Basic information Indications and Usage Mechanisms of Action Pharmacokinetics Safety Related Supplier
L-carnitine Chemical Properties
- Melting point:197-212 °C(lit.)
- Boiling point:287.5°C (rough estimate)
- alpha -31 º (c=10, H2O)
- Density 0.64 g/cm3
- refractive index -32 ° (C=1, H2O)
- storage temp. Store below +30°C.
- solubility H2O: 0.1 g/mL at 20 °C, clear, colorless
- form Crystals or Crystalline Powder
- pka3.80(at 25℃)
- color White
- PH6.5-8.5 (50g/l, H2O)
- Water Solubility 2500 g/L (20 ºC)
- Merck 14,1849
- BRN 4292315
- CAS DataBase Reference541-15-1(CAS DataBase Reference)
L-carnitine Usage And Synthesis
- Indications and UsageCarnitine is a type of vitamin B, and its structure is similar to that of amino acids. It is mainly used to help transport long-chain fatty acids to provide energy and to prevent fat from collecting in the heart, liver, and skeletal muscles. Carnitine can prevent disordered fat metabolism due to diabetes, fatty liver disease and heart disease, and it can reduce heart damage, lower blood triglyceride, aid in weight loss, and increase the antioxidant effects of vitamin E and C. Meats and giblets are high in carnitine. Artificially synthesized carnitine includes L-carnitine, D-carnitine, and DL-carnitine, and only L-carnitine has physiological activities. On the other hand, D-carnitine and DL-carnitine competitively inhibit the activity of carnitine acetyltransferase (CAT) and carnitine palmitoyltransferase (PTC) to prevent cells’ fat metabolism, thus harming human nutrition. L-carnitine was first discovered in 1905 by Russian chemists Gulewitsch and Krimberg in infusion broth, and its chemical structure was determined in 1927 by Tomita and Senju. L-carnitine is a white crystalline or transparent powder, and its melting point is 200℃ (decompose). It is easily soluble in water, lye, methanol and ethanol, barely soluble in acetone and acetate, and insoluble in chloroform. It is hygroscopic. L-carnitine can be used as an animal nutrition enhancer, and it is mainly used to enhance protein-based food additives to promote fat absorption and utilization. L-carnitine also is a nutrition enhancer that is mainly used in soy-based infant foods, sports nutritional foods and weight loss foods to promote fat absorption and utilization. According to China’s regulations, the permitted amount in biscuits, drinks, and dairy beverages is 600-3000mg/kg; in solid beverages, liquids, and gel capsules, 250-600mg/kg; in formula, 300-400mg/kg; in infant foods, 70-90mg/kg (1g tartrate is equivalent to 0.68g l-carnitine). L-carnitine can also be used as an appetite booster. L-carnitine affects the elimination and utilization of ketone bodies, so it can be used as a biological antioxidant to eliminate free radicals, maintain membrane stability, increase animal immunity and resistance to disease and stress. Oral L-carnitine can increase the speed of sperm maturation and sperm vitality, it can increase the number of forward-moving sperm and motile sperm in oligospermia and asthenospermia patients, thus increasing the women’s clinical pregnancy rate, and it does so safely and effectively. L-carnitine can bind with organic acids and the large amounts of acyl coenzyme derivatives produced in children with fatty acid metabolism disorder and turn them into water soluble acylcarnitine to be excreted through urine. This not only aids in controlling acute acidosis occurrences, but also effectively improves long-term prognosis.
- Mechanisms of ActionL-carnitine cannot participate in protein biosynthesis, but it promotes ketone body utilization and nitrogen generation to an extent. Its main function is to promote fatty acid beta oxidation, which occurs in the liver and the mitochondria of other tissue cells. It is known that free fatty acids and acyl coenzyme A cannot penetrate the inner mitochondrial membrane, but acylcarnitine can do so swiftly. Thus, it is determined that L-carnitine is the carrier that transports fatty acid and acyl forms into the mitochondrial membrane. The mechanisms of this transporting process are still unknown, but it is certain that carnitine acyl-CoA transferase is the key enzyme in this process. It has two isoenzymes, one of which is carnitine acyl-CoA transferase I, positioned on the outer side of the membrane. When fatty acid is catalyzed by acyl-CoA-synthatase to produce acyl-CoA, it is transported by carnitine acyl-CoA transferase I into the membrane. After it has entered the membrane, it is catalyzed by the second isoenzyme - carnitine acyl-CoA transferase II – to turned into a form of acyl-CoA that can be directly utilized by fatty acid catabolic enzymes. Afterwards, it releases energy through processes such as dehydrogenation and deoxygenation.
L-carnitine can also adjust the acyl ratio in mitochondria, thus affecting energy metabolism. L-carnitine can participate in the transportation of branched chain amino acid metabolites, which encourages the regular metabolism of branched chain amino acid.
- PharmacokineticsL-Carnitine is very easily soluble in water, and can be entirely absorbed by the human body when consumed through food. It is known that the small intestine absorbs L-carnitine, but there is little known about the specific absorption process of carnitine (free or esterified) through intestine mucosa and about the specific absorption area. Besides external food sources of carnitine, humans can also synthesize carnitine with their own bodies. The liver and kidneys are mainly responsible for synthesizing carnitine. They progress from lysine into epsilon beta hydroxy three methyl lysine, and use aldolase and aldehyde oxidase to transform it into L-carnitine. Besides lysine, the body’s biosynthesis of L-carnitine also requires methionine, vitamin C, nicotinic acid and vitamin B6.
A rat dissection showed that carnitine is most concentrated in the adrenal gland, followed by the heart, bones, muscles, fat tissue, and liver, and the carnitine concentration in the kidneys and brain are 40 times that in blood. Human carnitine concentration has varied greatly due to inconsistencies in measuring method and test subject. The biological method of testing human blood carnitine content placed it between 0.86-2.87mg/100ml, and the enzymology method of testing muscle carnitine content placed it between 0.457-2.479μg/g. The absorbed carnitine is metabolized by the human body and excreted in urine as free carnitine.
- Chemical PropertiesWhite or almost white, crystalline powder or colourless crystals, hygroscopic.
- OriginatorCarnitene,Sigma Tau Industrie,Italy
- OccurrenceSynthetic. It is found in its natural state in food
- Usesantimethemoglobinemic, cyanide antidote
- UsesEssential 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 f ound in heart and skeletal muscle. Dietary sources include red meat, dairy products, beans, avocado.
- UsesCarniking(R) is a product for premix- and feed industry. It is particularly recommended for the enrichment of compound feed.
- UsesL-Carnitine is a natural, vitamin-like nutrient wich plays an important role inhuman metabolism. It is essential in the utilization of fatty acids and in transporting metabolic energy
- UsesNatrulon(R) RC-100 is 100% L-Carnitine. This white crystalline powder, highly hygroscopic and amino acid like material brings not only the exfoliation but also, an additional benefit of a high level of moisturization capability.
- UsesNatrulon(R) RC-50DG is a 50% solution of L-Carnitine in decaglycerol/water. Natrulon(R) RC-50DG to provide a truly multi-functional product: an exfoliating product with excellent moisturization capability.
- DefinitionChEBI: The (R)-enantiomer of carnitine.
- Manufacturing Process9.3 g of epichlorohydrin was added at a temperature of 40°-50°C under
stirring to 9.6 g of trimethylamine hydrochloride dissolved in 10 cc of water.
Continuing the reaction for an hour at the above temperature, the reaction
product was concentrated under reduced pressure to obtain the crystals of 3-
chloro-2-oxypropyl trimethyl ammonium chloride which were recrystallized
with 25 cc of ethanol. The crystals obtained by concentrating the mother
liquor were also recrystallized. The yield was 17.4 g (MP 190°C, yield 91.5%).
This substance occurs as white, somewhat hygroscopic crystals and is readily
soluble in water or alcohol, but insoluble in benzene, toluene, ether, acetone
The result of analysis assuming (C6H15C10N)+Cl--calculated value: N, 7.45%; total Cl, 37.7%; Cl-, 18.88%. Observed value: N, 7.36%; total Cl, 37.54%; Cl-, 18.98%.
18.8 g of 3-chloro-2-oxypropyl trimethyl ammonium chloride was dissolved in a mixed solvent composed of 19 cc of methanol and 1 cc of water. 5.1 g of sodium cyanide dissolved in 8 cc of water was dropped into the solution at 50°C under stirring. After dropping, the mixture was held at this temperature for 30 minutes under stirring. The reaction product was then neutralized with 6 N hydrochloric acid toward pH 5, and, after cooling, sodium chloride separated out and was filtered. The filtrate was concentrated to dryness under reduced pressure, and the residue was washed with small quantity of ethanol. Drying the residue, dissolving in hot methanol, filtering off insoluble matters, and cooling mother liquor, the crystals of 3-cyano-2-axypropyl trimethyl ammonium chloride which deposited out were filtered and dried. Yield 16.7 g [MP (decomposition) 220°-223°C, yield 93.4%].
12.5 cc of concentrated hydrochloric acid was added to 17.9 g of 3-cyano-2- oxypropyl trimethyl ammonium chloride. Gradually heating the mixture on a water bath under stirring, so bringing the temperature up to 98°C at the end of about 3 hours, 9 cc of water was added. After cooling, free hydrochloric acid was neutralized with 3 cc of 6 N sodium hydroxide, and then by adding 1 g of active charcoal, the reaction product was decolorized and filtered. The filtrate was concentrated to almost dryness under reduced pressure. Then, this concentrate was, after washing with 10 cc of ethanol, dried. Yield 24.7 g.
The dried product was dissolved in 46.5 cc of glacial acetic acid by heating on a boiling water bath. The insoluble matter is removed by filtering hot, and on cooling the mother liquor, crystals of carnitine hydrochloride separated out. The crystals were filtered, washed with 10 cc of ethanol, and dried. Recrystallizing 19.7 g of the crude carnitine with methanol, 17 g of the refined carnitine was obtained [MP 195°-198°C (decomposing point), yield 86%], The overall yield of the refined carnitine through whole steps was about 74%. Carnitine thus prepared was an odorless, white, crystalline powder, having a strong acid taste.
- brand nameCarni tor (Sigma-Tau).
- Therapeutic FunctionAppetite stimulant
- Purification MethodsThe S(L) isomer is levocarnitine, Vitamin B7. The R or S isomers crystallise from EtOH/Me2CO (hygroscopic). The R or S hydrochlorides crystallise from hot EtOH or EtOH/Et2O and have m 142o(dec). The RS-isomer crystallises from hot EtOH (hygroscopic). The RS hydrochloride crystallises in needles from hot EtOH and has m 196o(dec). [(±) Mazzetti & Lemmon J Org Chem 22 228 1957, Beilstein 4 H 513, 4 I 548, 4 II 937-8, 4 III 1632-5, 4 IV 3185.]
L-carnitine Preparation Products And Raw materials
- L-Carnitine-L-tartrate L-Carnitine fumarate L-CARNITINE HYDROCHLORIDE, SYNTHETIC,L-CARNITINE HYDROCHLORIDE, SYNTHETIC Levosulpiride Levofloxacin carboxylic acid (R)-(-)-Epichlorohydrin (2R)-Bornane-10,2-sultam (1R,2R)-(-)-1,2-Diaminocyclohexane Levodopa L(-)-Carvone 4-CHLORO-3-HYDROXY BUTYRONITRILE Levocarnitine iMpurity 2-Propen-1-aminium, 3-carboxy-N,N,N-trimethyl-, chloride (1:1), (2Z)- D-(+)-Camphoric acid Levocarnitine Impurity 2 (3-methoxycarbonyl-allyl)-trimethyl-ammonium Levocarnitine Impurity 3 [(±)-(4-amino-2-hydroxy-4-oxobutyl)trimethylammonium] chloride
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