Riboflavin

Riboflavin

Chemical structure
Clinical data
Trade names	Many[1]
Other names	lactochrome, lactoflavin, vitamin G[2]
AHFS/Drugs.com	Monograph
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-life	66 to 84 minutes
Excretion	Urine
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  Y
PubChem CID	493570
IUPHAR/BPS	6578
DrugBank	DB00140 Y
ChemSpider	431981 Y
UNII	TLM2976OFR
KEGG	D00050 Y
ChEBI	CHEBI:17015 Y
ChEMBL	ChEMBL1534 Y[EMBL]
E number	E101, E101(iii) (colours)
CompTox Dashboard (EPA)	DTXSID8021777
ECHA InfoCard	100.001.370
Chemical and physical data
Formula	C17H20N4O6
Molar mass	376.369 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 Y Key:AUNGANRZJHBGPY-SCRDCRAPSA-N Y

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.