Acetyl-L-carnitine

Base Information

• Chemical Name: Acetyl-L-carnitine
• CAS No.: 5080-50-2
• Deprecated CAS: 461-77-8,541-68-4,3624-25-7,74832-89-6
• Molecular Formula: C9H17NO4.HCl
• Molecular Weight: 239.699
• Hs Code.: 29239000
• European Community (EC) Number: 608-476-7,610-570-8,690-015-4
• UNII: 6DH1W9VH8Q
• DSSTox Substance ID: DTXSID1040956
• Wikipedia: Acetylcarnitine
• Wikidata: Q311992
• NCI Thesaurus Code: C87329
• Metabolomics Workbench ID: 49952
• ChEMBL ID: CHEMBL1697733
• Mol file: 5080-50-2.mol

Synonyms:Acetyl Carnitine;Acetyl L Carnitine;Acetyl-L-Carnitine;Acetylcarnitine;Acetylcarnitine, (R)-Isomer;Alcar;Branigen;Carnitine, Acetyl;Levocarnitine Acetyl;Medosan

Chemical Property of Acetyl-L-carnitine

Chemical Property:

• Appearance/Colour: Crystallline powder
• Melting Point: 194 °C (dec.)(lit.)
• Refractive Index: -28 ° (C=1, H2O)
• PSA: 63.60000
• LogP: -2.89700
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: 100 mg/mL
• Water Solubility.: soluble
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 203.11575802
• Heavy Atom Count: 14
• Complexity: 214

Purity/Quality:

99.5% ^*data from raw suppliers

Acetyl-L-carnitine Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC(CC(=O)[O-])C[N+](C)(C)C
• Isomeric SMILES: CC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C
• Recent ClinicalTrials: Enhancing the Effects of Adolescent Alcohol Treatment With Acetyl-L-Carnitine
• Recent EU Clinical Trials: Electroneurographic and clinical evaluation in patients with mild / moderate Carpal Tunnel Syndrome , following conservative pharmacological treatment with Nicetile?.
• Description: Levacecarnine hydrochloride is a nootropic agent structurally related to the natural substance L-carnitine. It is reported to be useful in the treatment of cognition disorders in the elderly, perhaps due to its weak cholinergic properties. Acetyl-L-carnitine is an acetylated form of the essential mitochondrial metabolite L-carnitine that is catabolized by plasma esterases into carnitine. Acetyl-L-carnitine facilitates the uptake of acetyl-CoA into mitochondria during fatty acid oxidation, enhances acetylcholine production, and stimulates protein and membrane phospholipid synthesis. In vivo, acetyl-L-carnitine (100 mg/kg) increases mGlu2/3 receptor protein levels and mechanical pain thresholds in a mouse model of chronic inflammatory pain induced by complete Freund''s adjuvant.
• Uses: O-Acetyl-L-carnitine hydrochloride is used as a cholinergic agonist that stimulates neuronal response to serotonin and acetylcholine. Acetylcarnitine has antinociceptive activity that may be mediated by enhanced activity of muscarinic cholinergic receptors or mGlu2 glutamate receptors. Acetyl-L-Carnitine (ALC) is an important dietary supplement. ALC is a natural substance, present in the human body, especially in muscles, in the brain, and in the male testicles. ALC is the acetylated, high-energy form of L-Carnitine. O-Acetyl-L-carnitine hydrochloride may be used as a precursor for the preparation of O-Acetyl-L-carnitine, which in turn may be used as an analytical reference standard for the determination of the analyte in biological samples by hydrophilic interaction liquid chromatography-tandem mass spectrometry (HILIC-MS/MS) technique.

Technology Process of Acetyl-L-carnitine

There total 12 articles about Acetyl-L-carnitine 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: 89.0%

Acetyl-L-carnitine (3040-38-8,3624-25-7,541-68-4,74832-89-6,870-77-9,461-77-8) → O-acetyl-L-carnitine hydrochloride (5080-50-2)

Guidance literature:

With hydrogenchloride; In water; Sealed tube; Darkness;

DOI:10.1016/j.ijpharm.2021.121148

Reference yield: 86.3%

L-carnitine (541-15-1,44985-79-7) + acetyl chloride (75-36-5) → O-acetyl-L-carnitine hydrochloride (5080-50-2)

Guidance literature:

With acetic acid; In Isopropyl acetate; at 10 - 60 ℃; for 8h; Solvent; Large scale;

Reference yield:

acetic anhydride (108-24-7) + L-carnitine chloride (6645-46-1) → O-acetyl-L-carnitine hydrochloride (5080-50-2)

Guidance literature:

With toluene-4-sulfonic acid; at 70 - 75 ℃; for 1.5h;

upstream raw materials:

acetylthiocholine iodide

dl-carnitine hydrochloride

acetyl phosphate K⁺, Li⁺ salt

L-carnitine

Downstream raw materials:

Acetyl-L-carnitine

Refernces

• 1、 Baradaran, Behzad,Mahmoudian, Mohammad,Sarfraz, Muhammad,Shahbazi Mojarrad, Javid,Valizadeh, Hadi,Zahednezhad, Fahimeh,Zakeri-Milani, Parvin. "Surface modification with cholesteryl acetyl carnitine, a novel cationic agent, elevates cancer cell uptake of the PEGylated liposomes". . . Retrieved 2021/11/01.
• 2、 -. "Acetyl L-carnitine hydrochloride preparation method". Paragraph 0017; 0018; 0019; 0020; 0021; 0022; 0023-0031. . Retrieved 2017/02/09.