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F6750

Sigma-Aldrich

Riboflavin 5′-monophosphate sodium salt hydrate

73-79% (fluorimetric)

Synonyme(s) :

FMN-Na, Flavin mononucleotide, Riboflavin 5′-phosphate sodium salt

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About This Item

Formule empirique (notation de Hill):
C17H20N4NaO9P · xH2O
Numéro CAS:
130-40-5
Poids moléculaire :
478.33 (anhydrous basis)
Numéro Beilstein :
4106529
Numéro MDL:
MFCD00150992
Code UNSPSC :
41106305
eCl@ss :
34058005
ID de substance PubChem :
24894910
Nomenclature NACRES :
NA.51

Pureté

73-79% (fluorimetric)

Forme

powder

Solubilité

water: 50 mg/mL, clear, orange

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

BHRVCJBIICJWTH-APQIITSESA-M

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Catégories apparentées

Description générale

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

Actions biochimiques/physiologiques

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.

Qualité

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Arie L Marcovich et al.
Translational vision science & technology, 9(6), 4-4 (2020-08-22)
To evaluate the riboflavin (RF) concentration and distribution in the corneal stroma and the risk for endothelial photodamage during corneal crosslinking (CXL) following 10- and 30-minute impregnation. De-epithelialized rabbit corneas were subjected to impregnation for 10 and 30 minutes with
Arie L Marcovich et al.
Investigative ophthalmology & visual science, 53(10), 6378-6388 (2012-08-09)
We evaluated the efficacy and safety of photochemical corneal stiffening by palladium bacteriochlorin 13'-(2-sulfoethyl)amide dipotassium salt (WST11) and near infrared (NIR) illumination, using ex vivo and in vivo rabbit eye models. Corneas of post mortem rabbits and living rabbits were
Mieke M E Huijbers et al.
Scientific reports, 7, 43880-43880 (2017-03-04)
Flavoenzymes are versatile biocatalysts containing either FAD or FMN as cofactor. FAD often binds to a Rossmann fold, while FMN prefers a TIM-barrel or flavodoxin-like fold. Proline dehydrogenase is denoted as an exception: it possesses a TIM barrel-like fold while
Arie L Marcovich et al.
Translational vision science & technology, 9(6), 4-4 (2020-08-22)
To evaluate the riboflavin (RF) concentration and distribution in the corneal stroma and the risk for endothelial photodamage during corneal crosslinking (CXL) following 10- and 30-minute impregnation. De-epithelialized rabbit corneas were subjected to impregnation for 10 and 30 minutes with
Decreased Riboflavin Impregnation Time Does Not Increase the Risk for Endothelial Phototoxicity During Corneal Cross-Linking
Marcovich AL, et al.
Translational vision science & technology (2020)
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