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 hydrochloride is a naturally occurring carnitine derivative that plays a crucial role in the metabolism of fatty acids and the maintenance of cardiovascular health. It is formed by carnitine acetyltransferase during β-oxidation of uneven chain fatty acids and exhibits various beneficial effects on the heart and blood vessels.

Uses

Used in Pharmaceutical Industry:
Propionyl-L-carnitine hydrochloride is used as an antihypertensive agent for its ability to help regulate blood pressure and improve cardiovascular health.
Used in Cardiology:
Propionyl-L-carnitine hydrochloride is used as a therapeutic agent for improving the heart's mechanical recovery and other metabolic parameters after ischemia-reperfusion. It helps in reducing mitochondrial dysfunction induced by ischemia, preventing mitochondrial calcium overload, and depletion of ATP tissue stores.
Used in Cardiovascular Research:
Propionyl-L-carnitine hydrochloride is used as a research compound for studying its effects on the cardiovascular system, including its role in reducing the production of reactive oxygen species (ROS) and decreasing the expression of NADPH oxidase 2 (NOX2), NOX4, and ICAM-1 in human umbilical vein endothelial cells (HUVECs).
Chemical Properties:
Propionyl-L-carnitine hydrochloride is a white solid with specific chemical properties that contribute to its effectiveness in various applications.
Brand Name:
One of the brand names for Propionyl-L-carnitine hydrochloride is Drosos, manufactured by 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.