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F2253

Riboflavin 5′-monophosphate sodium salt hydrate

Name: Riboflavin 5′-monophosphate sodium salt hydrate
Brand: SIGMA

synthetic, ≥70% (HPLC)

Synonym(s):

FMN-Na, Flavin mononucleotide, Riboflavin 5′-phosphate sodium salt

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About This Item

Empirical Formula (Hill Notation):

C₁₇H₂₀N₄NaO₉P · xH₂O

CAS Number:

130-40-5

Molecular Weight:

478.33 (anhydrous basis)

NACRES:

NA.51

PubChem Substance ID:

24894817

eCl@ss:

34058005

UNSPSC Code:

41106305

MDL number:

MFCD00150992

Beilstein/REAXYS Number:

4106529

Assay:

≥70% (HPLC)

Biological source:

synthetic

Form:

powder

Solubility:

water: 50 mg/mL

Storage temp.:

−20°C

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Properties

biological source

synthetic

Quality Level

200

assay

≥70% (HPLC)

form

powder

impurities

≤0.3% Riboflavin

solubility

water: 50 mg/mL

storage temp.

−20°C

SMILES string

O.[Na+].Cc1cc2N=C3C(=O)NC(=O)N=C3N(C[C@H](O)[C@H](O)[C@H](O)COP(O)([O-])=O)c2cc1C

InChI

1S/C17H21N4O9P.Na.H2O/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29;;/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29);;1H2/q;+1;/p-1/t11-,12+,14-;;/m0../s1

InChI key

BHRVCJBIICJWTH-APQIITSESA-M

Description

Application

Riboflavin 5′-monophosphate sodium salt hydrate has been used:

as a component of assay buffer to determine the luminescence of L. lactis cells
as a component of the reaction mixture in nitric oxide synthase (NOS) enzymatic activity assay
in the high performance liquid chromatography (HPLC) analysis of Flavin mononucleotide (FMN) cyclase products
in luciferase assay with firefly luciferase

Biochem/physiol Actions

Riboflavin 5′-monophosphate (FMN), a derivative of riboflavin, is used as a prosthetic group for one and two-electron transfer in oxidation/reduction reactions. It acts as a cofactor for enzymes such as reduced nicotinamide adenine dinucleotide (NADH) dehydrogenase, nitric oxide synthase, and nitrilotriacetate monooxygenase. Riboflavin 5′-monophosphate is used as a substrate to study the specificity and kinetics of FMN phosphohydrolases and to study molecular sensing-based gene regulation by riboswitches.

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Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Luciferase detection during stationary phase in Lactococcus lactis

Bachmann H, et al.

Applied and Environmental Microbiology, 73(14), 4704-4706 (2007)

Flavin adenine dinucleotide and flavin mononucleotide metabolism in rat liver--the occurrence of FAD pyrophosphatase and FMN phosphohydrolase in isolated mitochondria.

M Barile et al.

European journal of biochemistry, 249(3), 777-785 (1997-12-12)

In order to gain some insight into mitochondrial flavin biochemistry, rat liver mitochondria essentially free of lysosomal and microsomal contamination were prepared and their capability to metabolise externally added and endogenous FAD and FMN tested both spectroscopically and via HPLC.

Establishment of patterned thalamocortical connections does not require nitric oxide synthase

Finney E M and Shatz C J

The Journal of Neuroscience, 18(21), 8826-8838 (1998)

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