RIBOFLAVIN-5'-PHOSPHATE SODIUM SALT DIHYDRATE Chemical Properties

Melting point:

>300°C

storage temp. 

2-8°C

solubility 

H₂O: 0.1 g/mL, clear, orange-yellow

form 

powder

color 

Orange to Dark Orange

Water Solubility 

Soluble in water at 50mg/ml

Merck 

14,8201

BRN 

4106529

Stability:

Stable. Incompatible with strong oxidizing agents.

Major Application

pharmaceutical (small molecule)

InChI

InChI=1/C17H21N4O9P.Na.H2O.H/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;/t11-,12+,14-;;;/s3

InChIKey

YDUBDYSQHQHEEE-GUYVJCBKNA-N

SMILES

C(N1C2=NC(=O)NC(=O)C2=NC2C=C(C)C(C)=CC1=2)[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O.[NaH].O |&1:19,21,23,r|

CAS DataBase Reference

6184-17-4(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

8

TSCA 

Yes

HS Code 

29362300

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

RIBOFLAVIN-5'-PHOSPHATE SODIUM SALT DIHYDRATE Usage And Synthesis

Description

Riboflavin 5''-monophosphate (FMN) is a coenzyme that is tightly bound to enzymes catalyzing oxidation and reduction reactions in a variety of biosynthetic pathways. FMN also binds the FMN riboswitch (RFN element) on RNA to alter gene regulation. FMN is a substrate of FMN phosphohydrolases and is used to study their function.

Chemical Properties

Yellowish crystalline powder

Uses

Riboflavin 5′-monophosphate (FMN) is used as a prosthetic group by oxidoreductase (one and two electron transfer) enzymes such as NADH dehydrogenases, nitric oxide synthases, and nitrilotriacetate monooxygenases. 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.

Uses

Riboflavin 5''-(Dihydrogen Phosphate) Monosodium Salt Dihydrate is a phosphated nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, leafy vegetables. Richest natural source is yeast. Minute amounts present in all plant and animal cells. Vitamin (enzyme cofactor).

General Description

Riboflavin 5′-monophosphate (FMN) is highly soluble in water. Flavins are considered as blue-light absorbing dyes.

Biochem/physiol Actions

Riboflavin 5′-monophosphate (FMN) acts as a cofactor in flavoproteins and possess biological activity in enzymes?and photoreceptors.

Synthesis

Synthesis steps of Riboflavin-5'-phosphate sodium salt dihydrate: in 1000ml three-necked bottle add 20ml water, 250ml tetrahydrofuran and 48g riboflavin stirring to dissolve into a mixture, cooled to 5 ~ 10 ??, slowly add 100ml of aqueous sodium metaphosphate (20.4g sodium metaphosphate dissolved in 100ml water), the temperature is controlled in the 28 ~ 30 ??, add the end of the temperature to 40 ??, the reaction 2 ~ 3 hours, stop the reaction, the reaction solution was poured into a large beaker, add 250ml of water with stirring while taking care of cooling to remove the insoluble material. ~3 hours, stop the reaction, cooled to 15 ~ 25 ??, the reaction solution was poured into a large beaker, added 250 ml of water, stirring at the same time pay attention to cooling, remove insoluble material. In the filtrate add 10% sodium hydroxide solution, adjust the PH value of 9, stirring at room temperature for 0.5 hours, filtration, mother liquor with hydrochloric acid to adjust the PH to 5 ~ 6, filtration, a white solid, with a small amount of 50% ethanol rinse, and then dissolve the product in 95% ethanol, filtration, crystallization and drying of the orange-yellow solid 59.2 grams, the yield is 92%.

Purification Methods

Purify FMN by paper chromatography using tert-butanol/water, cutting out the main spot and eluting it with water. It can also be purified by adsorption onto an apo-flavodoxin column, followed by elution and freeze drying. It crystallises from aqueous acidic solution. [Mayhew & Strating Eur J Biochem 59 539 1976, Beilstein 26 III/IV 2555.]

References

[1] WALSH C T, WENCEWICZ T A. Flavoenzymes: Versatile catalysts in biosynthetic pathways[J]. Natural Product Reports, 2012, 1: 175-200. DOI: 10.1039/c2np20069d
[2] CHANGJIAN FENG. Dissecting regulation mechanism of the FMN to heme interdomain electron transfer in nitric oxide synthases[J]. Journal of Inorganic Biochemistry, 2014, 130: Pages 130-140. DOI: 10.1016/j.jinorgbio.2013.09.005
[3] ALEXANDER SERGANOV  Dinshaw J P  Lili Huang. Coenzyme recognition and gene regulation by a flavin mononucleotide riboswitch[J]. Nature, 2009, 458 7235: 233-237. DOI: 10.1038/nature07642
[4] NORIHIKO TAKEMOTO  Masayuki I  Yuya Tanaka. Rho and RNase play a central role in FMN riboswitch regulation in Corynebacterium glutamicum.[J]. Nucleic Acids Research, 2015, 43 1: 520-529. DOI: 10.1093/nar/gku1281
[5] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.

RIBOFLAVIN-5'-PHOSPHATE SODIUM SALT DIHYDRATE(6184-17-4)Related Product Information

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