F6750
Riboflavin 5′-monophosphate sodium salt hydrate
70-79% (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:
Molecular Weight:
478.33 (anhydrous basis)
NACRES:
NA.51
PubChem Substance ID:
eCl@ss:
34058005
UNSPSC Code:
41106305
MDL number:
Beilstein/REAXYS Number:
4106529
Product Name
Riboflavin 5′-monophosphate sodium salt hydrate, 70-79% (fluorimetric)
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
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 key
BHRVCJBIICJWTH-APQIITSESA-M
biological source
non-animal source
description
(Clear to hazy)
assay
70-79% (fluorimetric)
form
powder
solubility
water: 50 mg/mL, orange
storage temp.
−20°C
Quality Level
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Analysis Note
Free Riboflavin: ≤6.0%
Riboflavin diphosphates: ≤6.0% (as riboflavin)
Riboflavin diphosphates: ≤6.0% (as riboflavin)
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.
General description
Riboflavin 5′-monophosphate is a derivative of riboflavin, a water-soluble vitamin.
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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.
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
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
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