406-76-8

Basic information

• Product Name: DL-Carnitine
• Synonyms: (3-carboxy-2-hydroxypropyl)trimethyl-,hydroxide,innersalt,dl-ammoniu;1-propanaminium,3-carboxy-2-hydroxy-n,n,n-trimethyl-,hydroxide,innersalt,;DL-CARNITINE;CARNITIN;(±)-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide;1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, inner salt;Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, hydroxide, inner salt, DL- (8CI);Cardiogen
• CAS NO: 406-76-8
• Molecular Formula: C₇H₁₅NO₃
• Molecular Weight: 161.2
• EINECS: 206-976-6
• Mol File: 406-76-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 197-198 °C (decomp)
• Appearance: /
• CAS DataBase Reference: DL-Carnitine(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Carnitine(406-76-8)
• EPA Substance Registry System: DL-Carnitine(406-76-8)

Safety Data

• Hazardous Substances Data: 406-76-8(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3

Upstream product

• 75-50-3 trimethylamine 
• 107-20-0 2-chloroethanal 
• 463-51-4 Ketene 
• 99211-78-6 (S)-4-Dimethylamino-3-hydroxy-butyric acid 
• 7013-07-2 (R)-4-Amino-3-hydroxybutanoic acid 
• 74-88-4 methyl iodide 
• 461-06-3 CARNITINE 
• 5261-99-4 (S)-(+)-Carnitinamid-Hydrochlorid 
• 32224-01-4 (S)-4-bromo-3-hydroxy-butyric acid ethyl ester 
• 133039-09-5 Toluene-4-sulfonate((S)-3-carboxy-2-hydroxy-propyl)-trimethyl-ammonium; 
• 1116-95-6 (D)-(+)-carnitinenitrile chloride 

Downstream Products

• 14548-19-7 (+)-Carnitin-aethylester 
• 6919-91-1 (+)-O-Lauroyl-carnitin 
• 6920-31-6 (+)-O-Isobutyryl-carnitin 
• 28330-02-1 palmitoyl carnitine chloride 
• 5469-16-9 (3S)-hydroxy-γ-butyrolactone 
• 5469-16-9 4-Hydroxy-dihydro-furan-2-on 

Relevant articles and documents

Resolution of the racemates of DL-carnitine

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PROCESS FOR THE PRODUCTION OF CARNITINE BY CYCLOADDITION

The invention relates to a method for the production of L-carnitine, wherein a chiral β-lactone carnitine precursor is obtained by a [2+2] cycloaddition of ketene with an aldehyde X—CH2—CHO, wherein X is selected from Cl, Br, I and trimethylamine, in the presence of a chiral catalyst.

Asymmetric synthesis of (S)-(+)-carnitine and analogs

A general asymmetric route to enantiomerically pure (S)-(+)-carnitine and analogs has been investigated that involves mono-addition of organometallic reagents to the lactone carbonyl group of (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin- 2-one and Lewis acid promoted stereoselective allylation of the resulting hemiacetals. The diastereomerically pure allyl oxazines thus obtained were readily converted into enantiomerically pure (S)-(+)-carnitine and two substituted analogs.

Phosphinyloxy propanaminium inner salt derivatives

Compounds of the formula STR1 where X1 and X2 are independently O or S, and R1 is as defined in the description R2, R3, and R4 are each independently straight or branched chain (C1-4)alkyl, and pharmaceutically acceptable salts, physiological hydrolysable esters, and pro-drug forms thereof are useful as hypoglycemic agents.