucine, which led to the theory that adding leucine to your diet in the form of BCAAs could help with muscular gains. The theory didn’t really pan out. Trouble is, muscle is still m...
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L-leucine
- Purity:99%Packing: 200kg/bag FOB
- Price: 1 USD/kilogram
- Time: 2023/06/02
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