2364-66-1

Basic information

• Product Name: 1-Propanaminium,3-carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-, inner salt, (2S)-
• Synonyms: 1-Propanaminium,3-carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-, inner salt, (S)-; Ammonium,(3-carboxy-2-hydroxypropyl)trimethyl-, hydroxide, inner salt, palmitate, D-(8CI); Palmitic acid, ester with (3-carboxy-2-hydroxypropyl)trimethylammoniumhydroxide inner salt, D- (8CI); (+)-Palmitoylcarnitine; (+)-Palmitylcarnitine; D-Palmitylcarnitine; Hexadecanoyl-D-(+)-carnitine; Palmitoyl d-carnitine; Palmitoyl-D-(+)-carnitine
• CAS NO: 2364-66-1
• Molecular Formula: C₂₃H₄₅NO₄
• Molecular Weight: 399.6077
• Mol File: 2364-66-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• CAS DataBase Reference: 1-Propanaminium,3-carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-, inner salt, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propanaminium,3-carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-, inner salt, (2S)-(2364-66-1)
• EPA Substance Registry System: 1-Propanaminium,3-carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-, inner salt, (2S)-(2364-66-1)

Safety Data

• Hazardous Substances Data: 2364-66-1(Hazardous Substances Data)

Usage

1-Propanaminium group

A positively charged nitrogen atom bonded to two methyl groups and an ethyl group.

3-Carboxy-N,N,N-trimethyl group

A carboxyl group (C=O(OH)) bonded to three methyl groups.

2-[(1-Oxohexadecyl)oxy] group

An alkoxy group (-O-) bonded to a 1-oxohexadecyl group, which is a long hydrocarbon chain with 16 carbon atoms and a carbonyl group at the end.

Inner salt

A compound formed by the reaction of an acid and a base without the release of a water molecule, resulting in a neutral compound with no net charge.

Chiral center

A carbon atom bonded to four different groups, resulting in two possible mirror-image isomers (enantiomers) with the (2S)configuration indicating the direction of the spiral.

Industrial and pharmaceutical applications

The compound is used as a surfactant, emulsifier, and stabilizer in various industries.

Unique structure and properties

The complex structure of the compound gives it special properties that make it valuable for a range of different purposes.

Upstream product

• 28330-02-1 o-palmitoyl-L-carnitine hydrochloride 
• 541-15-1 L-carnitine 
• 112-67-4 n-hexadecanoyl chloride 
• 57-10-3 1-hexadecylcarboxylic acid 
• 1763-10-6 S-palmitoyl-coenzyme A 
• 461-05-2 dl-carnitine hydrochloride 

Relevant articles and documents

NOVEL CRYSTALLINE FORMS

Preparation and characterization of novel forms of (1-hydroxy-2-imidazol-1-yl-1-phosphono-ethyl) phosphonic acid, suitable for pharmaceutical compositions in drug delivery systems for humans.

Stereoselective synthesis of a conformationally defined cyclohexyl carnitine analogue that binds CPT-1 with high affinity

Carnitine (1, 3-hydroxy-4-trimethylammoniobutyrate) is important in mammalian tissue as a carrier of acyl groups. In order to explore the binding requirements of the carnitine acyltransferases for carnitine, we designed conformationally defined cy- clohexyl carnitine analogues. These diastereomers contain the required gauche conformation between the trimethylammonium and hydroxy groups but vary the conformation between the hydroxy and carboxylic acid groups. Here we describe the synthesis and biological activity of the all-trans diastereomer (2), which was prepared by the ring opening of trans-methyl 2,3-epoxycylohex- anecarboxylate with NaN3 . Racemic 2 was a competitive inhibitor of neonatal rat cardiac myocyte CPT-1 (K(i) 0.5 mMfor racemic 2; K(m) 0.2 mM for L-carnitine) and a noncompetitive inhibitor of neonatal rat cardiac myocyte CPT-2 (K(i) 0.67 mM). These results suggest that 2 represents the bound conformation of carnitine for CPT-1. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.