D-carnitine

Base Information

• Chemical Name: D-carnitine
• CAS No.: 541-14-0
• Molecular Formula: C₇H₁₅NO₃
• Molecular Weight: 161.201
• Hs Code.: 29391900
• European Community (EC) Number: 625-884-0
• UNII: U9VY0ZOK7A
• Wikipedia: Carnitine
• Wikidata: Q27108687
• NCI Thesaurus Code: C82599
• RXCUI: 2106
• Metabolomics Workbench ID: 37052
• ChEMBL ID: CHEMBL503189
• Mol file: 541-14-0.mol

Synonyms:D-carnitine;541-14-0;(+)-Carnitine;(S)-3-Hydroxy-4-(trimethylammonio)butanoate;(S)-carnitine;Carnitine D-form;d(+)-carnitine;D-(+)-carnitine;(3S)-3-hydroxy-4-(trimethylazaniumyl)butanoate;Carnitine, (+)-;UNII-U9VY0ZOK7A;U9VY0ZOK7A;CHEBI:11060;D-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide, inner salt;(3S)-3-hydroxy-4-(trimethylammonio)butanoate;Carnitine;Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, hydroxide, inner salt, D-;CARNITINE, D-;(+)-D-CARNITINE;SCHEMBL94286;CARNITINE D-FORM [MI];CHEMBL503189;1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, hydroxide, inner salt, (S)-;PHIQHXFUZVPYII-LURJTMIESA-N;MFCD00083279;AKOS026751463;CS-W013266;AS-56612;S-(+)-3-hydroxy-4-trimethylaminobutyrate;(3S)-3-oxidanyl-4-(trimethylazaniumyl)butanoate;A829966;Q27108687;1-PROPANAMINIUM, 3-CARBOXY-2-HYDROXY-N,N,N-TRIMETHYL-, INNER SALT, (2S)-

Chemical Property of D-carnitine

Chemical Property:

• Melting Point: 197 °C
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 287.5°C (rough estimate)
• PSA: 60.36000
• Density: 1.1587 (rough estimate)
• LogP: -1.80650
• Storage Temp.: Store at 0°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• 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%,99%, ^*data from raw suppliers

D-Carnitine ^*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: C[N+](C)(C)CC(CC(=O)[O-])O
• Isomeric SMILES: C[N+](C)(C)C[C@H](CC(=O)[O-])O
• Uses: Essential cofactor of fatty acid metabolism; required for the transport of fatty acids through the inner mitochondrial membrane. Synthetized 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 D-carnitine

There total 14 articles about D-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:

(+)-Carnitin-aethylester

(+)-O-Lauroyl-carnitin

(+)-O-Isobutyryl-carnitin

palmitoyl carnitine chloride

Refernces

• 1、 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.
• 2、 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.