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F2253

Sigma-Aldrich

Riboflavin 5′-monophosphate sodium salt hydrate

synthetic, ≥70% (HPLC)

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Synonym(s):
FMN-Na, Flavin mononucleotide, Riboflavin 5′-phosphate sodium salt
Empirical Formula (Hill Notation):
C17H20N4NaO9P · xH2O
CAS Number:
Molecular Weight:
478.33 (anhydrous basis)
Beilstein:
4106529
MDL number:
eCl@ss:
34058005
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic

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

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This Item
77623F6750F8384
assay

≥70% (HPLC)

assay

-

assay

73-79% (fluorimetric)

assay

≥95%

form

powder

form

powder

form

powder

form

powder

impurities

≤0.3% Riboflavin

impurities

-

impurities

-

impurities

-

solubility

water: 50 mg/mL

solubility

water: soluble 100 g/L at 20 °C

solubility

water: 50 mg/mL, clear, orange

solubility

water: 50 mg/mL, clear

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

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.

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

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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)
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.
Enzymic formation of riboflavin 4?, 5?-cyclic phosphate from FAD: evidence for a specific low-Km FMN cyclase in rat liver1
FRAIZ F J, et al.
The Biochemical Journal, 330(2), 881-888 (1998)
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)
Steven O Mansoorabadi et al.
The Journal of organic chemistry, 72(17), 6329-6342 (2007-06-22)
Flavin coenzymes play a variety of roles in biological systems. This Perspective highlights the chemical versatility of flavins by reviewing research on five flavoenzymes that have been studied in our laboratory. Each of the enzymes discussed in this review [the

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