Nicotinic acid riboside

Base Information

• Chemical Name: Nicotinic acid riboside
• CAS No.: 17720-18-2
• Molecular Formula: C11H13 N O6
• Molecular Weight: 255.22402
• DSSTox Substance ID: DTXSID20938912
• Wikidata: Q27125847
• Metabolomics Workbench ID: 59971
• Mol file: 17720-18-2.mol

Synonyms:nicotinate ribonucleoside;nicotinate ribose;nicotinate riboside;nicotinic acid ribonucleoside

Chemical Property of Nicotinic acid riboside

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 113.93000
• Density: g/cm³
• LogP: -3.05090
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 255.07428713
• Heavy Atom Count: 18
• Complexity: 306

Purity/Quality:

98%,99%, ^*data from raw suppliers

NicotinicAcidRiboside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C[N+](=C1)C2C(C(C(O2)CO)O)O)C(=O)[O-]
• Isomeric SMILES: C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)[O-]
• Uses: An effective agent for increasing nicotinamide adenine dinucleotide (NAD) concentrations in mammalian cells.

Technology Process of Nicotinic acid riboside

There total 8 articles about Nicotinic acid riboside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

1-((2R,3R,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate → 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (17720-18-2)

Guidance literature:

With ammonia; In methanol; at -78 - -20 ℃; for 96h; Inert atmosphere; Sealed tube;

DOI:10.1039/c9ob01981b

Reference yield: 74.0%

1-(2’,3’,5’-triacetyl-beta-D-ribofuranosyl)-nicotinic acid → 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (17720-18-2)

Guidance literature:

With methanol; ammonia; at -78 - -20 ℃; for 96h; Sealed tube;

Reference yield:

5'-nicotinic acid ethyl ester ribose → 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium-3-carboxylate (17720-18-2)

Guidance literature:

With pig liver esterase; In phosphate buffer; for 12h; enzymatic hydrolysis;

DOI:10.1021/jm701001c

upstream raw materials:

C₂₅H₂₁NO₈

nicotinic acid

1,2,3,5-tetra-O-acetyl-D-ribofuranose

trimethylsilyl 3-pyridinecarboxylate

Downstream raw materials:

nicotinic acid riboside mononucleotide

Refernces

• 1、 -. "EFFICIENT AND SCALABLE SYNTHESES OF NICOTINOYL RIBOSIDES AND REDUCED NICOTINOYL RIBOSIDES, MODIFIED DERIVATIVES THEREOF, PHOSPHORYLATED ANALOGS THEREOF, ADENYLYL DINUCLEOTIDE CONJUGATES THEREOF, AND NOVEL CRYSTALLINE FORMS THEREOF". . . Retrieved 2018/05/26.
• 2、 Davies. "Simple synthesis of the 5-O-benzoylriboside of 1,4-dihydronicotinic acid; A cofactor for DT diaphorase and nitroreductase enzymes". . p. 311 - 312. Retrieved 2007/10/02.