160555-46-4

Basic information

• Product Name: (R,S)-1,2-O-Bis(hexadecanoyl)-3-O-(3-pyridylcarbonyl)glycerol
• Synonyms: S-16961-1; S-16961; (d,l)-1,2-O-Dipalmitoyl-3-O-nicotinoylglycerol; 2,3-bis(hexadecanoyloxy)propyl pyridine-3-carboxylate
• CAS NO: 160555-46-4
• Molecular Formula: C₄₁H₇₁NO₆
• Molecular Weight: 674.0055
• Mol File: 160555-46-4.mol

Chemical Properties

• Boiling Point: 695.8°C at 760 mmHg
• Flash Point: 374.6°C
• Density: 0.978g/cm³
• Vapor Pressure: 3.3E-19mmHg at 25°C
• Refractive Index: 1.483
• CAS DataBase Reference: (R,S)-1,2-O-Bis(hexadecanoyl)-3-O-(3-pyridylcarbonyl)glycerol(CAS DataBase Reference)
• NIST Chemistry Reference: (R,S)-1,2-O-Bis(hexadecanoyl)-3-O-(3-pyridylcarbonyl)glycerol(160555-46-4)
• EPA Substance Registry System: (R,S)-1,2-O-Bis(hexadecanoyl)-3-O-(3-pyridylcarbonyl)glycerol(160555-46-4)

Safety Data

• Hazardous Substances Data: 160555-46-4(Hazardous Substances Data)

Upstream product

• 20260-53-1 pyridine-3-carbonyl chloride hydrochloride 
• 40275-04-5 2,3-dihydroxypropyl nicotinate 
• 112-67-4 n-hexadecanoyl chloride 
• 1042289-75-7 rac-1,2-dipalmitoylglycerol 

Relevant articles and documents

Utility of Nicotinoyl Derivatives in Structural Studies of Mono- and Diacylglycerols by Gas Chromatography/Mass Spectrometry. Part 1

The 1- and 2-monoacylglycerols and 1,2- and 1,3-diacylglycerols of saturated and unbranched fatty acids with 8, 10, 12, 14, 16 and 18 carbon atoms were synthesized and subsequently derivatized with nicotinic acid chloride hydrochloride.The resulting nicotinoyl derivatives were examined by mass spectrometry in the case of pure substances and as mixtures by gas chromatography/mass spectrometry (GC/MS).From the electron impact mass spectra, differentiation between mono- and diacylglycerols and between the two positional isomers of monoacylglycerols and diacylglycerols is possible.The molecular masses of the partial acylglycerols and the identities of the bonded fatty acid were also determined.Similarly to the nicotinoyl derivatives of saturated fatty alcohols, the nicotinoyl derivatives of partial acylglycerols produce a fragmentation pattern that reflects every methylene group of the alkyl chains.These results offer rules for the structure elucidation of partially acylated acylglycerols and probably for mixed diacylglycerols by means of GC/MS, which includes the detection of double bonds and methyl branch positions at the fatty acid alkyl chains.The molecular formulae of all the important fragments in the mass spectra of the nicotinoyl derivatives were confirmed by high-resolution mass spectrometry.Their structures and fragmentation pathways are proposed.

Synthesis of 1,2-diacyl-3-nicotinoyl glycerol derivatives and evaluation of their acute effects on plasma lipids in the rat

Nicotinic acid (CAS 59-67-6) is the only hypolipidemic agent whose acitivity has been shown both on atherosclerotic lesions and on long term mortality. Unfortunately, its use is hindered by the frequent occurrence (> 70%) of adverse reactions (i.e. cutaneous rash, pruritus and, most significantly, flush). New prodrugs of nicotinic acid have been prepared by the use of diacylglycerol esters. In the rat, after acute oral administration of these products, a significant decrease of the free fatty acid plasma levels was obtained without the dramatic increase in nicotinic acid plasma levels observed after the oral administration of an equimolecular dose of nicotinic acid. The most interesting ester, S 16961 ((d,l)-1,2-dipalmitoyl-3-nicotinoyl glycerol, CAS 160555-46-4) is undergoing clinical trials.

Diacylglycerol nicotinates

Compounds of formula (I): STR1 in which: R1 and R2, which are identical or different, represent a higher alkyl or higher alkenyl radical, R3 represents a pyridyl or pyrazinyl radical, their isomers and their addition salts with a pharmaceutically acceptable acid and medicaments for the reduction of plasma lipids containing the same.