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riboflavin

File:Riboflavin_v2.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ130365· pop 78· linked from 1,094 articles

riboflavin

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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.

OverviewAI-generated

Riboflavin is a chemical compound with the formula C₁₇H₂₀N₄O₆. Its IUPAC name is 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione. The substance has a melting point of 310 and a mass of 376.138.

Chemical properties include a charge of 0, an xlogp of -1.5, and a topological polar surface area of 155. The molecule contains five hydrogen bond donors and seven hydrogen bond acceptors. A PubChem entry lists its weight as 376.4.

Riboflavin is referenced by 1,094 other encyclopedia articles. A PubMed search for the term yields a count of 23,369.

Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still 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 Ų
H-bond donors
5
H-bond acceptors
7
Formal charge
0

via PubChem

Research

23,369 papers

via PubMed

~27 min read

Encyclopedic overview

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, 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.

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.

Excerpted from Wikipedia’s “riboflavin” article, available under the CC BY-SA 4.0 licence.

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