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N1630

Sigma-Aldrich

β-Nicotinamide adenine dinucleotide 2′-phosphate reduced tetrasodium salt hydrate

≥93% (HPLC)

Synonym(s):
β-NADPH, 2′-NADPH hydrate, Coenzyme II reduced tetrasodium salt, Dihydronicotinamide adenine dinucleotide phosphate tetrasodium salt, NADPH Na4, TPNH2 Na4, Triphosphopyridine nucleotide reduced tetrasodium salt
Empirical Formula (Hill Notation):
C21H26N7Na4O17P3 · xH2O
CAS Number:
Molecular Weight:
833.35 (anhydrous basis)
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.51

Quality Level

assay

≥93% (HPLC)
≥93% (spectrophotometric assay)

form

powder

solubility

10 mM NaOH: soluble 50 mg/mL, clear

storage temp.

−20°C

SMILES string

[Na+].[Na+].[Na+].[Na+].NC(=O)C1=CN(C=CC1)[C@H]2O[C@@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]3O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@H](O)[C@@H]2O

InChI

1S/C21H30N7O17P3.4Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32;;;;/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35);;;;/q;4*+1/p-4/t10-,11+,13-,14+,15-,16+,20-,21+;;;;/m0..../s1

InChI key

WYWWVJHQDVCHKF-MPUNMZHWSA-J

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Application

β-NADPH is suitable for use in:
  • desaturation of fatty acids
  • an assay of desaturase activity
  • the histochemical detection of NADPH diaphorase activity in rat, rabbit and pheasant thoracic spinal cord
  • the measurement of glutathione in oligodendrocyte cultures

Packaging

25, 50, 100, 250, 500 mg in poly bottle
1, 5 g in poly bottle

Biochem/physiol Actions

β-NADPH is the reduced form of NADP+ generated by the pentose phosphate pathway. It serves as a carrier of reducing power and transfers H+ and 2 e to the oxidized precursors in the reduction reactions of biosynthesis. It is an essential coenzyme for the catalytic activity of enzymes such as glutathione reductase, diacetyl reductase, dihydrofolate reductase, glutamic dehydrogenase, p-hydroxybenzoate hydroxylase, NADPH-FMN oxidoreductase, nitrate reductase, and thioredoxin reductase. It is also a part of cytochrome P450 electron transport systems.
NADPH is an electron donor and a cofactor for many redox enzymes including nitric oxide synthetase.

Preparation Note

Chemically reduced.

Other Notes

Packaged based on solid weight.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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Product Information Sheet

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