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Merck

F6750

Sigma-Aldrich

Riboflavin 5′-Monophosphat Natriumsalz Hydrat

73-79% (fluorimetric)

Synonym(e):

FMN-Na, Flavin-mononucleotid

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About This Item

Empirische Formel (Hill-System):
C17H20N4NaO9P · xH2O
CAS-Nummer:
Molekulargewicht:
478.33 (anhydrous basis)
Beilstein:
4106529
MDL-Nummer:
UNSPSC-Code:
41106305
eCl@ss:
34058005
PubChem Substanz-ID:
NACRES:
NA.51

Qualitätsniveau

Assay

73-79% (fluorimetric)

Form

powder

Löslichkeit

water: 50 mg/mL, clear, orange

Lagertemp.

−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

InChIKey

BHRVCJBIICJWTH-APQIITSESA-M

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Allgemeine Beschreibung

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

Anwendung

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. Wirkung

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.

Qualität

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 1

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


Analysenzertifikate (COA)

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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)
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
Tamilarasan Udhayabanu et al.
Journal of clinical medicine, 6(5) (2017-05-06)
Mitochondria are the repository for various metabolites involved in diverse energy-generating processes, like the TCA cycle, oxidative phosphorylation, and metabolism of amino acids, fatty acids, and nucleotides, which rely significantly on flavoenzymes, such as oxidases, reductases, and dehydrogenases. Flavoenzymes are
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

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