riboflavin

Also known as 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione, 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine, 6,7-dimethyl-9-D-ribitylisoalloxazine, 1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol, vitamin G, vitamin B2, E101, Flavaxin

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, 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.

AI overview

Riboflavin, also known as vitamin B2, is a nutrient found in foods and supplements that your body uses to create important molecules involved in energy production, immune function, and normal growth. It also plays a role in how your body processes other B vitamins, and may help prevent migraines and treat certain eye conditions.

AI-generated from the Wikipedia summary — may contain errors.

Key facts

Drug.IUPAC_name: 7,8-Dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
Drug.image: Riboflavin_v2.svg
Drug.image_class: skin-invert-image
Drug.image2: Riboflavin-based-on-xtal-3D-bs-17.png
Drug.image_class2: bg-transparent
Drug.caption: Chemical structure
Drug.tradename: Many
Drug.DailyMedID: Riboflavin
Drug.routes_of_administration: By mouth, intramuscular, intravenous
Drug.ATC_prefix: A11
Drug.ATC_suffix: HA04
Drug.legal_US: OTC
Drug.legal_US_comment: / Rx-only
Drug.elimination_half life: 66 to 84 minutes
Drug.excretion: Urine
Drug.CAS_number: 83-88-5
Drug.PubChem: 493570
Drug.IUPHAR_ligand: 6578

via Wikipedia infobox

Chemical data

Formula: C17H20N4O6
Molecular weight: 376.4 g/mol
IUPAC name: 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
SMILES: CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@@H]([C@@H](CO)O)O)O
InChIKey: AUNGANRZJHBGPY-SCRDCRAPSA-N
XLogP: -1.5
Polar surface area: 155 Å²
H-bond donors: 5
H-bond acceptors: 7
Formal charge: 0

via PubChem

Research

23,369 papers

Riboflavin.Advances in nutrition (Bethesda, Md.) · 2016Pinto JT, Zempleni JDOI: 10.3945/an.116.012716
Riboflavin in Human Health: A Review of Current Evidences.ReviewAdvances in food and nutrition research · 2018Saedisomeolia A, Ashoori MDOI: 10.1016/bs.afnr.2017.11.002
Overlapping riboflavin supply pathways in bacteria.ReviewCritical reviews in microbiology · 2017García-Angulo VADOI: 10.1080/1040841X.2016.1192578
Riboflavin metabolism.ReviewThe New England journal of medicine · 1970Rivlin RSDOI: 10.1056/NEJM197008272830906
Riboflavin and health: A review of recent human research.ReviewCritical reviews in food science and nutrition · 2017Thakur K, Tomar SK, Singh AK et al.DOI: 10.1080/10408398.2016.1145104
Riboflavin for corneal cross-linking.ReviewDrugs of today (Barcelona, Spain : 1998) · 2016O'Brart DPDOI: 10.1358/dot.2016.52.6.2494140
Riboflavin (vitamin B-2) and health.ReviewThe American journal of clinical nutrition · 2003Powers HJDOI: 10.1093/ajcn/77.6.1352
Riboflavin production by Ashbya gossypii.ReviewBiotechnology letters · 2012Kato T, Park EYDOI: 10.1007/s10529-011-0833-z

via PubMed

Wikidata facts

Mass: 376.138

Show 6 more facts

Commons category: Riboflavin
chemical formula: C₁₇H₂₀N₄O₆
canonical SMILES: CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(CO)O)O)O
isomeric SMILES: CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@@H]([C@@H](CO)O)O)O
World Health Organisation international non-proprietary name: riboflavin
melting point: 310

Sources (8)

via Wikidata · CC0

~27 min read

Article

27 sections

Contents

Definition
Functions
Redox reactions
Micronutrient metabolism
Synthesis
Biosynthesis
Industrial synthesis
Laboratory synthesis
Uses
Treatment of corneal thinning
Migraine prevention
Food coloring
Dietary recommendations
Safety
Labeling
Sources
Fortification
Absorption, metabolism, excretion
Deficiency
Prevalence
Signs and symptoms
Risk factors
Causes
Diagnosis and assessment
History
See also
References

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.