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Riboflavin information


Riboflavin
Chemical structure
Clinical data
Trade namesMany[1]
Other nameslactochrome, lactoflavin, vitamin G[2]
AHFS/Drugs.comMonograph
License data
  • US DailyMed: Riboflavin
Routes of
administration
By mouth, intramuscular, intravenous
ATC code
  • A11HA04 (WHO) S01XA26 (WHO)
Legal status
Legal status
  • US: Dietary supplement
Pharmacokinetic data
Elimination half-life66 to 84 minutes
ExcretionUrine
Identifiers
IUPAC name
  • 7,8-Dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
CAS Number
  • 83-88-5  checkY
PubChem CID
  • 493570
IUPHAR/BPS
  • 6578
DrugBank
  • DB00140 checkY
ChemSpider
  • 431981 checkY
UNII
  • TLM2976OFR
KEGG
  • D00050 checkY
ChEBI
  • CHEBI:17015 checkY
ChEMBL
  • ChEMBL1534 checkY[EMBL]
E numberE101, E101(iii) (colours) Edit this at Wikidata
CompTox Dashboard (EPA)
  • DTXSID8021777 Edit this at Wikidata
ECHA InfoCard100.001.370 Edit this at Wikidata
Chemical and physical data
FormulaC17H20N4O6
Molar mass376.369 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • c12cc(C)c(C)cc1N=C3C(=O)NC(=O)N=C3N2C[C@H](O)[C@H](O)[C@H](O)CO
InChI
  • InChI=InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1 checkY
  • Key:AUNGANRZJHBGPY-SCRDCRAPSA-N checkY

Riboflavin, also known as vitamin B2, is a vitamin found in food and sold as a dietary supplement.[3] It is essential to the formation of two major coenzymes, flavin mononucleotide and flavin adenine dinucleotide. These coenzymes are involved in energy metabolism, cellular respiration, and antibody production, as well as normal growth and development. The coenzymes are also required for the metabolism of niacin, vitamin B6, and folate. Riboflavin is prescribed to treat corneal thinning, and taken orally, may reduce the incidence of migraine headaches in adults.

Riboflavin deficiency is rare and is usually accompanied by deficiencies of other vitamins and nutrients. It may be prevented or treated by oral supplements or by injections. As a water-soluble vitamin, any riboflavin consumed in excess of nutritional requirements is not stored; it is either not absorbed or is absorbed and quickly excreted in urine, causing the urine to have a bright yellow tint. Natural sources of riboflavin include meat, fish and fowl, eggs, dairy products, green vegetables, mushrooms, and almonds. Some countries require its addition to grains.[3]

Riboflavin was discovered in 1920, isolated in 1933, and first synthesized in 1935. In its purified, solid form, it is a water-soluble yellow-orange crystalline powder. In addition to its function as a vitamin, it is used as a food coloring agent. Biosynthesis takes place in bacteria, fungi and plants, but not animals. Industrial synthesis of riboflavin was initially achieved using a chemical process, but current commercial manufacturing relies on fermentation methods using strains of fungi and genetically modified bacteria.

  1. ^ "Riboflavin". Drugs.com. 22 July 2021. Archived from the original on 30 December 2016. Retrieved 8 October 2021.
  2. ^ Cite error: The named reference anm was invoked but never defined (see the help page).
  3. ^ a b c "Riboflavin: Fact Sheet for Health Professionals". Office of Dietary Supplements, US National Institutes of Health. 11 May 2022. Archived from the original on 24 February 2020. Retrieved 20 August 2023.

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Riboflavin

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Riboflavin, also known as vitamin B2, is a vitamin found in food and sold as a dietary supplement. It is essential to the formation of two major coenzymes...

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Flavin mononucleotide

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mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as...

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B vitamins

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referred to by B-number or by chemical name, such as B1 for thiamine, B2 for riboflavin, and B3 for niacin, while some are more commonly recognized by name than...

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Kinase

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phosphoglycerate, riboflavin, dihydroxyacetone, shikimate, and many others. Riboflavin kinase catalyzes the phosphorylation of riboflavin to create flavin...

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Riboflavin kinase

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In enzymology, a riboflavin kinase (EC 2.7.1.26) is an enzyme that catalyzes the chemical reaction ATP + riboflavin ⇌ {\displaystyle \rightleftharpoons...

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Riboflavin synthase

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Riboflavin synthase is an enzyme that catalyzes the final reaction of riboflavin biosynthesis. It catalyzes the transfer of a four-carbon unit from one...

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Riboflavin phosphotransferase

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enzymology, a riboflavin phosphotransferase (EC 2.7.1.42) is an enzyme that catalyzes the chemical reaction alpha-D-glucose 1-phosphate + riboflavin ⇌ {\displaystyle...

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Pathogen reduction using riboflavin and UV light

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reduction using riboflavin and UV light is a method by which infectious pathogens in blood for transfusion are inactivated by adding riboflavin and irradiating...

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Prokaryotic riboflavin biosynthesis protein

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prokaryotic riboflavin biosynthesis protein is a bifunctional enzyme found in bacteria that catalyzes the phosphorylation of riboflavin into flavin mononucleotide...

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Flavin group

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derivatives thereof. The biochemical source of flavin is the yellow B vitamin riboflavin. The flavin moiety is often attached with an adenosine diphosphate to...

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Riboflavin carrier protein

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Riboflavin carrier proteins (RFCPs) together with human serum albumin transport flavin mononucleotide (FMN) in the blood circuit. RFCPs are important in...

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Flavin reductase

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bonding, catalyze the reduction of these molecules to a reduced flavin. Riboflavin, or vitamin B, and flavin mononucleotide are two of the most well known...

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Guanosine triphosphate

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ribulose 5-phosphate, are the precursor compounds for the synthesis of riboflavin (vitamin B2). In the cell, GTP is synthesised through many processes including:...

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Flavin adenine dinucleotide

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together would restore activity. Theorell confirmed the pigment to be riboflavin's phosphate ester, flavin mononucleotide (FMN) in 1937, which was the first...

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Bell pepper

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– vitamin A (20%), and vitamin B6 (23% DV), with moderate contents of riboflavin (12%), folate (12% DV), and vitamin E (11% DV). A red bell pepper supplies...

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Yogurt

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(DV), a serving of yogurt is a rich source of vitamin B12 (31% DV) and riboflavin (23% DV), with moderate content of protein, phosphorus, and selenium (14...

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Raisin

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amounts (10–19% DV) of the Daily Value for several dietary minerals, riboflavin, and vitamin B6. Raisins can cause kidney failure in both cats and dogs...

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HEPES

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unwanted photochemical process wherein HEPES catalyzes a reaction with riboflavin when exposed to ambient light to produce hydrogen peroxide. This is not...

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Tapetum lucidum

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and makeup: dogs and ferrets use zinc, cats use riboflavin and zinc, and lemurs use only riboflavin.: 17  Choroidal tapetum fibrosum, as seen in cows...

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Marmite

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thiamin (B1), riboflavin (B2), niacin (B3), and folic acid (B9). Vitamin B12 is only available through artificial enrichment; riboflavin and folic acid...

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Industrial microbiology

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produce riboflavin. The most common organism used for production of riboflavin through fermentation is Eremothecium ashbyii. Once riboflavin is produced...

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E101

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may refer to: Riboflavin, food additive which has been assigned E number 101 Flavin mononucleotide, biomolecule produced from riboflavin European route...

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Banana

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33 g Protein 1.09 g Vitamins Quantity %DV† Thiamine (B1) 3% 0.031 mg Riboflavin (B2) 6% 0.073 mg Niacin (B3) 4% 0.665 mg Pantothenic acid (B5) 7% 0.334...

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Sugar

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Fat 0 g Protein 0 g Vitamins Quantity %DV† Thiamine (B1) 1% 0.008 mg Riboflavin (B2) 1% 0.007 mg Niacin (B3) 1% 0.082 mg Vitamin B6 2% 0.026 mg Folate...

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