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E101 riboflavin 5'-phosphate is a coenzyme that is tightly bound to enzymes catalyzing oxidation and reduction reactions in a variety of biosynthetic pathways.
E101 riboflavin 5'-phosphate also binds the FMN riboswitch (RFN element) on RNA to alter gene regulation.
E101 riboflavin 5'-phosphate is a substrate of FMN phosphohydrolases and is used to study their function.
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)
E101 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.
E101 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.
E101 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.
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.
E101 riboflavin 5'-phosphate is water-soluble and readily absorbed, it is often used in pharmaceutical and dietary supplements to treat or prevent riboflavin deficiency.
E101 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.
E101 riboflavin 5'-phosphate, also known as riboflavin phosphate sodium, is a water-soluble derivative of vitamin B2, widely used as a colorant and nutritional supplement in food, pharmaceutical, and feed applications.
It is the phosphorylated form of riboflavin.
E101 riboflavin 5'-phosphate belongs to the class of flavin compounds.
Chemically, it consists of riboflavin (isoalloxazine ring system) esterified with phosphoric acid at the 5′ position, usually present as the sodium salt.
This modification increases water solubility.
E101 riboflavin 5'-phosphate retains vitamin activity.
E101 riboflavin 5'-phosphate appears as a yellow to orange crystalline powder.
It is highly soluble in water, forming bright yellow solutions.
E101 riboflavin 5'-phosphate is odorless with a slightly bitter taste.
E101 riboflavin 5'-phosphate exhibits strong yellow fluorescence under UV light, characteristic of flavins.
It absorbs light in the visible range.
E101 riboflavin 5'-phosphate functions as a vitamin (B2) source, playing a key role in metabolic processes as part of coenzymes (FMN, FAD).
It is essential for energy metabolism.
This supports biological functions.
E101 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.
E101 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.
E101 riboflavin 5'-phosphate is the principal form in which riboflavin is found in cells and tissues.
E101 riboflavin 5'-phosphate requires more energy to produce, but is more soluble than riboflavin.
In cells, E101 riboflavin 5'-phosphate occurs freely circulating but also in several covalently bound forms.
Covalently or non-covalently bound FMN 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.
E101 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 more stable and more soluble than riboflavin, especially in aqueous systems.
However, it is sensitive to light.
Light exposure can cause degradation.
E101 riboflavin 5'-phosphate is chemically stable under normal conditions, but degrades when exposed to UV or strong light, especially in solution.
Proper storage in light-protective containers is required.
This preserves quality.
E101 riboflavin 5'-phosphate is best described as a water-soluble vitamin B2 derivative with strong yellow coloring, fluorescence, and nutritional functionality, widely used in food and pharmaceutical applications.
E101 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, E101 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.
E101 riboflavin 5'-phosphates ability to absorb UV light also provides a protective effect to deeper structures of the eye during these procedures.
E101 riboflavin 5'-phosphate is highly soluble in water. Flavins are considered as blue-light absorbing dyes.
E101 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 E101 riboflavin 5'-phosphate, which consists mainly of the monosodium salt of the 5′-monophosphate ester of riboflavin.
It is rapidly turned to free riboflavin after ingestion.
It is found in many foods for babies and young children as well as jams, milk products, and sweets and sugar products.
E101 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.
E101 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, E101 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 E101 riboflavin 5'-phosphate, energy metabolism can be severely impaired, leading to fatigue and other metabolic dysfunctions.
Beyond its metabolic roles, E101 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, E101 riboflavin 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, E101 riboflavin 5'-phosphatee’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.
E101 riboflavin 5'-phosphate exhibits excellent water solubility compared to riboflavin, allowing it to be easily incorporated into aqueous formulations.
It dissolves rapidly without the need for special conditions.
This improves formulation efficiency.
E101 riboflavin 5'-phosphate functions as a precursor to flavin mononucleotide (FMN), an essential coenzyme in redox reactions.
It participates in electron transfer processes.
This is critical for cellular metabolism.
The compound shows bright yellow coloration even at low concentrations.
E101 riboflavin 5'-phosphate provides effective coloring in foods and pharmaceuticals.
Uses Of E101 riboflavin 5'-phosphate:
E101 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.
E101 riboflavin 5'-phosphate is used as a substrate to study the specificity and kinetics of FMN phosphohydrolases.
E101 riboflavin 5'-phosphate is used to study molecular sensing based gene regulation by riboswitches.
E101 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).
E101 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.
It 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, E101 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, E101 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.
E101 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.
E101 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, E101 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.
E101 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.
E101 riboflavin 5'-phosphate is widely used in the food industry as a yellow colorant.
It imparts a bright yellow to orange color to products.
In fortified foods and beverages, it is used as a vitamin B2 source.
E101 riboflavin 5'-phosphate improves nutritional value.
This supports dietary supplementation.
E101 riboflavin 5'-phosphate is applied in soft drinks, energy drinks, and juices, where its high water solubility allows easy incorporation.
It provides uniform coloration.
This improves product consistency.
E101 riboflavin 5'-phosphate is used in dairy products and dairy alternatives to enhance color and nutritional content.
It mimics natural yellow tones.
This improves appearance.
In pharmaceutical formulations, it is used as a vitamin supplement and excipient.
E101 riboflavin 5'-phosphate supports metabolic functions.
This enhances therapeutic value.
E101 riboflavin 5'-phosphate is widely used in nutritional supplements and multivitamin products.
It provides a bioavailable form of vitamin B2.
This improves absorption.
In animal feed, it is added as a nutritional additive to support growth and metabolism.
E101 riboflavin 5'-phosphate ensures adequate vitamin intake.
This improves animal health.
E101 riboflavin 5'-phosphate is applied in cosmetic products, where it may act as a coloring agent and antioxidant component.
It enhances formulation appearance.
This supports product development.
In biochemical and laboratory applications, it is used as a coenzyme precursor in enzymatic studies.
E101 riboflavin 5'-phosphate supports metabolic research.
E101 riboflavin 5'-phosphate is used wherever coloring, vitamin supplementation, and metabolic support are required across food, pharmaceutical, feed, cosmetic, and research applications.
Safety Profile Of E101 riboflavin 5'-phosphate:
While E101 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.
E101 riboflavin 5'-phosphate is not flammable under normal conditions, though organic dust may present a combustible dust risk in industrial settings.
Standard fire safety precautions should be followed.
E101 riboflavin 5'-phosphate is chemically stable under normal conditions, but is sensitive to light (especially UV), leading to degradation and loss of activity.
E101 riboflavin 5'-phosphate presents very low hazard potential, as it is a water-soluble vitamin (B2 derivative) widely used in foods, pharmaceuticals, and supplements and generally recognized as safe.
E101 riboflavin 5'-phosphate has a well-established safety profile.
However, standard handling precautions apply in concentrated or industrial forms.
Skin contact is typically low risk, but prolonged exposure to concentrated powder or solutions may cause mild irritation in sensitive individuals.
No significant toxicity is expected.
Basic protective measures are recommended.
Eye contact may cause mild irritation.
Symptoms can include redness and discomfort.
Eyes should be rinsed thoroughly with water if exposure occurs.
Inhalation of dust (powder form) may cause minor respiratory irritation.
Fine particles can irritate the nose and throat.
Adequate ventilation is recommended.
Ingestion is considered safe at normal dietary and supplemental levels, as it is an essential vitamin.
Excess intake is generally excreted in urine, sometimes causing a harmless bright yellow coloration.
