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F6750

Sigma-Aldrich

Riboflavin 5′-monophosphate sodium salt hydrate

73-79% (fluorimetric)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C17H20N4NaO9P · xH2O
CAS Number:
130-40-5
Molecular Weight:
478.33 (anhydrous basis)
Beilstein/REAXYS Number:
4106529
MDL number:
MFCD00150992
UNSPSC Code:
41106305
eCl@ss:
34058005
PubChem Substance ID:
24894910
NACRES:
NA.51

Quality Level

200

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

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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)

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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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
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
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