riboflavin 5'-phosphate

vitamin B2 phosphate

CAS: 146-17-8 C17 H21 N4 O9 P MW: 456.34893200

Identification

Nameriboflavin 5'-phosphate
IUPAC[(2S,3R,4R)-5-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] dihydrogen phosphate
CAS Number146-17-8
EINECS205-664-7
FDA UNII7N464URE7E
Molecular FormulaC17 H21 N4 O9 P
Molecular Weight456.34893200
Beilstein0068086
XlogP3-2.60 (est)

Regulatory

FDA/DG SANTE Petitions, Reviews, Notices184.1697
FDA Mainterm (SATF)146-17-8 ; RIBOFLAVIN 5'-PHOSPHATE

Physical Properties

Food Chemicals Codex Listed No
Flash Point 32.00 °F. TCC ( 0.00 °C. ) (est)
logP (o/w) -1.747 (est)
Soluble in water, 1996 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral Toxicityintravenous-mouse LD50 365 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynutrient supplements
Recommendation for riboflavin 5'-phosphate usage levels up tonot for fragrance use.
Recommendation for riboflavin 5'-phosphate flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

[(2S,3R,4R)-5-(7,8- dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] dihydrogen phosphate flanin riboflavin mononucleotide riboflavine dihydrogen phosphate vitamin B2 phosphate PubMed: A thixotropic supramolecular hydrogel of adenine and riboflavin-5'-phosphate sodium salt showing enhanced fluorescence properties. PubMed: Matrix tablets based on a carrageenan with the modified-release of sodium riboflavin 5'-phosphate. PubMed: Evaluating in vivo delivery of riboflavin with coulomb-controlled iontophoresis for corneal collagen cross-linking: a pilot study. PubMed: [Ion-pair HPLC analysis of B vitamins in syrup products in Indonesia]. PubMed: Modified-release capsules containing sodium riboflavin 5'-phosphate. PubMed: Tailored beads made of dissolved cellulose--investigation of their drug release properties. PubMed: Electron acceptor dependence of electron shuttle secretion and extracellular electron transfer by Shewanella oneidensis MR-1. PubMed: Enhancement of corneal permeation of riboflavin-5'-phosphate through vitamin E TPGS: a promising approach in corneal trans-epithelial cross linking treatment. PubMed: Oxidative mechanisms for the biotransformation of 1-methyl-1,6-dihydropyridine-2-carbaldoxime to pralidoxime chloride. PubMed: The antibiotics roseoflavin and 8-demethyl-8-amino-riboflavin from Streptomyces davawensis are metabolized by human flavokinase and human FAD synthetase. PubMed: Simultaneous controlled vitamin release from multiparticulates: theory and experiment. PubMed: A novel riboflavin gastro-mucoadhesive delivery system based on ion-exchange fiber. PubMed: Simultaneous determination of some water-soluble vitamins and preservatives in multivitamin syrup by validated stability-indicating high-performance liquid chromatography method. PubMed: Shewanella secretes flavins that mediate extracellular electron transfer. PubMed: Molecular determinants for FMN-binding in Desulfovibrio gigas flavoredoxin. PubMed: Relationship between the redox change in yellow fluorescent protein of Vibrio fischeri strain Y1 and the reversible change in color of bioluminescence in vitro. PubMed: Activity coupling of Vibrio harveyi luciferase and flavin reductase (FRP): oxygen as a probe. PubMed: Kinetic mechanism and quaternary structure of Aminobacter aminovorans NADH:flavin oxidoreductase: an unusual flavin reductase with bound flavin. PubMed: Energy transfer evidence for in vitro and in vivo complexes of Vibrio harveyi flavin reductase P and luciferase. PubMed: A two [4Fe-4S]-cluster-containing ferredoxin as an alternative electron donor for 2-hydroxyglutaryl-CoA dehydratase from Acidaminococcus fermentans. PubMed: Automated determination of selected water-soluble vitamins in tablets using a bench-top robotic system coupled to reversed-phase (RP-18) HPLC with UV detection. PubMed: Rapid determination of thiamine, riboflavin, pyridoxine, and niacinamide in infant formulas by liquid chromatography. PubMed: The iron-sulfur clusters in 2-hydroxyglutaryl-CoA dehydratase from Acidaminococcus fermentans. Biochemical and spectroscopic investigations. PubMed: Activities of the bimodal fluorescent protein produced by Photobacterium phosphoreum strain bmFP in the luciferase reaction in vitro. PubMed: 2-hydroxyglutaryl-CoA dehydratase from Clostridium symbiosum. PubMed: Antimutagenic effects and possible mechanisms of action of vitamins and related compounds against genotoxic heterocyclic amines from cooked food. PubMed: Computational analysis of the oxygen addition at the C4a site of reduced flavin in the bacterial luciferase bioluminescence reaction. PubMed: Effects of mutations of the alpha His45 residue of Vibrio harveyi luciferase on the yield and reactivity of the flavin peroxide intermediate. PubMed: Preparation of riboflavin 4',5'-cyclic phosphate by incubation of flavin-adenine dinucleotide with Mn2+ in the absence of riboflavin 5'-phosphate cyclase. PubMed: Development of a novel controlled-release system for gastric retention. PubMed: Extent of Intramolecular Aromatic-Ring Stacking in Ternary Cu(2+) Complexes Formed by 2,2'-Bipyridyl or 1,10-Phenanthroline and Flavin Mononucleotide (FMN(2)(-))(1)(,)(2). PubMed: Inhibition of the mutagenicity of 2-nitrofluorene, 3-nitrofluoranthene and 1-nitropyrene by vitamins, porphyrins and related compounds, and vegetable and fruit juices and solvent extracts. PubMed: Binding of the oxidized, reduced, and radical flavin species to chorismate synthase. An investigation by spectrophotometry, fluorimetry, and electron paramagnetic resonance and electron nuclear double resonance spectroscopy. PubMed: Kinetics and thermodynamics of the binding of riboflavin, riboflavin 5'-phosphate and riboflavin 3',5'-bisphosphate by apoflavodoxins. PubMed: Cloning and analysis of structural genes from Streptomyces pristinaespiralis encoding enzymes involved in the conversion of pristinamycin IIB to pristinamycin IIA (PIIA): PIIA synthase and NADH:riboflavin 5'-phosphate oxidoreductase. PubMed: Purification of the two-enzyme system catalyzing the oxidation of the D-proline residue of pristinamycin IIB during the last step of pristinamycin IIA biosynthesis. PubMed: Catalytically active forms of the individual subunits of Vibrio harveyi luciferase and their kinetic and binding properties. PubMed: Probing the Vibrio harveyi luciferase beta subunit functionality and the intersubunit domain by site-directed mutagenesis. PubMed: Mechanism of aldehyde inhibition of Vibrio harveyi luciferase. Identification of two aldehyde sites and relationship between aldehyde and flavin binding. PubMed: Purification and characterization of a NADH oxidase from the thermophile Thermus thermophilus HB8. PubMed: Flavin levels in the rat retina. PubMed: [Effect of preliminarily administered aspartate to the body and its combination with a vitamin-coenzyme complex on the catabolism of L-[14C]-aspartate in tissues of various mouse organs in hermetically closed space]. PubMed: Amplified colorimetric assay of alkaline phosphatase using riboflavin 4'-phosphate: a simple method for measuring riboflavin and riboflavin 5'-phosphate. PubMed: A new reducing agent of flavins and its application to the assay of bacterial luciferase. PubMed: Effect of vitamin B2 deficiency on rat liver dihydropyrimidine dehydrogenase activity. PubMed: [Mechanisms of organic drug electrophoresis]. PubMed: Analysis of water-soluble vitamins in total parenteral nutrition solution by high pressure liquid chromatography. PubMed: Enhancement of adriamycin-induced mortality during riboflavin administration and riboflavin deficiency in rats. PubMed: The simultaneous assay of riboflavin 5-phosphate sodium and other water-soluble vitamins in liquid multivitamin formulations by liquid chromatograph. PubMed: Quantification of riboflavin, riboflavin 5'-phosphate and flavin adenine dinucleotide in plasma and urine by high-performance liquid chromatography. PubMed: Riboflavin metabolism in the hypothyroid human adult. PubMed: A comparative carbon-13, nitrogen-15, and phosphorus-31 nuclear magnetic resonance study on the flavodoxins from Clostridium MP, Megasphaera elsdenii, and Azotobacter vinelandii. PubMed: Vitamin stability in a TPN mixture stored in an EVA plastic bag. PubMed: [A variant of pathogenetic therapy in the acute period of perinatal hypoxic-traumatic brain lesions in premature infants]. PubMed: Carbon-13 and nitrogen-15 nuclear-magnetic-resonance investigation on Desulfovibrio vulgaris flavodoxin. PubMed: Effects of vitamins on lipid peroxidation and suppression of DNA synthesis induced by adriamycin in Ehrlich cells. PubMed: Factors modulating the formation of DNA adduct by aflatoxin B1 in vitro. PubMed: Metabolism of vitamin B-6 by human liver. PubMed: Direct cross-linking of three domains in the myosin head. PubMed: In-vitro riboflavin binding and endogenous flavins in Phycomyces blakesleeanus. PubMed: On the mobility of riboflavin 5'-phosphate in Megasphaera elsdenii flavodoxin as studied by 13C-nuclear-magnetic-resonance relaxation. PubMed: Phosphates of riboflavin and riboflavin analogs: a reinvestigation by high-performance liquid chromatography. PubMed: Isolation of bacterial luciferases by affinity chromatography on 2,2-diphenylpropylamine-Sepharose: phosphate-mediated binding to an immobilized substrate analogue. PubMed: Mechanism of the inhibition of mutagenicity of a benzo[a]pyrene 7,8-diol 9,10-epoxide by riboflavin 5'-phosphate. PubMed: Studies on the NADH and NADPH: riboflavin 5'-phosphate (FMN) oxidoreductases from Beneckea harveyi: characterization of the FMN binding sites. PubMed: New polyacrylamide matrices for drift-free isoelectric focusing. PubMed: Structural and dynamic information on the complex of Megasphaera elsdenii apoflavodoxin and riboflavin 5'-phosphate. A phosphorus-31 nuclear magnetic resonance study. PubMed: Binding of 2,2-diphenylpropylamine at the aldehyde site of bacterial luciferase increases the affinity of the reduced riboflavin 5'-phosphate site. PubMed: Interaction of riboflavin-5'-phosphate with poly-(alpha-L-lysine) & poly-(alpha-L-histidine) in aqueous medium. PubMed: Apoflavodoxin aggregation following dissociation of flavin. PubMed: Preparation and properties of immobilized flavokinase. PubMed: Spectroscopic studies of pyridoxamine (pyridoxine) 5'-phosphate oxidase. Equilibrium dissociation constants and spectra for riboflavin 5'-phosphate and analogues. PubMed: Solubilization and properties of a particulate hydrogenase from Methanobacterium strain G2R. PubMed: Purification and properties of nitroalkane oxidase from Fusarium oxysporum. PubMed: In vitro photodecomposition of uric acid in presence of riboflavin II. PubMed: A route dependent bioavailability in active metabolite suggested in riboflavin-5'-phosphate pharmacokinetics. PubMed: A continuous fluorometric assay for flavokinase. Properties of flavokinase from Peptostreptococcus elsdenii. PubMed: 15N nuclear magnetic resonance of flavins. PubMed: Histochemistry of normal and diseased human lymph nodes. PubMed: Properties of immobilized flavodoxin from Peptostreptococcus elsdenii. An affinity ligand for the purification of riboflavin 5'-phosphate (FMN) and its analogues. PubMed: Fluorescence titration with apoflavodoxin: a sensitive assay for riboflavin 5'-phosphate and flavin adenine dinucleotide in mixtures. PubMed: Effect of carbonated beverages and of an antiemetic containing carbohydrate and phosphoric acid on riboflavin bioavailability and salicylamide biotransformation in humans. PubMed: [Effect of riboflavin mononucleotide, ATP and nospanum hydrochloricum on the electric activity of the retina, ocular hemodynamics and ophthalmotonus (experimental-clinical study)]. PubMed: [Characteristics of the subconjunctival administration of a riboflavin-mononucleotide solution]. PubMed: The binding of riboflavin-5'-phosphate in a flavoprotein: flavodoxin at 2.0-Angstrom resolution. PubMed: [Riboflavin-mononucleotide in the ophthalmic practice]. PubMed: [Riboflavin mononucleotide]. PubMed: Riboflavin 5'-phosphate: a potent activator or brain glutaminase. PubMed: Studies on riboflavin metabolism in the rat. 3. Disappearance rate and urinary excretion rate of flavin after intravenous infusion of riboflavin-5'-phosphate. PubMed: Studies on riboflavin metabolism in the rat. I. Urinary and faecal excretion after oral administration of riboflavin-5'-phosphate. PubMed: Plasma protein binding of riboflavin and riboflavin-5'-phosphate in man. PubMed: Studies on riboflavin metabolism in the rat. II. Metabolic flavin elimination after oral or intraperitoneal administration of riboflavin-5'-phosphate. PubMed: Absorption, metabolism, and excretion of riboflavin-5'-phosphate in man. PubMed: Hydrolysis of riboflavin 5'-phosphate by phosphatases of rat kidney. PubMed: [Resorption of cocarboxylase, riboflavin-5'-phosphate sodium and vitamin A in the colon]. PubMed: [Riboflavin-5'-phosphate as electron donor in photosensibilized reduction of oxidized glutathione]. PubMed: [Riboflavin-5'-phosphate and hematoporphyrin sensitized by photooxidation of yeast alcohol dehydrogenase]. PubMed: Interaction between riboflavin and rutin. PubMed: Metal chelates and antitubercular activity. V. Riboflavin, riboflavin-5'-phosphate, alloxan, phthaloylhydrazine. PubMed: Photooxidations catalyzed by plant and bacterial extracts and by riboflavin-5'-phosphate. PubMed: [Influence of the reaction of the medium on the chemical hydrolysis of riboflavin-5'-phosphate]. PubMed: Synthetic riboflavin-5'-phosphate.