DL-Carnitine

Base Information

• Chemical Name: DL-Carnitine
• CAS No.: 406-76-8
• Deprecated CAS: 461-06-3,122195-30-6,15183-21-8
• Molecular Formula: C₇H₁₅NO₃
• Molecular Weight: 161.201
• Hs Code.: 2923900090
• European Community (EC) Number: 207-309-1
• UNII: S7UI8SM58A
• DSSTox Substance ID: DTXSID3022744
• Wikipedia: Carnitine
• Wikidata: Q243309
• NCI Thesaurus Code: C82599
• RXCUI: 2106
• Metabolomics Workbench ID: 124264
• ChEMBL ID: CHEMBL172513
• Mol file: 406-76-8.mol

Synonyms:Bicarnesine;Carnitine;L Carnitine;L-Carnitine;Levocarnitine;Vitamin BT

Chemical Property of DL-Carnitine

Chemical Property:

• Melting Point: 197-198 °C (decomp)
• PSA: 60.36000
• LogP: -1.80650
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 161.10519334
• Heavy Atom Count: 11
• Complexity: 134

Purity/Quality:

98%, ^*data from raw suppliers

DL-Carnitine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+](C)(C)CC(CC(=O)[O-])O
• Recent ClinicalTrials: CARNIVAL Study: Gut Flora Dependent Metabolism of Dietary CARNItine and Phosphatidylcholine and cardioVAscuLar Disease
• Recent NIPH Clinical Trials: Supportive effect of carnitine on hepatitis C virus eradication therapy
• Uses: DL-Carnitine is a Chloride salt free form of D,L-Carnitine Chloride (C184100). Carnitine is a vitamin, essential cofactor of fatty acid metabolism. It is required for the transport of fatty acids through the inner mitochondrial membrane. Synthesized primarily in the liver and kidney; highest concentrations found in heart and skeletal muscle. Dietary sources include red meat, dairy products, beans, avocado.

Technology Process of DL-Carnitine

There total 14 articles about DL-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: 80.0%

Toluene-4-sulfonate((S)-3-carboxy-2-hydroxy-propyl)-trimethyl-ammonium; (133039-09-5) → (S)-carnitin (406-76-8,461-06-3,541-14-0,541-15-1,44985-79-7)

Guidance literature:

by ion exchange;

DOI:10.1016/S0040-4039(00)88555-X

Reference yield:

4-(chloromethyl)oxetane-2-one + trimethylamine (75-50-3) → (2E)-4-hydroxybut-2-enoic acid (24587-49-3) + L-carnitine (541-15-1,44985-79-7) + (S)-carnitin (406-76-8,461-06-3,541-14-0,541-15-1,44985-79-7)

Guidance literature:

With sodium hydroxide; In water; at 0 - 20 ℃; for 2h; Product distribution / selectivity;

Reference yield:

tetrafluoroborate salt of L-carnitine + dichlorotetradecylphosphite → (R)-3-carboxy-N,N,N-trimethyl-2-{[hydroxy(tetradecyloxy)phosphinyl]oxy}-1-propanaminium hydroxide + (S)-carnitin (406-76-8,461-06-3,541-14-0,541-15-1,44985-79-7)

Guidance literature:

In 2,3,5-trimethyl-pyridine; methanol; water; acetonitrile;

upstream raw materials:

CARNITINE

(D)-(+)-carnitinenitrile chloride

Toluene-4-sulfonate((S)-3-carboxy-2-hydroxy-propyl)-trimethyl-ammonium;

(S)-4-bromo-3-hydroxy-butyric acid ethyl ester

Downstream raw materials:

palmitoyl carnitine chloride

4-Hydroxy-dihydro-furan-2-on

(3S)-hydroxy-γ-butyrolactone

(+)-O-Isobutyryl-carnitin

Refernces

• 1、 Strack,Lorenz. "On the preparation of carnitinbetaine". . p. 276 - 277. Retrieved 1966.
• 2、 Bose, D. Subhas,Fatima, Liyakat,Rajender, Salla. "An efficient, highly enantioenriched route to L-carnitine and α-lipoic acid via hydrolytic kinetic resolution". . p. 1863 - 1867. Retrieved 2008/01/27.
• 3、 Berthod,Valleix,Tizon,Leonce,Caussignac,Armstrong. "Retention and selectivity of teicoplanin stationary phases after copper complexation and isotopic exchange". . p. 5499 - 5508. Retrieved 2007/10/03.