17720-18-2

Basic information

• Product Name: nicotinic acid ribonucleoside
• Synonyms: nicotinic acid ribonucleoside;3-Carboxy-1-β-D-ribofuranosyl- pyridiniuM Hydroxide Inner Salt;3-Carboxy-1-β-D-ribofuranosylpyridiniuM Inner Salt;Nicotinic Riboside;NARH - oxidized form
• CAS NO: 17720-18-2
• Molecular Formula: C₁₁H₁₃NO₆
• Molecular Weight: 255.22402
• Mol File: 17720-18-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: nicotinic acid ribonucleoside(CAS DataBase Reference)
• NIST Chemistry Reference: nicotinic acid ribonucleoside(17720-18-2)
• EPA Substance Registry System: nicotinic acid ribonucleoside(17720-18-2)

Safety Data

• Hazardous Substances Data: 17720-18-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

An effective agent for increasing nicotinamide adenine dinucleotide (NAD) concentrations in mammalian cells.

InChI:InChI=1/C11H13NO6/c13-5-7-8(14)9(15)10(18-7)12-3-1-2-6(4-12)11(16)17/h1-4,7-10,13-15H,5H2/t7-,8-,9-,10-/m1/s1

Upstream product

• 25436-37-7 trimethylsilyl 3-pyridinecarboxylate 
• 28708-32-9 1,2,3,5-tetra-O-acetyl-D-ribofuranose 
• 59-67-6 nicotinic acid 
• 143678-99-3 C₂₅H₂₁NO₈ 

Downstream Products

• 321-02-8 nicotinic acid riboside mononucleotide 

Relevant articles and documents

Scalable syntheses of traceable ribosylated NAD+ precursors

Nicotinamide adenine dinucleotide, NAD+, is an essential cofactor and substrate for many cellular enzymes. Its sustained intracellular levels have been linked to improved physiological end points in a range of metabolic diseases. Biosynthetic precursors to NAD+ include nicotinic acid, nicotinamide, the ribosylated parents and the phosphorylated form of the ribosylated parents. By combining solvent-assisted mechanochemistry and sealed reaction conditions, access to the ribosylated NAD+ precursors and to the isotopologues of NAD+ precursors was achieved in high yields and levels of purity. The latter is critical as it offers means to better trace biosynthetic pathways to NAD+, investigate the multifaceted roles of the intracellular NAD+ pools, and better exploit NAD+ biology.

Syntheses of nicotinamide riboside and derivatives: Effective agents for increasing nicotinamide adenine dinucleotide concentrations in mammalian cells

A new two-step methodology achieves stereoselective synthesis of β-nicotinamide riboside and a series of related amide, ester, and acid nucleosides. Compounds were prepared through a triacetylatednicotinate ester nucleoside, via coupling of either ethylnicotinate or phenylnicotinate with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose. Nicotinamide riboside, nicotinic acid riboside, O-ethylnicotinate riboside, O-methylnicotinate riboside, and several N-alkyl derivatives increased NAD+ concentrations from 1.2-2.7-fold in several mammalian cell lines. These findings establish bioavailability and potent effects of these nucleosides in stimulating the increase of NAD+ concentrations in mammalian cells.