Nicotinamide ribose supplier

Name
NICOTINAMIDE RIBOSIDE
EINECS 1308068-626-2
CAS No. 1341-23-7
Article Data15
CAS DataBase
Density 1.201g/cm³
Solubility
Melting Point
Formula C₁₁H₁₅ N₂ O₅
Boiling Point 646.2 °C at 760 mmHg
Molecular Weight 255.25
Flash Point 344.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Pyridinium,3-carbamoyl-1-b-D-ribofuranosyl-(8CI);3-Pyridinecarboxamide, 1-b-D-ribosyl-;Nicotinamide ribonucleoside;Nicotinamide ribose;Nicotinamide riboside;Ribosylnicotinamide;1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridine-5-carboxamide;nicotinamide-beta-riboside;
PSA 116.25000
LogP -1.69540

Synthetic route

: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 98-92-0
nicotinamide

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
Stage #1: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose With hydrogen bromide; acetic acid In toluene at 0℃; for 2h; Stage #2: nicotinamide In toluene Stage #3: With ammonia In methanol at 0℃; Concentration;	86.8%

: 98-92-0
nicotinamide

: 13035-61-5
1,2,3,5-tetraacetylribose

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
Stage #1: nicotinamide; 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 1.5h; Stage #2: With methanol at 20℃; for 1h;
Stage #1: nicotinamide; 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 30 - 40℃; Large scale; Stage #2: With potassium carbonate In dichloromethane at 15℃; for 1h; Large scale;

: 2',3',5'-triacetyl ethyl nicotinate riboside trifluoroacetate

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
With ammonium hydroxide In methanol at 4℃; for 16h;

: 2',3',5'-triacetyl ethyl nicotinate riboside

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
With ammonia In methanol at 4℃; for 7h;
Stage #1: 2',3',5'-triacetyl ethyl nicotinate riboside With ammonia at -5 - 5℃; for 1h; Stage #2: With sodium ethanolate In ethanol at -5 - 5℃; for 1h;

: 53-84-9
NAD

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: zirconium(IV) chloride; water / 0.5 h / 80 °C 2: calcium L-ascorbate; water / 48 h / 80 °C View Scheme

: 1094-61-7
nicotinamide mononucleotide

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
With water; calcium L-ascorbate at 80℃; for 48h; Reagent/catalyst;

: 5'-nicotinic acid ethyl ester ribose

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
With ammonia In acetonitrile at -5 - 5℃; for 1h;

: 1-(2',3',5'-triacetyl-β-D-ribofuranosyl)nicotinamide

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
With methanol at 25℃; for 0.5h; Large scale;	0.71 kg
With sodium ethanolate In ethanol at -5 - 5℃; for 1h;
With methanol; sodium methylate at -5 - 0℃; for 5h; Inert atmosphere;	8.5 g

: nicotinamide riboside glycine

A: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

B: 56-40-6
glycine

Conditions

Conditions	Yield
In aq. buffer pH=7;

: 13035-61-5
1,2,3,5-tetraacetylribose

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C 2.1: ammonia / 1 h / -5 - 5 °C 2.2: 1 h / -5 - 5 °C View Scheme
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C 2: sodium ethanolate / ethanol / 1 h / -5 - 5 °C View Scheme
Multi-step reaction with 4 steps 1: acetonitrile / 8 h / -5 °C / Inert atmosphere 2: sodium hydrogencarbonate; sodium hydroxide / water / 45 °C / Inert atmosphere 3: chloranil / tetrahydrofuran / 0 °C / Inert atmosphere 4: sodium methylate; methanol / 5 h / -5 - 0 °C / Inert atmosphere View Scheme

: 614-18-6
3-pyridinecarboxylic acid ethyl ester

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C 2.1: ammonia / 1 h / -5 - 5 °C 2.2: 1 h / -5 - 5 °C View Scheme

: 98-92-0
nicotinamide

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C 2: sodium ethanolate / ethanol / 1 h / -5 - 5 °C View Scheme
Multi-step reaction with 4 steps 1: acetonitrile / 8 h / -5 °C / Inert atmosphere 2: sodium hydrogencarbonate; sodium hydroxide / water / 45 °C / Inert atmosphere 3: chloranil / tetrahydrofuran / 0 °C / Inert atmosphere 4: sodium methylate; methanol / 5 h / -5 - 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: dichloromethane / 10 h / 0 °C / Inert atmosphere 2: sodium dithionite; potassium carbonate / water / 20 °C / Inert atmosphere 3: sodium periodate / 1,4-dioxane / 20 °C / Inert atmosphere 4: sodium methylate; methanol / 8 h / -10 - 0 °C / Inert atmosphere View Scheme

: 69216-50-8
1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-3-carbamoyl-pyridinium

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
With methanol; sodium methylate at -10 - 0℃; for 5h; Inert atmosphere;

: C13H6F12O9

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: dichloromethane / 10 h / 0 °C / Inert atmosphere 2: sodium dithionite; potassium carbonate / water / 20 °C / Inert atmosphere 3: sodium periodate / 1,4-dioxane / 20 °C / Inert atmosphere 4: sodium methylate; methanol / 8 h / -10 - 0 °C / Inert atmosphere View Scheme

: CF3O3S(1-)*C17H12F9N2O8(1+)

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium dithionite; potassium carbonate / water / 20 °C / Inert atmosphere 2: sodium periodate / 1,4-dioxane / 20 °C / Inert atmosphere 3: sodium methylate; methanol / 8 h / -10 - 0 °C / Inert atmosphere View Scheme

: C17H13F9N2O8

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium periodate / 1,4-dioxane / 20 °C / Inert atmosphere 2: sodium methylate; methanol / 8 h / -10 - 0 °C / Inert atmosphere View Scheme

: C17H12F9N2O8(1+)

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
With methanol; sodium methylate at -10 - 0℃; for 8h; Inert atmosphere;

: C32H24N5O14(1+)

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
With methanol; sodium methylate at -10 - 0℃; for 3h; Inert atmosphere;

: 3-carbamoyl-1-((2R,3R,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate; sodium hydroxide / water / 45 °C / Inert atmosphere 2: chloranil / tetrahydrofuran / 0 °C / Inert atmosphere 3: sodium methylate; methanol / 5 h / -5 - 0 °C / Inert atmosphere View Scheme

: [(2R,5R)-3,4-diacetoxy-5-(3-carbamoyl-4H-pyridin-1-yl)tetrahydrofuran-2-yl]methyl acetate

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: chloranil / tetrahydrofuran / 0 °C / Inert atmosphere 2: sodium methylate; methanol / 5 h / -5 - 0 °C / Inert atmosphere View Scheme

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: 19132-12-8
1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofur-2-yl]-1,4-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate; sodium dithionite at 0℃; for 0.5h; pH=8; Inert atmosphere;	70%

: 617-48-1
malic acid

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: C11H15N2O5(1+)*C4H5O5(1-)*C4H6O5

Conditions

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	60.51%

: 617-48-1
malic acid

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: nicotinamide ribose malate

Conditions

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	60.51%

: 617-48-1
malic acid

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: C11H15N2O5(1+)*C4H5O5(1-)

Conditions

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	57%

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: 77-92-9
citric acid

: C11H15N2O5(1+)*C6H8O7*C6H7O7(1-)

Conditions

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	56.82%

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: 77-92-9
citric acid

: nicotinamide ribose citrate

Conditions

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	56.82%

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: 1094-61-7
nicotinamide mononucleotide

Conditions

Conditions	Yield
With trichlorophosphate In tetrahydrofuran at 0 - 20℃; for 12h;	56%

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: 77-92-9
citric acid

: C11H15N2O5(1+)*C6H7O7(1-)

Conditions

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	55.91%

: 765-01-5
10-hydroxy-2-decenoic acid

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: C11H15N2O5(1+)*C10H17O3(1-)*C10H18O3

Conditions

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	50%

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: 98-92-0
nicotinamide

Conditions

Conditions	Yield
With potassium hydroxide; CAPS buffer (pH > 7); potassium chloride In water at 37℃; Product distribution; Mechanism; Kinetics;
With human CD157; water In aq. phosphate buffer pH=7; Kinetics; Enzymatic reaction;

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: nicotinamide mononucleotide

Conditions

Conditions	Yield
With trichlorophosphate In various solvent(s) at 0℃; for 4h;
With human nicotinamide riboside kinase-1; ATP; magnesium chloride at 37℃; for 2h; pH=7.5; aq. phosphate buffer; Enzymatic reaction;

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: 938173-81-0
imidazolide nicotinamide monophosphate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: POCl3 / various solvent(s) / 4 h / 0 °C 2: Et3N / dimethylformamide / 3 h / 20 °C View Scheme

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: C28H35N7O17P3(1+)

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: POCl3 / various solvent(s) / 4 h / 0 °C 2: Et3N / dimethylformamide / 3 h / 20 °C 3: dimethylformamide / 24 h / 20 °C 4: 22 percent / TBAF; AcOH / tetrahydrofuran / 3 h / 0 °C View Scheme

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: (C3H7)4Si2OOH(C10H10N5O4)(PO(OC7H7)2)(POOH)O(H2NCOC5H3NC5O4H9POOH)(1+)

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: POCl3 / various solvent(s) / 4 h / 0 °C 2: Et3N / dimethylformamide / 3 h / 20 °C 3: dimethylformamide / 24 h / 20 °C View Scheme

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: 604-79-5
nicotinamide adenine dinucleotide phosphate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: POCl3 / various solvent(s) / 4 h / 0 °C 2: Et3N / dimethylformamide / 3 h / 20 °C 3: dimethylformamide / 24 h / 20 °C 4: 22 percent / TBAF; AcOH / tetrahydrofuran / 3 h / 0 °C 5: 77 percent / cyclohexadiene / Pd/C / methanol; H2O / 2 h / 20 °C View Scheme

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: 1-[(2R,3R,4S,5R)-5-[[[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxyhydroxyphosphoryl]oxyhydroxyphosphoryl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyridin-1-ium-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: POCl3 / various solvent(s) / 4 h / 0 °C 2: Et3N / dimethylformamide / 3 h / 20 °C 3: dimethylformamide / 24 h / 20 °C 4: 22 percent / TBAF; AcOH / tetrahydrofuran / 3 h / 0 °C 5: 77 percent / cyclohexadiene / Pd/C / methanol; H2O / 2 h / 20 °C 6: 63 percent / aq. NaOAc / Aplysia ADP-ribosyl cyclase / 5 h / 20 °C / pH 4 View Scheme

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: 56-65-5
ATP

: 865-05-4
nicotinamide adenine dinucleotide

Conditions

Conditions	Yield
With human nicotinamide mononucleotide adenylyltransferase 1; human nicotinamide riboside kinase 1 at 20℃; for 4h; Enzymatic reaction;

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

A: α-D-ribofuranosyl-1-phosphate

B: 98-92-0
nicotinamide

Conditions

Conditions	Yield
With potassium dihydrogenphosphate; purine nucleoside phosphorylase In aq. buffer pH=7; Enzymatic reaction;

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: C4H5O5(1-)*C4H6O5*(x)C6H4NO2(1-)*C11H15N2O5(1+)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 2 h / -10 - -5 °C / Inert atmosphere 2: 0.17 h / 16 °C / Inert atmosphere View Scheme

: 1341-23-7
1-(β-D-ribofuranosyl)-nicotinamide

: C4H5O5(1-)*C4H6O5*(x)C5H8NO4(1-)*C11H15N2O5(1+)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 2 h / -10 - -5 °C / Inert atmosphere 2: 0.17 h / Inert atmosphere View Scheme

Nicotinamide ribose Specification

The Nicotinamide ribose with cas registry number of 1341-23-7, is also called Pyridinium,3-carbamoyl-1-b-D-ribofuranosyl-(8CI) ;3-Pyridinecarboxamide, 1-b-D-ribosyl- .

Physical properties of Nicotinamide ribose :(1)# of Rule of 5 Violations: 1; (2)#H bond acceptors: 8; (3)#H bond donors: 6; (4)#Freely Rotating Bonds: 9; (5)Polar Surface Area: 153.97 Å²; (6)Enthalpy of Vaporization: 100.16 kJ/mol; (7)Vapour Pressure: 1.39E-17 mmHg at 25°C .

You can still convert the following datas into molecular structure:(1)SMILES:NC(=O)c1cccnc1.O=C[C@H](O)[C@H](O)[C@H](O)CO; (2)InChI:InChI=1/C6H6N2O.C5H10O5/c7-6(9)5-2-1-3-8-4-5;6-1-3(8)5(10)4(9)2-7/h1-4H,(H2,7,9);1,3-5,7-10H,2H2/t;3-,4+,5-/m.0/s1; (3)InChIKey:JQZBTYOVGMGUST-HEEXEHOYBT; (4)Std. InChI:InChI=1S/C6H6N2O.C5H10O5/c7-6(9)5-2-1-3-8-4-5;6-1-3(8)5(10)4(9)2-7/h1-4H,(H2,7,9);1,3-5,7-10H,2H2/t;3-,4+,5-/m.0/s1; (5)Std. InChIKey:JQZBTYOVGMGUST-HEEXEHOYSA-N.

Product Name

NICOTINAMIDE RIBOSIDE

Synthetic route

Nicotinamide ribose Specification

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