L-Carnitine CAS 541-15-1 is a naturally occurring, quaternary ammonium compound biosynthesized from the amino acids lysine and methionine. It is a chiral molecule, with the L-enantiomer being the biologically active form. Structurally, it functions as a carrier molecule for long-chain fatty acids. L-Carnitine is the essential biological shuttle required for transporting long-chain fatty acids into the mitochondria for energy production. It is a conditionally essential nutrient that optimizes cellular energy metabolism, making it fundamental for muscular, cardiovascular, and metabolic health.
Nombre :
L-CarnitineN.º CAS :
541-15-1MF :
C₇H₁₅NO₃MW :
161.20Pureza :
99%Apariencia :
White, crystalline, hygroscopic powderCondición de almacenamiento :
Store in a tightly sealed container in a cool, dry place.Chemical Properties
IUPAC Name: (3R)-3-Hydroxy-4-(trimethylazaniumyl)butanoate
Other Common Names: Levocarnitine, Vitamin B₇ (obsolete), L-Carnitine
Chemical Formula: C₇H₁₅NO₃
Molecular Weight: 161.20 g/mol
Structure: A small, water-soluble molecule with a hydroxyl group (-OH) and a trimethylammonium group [-N⁺(CH₃)₃] at opposite ends of a short carbon chain.
Appearance: White, crystalline, hygroscopic powder. It is commonly supplied as the base or in salt forms like L-carnitine-L-tartrate or L-carnitine fumarate for improved stability.
Melting Point: Decomposes at ~197-212°C.
Solubility: Highly soluble in water (~2500 g/L). Soluble in hot ethanol, practically insoluble in acetone or ether.
Stability: Stable under dry, cool conditions. It is hygroscopic (absorbs moisture from air). Aqueous solutions are stable at acidic pH but are susceptible to microbial growth.
Optical Activity: The naturally occurring and bioactive form is the L-enantiomer. The D-enantiomer is biologically inactive and may even inhibit the function of L-carnitine.
Key Reactivity: Its primary biological function is to form esters (acyl-carnitines) with fatty acids via its hydroxyl group, a reaction catalyzed by carnitine palmitoyltransferase enzymes.
Biological Activities
L-Carnitine plays an indispensable role in cellular energy metabolism.
Essential Role in Fatty Acid Oxidation: Its primary and most critical function is to transport long-chain fatty acids (LCFAs) from the cytosol into the mitochondrial matrix, where they undergo β-oxidation to produce acetyl-CoA and energy (ATP). Carnitine acts as a molecular shuttle.
Mitochondrial Health & Bioenergetics: By facilitating fat burning for fuel, it helps maintain energy homeostasis, supports mitochondrial function, and prevents the toxic accumulation of fatty acids in the cytoplasm.
Buffer for Acetyl Groups: It modulates the intramitochondral acetyl-CoA/CoA ratio by forming acetyl-L-carnitine, which can transport acetyl groups out of the mitochondria. This is crucial for maintaining metabolic flexibility.
Antioxidant & Cell Signaling: Exhibits indirect antioxidant properties by improving mitochondrial efficiency and reducing oxidative stress. It may also influence gene expression related to fat metabolism.
Deficiency: Can be primary (genetic defects in biosynthesis or transport) or secondary (due to conditions like liver disease, pregnancy, or valproate therapy). Deficiency leads to muscle weakness, hypoglycemia, cardiomyopathy, and fatigue due to impaired energy production.
Biosynthesis
Endogenous Production: Humans synthesize L-carnitine primarily in the liver and kidneys from the essential amino acids lysine (which provides the carbon backbone) and methionine (which provides the methyl groups), with essential cofactors Vitamin C (ascorbic acid), iron (Fe²⁺), Vitamin B₆ (pyridoxine), and niacin.
Dietary Sources: Rich sources include red meat (especially lamb and beef), poultry, fish, and dairy products. Plant-based foods contain very little. An average omnivorous diet provides about 60-180 mg per day.
Absorption & Transport: Dietary L-carnitine is absorbed in the small intestine via both passive diffusion and active transport (OCTN2 transporter). It is distributed to tissues, with the highest concentrations found in cardiac and skeletal muscle.
Applications
Key Advantages & Benefits
1. Fundamental Role in Cellular Energy Production
Benefit: Serves as the indispensable carrier molecule that enables long-chain fatty acids to cross the inner mitochondrial membrane, where they are oxidized to produce ATP. This process is critical for sustained energy, especially in tissues with high energy demands like cardiac and skeletal muscle.
Application Scenario: For an endurance athlete like a marathon runner, supplemental L-Carnitine helps maximize the utilization of fat stores as fuel during prolonged exercise. This spares muscle glycogen (carbohydrate stores), potentially delaying fatigue and "hitting the wall," leading to improved performance and endurance.
2. Clinically Validated for Specific Deficiencies & Conditions
Benefit: It is the standard, life-saving therapy for primary systemic carnitine deficiency and effectively manages secondary deficiencies. Its role in cardiac energy metabolism provides adjunctive support in validated clinical contexts.
Application Scenario: In a clinical setting for a patient with congestive heart failure, adjunctive L-Carnitine supplementation (as prescribed) supports the heart's compromised energy production by enhancing fatty acid oxidation in cardiac myocytes, potentially improving symptoms like exercise intolerance and quality of life.
3. Supports Metabolic Detoxification & Homeostasis
Benefit: Acts as a metabolic buffer by facilitating the removal of excess acyl groups from mitochondria. This prevents the accumulation of toxic metabolic intermediates and helps maintain a healthy acetyl-CoA/CoA ratio, crucial for efficient function of mitochondrial enzymes.
Application Scenario: For patients undergoing hemodialysis, who are prone to carnitine depletion, supplementation helps prevent the buildup of fatty acid metabolites, reducing complications such as muscle weakness, cardiomyopathy, and intradialytic cramps, thereby improving patient outcomes.
4. Safe, Well-Tolerated, and Versatile in Formulation
Benefit: As a naturally occurring substance, it exhibits an excellent safety profile at recommended doses. Its high solubility and stability allow for versatile delivery in tablets, capsules, powders, liquids, and functional beverages.
Application Scenario: A sports nutrition company formulating a post-workout recovery powder uses L-Carnitine base due to its neutral taste, excellent mixability, and compatibility with other ingredients like carbohydrates and protein, creating a convenient product aimed at reducing muscle soreness and enhancing recovery.
L-Carnitine (CAS 541-15-1) is not a mere "fat burner" supplement but a fundamental micronutrient that optimizes a core metabolic pathway. Its greatest advantage lies in its physiological necessity and role in energy homeostasis, particularly under conditions of high demand or deficiency. While specialized forms like ALCAR excel for brain health, base L-Carnitine remains the most cost-effective and well-researched form for systemic metabolic and muscular support. For athletes, it is a recovery and endurance aid; for clinicians, a therapeutic agent; and for the general health-conscious individual, a safe means to support cellular energy production. Its value is rooted in science, not stimulant-driven hype.
FAQs
Q1: What are the proven benefits of L-carnitine supplementation?
A: The strongest evidence supports its use for:
1)Treating diagnosed carnitine deficiency.
2)Improving symptoms in patients with angina or heart failure.
3)Enhancing recovery (reducing muscle soreness and damage markers) in athletes.
Evidence for direct performance enhancement or fat loss in healthy, well-nourished individuals is more mixed and often shows modest effects at best.
Q2: Is L-carnitine safe? Are there any side effects?
A: It is generally very safe at recommended doses (500-2000 mg/day). High doses (>3-5 g/day) may cause:
Gastrointestinal distress: Nausea, vomiting, diarrhea, abdominal cramps.
"Fishy" body odor: Due to bacterial metabolism of excess carnitine to trimethylamine (TMA).
Rare interactions: May potentiate the effects of blood-thinners like warfarin.
Q3: Who is most likely to benefit from supplementation?
A:
Vegans & Vegetarians: Due to very low dietary intake.
Athletes & Active Individuals: For potential recovery benefits.
Older Adults: Endogenous synthesis may decline with age.
Individuals with Specific Medical Conditions: As directed by a physician (e.g., heart disease, kidney dialysis, male infertility).
Q4: What is the difference between L-carnitine, Acetyl-L-carnitine (ALCAR), and L-carnitine L-tartrate?
A:
L-Carnitine Base: The standard form, best for general supplementation and addressing deficiency.
Acetyl-L-Carnitine (ALCAR): The acetylated ester. It crosses the blood-brain barrier more easily and is often preferred for cognitive support, neurohealth, and mood due to its role in acetylcholine production and mitochondrial function in neurons.
L-Carnitine L-Tartrate: A salt form commonly used in sports nutrition due to its rapid absorption and studies showing efficacy in reducing exercise-induced muscle damage and soreness.
Q5: When is the best time to take it, and what is the typical dose?
A:
Timing: For exercise-related benefits, 30-60 minutes before a workout. For general health, it can be taken with meals to improve tolerance.
Dose: Varies by goal. General health: 500-1000 mg/day. Athletic performance/recovery: 1000-2000 mg/day. Always follow product label instructions or a healthcare provider's advice.
Q6: Can I get enough from my diet alone?
A: Yes, if you are an omnivore. A 4-oz steak provides about 56-162 mg of carnitine. The body also synthesizes it. Deficiency in healthy individuals eating a balanced diet is rare. Supplements are most useful for targeted needs (athletic recovery) or populations with low intake/ increased requirements (vegans, elderly).
Q7: Are there any contraindications?
A: People with seizure disorders should use caution, as carnitine may interact with certain anti-seizure medications like valproate. Those with hypothyroidism should consult a doctor, as carnitine may inhibit thyroid hormone action in high doses. As always, consult a healthcare professional before starting any new supplement, especially if you have underlying health conditions or are taking medications.
Clorhidrato de procaína CAS 51-05-8 Es la sal hidrocloruro de procaína soluble en agua. Es la formulación específica utilizada en medicina clínica, conocida por su nombre comercial:NovocaínaSi bien su uso en la práctica general ha disminuido, sigue siendo un fármaco históricamente fundamental y aún se emplea en contextos médicos y terapéuticos específicos.
Detalles
L(+)-Choline bitartrate CAS 87-67-2 is an organic salt compound formed from one molecule of choline (a quaternary ammonium cation and essential nutrient) and one molecule of L(+)-tartaric acid (a natural dicarboxylic acid). It is a specific, enantiomerically pure form of choline salt where the counterion is derived from natural tartaric acid.It is a high-purity, stable, and highly bioavailable source of essential choline, combining the vital nutrient with a natural, food-grade organic acid. It offers a superior balance of safety, solubility, and cost-effectiveness for dietary supplementation and food fortification.
Detalles
L-Carnitine CAS 541-15-1 is a naturally occurring, quaternary ammonium compound biosynthesized from the amino acids lysine and methionine. It is a chiral molecule, with the L-enantiomer being the biologically active form. Structurally, it functions as a carrier molecule for long-chain fatty acids. L-Carnitine is the essential biological shuttle required for transporting long-chain fatty acids into the mitochondria for energy production. It is a conditionally essential nutrient that optimizes cellular energy metabolism, making it fundamental for muscular, cardiovascular, and metabolic health.
Detalles
L-Carnitine-L-tartrate CAS 36687-82-8 is a well-defined, crystalline salt formed through the ionic bonding of one molecule of L-carnitine (the biologically active enantiomer) and one molecule of L-tartaric acid (the naturally occurring enantiomer). It is specifically engineered as a superior solid form of carnitine for dietary supplements and functional foods. L-Carnitine-L-tartrate is a non-hygroscopic, highly stable salt form of L-carnitine, specifically engineered for superior manufacturing and performance. It delivers the essential metabolic benefits of L-carnitine with added advantages for physical recovery, excelling in solid-dose and powdered supplement formulations where stability and clinical validation are paramount.
Detalles
Trimethylamine hydrochloride (TMA·HCl) CAS 593-81-7 is the hydrochloride salt of trimethylamine (TMA), a simple tertiary alkylamine. It is a solid, crystalline form of the normally gaseous and foul-smelling trimethylamine, which makes it much more convenient to handle, store, and weigh precisely.Trimethylamine Hydrochloride is the safe, stable, and precisely weighable solid equivalent of gaseous trimethylamine (TMA). It transforms a hazardous, malodorous gas into a controllable reagent, eliminating the major handling and safety challenges while enabling exact stoichiometry in critical synthetic steps.
Detalles
(S)-4-Chloro-3-hydroxybutyronitrile CAS 127913-44-4 is a chiral, bifunctional organic molecule serving as a versatile building block in asymmetric synthesis. It features a nitrile group, a secondary alcohol with defined (S)-stereochemistry, and a terminal chloro substituent, allowing for multiple divergent chemical transformations from a single, enantiomerically pure scaffold.(S)-4-Chloro-3-hydroxybutyronitrile is a privileged, enantiomerically pure chiral building block that provides a compact, multifunctional scaffold with three differentiable reaction sites. Its core value lies in enabling the efficient, stereocontrolled synthesis of complex chiral molecules, particularly pharmacologically active intermediates, with high atom economy and strategic flexibility.
Detalles
Ethyl (S)-4-chloro-3-hydroxybutyrate CAS 86728-85-0 is a chiral, bifunctional ester and a highly valuable building block in asymmetric synthesis. It features a terminal chloro group, a secondary alcohol with defined (S)-stereochemistry, and an ethyl ester, providing three distinct reactive handles for chemical transformation from a single enantiomerically pure scaffold. This compound is a chirally pure, trifunctional building block that integrates a reactive ethyl ester, a stereodefined secondary alcohol, and a terminal chloride into a compact C4 skeleton. It is the preferred industrial precursor for synthesizing the chiral side chain of blockbuster statin drugs due to its optimal balance of reactivity, stability, and efficient biocatalytic production.
Detalles
Ethyl (R)-4-cyano-3-hydroxybutyrate CAS 141942-85-0 is a chiral, bifunctional building block of significant importance in asymmetric synthesis. It contains a stereogenic center with (R)-configuration, an ethyl ester group, and a terminal nitrile group, making it a versatile precursor for constructing complex chiral molecules, particularly in pharmaceutical applications. This compound is a stereodefined, multifunctional chiral building block where the (R)-configured alcohol and versatile cyano group provide unique synthetic leverage. It serves as a privileged precursor for high-value pharmaceutical intermediates, particularly statin side chains, by offering superior and orthogonal reactivity compared to its chloro analog.
Detalles
CONTÁCTENOS
1st Floor, No. 477, Huancheng West Road, Nanqiao Town, Fengxian District, Shanghai,China
sales@qxscientific.com
+86 -13701740203
IPv6 RED SOPORTADA
|
Mapa del sitio
|
XML |
Blog |
política de privacidad
Dejar un mensaje
Scan to Wechat/Whatsapp :
Español
English
Español
Português
