F1392

Riboflavin 5′-monophosphate sodium salt hydrate

suitable for electrophoresis, suitable for acrylamide photopolymerization, ≥70%, powder

• 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
• EC Number: 204-988-6
• MDL number: MFCD00150992
• UNSPSC Code: 41106305
• PubChem Substance ID: 24894764
• NACRES: NA.51

Properties

• Assay: ≥70%
• form: powder
• optical activity: [α]20/D +37 to +42°, c = 1.5 in 5 M HCl(lit.)
• technique(s): electrophoresis: suitable
• solubility: H₂O: soluble 50 mg/mL, clear, orange
• ε (extinction coefficient): 12.5 at 445 nm at 1 mM
• suitability: suitable for acrylamide photopolymerization
• foreign activity: Protease, none detected
• 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 or FMN is suitable:

• to study its mechanism of inhibition of mutagenicity of a benzo[a]pyrene 7,8-diol 9,10-epoxide, a carcinogenic metabolite of benzo[a]pyrene
• along with flavin adenine dinucleotide for reactivation of the enzyme that catalyzes the oxidation of pyridoxamine to pyridoxal in a study
• to study the reduction of polymeric azo and nitro dyes by intestinal bacteria
• to study the effect of FMN on ferrisiderophore reductase activity in the cytoplasmic fraction of Agrobacterium tumefaciens.

Biochem/physiol Actions

FMN is a coenzyme synthesized from riboflavin (vitamin B2). It acts as a component of complex I of the electron transport chain. The enzymes containing FMN are called as flavin enzymes and are involved in oxidation-reduction mechanisms.
FMN is suitable as a photopolymerization reagent in polyacrylamide gel electrophoresis (PAGE) by forming free radicals in aqueous solution in the presence of light. FMN photodecomposes to leucoflavin. No free radicals are formed in the absence of oxygen, but traces of oxygen allow for leucoflavin to reoxidize with free-radical generation. The catalysts, tetramethylethylenediamine (TEMED) or 3-dimethylaminopropionitrile (DMAPN), are commonly added to speed up the free radical formation. Free radicals will cause acrylamide and bis-acrylamide to polymerize to form a gel matrix which can be used for sieving macromolecules. FMN is commonly used in the stacking gel for non-denaturing PAGE because native proteins can be sensitive to persulfate ions from ammonium persulfate. Another advantage of FMN over ammonium persulfate is that it will not start polymerizing until the gel is illuminated.

Riboflavin 5′-monophosphate or Flavin mononucleotide (FMN) serves as a prosthetic group for flavoenzymes. It is a part of the mitochondrial respiratory chain complex I and acts as a redox carrier. FMN is unstable in alkaline solution and is highly stable at pH 6.

Safety Information

• 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