541-14-0

Basic information

• Product Name: D(+)-Carnitine
• Synonyms: (3-carboxy-2-hydroxypropyl)trimethyl-,hydroxide,innersalt,d-ammoniu;d-(3-carboxy-2-hydroxypropyl)trimethylammoniumhydroxide,innersalt;DL-CARNITINE BENZYL ESTER CHLORIDE;D-CARNITINE HYDROCHLORIDE;(+)-BETA-HYDROXY-GAMMA-(TRIMETHYLAMMONIO)BUTYRATE HYDROCHLORIDE;2-HYDROXY-N,N,N-TRIMETHYL-4-OXO-4-(PHENYLMETHOXY)-1-BUTANAMINIUM CHLORIDE;(3-CARBOXY-2-HYDROXYPROPYL)TRIMETHYLAMMONIUM CHLORIDE;(+)-β-Hydroxy-γ-(trimethylammonio)butyrate
• CAS NO: 541-14-0
• Molecular Formula: C₇H₁₅NO₃
• Molecular Weight: 161.2
• Product Categories: chiral;Aliphatics;Amino Acids & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 541-14-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 197 °C
• Boiling Point: 287.5°C (rough estimate)
• Appearance: /
• Density: 1.1587 (rough estimate)
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Store at 0°C
• Solubility: Methanol (Slightly), Water (Slightly)
• Merck: 13,1862
• CAS DataBase Reference: D(+)-Carnitine(CAS DataBase Reference)
• NIST Chemistry Reference: D(+)-Carnitine(541-14-0)
• EPA Substance Registry System: D(+)-Carnitine(541-14-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: BP2979850
• HazardClass: IRRITANT
• Hazardous Substances Data: 541-14-0(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

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.

Definition

ChEBI: The (S)-enantiomer of carnitine.

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

Upstream product

• 7013-07-2 (R)-4-Amino-3-hydroxybutanoic acid 
• 74-88-4 methyl iodide 
• 75-50-3 trimethylamine 
• 107-20-0 2-chloroethanal 
• 463-51-4 Ketene 
• 99211-78-6 (S)-4-Dimethylamino-3-hydroxy-butyric acid 
• 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

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.

Retention and selectivity of teicoplanin stationary phases after copper complexation and isotopic exchange

Teicoplanin is a macrocyclic glycopeptide that is highly effective as a chiral selector for LC enantiomeric separations. Two possible interaction paths were investigated and related to solute retention and selectivity: (1) interactions with the only teicoplanin amine group and (2) role of hydrogen bonding interactions. Mobile phases containing 0.5 and 5 mM copper ions were used to try to block the amine group. In the presence of copper ions, it was found that the teicoplanin stationary phase has a decreased ability to separate most underivatized racemic amino acids. However, it maintained its ability to separate enantiomers that were not α - amino acids. It is established that there is little copper - teicoplanin complex formation. The effect of Cu2+ on the enantioseparation of some α - amino acids appears to be due to the fact that these solutes are good bidentate ligands and form complexes with copper ions in the mobile phase. Isotopic exchange with deuterium oxide was performed using acetonitrile - heavy water mobile phases. It was found that the retention times of all amino acids were lower with deuterated mobile phases. The retention times of polar or apolar molecules without amine groups were higher with deuterated mobiles phases. In all cases, the enantio-selectivity factors were unaffected by the deuterium exchange. It is proposed that the electrostatic interactions are decreased in the deuterated mobile phases and the solute-accessible stationary-phase volume is somewhat swollen by deuterium oxide. The balance of these effects is a decrease in the amino acid retention times and an increase in the apolar solute retention time. The enantio-selectivity factors of all of the molecules remain unchanged because all of the interactions are changed equally. We propose a new global quality criterion (the E factor) for comparing and evaluating enantiomeric separations.

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.