N-Acetyl-L-leucine

Base Information

• Chemical Name: N-Acetyl-L-leucine
• CAS No.: 1188-21-2
• Deprecated CAS: 24160-46-1,90243-88-2,90243-88-2
• Molecular Formula: C8H15NO3
• Molecular Weight: 173.212
• Hs Code.: 29241900
• European Community (EC) Number: 214-706-3
• NSC Number: 758152
• UNII: E915HL7K2O
• DSSTox Substance ID: DTXSID6045870
• Nikkaji Number: J23.189D
• Metabolomics Workbench ID: 41523
• ChEMBL ID: CHEMBL56021
• Mol file: 1188-21-2.mol

Synonyms:acetyl-DL-leucine;acetylleucine;acetylleucine, L-;Lasdol;N-acetyl-L-leucine;N-acetylleucine;Tanganil

Chemical Property of N-Acetyl-L-leucine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.77E-06mmHg at 25°C
• Melting Point: 187-190 °C(lit.)
• Refractive Index: -22 ° (C=5, EtOH)
• Boiling Point: 369.7 °C at 760mmHg
• PKA: 3.67±0.10(Predicted)
• Flash Point: 177.4 °C
• PSA: 66.40000
• Density: 1.069 g/cm³
• LogP: 1.01270
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Water (Slightly, Heated)
• Water Solubility.: 0.81 g/100 mL (20 ºC)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 173.10519334
• Heavy Atom Count: 12
• Complexity: 177

Purity/Quality:

99% ^*data from raw suppliers

N-Acetyl-L-leucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)O)NC(=O)C
• Isomeric SMILES: CC(C)C[C@@H](C(=O)O)NC(=O)C
• Recent ClinicalTrials: A Pivotal Study of N-Acetyl-L-Leucine on Niemann-Pick Disease Type C
• Recent EU Clinical Trials: Effects of N-Acetyl-L-Leucine on Niemann-Pick disease type C (NPC): A Phase III, randomized, placebo-controlled, double-blind, crossover study
• Uses: N-Acetyl-L-(-)-leucine is used in the preparation of small molecule inhibitors of anti-apoptotic Bcl-2 family proteins. Also used in the preparation of amphiphilic copolymers involving hydrophobic amino acid and oligopeptide side chains for optical tumor imaging in vivo.

Technology Process of N-Acetyl-L-leucine

There total 25 articles about N-Acetyl-L-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: 100.0%

(Z)-2-Acetylamino-4-methyl-pent-2-enoic acid (64896-30-6) → N-Ac-Leu (1188-21-2)

Guidance literature:

With hydrogen; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; triethylamine; (2R,2'R)-bis(diphenylphosphino)-(1R,1'R)-dicyclopentane; In tetrahydrofuran; at 20 ℃; for 24h; under 750.075 Torr;

Reference yield: 98.0%

L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + acetic anhydride (108-24-7) → N-Ac-Leu (1188-21-2)

Guidance literature:

In water; for 0.0666667h; Irradiation;

DOI:10.1080/00397919208021300

Reference yield: 91.0%

methyl N-acetyl-leucinate (57289-25-5) → N-Ac-Leu (1188-21-2) + methyl (R)-2-(N-acetylamino)-4-methylpentanoate (35799-87-2)

Guidance literature:

With sodium hydroxide; phosphate buffer; pronase EC 3.4.24.4; In tetrahydrofuran; Ambient temperature;

upstream raw materials:

Ketene

L-leucine

N-acetylleucine

acetic anhydride

Downstream raw materials:

N-acetyl-DL-leucine anilide

N-acetyl-N'-methylleucinamide

Ac-Leu-NHMe

(S)-2-Acetylamino-4-methyl-pentanoic acid; compound with (S)-1-(4-trifluoromethyl-phenyl)-ethylamine

Refernces

• 1、 Huffman,Ingersoll. "-". . p. 3366,3368. Retrieved 1951.
• 2、 Cesarotti, E.,Chiesa, A.,Ciani, G.,Sironi, A.. "ASYMMETRIC HYDROGENATION CATALYZED BY AMINOPHOSPHINE-PHOSPHINITERHODIUM COMPLEXES DERIVED FROM NATURAL AMINOALCOHOLS AND X-RAY CRYSTAL STRUCTURE OF (1,5-CYCLOOCTADIENE)-(S)-N-(DIPHENYLPHOSPHINO)-2-DIPHENYLPHOSPHINOXYMETHYLPYRROLIDINERHODIUM(I) PERCHLORATE". . p. 79 - 92. Retrieved 1983.
• 3、 Veera Reddy,Ravindranath. "Acetylation under ultrasonic conditions: Convenient preparation of N-acetylamino acids". . p. 257 - 264. Retrieved 1992.
• 4、 Kwon, Hongmok,Ha, Hyunsoo,Jeon, Hayoung,Jang, Jaebong,Son, Sang-Hyun,Lee, Kiho,Park, Song-Kyu,Byun, Youngjoo. "Structure-activity relationship studies of dipeptide-based hepsin inhibitors with Arg bioisosteres". supporting information. . Retrieved 2020/12/25.
• 5、 Nathanael, Joses G.,Wille, Uta. "Oxidative Damage in Aliphatic Amino Acids and Di- and Tripeptides by the Environmental Free Radical Oxidant NO3?: the Role of the Amide Bond Revealed by Kinetic and Computational Studies". . p. 3405 - 3418. Retrieved 2019/03/11.