125377-87-9

Basic information

• Product Name: (S)-Amino Carnitine
• Synonyms: (2S)-2-Amino-3-carboxy-N,N,N-trimethyl-1-propanaminium Inner Salt;(S)-3-Amino-4-(trimethylammonio)butyrate;(S)-Amino Carnitine;(S)-Emeriamine
• CAS NO: 125377-87-9
• Molecular Formula: C7H16N2O2
• Molecular Weight: 0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals;Chemical Amines;Amines;Inhibitors
• Mol File: 125377-87-9.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: (S)-Amino Carnitine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Amino Carnitine(125377-87-9)
• EPA Substance Registry System: (S)-Amino Carnitine(125377-87-9)

Safety Data

• Hazardous Substances Data: 125377-87-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-Amino Carnitine is used as an inhibitor of fatty acid oxidation for its ability to regulate lipid metabolism. It functions as a hypoglycemic and antiketogenic compound, making it a potential candidate for the treatment of diabetes and related metabolic disorders.
Used in Metabolic Research:
(S)-Amino Carnitine is used as a research tool for studying the role of carnitine acetyltransferase (CAT) and carnitine palmitoyltransferase (CPT) in lipid metabolism. By inhibiting these enzymes, researchers can gain insights into the underlying mechanisms of fatty acid oxidation and its impact on overall metabolism.
Used in Nutritional Supplements:
(S)-Amino Carnitine is used as an ingredient in nutritional supplements designed to support healthy lipid metabolism and energy production. Its role in inhibiting fatty acid oxidation may contribute to improved athletic performance and overall health.
Used in Drug Development:
(S)-Amino Carnitine's ability to alter lipidic metabolism and inhibit key enzymes makes it a promising candidate for the development of new drugs targeting metabolic disorders and related health issues. Its potential applications in this field are currently under investigation.

Upstream product

• 108919-55-7 (R)-3-(tosylamino)-4-(trimethylammonio)butanoate 
• 108-95-2 phenol 

Downstream Products

• 1228293-55-7 C₂₂H₂₉N₃O₅ 
• 250694-23-6 C₂₄H₄₁N₃O₄ 
• 1228293-56-8 C₂₁H₂₇N₃O₄ 
• 1228293-58-0 C₁₈H₂₉N₃O₃ 
• 1228293-57-9 C₁₆H₂₅N₃O₃ 
• 1059703-04-6 (R)-3-(N-(4-heptylphenyl)sulfamoylamino)-4-(trimethylammonio)-butanoate 
• 1059703-07-9 (R)-3-(N-(4-octylphenyl)sulfamoylamino)-4-(trimethylammonio)-butanoate 
• 1059703-90-0 (R)-3-(N-methyl-N-(4-octylphenyl)sulfamoylamino)-4-(trimethylammonio)butanoate 

Relevant articles and documents

INHIBITORS OF CARNITINE PALMITOYLTRANSFERASE AND TREATING CANCER

A CPT inhibitor compound is represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof: or a pharmaceutically acceptable salt thereof. A pharmaceutical composition comprises a compound represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof. A method of treating a subject having cancer comprises administering to the subject a therapeutically effective amount of a compound represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof.

Synthesis of (R) and (S)-aminocarnitine, (R) and (S)-4-phosphonium-3-amino-butanoate, (R) and (S) 3,4-diaminobutanoic acid, and their derivatives starting from D- and L-aspartic acid

R or S aminocarnitine, R or S phosphonium aminocarnitine and R and S 3,4 diaminobutanoic acid, and their derivatives are prepared using starting from aspartic acid with the same configuration as the desired compounds. This process is advantageous from the industrial point of view in terms of the type of reactants used, the reduced volumes of solvents and the possibility of avoiding purification of the intermediate products.

Synthesis of (R) and (S)-aminocarnitine, (R) and (S)-4-phosphonium-3-amino-butanoate, (R) and (S) 3,4-diaminobutanoic acid, and their derivatives starting from D- and L-aspartic acid

A process is described for the preparation of R or S aminocarnitine, R or S phosphonium aminocarnitine and R and S 3,4 diaminobutanoic acid, and their derivatives with the following formula: 1where Y is as described in the attached description, starting from aspartic acid with the same configuration as the desired compounds. This process is advantageous from the industrial point of view in terms of the type of reactants used, the reduced volumes of solvents and the possibility of avoiding purification of the intermediate products.

Synthesis of (R) and (S)-aminocarnitine, (R) and (S)-4-phosphonium-3-amino-butanoate, (R) and (S) 3,4-diaminobutanoic acid, and their derivatives starting from D- and L-aspartic acid

A process is described for the preparation of R or S aminocarnitine, R or S phosphonium aminocarnitine and R and S 3,4 diaminobutanoic acid, and their derivatives with the following formula: where Y is as described in the attached description, starting from aspartic acid with the same configuration as the desired compounds. This process is advantageous from the industrial point of view in terms of the type of reactants used, the reduced volumes of solvents and the possibility of avoiding purification of the intermediate products.

A Practical and Stereoconservative Synthesis of (R)-3-Amino-4-(trimethyl-ammonio)butanoate [(R)-Aminocarnitine], and Its Trimethylphosphonium and Simple Ammonium Analogues Starting from D-Aspartic Acid

We have developed a new stereospecific synthesis of (R)-aminocarnitine using D-aspartic acid as the starting material. This strategy, which is simple and amenable to an industrial scale-up, gives the target compound in six steps and in fairly good overall

Synthesis of (R) and (S) -aminocarnitine and their derivatives starting from D- and L-aspartic acid

R or S aminocarnitine and their derivatives with formula (I) where Y is as described in the description, starting with aspartic acid with the same configuration as the aminocarnitine desired. This process has advantage in the type of reactants used, reduced volumes of solvents and the possibility of avoiding purification of intermediate products.

Process for producing R-aminocarnitine and S-aminocarnitine

A process for producing aminocarnitine is described, wherein methanesulfonylcarnitine is converted to a lactone which is reacted with an azide to give azidocarnitine. The catalytic hydrogenation of azidocarnitine gives aminocarnitine.

The β-Lactone Route to a Totally Stereoselective Synthesis of Carnitine Derivatives

The syntheses of the enantiomerically pure, carnitine-related β-lactones 10 and 12 starting from various carnitine precursors of opposite configuration (or carnitine itself) are described. (R)-3-Chlorocarnitine (20) has also been directly prepared from (S)-carnitine (14) and has been cyclized to 12 by a second inversion of configuration of the stereogenic centre.By nucleophilic attack at the carbonyl carbon, the β-lactone carnitine derivatives have been converted into esters, amides, and guanidino congeners.Following this route, it is possible to obtain the biologically active isomer (R)-carnitine (1) starting from the otherwise useless industrial by-product (S)-carnitine (14).Nucleophilic attack by selected ambident nucleophiles at the β-carbon of the same β-lactone derivatives results in a second inversion of configuration of the stereogenic centre.Besides aminocarnitine (3), chiral acetylcarnitine (2) and acetylthiocarnitine (5) have been synthesized in homochiral forms following this latter procedure. - Keywords: asymmetric ring-opening; carnitine; cyclizations; β-lactones; nucleophilic substitutions

Process for producing R-aminicarnitine and S-aminocarnitine

A process for producing aminocarnitine is described, wherein methanesulfonylcarnitine is converted to a lactone which is reacted with an azide to give azidocarnitine. The catalytic hydrogenation of azidocarnitine gives aminocarnitine.