DL-Leucine

Base Information

• Chemical Name: DL-Leucine
• CAS No.: 328-39-2
• Deprecated CAS: 1105707-16-1
• Molecular Formula: C6H13NO2
• Molecular Weight: 131.175
• Hs Code.: 2922.49
• European Community (EC) Number: 206-328-2
• NSC Number: 77687,46709,9252
• UNII: 1QSS9D5DR6
• DSSTox Substance ID: DTXSID00859050
• Nikkaji Number: J1.285H
• Wikidata: Q60662890
• Metabolomics Workbench ID: 1872
• ChEMBL ID: CHEMBL46575
• Mol file: 328-39-2.mol

Synonyms:DL-Leucine;328-39-2;2-Amino-4-methylpentanoic acid;H-DL-Leu-OH;Leucine, DL-;(RS)-Leucine;(+-)-Leucine;25322-63-8;MFCD00063087;2-amino-4-methyl-pentanoic acid;NSC46709;(+/-)-Amino-4-methylpentanoic acid;UNII-1QSS9D5DR6;1QSS9D5DR6;DL-LEUCINE (15N);CHEBI:25017;L-LEUCINE (U-13C6);L-LEUCINE-1-13C-15N;NSC 9252;NSC-9252;EINECS 206-328-2;( inverted exclamation markA)-Leucine;73579-45-0;AI3-26709;Leuzin;DL-LEUCINE-4,5,5,5,6,6,6-D7;Hleu;L(+)-Leucine;DL-2-Amino-4-methylpentanoic acid;Norvaline, 4-methyl-;2-amino-4-methylpentanoicacid;NSC9252;Valeric acid, 2-amino-4-methyl-;laevo-leucine;MFCD00002617;MFCD00063088;NSC-77687;d,l-leucine;3h-leucine;DL- leucine;d,1-leucine;Leucine #;.alpha.-Amino-.gamma.-methylvaleric acid;92751-17-2;(.+-.)-Leucine;(.+/-.)-Leucine;Leu247;LEUCINE,(L);DL-LEUCINE [FCC];SCHEMBL3888;.alpha.-Aminoisocaproic acid;CHEMBL46575;WLN: QVYZ1Y1&1 -L;2-amino-4-methyl pentanoic acid;DTXSID00859050;WLN: QVYZ1Y1 & 1-D;DL-Leucine, >=99% (HPLC);271247-12-2;HY-B1674;NSC77687;(2R)-2-ammonio-4-methylpentanoate;Pentanoic acid, 2-amino-4-methyl-;AC7886;DL-2-Aminmo-4-methylvalerianic acid;LMFA01100048;STL281857;AKOS000118923;AKOS016050505;CS-W020700;PB47827;7005-03-0;AC-24099;AS-12287;LS-87802;NCI60_004103;SY005863;SY006365;SY033229;AM20090485;DL-Leucine, Vetec(TM) reagent grade, 99%;FT-0602784;FT-0625480;FT-0627930;FT-0641848;FT-0670765;FT-0695062;FT-0695813;FT-0770717;FT-0771371;L0028;(+/-)-2-AMINO-4-METHYLVALERIC ACID;EN300-18048;A817787;A821451;SR-01000944477;Q-100404;SR-01000944477-1;L-Leucine-15N;H-[15N]LEU-OH;59935-31-8;Q60662890;Z57127546;F2191-0181;8EB2668C-D303-4401-A7D5-8ABD6B79B75F;25988-64-1

Chemical Property of DL-Leucine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.0309mmHg at 25°C
• Melting Point: 293-296 °C (subl.)(lit.)
• Refractive Index: 1.462
• Boiling Point: 225.772 °C at 760 mmHg
• PKA: pKa: 9.744(25°C)
• Flash Point: 90.344 °C
• PSA: 63.32000
• Density: 1.036 g/cm³
• LogP: 1.14470
• Storage Temp.: Store at RT.
• Solubility.: 1 M HCl: soluble
• Water Solubility.: soluble
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 131.094628657
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

99.3% ^*data from raw suppliers

DL-Leucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Safety Statements: 22-24/25-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(C(=O)O)N
• Uses: DL-Leucine is a racemic mixture of the D- and L- enantiomers of Leucine. DL-Leucine is used to form benzimidazole and pyrimidine hydroxy azo dyes with various transition metals. DL-Leucine may be used for the evaluation of chiral amino acid separation techniques.DL-Leucine is used for the following applications:Used as a standard for the measurement of free amino acidsUsed in the process of tritiated leucine uptakeUsed in solution preparation (various organics were used in different combinations and concentrations to model complex surface tension effects, DL-Leucine is one of them). It is chosen due to its presence in atmospheric aerosols and ice nucleation activity as well as for its surfactant character

Technology Process of DL-Leucine

There total 130 articles about DL-Leucine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

2-amino-4-methylpentan-1-ol (16369-17-8,14438-11-0) → LEUCINE (328-39-2,21675-61-6,25248-98-0,70-45-1)

Guidance literature:

2-amino-4-methylpentan-1-ol; With (6-di-tert-butylphosphinomethyl-2,2’-bipyridyl)Ru(CO)HCl; water; sodium hydroxide; In 1,4-dioxane; for 24h; Schlenk technique; Inert atmosphere; Glovebox; Reflux;

With hydrogenchloride; In 1,4-dioxane; water;

DOI:10.1021/jacs.6b03488

Reference yield: 69.0%

2-hydroxy-4-methylpentanoic acid (10303-64-7,498-36-2) → LEUCINE (328-39-2,21675-61-6,25248-98-0,70-45-1)

Guidance literature:

With ammonium hydroxide; hydrogen; at 219.84 ℃; for 2h; under 7500.75 Torr; Catalytic behavior; Autoclave; Alkaline conditions;

DOI:10.1073/pnas.1800272115

Reference yield: 68.0%

4-methyl-2-oxopentanoic acid (816-66-0) → LEUCINE (328-39-2,21675-61-6,25248-98-0,70-45-1)

Guidance literature:

With phenylglycin; In water; acetonitrile; for 24h; Reagent/catalyst; Solvent; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.8b03910

upstream raw materials:

(RS)-leucinonitrile

L-leucine

ethyl 2-acetyl-4-methylpentanoate

2-isobutyl-malonamic acid

Downstream raw materials:

N-(N-benzoyl-glycyl)-leucine

DL-leucine methyl ester

4-(2-methylpropyl)oxazolidine-2,5-dione

N-phthaloyl-DL-leucine

Refernces

Syntheses and lipophilicity measurement of N^α/N-terminus-1,1-dihydroperfluoroalkylated α-amino acids and small peptides

10.1016/j.jfluchem.2007.07.003

The research focuses on improving the bioavailability of peptide drugs, especially addressing the poor biological membrane permeability and rapid metabolism of drugs such as enkephalins. To overcome these challenges, the study investigated the synthesis and lipophilicity measurements of Na/N-terminal-1,1-dihydroperfluoroalkylated a-amino acids and small peptides. The experiments involved the synthesis of specific (1,1-dihydroperfluoroalkyl)phenyliodonium N,N-bis(trifluoromethylsulfonyl)imide, which was then used to transfer the 1,1-dihydroperfluoroalkyl group to the a-amino group of (L) tyrosine. The resulting Na-2,2,2-trifluoroethylated (L) tyrosine was used for the solid phase peptide synthesis of leucine enkephalin analogs. The lipophilicity of these perfluoroalkylated (L) tyrosine and N-terminal-2,2,2-trifluoroethylated leucine enkephalin analogs was measured and compared with the parent compound. Reactants included (L) tyrosine, iodine salts, and various reagents for the synthetic process, while analyses included NMR spectroscopy, UV measurements, and partition coefficient calculations to assess lipophilicity.

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