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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:
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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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.
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)
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)
Hannah Tabakh et al.
eLife, 10 (2021-05-07)
Pathogens encounter numerous antimicrobial responses during infection, including the reactive oxygen species (ROS) burst. ROS-mediated oxidation of host membrane poly-unsaturated fatty acids (PUFAs) generates the toxic alpha-beta carbonyl 4-hydroxy-2-nonenal (4-HNE). Although studied extensively in the context of sterile inflammation, research
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