119793-66-7

Basic information

• Product Name: Propionyl-L-carnitine hydrochloride
• Synonyms: PROPIONYL-L-CARNITINE CHLORIDE;PROPIONYL L-CARNITINE HCL;PROPIONYL-L-CARNITINE HYDROCHLORIDE;PROPIONYL-LEVO-CARNITINE HYDROCHLORIDE;(r)-2-propionyl-3-(trimethylaminium)butanoic acid chloride;Propionyl L-Carnitine;PROPIONYLLEVOCARNITINE HCL;Propionyllevocarnitine
• CAS NO: 119793-66-7
• Molecular Formula: C₁₀H₂₀NO₄*Cl
• Molecular Weight: 253.72
• EINECS: 1308068-626-2
• Product Categories: Amino Acids & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;ALDOMET
• Mol File: 119793-66-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 165-167°C
• Appearance: /
• Storage Temp.: Store at 0°C
• Solubility: Chloroform (Slightly), Water (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: Propionyl-L-carnitine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Propionyl-L-carnitine hydrochloride(119793-66-7)
• EPA Substance Registry System: Propionyl-L-carnitine hydrochloride(119793-66-7)

Safety Data

• Hazardous Substances Data: 119793-66-7(Hazardous Substances Data)

Usage

Description

Propionyl-L-carnitine is a naturally occurring carnitine derivative formed by carnitine acetyltransferase during β-oxidation of uneven chain fatty acids. Propionyl-L-carnitine increases the basal release of prostaglandin E2 (PGE2; ) and 6-keto-prostaglandin F1α in carrageenan-stimulated isolated rat peritoneal cells contaminated with neutrophils and increases the basal release of thromboxane B2 (TXB2; ) in non-contaminated cells. It reduces the production of reactive oxygen species (ROS) and decreases the expression of NADPH oxidase 2 (NOX2), NOX4, and ICAM-1 in human umbilical vein endothelial cells (HUVECs). It also increases the rate of revascularization and the hind limb vascular area in a rabbit model of hind limb ischemia when administered at a dose of 10 mg per animal. Propionyl-L-carnitine reduces mitochondrial dysfunction induced by ischemia, preventing mitochondrial calcium overload, and depletion of ATP tissue stores in a rabbit model of ischemia.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 119793-66-7 differently. You can refer to the following data:
1. antihypertensive
2. L-Propionyl carnitine has been shown to improve the heart's mechanical recovery and other metabolic parameters after ischemia-reperfusion.
3. L-Propionyl carnitine has been shown to improve the heart''s mechanical recovery and other metabolic parameters after ischemia-reperfusion.

Brand name

Dromos (Biosint S.p.A.).

InChI:InChI=1/C10H19NO4.ClH/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4;/h8H,5-7H2,1-4H3;1H/t8-;/m1./s1

Synthetic route

propionyl chloride (79-03-8) + L-carnitine chloride (6645-46-1) → (R)-3-carboxy-N,N,N-trimethyl-2-(propionyloxy)propan-1-ammonium chloride (119793-66-7)

Conditions	Yield
With trifluoroacetic acid at 40 - 50℃; for 20h;

(R)-3-carboxy-N,N,N-trimethyl-2-(propionyloxy)propan-1-ammonium chloride (119793-66-7) + glycine (56-40-6) → glycine propionyl-L-carnitine hydrochloride

Conditions	Yield
Stage #1: (R)-3-carboxy-N,N,N-trimethyl-2-(propionyloxy)propan-1-ammonium chloride In ethanol at 50℃; Stage #2: glycine In ethanol at 70℃; for 2h; Concentration; Temperature; Solvent;	98.7%

(R)-3-carboxy-N,N,N-trimethyl-2-(propionyloxy)propan-1-ammonium chloride (119793-66-7) → C10H19ClNO3(1+)*Cl(1-)

Conditions	Yield
With oxalyl dichloride In dichloromethane at 40 - 50℃;

Upstream product

• 79-03-8 propionyl chloride 
• 6645-46-1 L-carnitine chloride 

Relevant articles and documents

Synthesis of carnitine benzyl esters as prodrugs

The introduction of C-2 acyl groups and a benzyl ester onto L-carnitine generated a series of carnitine benzyl esters as prodrug with improved liposolubility, stability and bioavailability.