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F2253

Sigma-Aldrich

Riboflavin 5′-monophosphate sodium salt hydrate

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)
Beilstein:
4106529
MDL number:
MFCD00150992
UNSPSC Code:
41106305
eCl@ss:
34058005
PubChem Substance ID:
24894817
NACRES:
NA.51

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

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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.

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Luciferase detection during stationary phase in Lactococcus lactis
Bachmann H, et al.
Applied and Environmental Microbiology, 73(14), 4704-4706 (2007)
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
Nathan J Baird et al.
RNA biology, 7(3), 328-332 (2010-05-12)
Riboswitches are structured mRNA elements involved in gene regulation that respond to the intracellular concentration of specific small molecules. Binding of their cognate ligand is thought to elicit a global conformational change of the riboswitch, in addition to modulating the
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