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Cas Database

146-17-8

146-17-8

Identification

  • Product Name:Riboflavin5'-(dihydrogen phosphate)

  • CAS Number: 146-17-8

  • EINECS:205-664-7 (Base)204-988-6

  • Molecular Weight:456.349

  • Molecular Formula: C17H21 N4 O9 P

  • HS Code:HOSPHATE SODIUM PRODUCT IDENTIFICATION

  • Mol File:146-17-8.mol

Synonyms:Riboflavine5-phosphate (6CI); Benzo[g]pteridine, riboflavin 5'-(dihydrogen phosphate)deriv.; Alloxazine mononucleotide; Bisulase; E 101; E 101a; FMN; Flanin; Flavinmononucleotide; Flavine mononucleotide; Flavol; Riboflavin 5'-monophosphate;Riboflavin 5'-phosphate; Riboflavin mononucleotide; Riboflavin monophosphate;Riboflavin phosphate; Riboflavine 5'-monophosphate; Riboflavine 5'-phosphate;Riboflavine dihydrogen phosphate; Riboflavine monophosphate; Riboflavinephosphate; Vitamin B2 phosphate

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Safety information and MSDS view more

  • Pictogram(s):Not regulated UN NO.

  • Hazard Codes:Not regulated UN NO.

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 7 Articles be found

Human riboflavin kinase: Species-specific traits in the biosynthesis of the FMN cofactor

Anoz-Carbonell, Ernesto,Rivero, Maribel,Polo, Victor,Velázquez-Campoy, Adrián,Medina, Milagros

, p. 10871 - 10886 (2020)

Human riboflavin kinase (HsRFK) catalyzes vitamin B2 (riboflavin) phosphorylation to flavin mononucleotide (FMN), obligatory step in flavin cofactor synthesis. HsRFK expression is related to protection from oxidative stress, amyloid-β toxicity, and some malignant cancers progression. Its downregulation alters expression profiles of clock-controlled metabolic-genes and destroys flavins protection on stroke treatments, while its activity reduction links to protein-energy malnutrition and thyroid hormones decrease. We explored specific features of the mechanisms underlying the regulation of HsRFK activity, showing that both reaction products regulate it through competitive inhibition. Fast-kinetic studies show that despite HsRFK binds faster and preferably the reaction substrates, the complex holding both products is kinetically most stable. An intricate ligand binding landscape with all combinations of substrates/products competing with the catalytic complex and exhibiting moderate cooperativity is also presented. These data might contribute to better understanding the molecular bases of pathologies coursing with aberrant HsRFK availability, and envisage that interaction with its client-apoproteins might favor FMN release. Finally, HsRFK parameters differ from those of the so far evaluated bacterial counterparts, reinforcing the idea of species-specific mechanisms in RFK catalysis. These observations support HsRFK as potential therapeutic target because of its key functions, while also envisage bacterial RFK modules as potential antimicrobial targets.

Spectroscopic study of molecular associations between FMN and β-carbolines

Codoner, Armando,Medina, Piedad,Jover, Enrique,Sanchez, Jesus A.

, p. 1793 - 1800 (1993)

The spectrophotometric and thermodynamic properties of molecular complexes of flavin mononucleotide (FMN) (riboflavin 5'-phosphate) with some β-carboline derivatives have been investigated in aqueous solution.The molecular associations have been examined by means of electronic absorption spectra, since in each a new charge-transfer band has been located, and also the variation of the fluorescenece emission of FMN on the solutions has been observed.The formation constants for the molecular complexes were determined from absorption data using the Foster-Hammick-Wardley method.The quenching phenomenon observed in FMN fluorescence is related to the concentration of the β-carboline derivatives, allowing the calculation of the quenching constants for FMN-β-carboline complexes.Thermodynamic parameters have been determined from the values of association constants for the molecular complexes at various temperatures.The influence of substituents in the β-carboline molecule on the stability of the complexes formed was also investigated.

Catalytic role of a conserved cysteine residue in the desulfonation reaction by the alkanesulfonate monooxygenase enzyme

Carpenter, Russell A.,Zhan, Xuanzhi,Ellis, Holly R.

, p. 97 - 105 (2010)

Detailed kinetic studies were performed in order to determine the role of the single cysteine residue in the desulfonation reaction catalyzed by SsuD. Mutation of the conserved cysteine at position 54 in SsuD to either serine or alanine had little effect on FMNH2 binding. The kcat/Km value for the C54S SsuD variant increased 3-fold, whereas the kcat/Km value for C54A SsuD decreased 6-fold relative to wild-type SsuD. An initial fast phase was observed in kinetic traces obtained for the oxidation of flavin at 370 nm when FMNH2 was mixed against C54S SsuD (kobs, 111 s- 1) in oxygenated buffer that was 10-fold faster than wild-type SsuD (kobs, 12.9 s- 1). However, there was no initial fast phase observed in similar kinetic traces obtained for C54A SsuD. This initial fast phase was previously assigned to the formation of the C4a-(hydro)peroxyflavin in studies with wild-type SsuD. There was no evidence for the formation of the C4a-(hydro)peroxyflavin with either SsuD variant when octanesulfonate was included in rapid reaction kinetic studies, even at low octanesulfonate concentrations. The absence of any C4a-(hydro)peroxyflavin accumulation correlates with the increased catalytic activity of C54S SsuD. These results suggest that the conservative serine substitution is able to effectively take the place of cysteine in catalysis. Conversely, decreased accumulation of the C4a-(hydro)peroxyflavin intermediate with the C54A SsuD variant may be due to decreased activity. The data described suggest that Cys54 in SsuD may be either directly or indirectly involved in stabilizing the C4a-(hydro)peroxyflavin intermediate formed during catalysis through hydrogen bonding interactions.

Photochemically induced dynamic nuclear polarization in a C450A mutant of the LOV2 domain of the Avena sativa blue-light receptor phototropin

Richter, Gerald,Weber, Stefan,Roemisch, Werner,Bacher, Adelbert,Fischer, Markus,Eisenreich, Wolfgang

, p. 17245 - 17252 (2005)

Phototropin is a blue-light receptor involved in the phototropic response of higher plants. The photoreceptor comprises a protein kinase domain and two structurally similar flavin-mononucleotide (FMN) binding domains designated LOV1 and LOV2. Blue-light irradiation of recombinant LOV2 domains induces the formation of a covalent adduct of the thiol group of a functional cysteine in the cofactor-binding pocket to C(4a) of the FMN. Cysteine-to-alanine mutants of LOV domains are unable to form that adduct but generate an FMN radical upon illumination. The recombinant C450A mutant of the LOV2 domain of Avena sativa phototropin was reconstituted with universally and site-selectively 13C-labeled FMN and the 13C NMR signals were unequivocally assigned. 13C NMR spectra were acquired in darkness and under blue-light irradiation. The chemical shifts and the coupling patterns of the signals were not affected by irradiation. However, under blue-light exposure, exceptionally strong nuclear-spin polarization was developed in the resonances belonging to certain carbons of the FMN's isoalloxazine moiety. An enhancement of the NMR absorption was observed for the signals of C(5a), C(7), and C(9). NMR lines in emission were detected for the signals belonging to C(2), C(4), C(4a), C(6), C(8), and C(9a). The signal of C(10a) remained in absorption but was slightly attenuated. In contrast, the intensities of the NMR signals belonging to the carbons of the ribityl side chain of FMN were not affected by light. The observation of spin-polarized 13C-nuclei in the NMR spectra of the mutant LOV2 domain is clear evidence for radical-pair intermediates in the reaction steps following optical sample excitation.

Site-Selective Synthesis of 15N- and 13C-Enriched Flavin Mononucleotide Coenzyme Isotopologues

Neti, Syam Sundar,Poulter, C. Dale

, p. 5087 - 5092 (2016/07/06)

Flavin mononucleotide (FMN) is a coenzyme for numerous proteins involved in key cellular and physiological processes. Isotopically labeled flavin is a powerful tool for studying the structure and mechanism of flavoenzyme-catalyzed reactions by a variety of techniques, including NMR, IR, Raman, and mass spectrometry. In this report, we describe the preparation of labeled FMN isotopologues enriched with 15N and 13C isotopes at various sites in the pyrazine and pyrimidine rings of the isoalloxazine core of the cofactor from readily available precursors by a five-step chemo-enzymatic synthesis.

Fluorescent assay of cyclic nucleotide phosphodiesterase activity in a neutral aqueous solution

Choi, So Jung,Rhee, Hyun-Woo,Kim, Jihye,Chung, Doo Soo,Hong, Jong-In

, p. 31 - 32 (2013/08/24)

-

Process route upstream and downstream products

Process route

water
7732-18-5

water

flavin adenine dinucleotide
146-14-5,887565-61-9

flavin adenine dinucleotide

lumiflavin
1088-56-8

lumiflavin

5'-adenosine monophosphate
61-19-8,24937-83-5,67583-85-1

5'-adenosine monophosphate

Flavin mononucleotide
146-17-8,69680-01-9

Flavin mononucleotide

Conditions
Conditions Yield
vom pH 3-9;
bei der Einwirkung von Sonnenlicht;
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

flavin adenine dinucleotide
146-14-5,887565-61-9

flavin adenine dinucleotide

lumiflavin
1088-56-8

lumiflavin

5'-adenosine monophosphate
61-19-8,24937-83-5,67583-85-1

5'-adenosine monophosphate

Flavin mononucleotide
146-17-8,69680-01-9

Flavin mononucleotide

Conditions
Conditions Yield
Adenin, O5-Phosphono-D-ribose und H3PO4;
Phosphoric acid mono-[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] ester; compound with 9H-β-carboline

Phosphoric acid mono-[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] ester; compound with 9H-β-carboline

betacarboline
244-63-3

betacarboline

Flavin mononucleotide
146-17-8,69680-01-9

Flavin mononucleotide

Conditions
Conditions Yield
With phosphate buffer pH 6; In water; at 5 - 25 ℃; Equilibrium constant; investigated with absorption spectroscopy;
Phosphoric acid mono-[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] ester; compound with 7-methoxy-1-methyl-9H-β-carboline

Phosphoric acid mono-[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] ester; compound with 7-methoxy-1-methyl-9H-β-carboline

harmine
442-51-3

harmine

Flavin mononucleotide
146-17-8,69680-01-9

Flavin mononucleotide

Conditions
Conditions Yield
With phosphate buffer pH 6; In water; at 5 - 45 ℃; Equilibrium constant; investigated with absorption spectroscopy;
Phosphoric acid mono-[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] ester; compound with 1-methyl-9H-β-carboline

Phosphoric acid mono-[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] ester; compound with 1-methyl-9H-β-carboline

harmane
486-84-0

harmane

Flavin mononucleotide
146-17-8,69680-01-9

Flavin mononucleotide

Conditions
Conditions Yield
With phosphate buffer pH 5.5; In water; at 5 - 45 ℃; Equilibrium constant; investigated with absorption spectroscopy;
Phosphoric acid mono-[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] ester; compound with 1-methyl-9H-β-carbolin-7-ol

Phosphoric acid mono-[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] ester; compound with 1-methyl-9H-β-carbolin-7-ol

harmol
487-03-6

harmol

Flavin mononucleotide
146-17-8,69680-01-9

Flavin mononucleotide

Conditions
Conditions Yield
With phosphate buffer pH 6; In water; at 5 - 45 ℃; Equilibrium constant; investigated with absorption spectroscopy;
Flavin mononucleotide
146-17-8,69680-01-9

Flavin mononucleotide

Conditions
Conditions Yield
With meta-phosphoric acid; Erwaermen des Reaktionsprodukts mit wss.HCl;
With chlorophosphonic acid; Behandeln des Reaktionsprodukts mit H2O;
With chloroform; phosphorus pentoxide; phenol; Behandeln des Reaktionsprodukts mit wss.HCl;
With pyruvate kinase; phosphoenolpyruvic acid; ATP; riboflavin kinase; magnesium chloride; In various solvent(s); at 37 ℃; for 16h; pH=8;
With human riboflavin kinase from the yeast Schizosaccharomyces pombe; ATP; magnesium chloride; 2,2'-piperazine-1,4-diyl-bis-ethanesulfonic acid; at 25 - 100 ℃; for 0.1h; pH=7; Concentration; Reagent/catalyst; Temperature; Catalytic behavior; Kinetics; Enzymatic reaction;
Phosphoric acid mono-[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] ester; compound with 7-methoxy-1,2-dimethyl-2H-β-carboline

Phosphoric acid mono-[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] ester; compound with 7-methoxy-1,2-dimethyl-2H-β-carboline

2-methyl-2H-harmine
6519-18-2

2-methyl-2H-harmine

Flavin mononucleotide
146-17-8,69680-01-9

Flavin mononucleotide

Conditions
Conditions Yield
With phosphate buffer pH 6; In water; at 5 - 45 ℃; Equilibrium constant; investigated with absorption spectroscopy;
Flavin mononucleotide
146-17-8,69680-01-9

Flavin mononucleotide

Conditions
Conditions Yield
With potassium permanganate;
1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-5-hydroxypentane-2,3,4-triyl triacetate
116081-53-9

1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-5-hydroxypentane-2,3,4-triyl triacetate

Flavin mononucleotide
146-17-8,69680-01-9

Flavin mononucleotide

Conditions
Conditions Yield
With pyridine; trichlorophosphate; Behandeln des Reaktionsprodukts mit wss.Alkalilauge;

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