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

Description

D(+)-Carnitine, also known as the (S)-enantiomer of carnitine, is an essential cofactor of fatty acid metabolism that plays a crucial role in the transport of fatty acids through the inner mitochondrial membrane. It is primarily synthesized in the liver and kidney, with the highest concentrations found in heart and skeletal muscle. D(+)-Carnitine is a white to light yellow crystal powder and can be obtained from dietary sources such as red meat, dairy products, beans, and avocado.

Uses

Used in Pharmaceutical Industry:
D(+)-Carnitine is used as a therapeutic agent for various conditions related to fatty acid metabolism, including cardiovascular diseases, metabolic disorders, and muscle fatigue. Its role in the transport of fatty acids across the inner mitochondrial membrane aids in energy production and supports overall cellular function.
Used in Sports Nutrition:
D(+)-Carnitine is used as a supplement in the sports nutrition industry to enhance endurance, improve athletic performance, and reduce muscle fatigue. Its involvement in fatty acid metabolism helps in providing energy during intense physical activities.
Used in Weight Management:
D(+)-Carnitine is used as a weight management aid, as it may help in the breakdown of fats for energy production, thus supporting weight loss and maintaining a healthy body composition.
Used in Animal Nutrition:
D(+)-Carnitine is used as a feed additive in the animal nutrition industry to improve the health and performance of livestock, particularly in poultry and pigs. It helps in enhancing energy metabolism, growth, and overall productivity.
Used in Cosmetics:
D(+)-Carnitine is used in the cosmetics industry for its potential anti-aging and skin health benefits. It may help in improving skin elasticity, reducing the appearance of fine lines and wrinkles, and promoting a more youthful complexion.

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

Upstream product

• 461-06-3 CARNITINE 
• 1116-95-6 (D)-(+)-carnitinenitrile chloride 
• 133039-09-5 Toluene-4-sulfonate((S)-3-carboxy-2-hydroxy-propyl)-trimethyl-ammonium; 
• 32224-01-4 (S)-4-bromo-3-hydroxy-butyric acid ethyl ester 
• 5261-99-4 (S)-(+)-Carnitinamid-Hydrochlorid 
• 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 

Downstream Products

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

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.