F6750

Riboflavin 5′-monophosphate sodium salt hydrate

73-79% (fluorimetric)

• 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: 24894910
• NACRES: NA.51

Properties

• Assay: 73-79% (fluorimetric)
• form: powder
• solubility: water: 50 mg/mL, clear, orange
• 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

General description

Riboflavin 5′-monophosphate is a derivative of riboflavin, a water-soluble vitamin.

Application

Riboflavin 5′-monophosphate is used as a substrate to study the specificity and kinetics of FMN phosphohydrolases. FMN is used to study molecular sensing based gene regulation by riboswitches.

Riboflavin 5′-monophosphate sodium salt hydrate has been used in the preparation of hypo-osmolar riboflavin formulation:

• to evaluate the riboflavin (RF) concentration and distribution in the corneal stroma
• to study corneal resistance to enzymatic digestion
• as a photosensitizer to evaluate the efficacy and safety of photochemical corneal stiffening using ex vivo and in vivo rabbit eye models

Biochem/physiol Actions

Riboflavin 5′-monophosphate (FMN) serves as a cofactor for flavoenzymes. It is used as a prosthetic group by oxidoreductase (one and two-electron transfer) enzymes, also called flavoproteins, such as nicotinamide adenine dinucleotide (NADH) dehydrogenases, nitric oxide synthases, nitric oxide reductase, and nitrilotriacetate monooxygenases. These enzymes protect cells from oxidative stress and apoptosis. Any alteration in the levels of FMN caused due to abnormal riboflavin metabolism leads to mitochondrial dysfunction and diminished energy levels. This results in disorders related to riboflavin such as cataracts, neurodegenerative and cardiovascular diseases. FMN is associated with metabolic pathways of amino acids, fatty acids, and purines. It is involved in cellular growth and development mediated by the oxidation-reduction reaction.

Quality

Free Riboflavin: ≤6.0%
Riboflavin diphosphates: ≤6.0% (as riboflavin)

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