Acetyl-L-carnitine

Base Information

• Chemical Name: Acetyl-L-carnitine
• CAS No.: 3040-38-8
• Deprecated CAS: 461-77-8,541-68-4,3624-25-7,74832-89-6
• Molecular Formula: C9H17 N O4
• Molecular Weight: 203.238
• 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: 3040-38-8.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:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 66.43000
• Density: g/cm³
• LogP: -1.23570
• 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% ^*data from raw suppliers

ACETYL-L-CARNITINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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: L-Acetylcarnitine is a endogenous substance, synthesized in the mitochondria, that increases cellular oxidative metabolism and cholinergic activity. It has a good penetration in the CNS when administered orally and intravenously, and no side effects have been observed. L-Acetylcarnitine has a large variety of interesting pharmacological properties:It is a cholinergic agent because it promotes the synthesis and freeing of acetylcholine.It reduces oxidation processes, thus reducing lipofuscin deposits in the brain.It acts on the hypothalamic-hypophyseal-adrenal axis, antagonizing the existing downregulation (Carta and Calvani 1991).In a 1-year study of 130 patients with AD (63 in treatment with L-acetylcarnitine and 67 with placebo), an improvement in the cognitive decline measured through neuropsychiatric batteries was observed (Spagnoli et al. 1991).
• Uses: Acetylcarnitine may be a useful for treatment of male infertility caused by low quantities of immobile sperm.Acetyl-L-carnitine (ALC) is produced naturally in humans, and can be found in the brain, liver, and kidneys. ALC is also available as a dietary supplement. ALC has been studied for its potential use in slowing the progression of age-related memory loss and Alzheimer’s disease. ALC may also have a potential use in the treatment of neuropathy (nerve pain) associated with diabetes and HIV disease.

Technology Process of Acetyl-L-carnitine

There total 14 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: 88.9%

acetic anhydride (108-24-7) + L-carnitine (541-15-1,44985-79-7) → Acetyl-L-carnitine (3040-38-8,3624-25-7,541-68-4,74832-89-6,870-77-9,461-77-8)

Guidance literature:

With acetic acid; at 80 ℃; for 12h; Temperature;

Reference yield: 71.4%

L-carnitine (541-15-1,44985-79-7) + acetyl chloride (75-36-5) → Acetyl-L-carnitine (3040-38-8,3624-25-7,541-68-4,74832-89-6,870-77-9,461-77-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 5 ℃; for 12h; Concentration;

Reference yield: 68.3%

L-carnitine chloride (6645-46-1) + acetyl chloride (75-36-5) → Acetyl-L-carnitine (3040-38-8,3624-25-7,541-68-4,74832-89-6,870-77-9,461-77-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 5 ℃; for 12h; Concentration;

upstream raw materials:

sodium acetate

L-carnitine chloride

(S)-(+)-3-hydroxy-4-(trimethylammonio)-butanoic acid chloride

(R)-carnitine mesylate mesylate

Downstream raw materials:

2-buten-4-olide

O-acetyl-L-carnitine hydrochloride

Refernces

• 1、 -. "Preparation method of acetyl-L-carnitine nitrate". Paragraph 0021; 0023. . Retrieved 2020/06/09.
• 2、 Ginzinger, Werner,Egger, Alexander,Muehlgassner, Gerhard,Arion, Vladimir B.,Jakupec, Michael A.,Galanski, Markus,Berger, Walter,Keppler, Bernhard K.. "Water-soluble cationic derivatives of indirubin, the active anticancer component from indigo naturalis". . p. 2175 - 2185. Retrieved 2013/01/15.