Riboflavin 5'-Monophosphate Sodium Salt

Description

Riboflavin-5-phosphate sodium (sodium FMN,130-40-5) 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

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).

Uses

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.

Uses

Riboflavin 5′-monophosphate sodium salt hydrate has been used:

• as a component of assay buffer to determine the luminescence of L. lactis cells
• as a component of the reaction mixture in nitric oxide synthase (NOS) enzymatic activity assay
• in the high performance liquid chromatography (HPLC) analysis of Flavin mononucleotide (FMN) cyclase products
• in luciferase assay with firefly luciferase

Definition

ChEBI: Riboflavin sodium phosphate is a ribitol phosphate and a vitamin B2. It is functionally related to a riboflavin.

Application

Riboflavin 5'-Monophosphate Sodium Salt is a coenzyme that is tightly bound to enzymes catalyzing substrate oxidations and reductions, enable an enormous range of chemical transformations in biosynthetic pathways. Riboflavin 5'-Monophosphate Sodium Salt can be used as:
(1) A stable isotope internal standard for the interpretation of data in specific biological samples.
(2) An effective NAD+ reducing agent.
(3) To study progressive keratitis, corneal ectasia and irregular astigmatism.

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 Sodium Salt Hydrate (Vitamin B2 Salt) may serve as both a carbon source and reducing agent for synthesising luminescent carbon dots and carbon-encapsulated metal (Au, Pt, Pd) particles. Simultaneous hydrothermal heating of B2salt and metal salt solutions yields water-soluble carbon dots in the supernatant and carbon-coated metal particles in the precipitate. The resulting carbon dots exhibit dual nitrogen and phosphorus doping, enhancing their luminescent properties, while the metal-loaded carbon particles hold significant potential for catalytic applications.

Biochem/physiol Actions

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

Synthesis

The current synthesis method mainly involves phosphorylation of riboflavin with phosphorus trichloride in a mixed solvent of pyridine and acetonitrile, followed by hydrolysis of the reaction mixture and neutralization with sodium hydroxide to obtain sodium riboflavin phosphate. There is also a synthetic method in which -butyrolactone is used for the reaction instead of pyridine. The products produced by the above synthesis methods have low content of sodium riboflavin phosphate, which is difficult to meet the requirements of the Chinese Pharmacopoeia, high content of riboflavin diphosphate and high content of free phosphoric acid; more impurities, low quality; and large amount of contaminated waste liquid disposal. The main factors affecting the quality of sodium riboflavin phosphate are related substances and free phosphoric acid content, the relevant substances are riboflavin diphosphate and free riboflavin, of which riboflavin diphosphate is 3,4-riboflavin diphosphate, 3,5-riboflavin diphosphate, 4,5-riboflavin diphosphate and its sum; pharmacopoeia standard content control upper limit is 6%.

IC 50

Cryptosporidium hominis TS-DHFR: IC50 = 55 μM; Dihydrofolate reductase: IC50 = 325 μM (human); Thymidylate synthase: IC50 >500 μM (human); Dihydrofolate reductase: IC50 >500 μM (Toxoplasma gondii)

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.]