130-40-5

Basic information

• Product Name: Riboflavin-5-phosphate sodium
• Synonyms: riboflavin5’-(dihydrogenphosphate),monosodiumsalt;Riboflavin 5′-monophosphate sodium salt;flavin mononucleotide sodium*electrophoresis reag;riboflavin 5-(sodium hydrogen phosphate);SODIUM RIBOFLAVIN PHOSPHATE;RIBOFLAVIN 5-PHOSPHATE SODIUM USP;Riboflavine 5'-monophosphate Sodium salt, Ph Eur;FLAVIN MONONUCLEOTIDE SODIUM*ELECTROPHOR ESIS REAGEN
• CAS NO: 130-40-5
• Molecular Formula: C17H20N4NaO9P
• Molecular Weight: 478.33
• EINECS: 204-988-6
• Product Categories: Biochemistry;Vitamins;Vitamins and derivatives;Vitamin Ingredients;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Phosphorylating and Phosphitylating Agents;Vitamin series;TAZIDIME;vitamin;Inhibitors
• Mol File: 130-40-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: >300°C
• Appearance: solid
• Refractive Index: 41 ° (C=1.5, 5mol/L HCl)
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble50mg/mL, clear, orange
• Water Solubility: almost transparency
• Stability: Stable. Incompatible with strong oxidizing agents, reducing agents, bases, calcium, metallic salts. Protect from light, air and
• Merck: 14,8201
• BRN: 4106529
• CAS DataBase Reference: Riboflavin-5-phosphate sodium(CAS DataBase Reference)
• NIST Chemistry Reference: Riboflavin-5-phosphate sodium(130-40-5)
• EPA Substance Registry System: Riboflavin-5-phosphate sodium(130-40-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• F: 3-8-10
• Hazardous Substances Data: 130-40-5(Hazardous Substances Data)

Usage

Description

Riboflavin-5-phosphate sodium (sodium FMN) consist mainly monosodium salt of Riboflavin 5-phophate (FMN), the 5-monophosphate ester of riboflavin. Riboflavin-5-phosphate sodium is produced by direct reaction of riboflavin with a phosphorylating agent such as phosphorous oxychloride in an organic solvent. Riboflavin 5-phophate (FMN) is essential as a coenzyme in various enzymic reactions in the body and is therefore used in the form of its salts, especially in the form of sodium FMN, as additive to drugs and human and animal food. Sodium FMN is also used as starting material for flavin adenine dinucleotide which is employed for treating vitamin B2 deficiency. It is used as a yellow food color additive (E106).? Riboflavin 5-phosphate sodium is fairly stable in air but is hygroscopic and sensitive to heat and light. The product may be stored for 33 months from the date of manufacture in the unopened original container and at a temperature below 15 °C.

References

[1] https://en.wikipedia.org/wiki/Flavin_mononucleotide [2] Scientific Opinion on the re-evaluation of riboflavin (E101(i)) and riboflavin-5’-phosphate sodium (E 101(ii)) as food additives, EFSA Journal 2013 [3] Patent US 5095115A: Preparation of riboflavin 5'-phosphate (fmn) and its sodium salt in a lactone

Chemical Properties

Riboflavin 5'-Monophosphate Sodium Salt is a yellow toorange-yellow, crystalline hygroscopic powder. It is odorless, and has a slightly bitter taste. It is soluble in water, and practically insoluble in ethanol(95), in chloroform and in diethyl ether. It is decomposed on exposure to light.

Uses

Different sources of media describe the Uses of 130-40-5 differently. You can refer to the following data:
1. One of the bioactive forms of Riboflavin. 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).
2. antibacterial. Riboflavin 5′-monophosphate sodium salt was used as water-soluble model drug in a combined conventional inkjet printing technology with flexographic printing for the fabrication of drug delivery systems.It may be employed as initiator for the photo-initiated polymerization of acrylamide.It may be employed in chronoamperometric assay for vanadium ions. Riboflavin 5′-monophosphate is also known as flavin mononucleotide (FMN). FMN is a water-soluble micronutrient. It is enzymatically produced from riboflavin (RF).Riboflavin 5′-monophosphate is one of the constituent of enzyme cofactor flavin-adenine dinucleotide.
3. Riboflavin 5′-monophosphate sodium salt hydrate has been used:as a component of assay buffer to determine the luminescence of L. lactis cellsas a component of the reaction mixture in nitric oxide synthase (NOS) enzymatic activity assayin the high performance liquid chromatography (HPLC) analysis of Flavin mononucleotide (FMN) cyclase productsin luciferase assay with firefly luciferase

Biological Functions

Riboflavin 5'-Phosphate Sodium is the phosphate sodium salt form of riboflavin, a water-soluble and essential micronutrient that is the principal growth-promoting factor in naturally occurring vitamin B complexes. Riboflavin phosphate sodium is converted to 2 coenzymes, flavin mononucleotide (FMN) and flavin adenine dinucleotide (FAD), which are necessary for energy production by aiding in the metabolism of fats, carbohydrates and proteins and are required for red blood cell formation and respiration, antibody production and for regulating human growth and reproduction. Riboflavin phosphate sodium is essential for healthy skin, nails and hair growth.

General Description

Riboflavin 5′-monophosphate is also known as flavin mononucleotide (FMN). FMN is a water-soluble micronutrient. It is enzymatically produced from riboflavin (RF). Riboflavin 5′-monophosphate is one of the constituent of enzyme cofactor flavin-adenine dinucleotide.

Biochem/physiol Actions

Riboflavin 5′-monophosphate or flavin mononucleotide (FMN) possesses fluorescence, photosensitivity and redox activities.

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.]

InChI:InChI=1/C17H21N4O9P.Na.2H2O/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);;2*1H2/q;+1;;/p-1/t11-,12+,14-;;;/m0.../s1

Synthetic route

1,5-dihydroflavin → sodium riboflavin-5'-monophosphate (130-40-5)

Conditions	Yield
With oxygen In aq. phosphate buffer at 24.84℃; for 0.166667h; pH=6; Kinetics; Inert atmosphere; Sealed tube;

riboflavin (83-88-5) → sodium riboflavin-5'-monophosphate (130-40-5)

Conditions	Yield
Stage #1: riboflavin With pyridine; water; trichlorophosphate In acetonitrile at 15℃; for 16h; Stage #2: With hydrogenchloride In water at 50℃; for 6h; Stage #3: With sodium hydroxide In water at 40℃; for 12h; pH=9;
Stage #1: riboflavin With pyridine; trichlorophosphate In water; acetonitrile at 15℃; for 16h; Stage #2: With hydrogenchloride In water; acetonitrile at 50℃; for 6h; Stage #3: With sodium hydroxide at 40℃; for 12h; pH=9;
Stage #1: riboflavin With pyridine; trichlorophosphate In water; acetonitrile at 15℃; for 16h; Stage #2: With hydrogenchloride In water; acetonitrile at 50℃; for 6h; Stage #3: With sodium hydroxide In water; acetonitrile at 50℃; for 12h; pH=9;
Stage #1: riboflavin With pyridine; trichlorophosphate In water; acetonitrile at 10 - 35℃; for 1.5h; Stage #2: With hydrogenchloride In water; acetonitrile at 50℃; for 3h; Stage #3: With sodium hydroxide In water; acetonitrile at 35℃; for 0.5h; pH=4.5; Temperature; pH-value;

N6-(trifluoroacetamidohexyl)adenosine 5'-monophosphate (66060-76-2) + sodium riboflavin-5'-monophosphate (130-40-5) → C35H45F3N10O16P2 + C36H43F3N10O17P2

Conditions	Yield
With 18-crown-6 ether; 1,1'-carbonyldiimidazole 1.) DMF, room temperature, 3 h, 2.) room temperature, overnight; 35-40 deg C, 20 h; Multistep reaction;

sodium riboflavin-5'-monophosphate (130-40-5) → 1,5-dihydroflavin

Conditions	Yield
With C15H12IrN2O2(1-); hydrogen In aq. phosphate buffer at 24.84℃; for 0.166667h; pH=6; Kinetics; Reagent/catalyst; Inert atmosphere; Sealed tube;

sodium riboflavin-5'-monophosphate (130-40-5) + 7H-purin-6-ylamine (73-24-5) → C5H5N5*C17H20N4O9P(1-)*Na(1+)

Conditions	Yield
In aq. buffer at 30 - 80℃; pH=4; Sonication;

sodium riboflavin-5'-monophosphate (130-40-5) → reduced flavin mononucleotide (5666-16-0)

Conditions	Yield
With hydrogen; hydrogenase 1 from Escherichia coli In aq. buffer at 25℃; under 750.075 Torr; for 3.5h; pH=8; Glovebox; Sealed tube; Enzymatic reaction;

Upstream product

• 83-88-5 riboflavin 

Downstream Products

• 5666-16-0 flavin mononucleotide 

Relevant articles and documents

Direct synthesis of hydrogen peroxide from hydrogen and oxygen by using a water-soluble iridium complex and flavin mononucleotide

H2, O2 to H2O2: The direct synthesis of hydrogen peroxide from hydrogen and oxygen in water has been made possible by using an iridium(III) complex, [IrIII(Cp)(4-(1H-pyrazol- 1-yl-κN2)benzoic acid-κC3)(H 2O)]2SO4, and flavin mononucleotide. This method gives hydrogen peroxide with a high turnover number (847) and yield (19.2 %) under normal pressure and at room temperature. Copyright

Riboflavin sodium phosphate synthesis method and process (by machine translation)

The invention relates to a method for producing medical products, in particular relates to a process for synthesis of riboflavin sodium phosphate, belongs to the technical field of pharmaceutical chemistry. The process mainly through ovoflavin and phosphorus oxychloride in a certain condition to produce riboflavin phosphate esterification reaction, filtering, removing the solid material, to hydrolyze the filtrate, to obtain crude sodium riboflavin phosphate, filter it, collecting filter cake, the filter cake to crystallization, the riboflavin sodium phosphate crystal, filtering, the filter cake by adding dryer are used for drying, to obtain the product. To the raw materials of this method, low cost, simple reaction, is easy to control, high yield, and can be used for mass production of the workshop. The Patent refers to the synthesis process of riboflavin sodium phosphate has broad application prospect. (by machine translation)

Synthetic method and technology of riboflavin sodium phosphate

The invention relates to a method used for producing medical products, more specifically relates to a synthetic method of riboflavin sodium phosphate, and belongs to the technical field of pharmaceutical chemistry. In the synthetic method, esterification reaction of riboflavin and phosphorus oxychloride is carried out at certain conditions so as to obtain a riboflavin phosphate product; the riboflavin phosphate product is filtered, solid substances are removed, and an obtained filtrate is subjected to hydrolysis so as to obtain a riboflavin sodium phosphate crude product; the riboflavin sodium phosphate crude product is filtered, a filter cake is collected, and is subjected to crystallization so as to obtain a riboflavin sodium phosphate crystal product; and the riboflavin sodium phosphate crystal product is filtered, and an obtained filter residue is dried in a drier so as to obtain a finished product. The raw materials are easily available; cost is low; reaction is simple, and is convenient to control; yield is high; and the synthetic method can be applied to workshop large batch production. Application prospect of the synthetic method in the field of riboflavin sodium phosphate synthesis is promising.