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Riboflavin 5'-phosphate, also known as flavin mononucleotide (FMN), is a phosphorylated derivative of riboflavin (vitamin B₂) that acts as an essential coenzyme in numerous biological redox reactions.
Riboflavin 5'-phosphate is formed in the body when riboflavin is converted to its active coenzyme form by the enzyme riboflavin kinase, which attaches a phosphate group to the riboflavin molecule.
Riboflavin 5'-phosphate plays a critical role as a precursor to flavin adenine dinucleotide (FAD), another vital coenzyme, and both FMN and FAD are required for the activity of many enzymes known as flavoproteins.
CAS Number: 6184-17-4
Molecular Formula: C17H24N4NaO10P
Molecular Weight: 498.36
EINECS Number: 201-507-1
Synonyms: 6184-17-4, Riboflavin 5'-phosphate sodium, Phosphated riboflavin, Flavin mononucleotide dihydrate, Riboflavin 5'-phosphate sodium dihydrate, Riboflavin sodium phosphate dihydrate, UNII-20RD1DZH99, 20RD1DZH99, PHOTREXA VISCOUS, Sodium Riboflavin Phosphate, INS NO.101(II), INS-101(II), E-101(II), Riboflavin 5'-phosphate sodium (USP), Riboflavin 5'-phosphate sodium [USP], Sodium riboflavin 5'-phosphate, NSC-759230, SODIUM RIBOFLAVIN 5'-PHOSPHATE DIHYDRATE, Riboflavine 5'-(sodium hydrogen phosphate), dihydrate, Riboflavin 5'-(dihydrogen phosphate), monosodium salt, dihydrate, COLLAGEX-RAPID COMPONENT RIBOFLAVIN 5'-PHOSPHATE SODIUM, COLLAGEX-HYPOTONIC COMPONENT RIBOFLAVIN 5'-PHOSPHATE SODIUM, PHOSPHATED RIBOFLAVIN (USP-RS), PHOSPHATED RIBOFLAVIN [USP-RS], RIBOFLAVIN 5'-(DIHYDROGEN PHOSPHATE), SODIUM SALT, HYDRATE (1:1:2), Riboflavin-5'-phosphate sodium, CHEBI:32098, RIBOFLAVIN 5'-PHOSPHATE SODIUM (USP MONOGRAPH), RIBOFLAVIN 5'-PHOSPHATE SODIUM [USP MONOGRAPH], RIBOFLAVIN SODIUM PHOSPHATE (MART.), RIBOFLAVIN SODIUM PHOSPHATE ANHYDROUS, RIBOFLAVIN SODIUM PHOSPHATE (EP MONOGRAPH), riboflavin 5-phosphate in 20% dextran ophthalmic, 204-988-6, 957E53WV42, Riboflavin 5'-phosphate sodium anhydrous, riboflavin sodium phosphate, Photrexa, Riboflavin-5'-phosphate sodium salt dihydrate, Vitamin B2 phosphate (sodium salt) dihydrate, MFCD00150993, Riboflavin 5'-phosphate sodium salt dihydrate, Riboflavine phosphate (sodium hydrate), sodium (2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-2,3,4-trihydroxypentyl hydrogenphosphate dihydrate, sodium;[(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] hydrogen phosphate;dihydrate, RIBOFLAVIN PHOSPHATE SODIUM, Riboflavin 5'-(Dihydrogen Phosphate) Monosodium Salt Dihydrate (~70%), Riboflavin sodium phosphate [JAN], riboflavin 5'-monophosphate sodium salt hydrate, Photrexa (TN), FMM-Na·2H2O, 130-40-5, MSK2571NaW, Riboflavin-5-phosphoric acid monosodium dihydrate, FMN-Na;Flavin mononucleotide, Riboflavin 5'-monophosphate sodium salt dihydrate, CHEMBL3989697, FMN-Na;Riboflavin 5'-phosphate sodium;Vitamin B2 Phosphate Sodium Salt, SCHEMBL21899339, Riboflavin 5''''-phosphate sodium, BDBM50523758, AKOS025312546, CS-W014429, FR45599, HY-W013713, RIBOFLAVIN 5''-PHOSPHATE SODIUM, Flavin mononucleotide sodium salt dihydrate, RIBOFLAVIN PHOSPHATE SODIUM [VANDF], RIBOFLAVIN 5'-PHOSPHATE SODIUM [FCC], D05725, F71324, Riboflavine-5'-monophosphate sodium salt hydrate, Q27253481, RIBOFLAVIN 5'-PHOSPHATE SODIUM [ORANGE BOOK], Riboflavin 5'-phosphate sodium salt dihydrate, USP grade, Riboflavin-5'-phosphate sodium salt dihydrate, AldrichCPR, Riboflavin 5 inverted exclamation marka-monophosphate sodium salt hydrate, Riboflavin 5'-(Dihydrogen Phosphate) Monosodium Salt Dihydrate (>80 per cent)
Riboflavin 5'-phosphate is a coenzyme that is tightly bound to enzymes catalyzing oxidation and reduction reactions in a variety of biosynthetic pathways.
Riboflavin 5'-phosphate also binds the FMN riboswitch (RFN element) on RNA to alter gene regulation.
Riboflavin 5'-phosphate is a substrate of FMN phosphohydrolases and is used to study their function.
These enzymes participate in key metabolic processes, including energy production in the electron transport chain, the metabolism of fats, drugs, and steroids, and the conversion of vitamin B₆ to its active form.
Because riboflavin 5'-phosphate is water-soluble and readily absorbed, it is often used in pharmaceutical and dietary supplements to treat or prevent riboflavin deficiency.
Riboflavin 5'-phosphate is also used in ophthalmology, particularly in corneal cross-linking procedures for keratoconus, where it acts as a photosensitizer that strengthens corneal tissue when activated by ultraviolet light.
Riboflavin 5'-phosphate, or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as the prosthetic group of various oxidoreductases, including NADH dehydrogenase, as well as a cofactor in biological blue-light photo receptors.
During the catalytic cycle, various oxidoreductases induce reversible interconversions between the oxidized (FMN), semiquinone (FMNH•), and reduced (FMNH2) forms of the isoalloxazine core.
Riboflavin 5'-phosphate is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers.
In its role as blue-light photo receptor, (oxidized) FMN stands out from the 'conventional' photo receptors as the signaling state and not an E/Z isomerization.
Riboflavin 5'-phosphate is the principal form in which riboflavin is found in cells and tissues.
Riboflavin 5'-phosphate requires more energy to produce, but is more soluble than riboflavin.
In cells, Riboflavin 5'-phosphate occurs freely circulating but also in several covalently bound forms.
Covalently or non-covalently bound Riboflavin 5'-phosphate is a cofactor of many enzymes playing an important pathophysiological role in cellular metabolism.
For example dissociation of flavin mononucleotide from mitochondrial complex I has been shown to occur during ischemia/reperfusion brain injury during stroke.
Riboflavin 5'-phosphate is considered the bioactive form of vitamin B2 because it can directly function as a coenzyme without further conversion in the body.
It is involved in numerous oxidative and reductive biochemical reactions by serving as a carrier of electrons and hydrogen atoms in flavoprotein enzymes.
These enzymes are critical for processes such as the metabolism of carbohydrates, amino acids, and lipids, making riboflavin 5'-phosphate indispensable for cellular energy production and growth.
Melting point: >300 °C
Storage temperature: 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 50 mg/mL
Merck: 14,8201
BRN: 4106529
Stability: Stable. Incompatible with strong oxidizing agents.
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@HC@HC@HCOP(O)(O)=O.[NaH].O |&1:19,21,23,r|
CAS Database Reference: 6184-17-4 (CAS Database Reference)
FDA UNII: 20RD1DZH99
UNSPSC Code: 41116107
Riboflavin 5'-phosphate is preferred over plain riboflavin in certain therapies because it has better solubility in water and faster bioavailability.
It is frequently used in intravenous solutions for patients who cannot adequately absorb vitamins through the gastrointestinal tract.
In ophthalmology, Riboflavin 5'-phosphate is a key component in corneal cross-linking treatments, where it penetrates the corneal tissue and, when exposed to ultraviolet A (UVA) light, triggers the formation of new bonds between collagen fibers.
This strengthens and stabilizes the cornea, which is especially beneficial for patients with keratoconus or corneal ectasia.
Its ability to absorb UV light also provides a protective effect to deeper structures of the eye during these procedures.
Riboflavin 5'-phosphate is highly soluble in water.
Flavins are considered as blue-light absorbing dyes.
Riboflavin 5'-phosphate is also used as an orange-red food colour additive, designated in Europe as E number E101a.
E106, a very closely related food dye, is Riboflavin 5'-phosphate sodium salt, which consists mainly of the monosodium salt of the 5′-monophosphate ester of riboflavin.
Riboflavin 5'-phosphate is rapidly turned to free riboflavin after ingestion.
Riboflavin 5'-phosphate is found in many foods for babies and young children as well as jams, milk products, and sweets and sugar products.
Riboflavin 5'-phosphate has been studied for its potential in reducing migraine frequency in some patients due to its role in mitochondrial energy production, although more research is still needed to confirm its effectiveness in this area.
Riboflavin 5'-phosphate is a vital molecule in biochemistry because it acts as an essential coenzyme involved in a wide range of enzymatic reactions necessary for maintaining normal cellular function and metabolism.
It belongs to the family of flavins, which are characterized by their ability to participate in redox (reduction-oxidation) reactions.
By cycling between oxidized and reduced forms, riboflavin 5'-phosphate enables enzymes to transfer electrons, which is a fundamental step in energy production within cells.
One of its most important roles is in the mitochondrial electron transport chain, where it contributes to the generation of adenosine triphosphate (ATP), the primary energy currency of the cell.
Without adequate levels of Riboflavin 5'-phosphate, energy metabolism can be severely impaired, leading to fatigue and other metabolic dysfunctions.
Beyond its metabolic roles, riboflavin 5'-phosphate is critical for the metabolism of other vitamins as well.
For example, it is involved in converting vitamin B6 into its active form, pyridoxal 5’-phosphate, and assists in the activation of niacin (vitamin B3) and folate.
This interconnectedness highlights its importance in maintaining overall nutritional balance and cellular health.
Pharmacologically, riboflavin 5'-phosphate is valued for its enhanced solubility and bioavailability compared to riboflavin itself.
This makes it a preferred form in supplements and medications designed to treat deficiencies or support increased metabolic demand, such as during illness, pregnancy, or intense physical activity.
In addition to its therapeutic uses, riboflavin 5'-phosphate’s role in corneal cross-linking has revolutionized treatment options for progressive eye disorders.
The photosensitizing property of this molecule allows it to produce reactive oxygen species when exposed to UVA light, which induces covalent bonding between collagen fibers in the cornea.
This process strengthens the corneal structure, preventing further deformation and vision loss.
Uses Of Riboflavin 5'-phosphate:
Riboflavin 5'-phosphate 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'-phosphate is used as a substrate to study the specificity and kinetics of FMN phosphohydrolases.
Riboflavin 5'-phosphate is used to study molecular sensing based gene regulation by riboswitches.
Riboflavin 5'-phosphate 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).
Riboflavin 5'-phosphate is widely used in both medical and nutritional fields due to its role as a bioactive form of vitamin B2, making it an essential ingredient in dietary supplements designed to prevent or treat riboflavin deficiency and related metabolic disorders.
Riboflavin 5'-phosphate is particularly valuable in clinical settings for patients who have impaired absorption of vitamins from the gastrointestinal tract, such as those with malabsorption syndromes or chronic illnesses, because its water solubility allows for more efficient uptake compared to regular riboflavin.
In addition to its nutritional applications, riboflavin 5'-phosphate is extensively utilized in ophthalmology, most notably in corneal cross-linking procedures aimed at treating keratoconus and other corneal thinning disorders.
In these treatments, the compound acts as a photosensitizer that, when activated by ultraviolet A (UVA) light, initiates a chemical reaction that strengthens the collagen fibers in the cornea, thus improving its mechanical stability and preventing progressive vision loss.
Beyond these clinical uses, Riboflavin 5'-phosphate is also incorporated in pharmaceutical formulations as a coenzyme in various enzyme preparations, supporting biochemical reactions essential for energy production and cellular metabolism.
Moreover, Riboflavin 5'-phosphate finds application in research and diagnostic laboratories as a standard compound for studying flavoprotein enzymes and their mechanisms.
Some emerging studies also suggest potential uses of riboflavin 5'-phosphate in neurological health, particularly in reducing the frequency and severity of migraines, possibly due to its involvement in mitochondrial energy metabolism, though these applications require further clinical validation.
Overall, the versatility of riboflavin 5'-phosphate in medical, nutritional, and scientific contexts highlights its importance as a multifunctional compound crucial for maintaining health and supporting specialized therapies.
Riboflavin 5'-phosphate is extensively used in nutritional supplements and fortified foods because it provides a more bioavailable and easily absorbed form of vitamin B2, which is vital for individuals with increased nutritional requirements, including pregnant women, athletes, and those recovering from illness or surgery.
By enhancing the intake of this active coenzyme form, supplements can more effectively support the body’s metabolic demands and help prevent symptoms associated with riboflavin deficiency, such as sore throat, skin disorders, and anemia.
In pharmaceutical applications, Riboflavin 5'-phosphate is often included in multivitamin preparations and vitamin B-complex formulations to ensure comprehensive nutritional support.
Its presence in these products helps optimize enzymatic functions across various biochemical pathways, including those involved in energy production, antioxidant defense, and cellular repair.
Riboflavin 5'-phosphate’s role in ophthalmology is particularly notable, where it is a key agent in the corneal collagen cross-linking procedure, a minimally invasive treatment that can halt the progression of keratoconus, a degenerative eye disease that thins and weakens the cornea.
During this procedure, riboflavin 5'-phosphate is applied topically to the cornea and activated with UVA light, facilitating the formation of stronger chemical bonds within corneal collagen fibers, thereby increasing the cornea’s rigidity and preserving vision.
In addition to its established uses, Riboflavin 5'-phosphate is under investigation for potential therapeutic roles in neurological and mitochondrial disorders.
Its involvement in mitochondrial energy metabolism suggests it may help improve cellular energy production in conditions characterized by mitochondrial dysfunction, which could translate into benefits for patients with chronic fatigue, neurodegenerative diseases, or migraine headaches.
Although promising, these applications are still the subject of ongoing research.
Safety Profile Of Riboflavin 5'-phosphate:
While Riboflavin 5'-phosphate is generally recognized as safe and non-toxic at typical dietary and therapeutic doses, excessive or inappropriate use—such as very high supplemental intake—may lead to adverse effects including mild gastrointestinal disturbances like diarrhea, increased urine production causing a bright yellow discoloration that is harmless but may be alarming, and, in some cases, skin reactions such as itching, redness, or rash, particularly in individuals with photosensitivity or allergies to flavins.
Furthermore, because riboflavin 5'-phosphate is a photosensitizing agent, exposure to high doses combined with intense sunlight or ultraviolet light could increase the risk of phototoxic reactions, which manifest as skin irritation or inflammation upon light exposure, necessitating caution when used topically or during procedures like corneal cross-linking.
Although serious toxic effects are rare, there is a theoretical risk that excessive riboflavin 5'-phosphate could interfere with the metabolism or absorption of other nutrients or medications by competing in enzymatic pathways, especially in vulnerable populations such as pregnant women, infants, or individuals with metabolic disorders, emphasizing the importance of adhering to recommended dosages and medical supervision.
