Riboflavin

HCID 493570CAS 83-88-5

Grundinformationen

Standard-SMILES
Cc1cc2nc3c(=O)[nH]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C
InChIKey
AUNGANRZJHBGPY-SCRDCRAPSA-N
Summenformel
C17H20N4O6
Durchschnittliche Molmasse
376,4 g/mol
Monoisotopische Masse
376,13828436

Überblick

Riboflavin is D-Ribitol in which the hydroxy group at position 5 is substituted by a 7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl moiety. It is a nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables, but the richest natural source is yeast. The free form occurs only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin-adenine dinucleotide. It has a role as an antioxidant, a cofactor, a photosensitizing agent, an anti-inflammatory agent, a mouse metabolite, a plant metabolite, an Escherichia coli metabolite, a food colouring, a fundamental metabolite and a human urinary metabolite. It is a vitamin B2 and a flavin. It is a conjugate acid of a riboflavin(1-).

Namen und Bezeichner

Bevorzugter Name
Riboflavin
IUPAC
7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
Lokaler Name
Riboflavin
Englischer Name
Riboflavin
Summenformel
C17H20N4O6
Molmasse
376.36

Namen und Synonyme

riboflavinvitamin B283-88-5RiboflavineLactoflavinVitamin GLactoflavineFlavaxinBeflavineBeflavinRibodermRibipca
Weitere Namen anzeigen
(-)-Riboflavinriboflavin (b2)Riboflavin UniversalRiboflavin Vitamin B2VIT B2Riboflavin CRSVitamin B2 (Riboflavine)
RibovelLactobeneRibocrisinaRiboflavinaRiboflavinumRibotoneVitaflavineFlaxain

Datenbank-Bezeichner

CAS
83-88-5
PubChem CID
493570
DTXSID
DTXSID8021777
ChEMBL
CHEMBL1534
ChEBI
CHEBI:17015
UNII
TLM2976OFR
EC Number
201-507-1
Nikkaji
J3.876H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-1,5
Polarare Oberfläche (TPSA)
155 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
7
Frei drehbare Bindungen
5
Schwere Atome
27

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Vitamins and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsCosmetic colorant; Skin conditioning; Hair dyeing
pHpH of saturated aqueous solution: about 6
SpringerMaterials PropertiesAngular frequency
LogP · 4 Einträge

log Kow = -1.46

-1.46

-1.46

-0.55

Physikochemische Eigenschaften

Schmelzpunkt
290 °C · 290 °C (dec.)(lit.)
Siedepunkt
504.93 °C · 504.93°C (rough estimate)
Dichte
1.2112 · 1.2112 (rough estimate)
Brechungsindex
-135 ° · -135 ° (C=0.5, JP Method)
Flammpunkt
9 ℃ · 9℃
storage temp.
2 · 2-8°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 3 Einträge

This chemical does not meet GHS hazard criteria for 98.4% (122 of 124) of all reports.

Not Classified

Aggregated GHS information provided per 124 reports by companies from 4 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: Riboflavin

Status: Active Update: 25-10-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20915

Riboflavin: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
Hazards SummaryNo listed effects of short-term or long-term exposure; [ICSC] Large doses may cause yellow perspiration; [Olson, p. 446] Acceptable daily intake (ADI) of 0-0.5 mg/kg; [JECFA] May cause irritation; [Sigma-Aldrich MSDS]
FDA Requirements · 4 Einträge

Certification of this color additive when used as a food is not necessary for the protection of the public health and therefore batches thereof are exempt from the requirements of section 706(c) of the Federal Food, Drug, and Cosmetic Act.

Substance added directly to human food affirmed as generally recognized as safe (GRAS).

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: riboflavin is included in weight control drug products.

Riboflavin used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

Special Reports · 1 Eintrag

NAS, Food and Nutrition Board, Institute of Medicine; Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline. National Academy Press, Washington, D.C. (1998).[Available from, as of March 2, 2010: http://www.nap.edu/catalog/6015.html]

Chemical DangersDecomposes on heating. This produces toxic fumes.

Sicherheit und Schutzausrüstung

Fire FightingUse coarse water spray, carbon dioxide.
First Aid Measures · 3 Einträge

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Safe StorageWell closed.
Storage ConditionsSolutions of riboflavin should be protected from air and light. Riboflavin tablets should be stored in tight, light-resistant containers at a temperature less than 40 degrees C, preferably between 15-30 degrees C.
Disposal Methods · 3 Einträge

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage DisposalSweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.

Toxikologische Informationen

Interactions · 5 Einträge

Riboflavin interrelates with other B vitamins, notably niacin, which requires riboflavin for its formation from tryptophan, and vitamin B6, which also requires riboflavin for a conversion to a conenzyme form. These interrelationships are not known to affect the requirement for riboflavin.

The rate and extent of absorption of riboflavin are reportedly affected by propantheline bromide. Prior administration of propantheline bromide delayed the rate of absorption of riboflavin but increased the total amount absorbed, presumably by increasing the residence time of riboflavin at GI absorption sites.

Alcohol impairs intestinal absorption of riboflavin.

Concurrent use /with probenecid/ decreases gastrointestinal absorption of riboflavin; requirements for riboflavin may be increased in patients receiving probenecid.

For more Interactions (Complete) data for Riboflavin (7 total), please visit the HSDB record page.

Adverse Effects · 1 Eintrag

Riboflavin is relatively safe to administer as it has limited water solubility, and enterocytes do not absorb the excess. However, caution is necessary when administering large doses to pregnant women. Riboflavin may cause benign urine discoloration.

Exposure Routes · 2 Einträge

The substance can be absorbed into the body by ingestion.

Vitamin B2 is readily absorbed from the upper gastrointestinal tract.

Milk Concentrations · 1 Eintrag

No difference in riboflavin content of human milk was found between supplemented and unsupplemented well-nourished mothers at 6 months postpartum. Previously, estimates of the riboflavin content of human milk from well-nourished, unsupplemented mothers included 0.37 +/- 0.13 (standard deviation) mg/L at 5 to 7 days postpartum, 0.49 +/- 0.12 mg/L at 43 to 45 days postpartum, 0.24 +/- 0.35 mg/L at 6 months postpartum, and 0.35 +/- 0.02 mg/L after 3 weeks postpartum. More recent studies in five subjects showed that riboflavin in milk may have been previously underestimated as a result of a lack of detection of flavin-adenine dinucleotide (FAD), ... On the basis of this and studies of microbiologically determined riboflavin in human milk, a riboflavin concentration of 0.35 mg/L will be used for human milk consumed by infants younger than 6 months.

Toxicity Summary · 2 Einträge

No observable toxicities with intakes of riboflavin are from food sources many times the recommended daily allowance. Riboflavin has high water solubility and limited absorption. No adverse effects are from high riboflavin intakes from foods or supplements up to 400 mg daily for at least 3 months. The Food and Nutrition Board has not established the upper limit for riboflavin as it has a good safety profile. High-dose riboflavin does not cause toxicity as excess riboflavin is excreted in the urine.

Binds to riboflavin hydrogenase, riboflavin kinase, and riboflavin synthase. Riboflavin is the precursor of flavin mononucleotide (FMN, riboflavin monophosphate) and flavin adenine dinucleotide (FAD). The antioxidant activity of riboflavin is principally derived from its role as a precursor of FAD and the role of this cofactor in the production of the antioxidant reduced glutathione. Reduced glutathione is the cofactor of the selenium-containing glutathione peroxidases among other things. The glutathione peroxidases are major antioxidant enzymes. Reduced glutathione is generated by the FAD-containing enzyme glutathione reductase.

Plant ConcentrationsPlants with the highest amount of Riboflavin(1). [Table#2208]

Regulatorische Informationen

FDA Requirements · 4 Einträge

Certification of this color additive when used as a food is not necessary for the protection of the public health and therefore batches thereof are exempt from the requirements of section 706(c) of the Federal Food, Drug, and Cosmetic Act.

Substance added directly to human food affirmed as generally recognized as safe (GRAS).

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: riboflavin is included in weight control drug products.

Riboflavin used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

Sicherheitsdaten

F
8-10-21
wgk
1
tsca
TSCA listed
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29362300
RTECS-Nr.
VJ1400000

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 5 Einträge

S - Sensory organs

A - Alimentary tract and metabolism

QS - Sensory organs

QA - Alimentary tract and metabolism

A11HA04

Bionecessity · 5 Einträge

Riboflavin (vitamin B2) functions as a coenzyme for numerous oxidation-reduction reactions in several metabolic pathways and in energy production. The rate of absorption is proportional to intake, and it increases when riboflavin is ingested along with other foods and in the presence of bile salts. The requirements for riboflavin are based on intake in relation to a combination of indicators, including the excretion of riboflavin and its metabolites, blood values for riboflavin, and the erythrocyte glutathione reductase activity coefficient ... DRI values are listed by life stage group in the table.

State of deficiency: ariboflavinosis is characterized by cheilosis, angular stomatitis, glossitis, seborrheic dermatitis of nose and scrotum, and corneal vascularization ... Riboflavin deficiency seldom occurs alone; it often is observed with pellagra and other B-complex deficiency states ...

State of deficiency: ocular symptoms /of ariboflavinosis/ include pruritis, burning, blepharospasm, photophobia, and visual impairment.

Women pregnant with more than one fetus and those breastfeeding more than one infant are also likely to require more riboflavin.

For more Bionecessity (Complete) data for Riboflavin (43 total), please visit the HSDB record page.

Protein Binding60%
Pharmacodynamics · 1 Eintrag

Riboflavin or vitamin B2 is an easily absorbed, water-soluble micronutrient with a key role in maintaining human health. Like the other B vitamins, it supports energy production by aiding in the metabolising of fats, carbohydrates, and proteins. Vitamin B2 is also required for red blood cell formation and respiration, antibody production, and for regulating human growth and reproduction. It is essential for healthy skin, nails, hair growth and general good health, including regulating thyroid activity. Riboflavin also helps in the prevention or treatment of many types of eye disorders, including some cases of cataracts.

Mechanism of Action · 6 Einträge

Binds to riboflavin hydrogenase, riboflavin kinase, and riboflavin synthase. Riboflavin is the precursor of flavin mononucleotide (FMN, riboflavin monophosphate) and flavin adenine dinucleotide (FAD). The antioxidant activity of riboflavin is principally derived from its role as a precursor of FAD and the role of this cofactor in the production of the antioxidant reduced glutathione. Reduced glutathione is the cofactor of the selenium-containing glutathione peroxidases among other things. The glutathione peroxidases are major antioxidant enzymes. Reduced glutathione is generated by the FAD-containing enzyme glutathione reductase.

Riboflavin is converted to 2 coenzymes, flavin mononucleotide (FMN) and flavin adenine dinucleotide (FAD), which are necessary for normal tissue respiration. Riboflavin is also required for activation of pyridoxine, conversion of tryptophan to niacin, and may be involved in maintaining erythrocyte integrity.

Riboflavin functions as the coenzyme for flavin adenine dinucleotide (FAD) and flavin mononucleotide (FMN), which primarily influence hydrogen transport in oxidative enzyme systems (eg, cytochrome C reductase, succinic dehydrogenase, xanthine oxidase).

Two active forms of riboflavin exist ... coenzyme flavin mononucleotide (FMN) and coenzyme flavin adenine dinucleotide (FAD). They are formed by reaction of riboflavin with 1 and 2 molecules of ATP as follow: riboflavin + ATP = riboflavin-P (FMN) + ADP; FMN + ATP = riboflavin-ADP (FAD) + PP.

Riboflavin is a water-soluble, yellow, fluorescent compound. The primary form of the vitamin is as an integral component of the coenzymes flavin mononucleotide (FMN) and flavin-adenine dinucleotide (FAD). It is in these bound coenzyme forms that riboflavin functions as a catalyst for redox reactions in numerous metabolic pathways and in energy production. ... The redox reactions in which flavocoenzymes participate include flavoprotein-catalyzed dehydrogenations that are both pyridine nucleotide (niacin) dependent and independent, reactions with sulfur-containing compounds, hydroxylations, oxidative decarboxylations (involving thiamin as its pyrophosphate), dioxygenations, and reduction of oxygen to hydrogen peroxide. There are obligatory roles of flavocoenzymes in the formation of some vitamins and their coenzymes. For example, the biosynthesis of two niacin-containing coenzymes from tryptophan occurs via FAD-dependent kynurenine hydroxylase, an FMN-dependent oxidase catalyzes the conversion of the 5'-phosphates of vitamin B6 to coenzymic pyridoxal 5'-phosphate, and an FAD-dependent dehydrogenase reduces 5,10-methylene-tetrahydrofolate to the 5'-methyl product that interfaces with the B12-dependent formation of methionine from homocysteine and thus with sulfur amino acid metabolism.

For more Mechanism of Action (Complete) data for Riboflavin (7 total), please visit the HSDB record page.

Biological Half-Life · 2 Einträge

66-84 minutes

The biologic half-life of riboflavin is about 66-84 minutes following oral or IM administration of a single large dose in healthy individuals.

Verwendung und Herstellung

Uses · 6 Einträge

Present in minute amounts in all plant and animal cells and especially in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables; Used as a food coloring and vitamin (enzyme cofactor); [Merck Index] Used as a medication, animal feed supplement, nutritional supplement, and to inactivate pathogens and viruses; [HSDB] Used as flavoring agent, color, and nutritional supplement for foods; [FDA] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]

Farming (Feed Additives) [Category: Industry]

Medicine, nutrition, animal feed supplement, enriched flours, dietary supplement

THERAPEUTIC CATEGORY: Vitamin (enzyme cofactor)

THERAPEUTIC CATEGORY (VETERINARY): Vitamin (enzyme cofactor)

Mirasol pathogen reduction technology (PRT) treatment uses riboflavin (vitamin B(2)) in combination with ultraviolet light (UV) to inactivate pathogens in platelet concentrates (PCs).

U.S. Exports · 2 Einträge

(1972) No data

(1975) No data

U.S. Imports · 2 Einträge

(1972) 7.24 X 10+7 g (Princpl Custms Dists)

(1975) 6.01 X 10+5 g (Princpl Custms Dists)

U.S. Production · 3 Einträge

(1972) 4.59 X 10+8 g

(1973) 3.35 X 10+8 g

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2209]

Methods of Manufacturing · 3 Einträge

The readily available compound 3,4-xylidine is reacted with D-ribose in methanol. The resulting riboside is catalytically hydrogenated to give N-(3,4-dimethylphenyl)-D-1'-ribamine without isolation, and the product is purified by crystallization. Coupling of /N-(3,4-dimethylphenyl)-D-1'-ribamine/ with phenyl diazonium salt in a buffered aqueous solution yields crystalline N-(2-phenylazo-4,5-dimethylphenyl)-D-1'-ribamine. Dry / N-(2-phenylazo-4,5-dimethylphenyl)-D-1'-ribamine/ is converted to riboflavin by cyclocondensation with barbituric acid in a weakly acidic medium. Mixtures of dioxane and acetic acid or di-alpha-substituted carboxylic acids have proved suitable as solvents. Crude /riboflavin/ can be purified by reprecipitation from hydrochloric acid or dilute sodium hydroxide solution, possibly with the addition of hydrogen peroxide.

Riboflavin can be produced microbiologically. At present, the microorganisms Bacillus subtilis, the ascomycetes Eremothecium ashbyii, Ashbya gossypii, and the yeasts Candida flareri and Saccharomyces cerevisiae are used. The nutrient media employed are molasses or plant oils as carbon source, inorganic salts, amino acids, animal or plant peptones and proteins, as well as vitamin additives. In a sterile aerobic submerged process, yields much higher than 10 grams of riboflavin per liter of culture broth are obtained in a few days with good aeration and stirring at temperatures below 30 °C. After separation of the biomass, evaporation and drying of the concentrate, an enriched product with a vitamin B2 content of up to 80% is obtained. The majority of the riboflavin produced by fermentation is used in animal feeds.

Condensation of d-ribose with 3,4-xylidine resulting in N-d -ribityl-3,4-xylidine, which is either coupled with a diazonium salt followed by reduction and reaction with alloxan, or reacted with barbituric acid; fermentation of carbohydrate materials by bacteria, yeast, or fungi

Formulations/PreparationsBulk: Powder. Oral: Tablets 25 mg, 50 mg, 100 mg. (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name.)
Anwendungen · 2 Einträge

BeschreibungA water-soluble B fraction was found in the 1920s to contain a yellow, fluorescent growth factor called riboflavin in England and vitamin G in the United States. In the early 1930s, several groups found the coenzyme forms of riboflavin 50-phosphate (flavin mononucleotide) and the further conjugate with adenylic acid (flavin adenine dinucleotide).

Verwendenriboflavin (Vitamin B2) is used in skin care preparations as an emollient. It can be found in sun care products as a suntan enhancer. Medicinally, it is used for the treatment of skin lesions.

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: D-Ribitol in which the hydroxy group at position 5 is substituted by a 7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl moiety. It is a nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vege ables, but the richest natural source is yeast. The free form occurs only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin-adenine dinucleotide.

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