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Riboflavin(CAS No. 83-88-5)

Riboflavin C17H20N4O6 (cas 83-88-5) Molecular Structure

83-88-5 Structure

Identification and Related Records

【Name】
Riboflavin
【Iupac name】
7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,
5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
【CAS Registry number】
83-88-5
【Synonyms】
Vitamin B2-Riboflavin(Vitamin B2)USP/BP/EP
VB2 (Riboflavin)
(-)-Riboflavin
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol
6,7-Dimethyl-9-ribitylisoalloxazine
Beflavin
Beflavine
Benzo[g]pteridine-2,4(3H,10H)-dione,7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-
C.I. 50900
C.I. FoodYellow 15
D-Ribitol,1-deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-
E101
E 101 (dye)
Flavaxin
Flavin BB
Flaxain
Food Yellow 15
Hyre
Lactobene
Lactoflavin
Lactoflavine
NCI 0033298
San Yellow B
Vitaflavine
Vitamin G
【EINECS(EC#)】
201-507-1
【Molecular Formula】
C17H20N4O6 (Products with the same molecular formula)
【Molecular Weight】
376.37
【Inchi】
InChI=1/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-/m1/s1
【InChIKey】
AUNGANRZJHBGPY-UHFFFAOYSA-N
【Canonical SMILES】
CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(CO)O)O)O
【Isomers 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
【MOL File】
83-88-5.mol

Chemical and Physical Properties

【Appearance】
Yellow to orange/yellow crystalline powd
【Density】
1.65
【Melting Point】
290℃
【Refractive Index】
-135 ° (C=0.5, JP Method)
【Alpha】
-135 o (C=5, 0.05 M NAOH)
【Water】
0.07 g/L (20℃)
【Solubilities】
Water solubility: 0.07 g/L (20 °C)
【Color/Form】
Fine orange-yellow needles from 2N acetic acid, alcohol, water, or pyridine ... three different crystal forms
Orange to yellow crystals or needles
【Stability】
Stable, but light-sensitive. Incompatible with strong oxidizing agents, reducing agents, bases, calcium, metallic salts. May be moisture sensitive.
【HS Code】
29362300
【Storage temp】
2-8°C
【Spectral properties】
Specific optical rotation: -112 to -122 deg at 25 deg C/D (0.0 N sodium hydroxide, 0.5%; -8.80 deg (water) sodium line
The specific optical rotation in acid or neutral solutions is +56.5-59.5 deg at 20 deg C (0.5%, dil HCl).
MAX ABSORPTION (WATER): 267 NM (LOG E= 4.51); 373 NM (LOG E= 4.02); 447 NM (LOG E= 4.09); SADTLER REF NUMBER: 10526 (IR, PRISM)
UV max absorption: 220-225 nm, 266 nm, 371 nm, 444 nm, 475 nm ... Aqueous solutions are yellow showing a green fluorescence with max at 565 nm
IR: 18248 (Sadtler Research Laboratories IR Grating Collection)
UV: 6-738 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
UV: 6-738 (Phillip et al; Organic Electronic Spectral Data, John Wiley & Sons, New York)
MASS: 16561 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 447 (National Bureau of Standards)
【Computed Properties】
Molecular Weight:376.3639 [g/mol]
Molecular Formula:C17H20N4O6
XLogP3:-1.5
H-Bond Donor:5
H-Bond Acceptor:7
Rotatable Bond Count:5
Tautomer Count:3
Exact Mass:376.138284
MonoIsotopic Mass:376.138284
Topological Polar Surface Area:155
Heavy Atom Count:27
Formal Charge:0
Complexity:680
Isotope Atom Count:0
Defined Atom Stereocenter Count:3
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:7
Feature 3D Donor Count:6
Feature 3D Ring Count:3
Effective Rotor Count:5
Conformer Sampling RMSD:0.8
CID Conformer Count:29

Safety and Handling

【Safety Statements 】
S24/25
【Safety】

Safety Statements: S24/25
S24/25:? Avoid contact with skin and eyes?

【Transport】
25kgs
【Formulations/Preparations】
Bulk: Powder. Oral: Tablets 25 mg, 50 mg, 100 mg. (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name.)
【Exposure Standards and Regulations】
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.
【Specification】

?Riboflavin , its cas register number is 83-88-5. It also can be called Araboflavin ; and Vitamin B2 . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately.
In addition, Riboflavin (CAS NO.83-88-5) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, reducing agents, bases, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products:?oxides of nitrogen, carbon monoxide, carbon dioxide.

【Octanol/Water Partition Coefficient】
log Kow = -1.46
【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

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 deg 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
U.S. Exports

(1972) No data
(1975) No data
U.S. Imports

(1972) 7.24 X 10+7 g (Princpl Custms Dists)
(1975) 6.01 X 10+5 g (Princpl Custms Dists)
U.S. Production

(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. Year Production Range (pounds) 1986 No Reports 1990 No Reports 1994 10 thousand - 500 thousand 1998 10 thousand - 500 thousand 2002 No Reports
【Usage】

Inhibitor of poly(ethylene glycol) oxidation.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms.
- A group of water-soluble vitamins, some of which are COENZYMES.
【Therapeutic Uses】
Riboflavin is used to prevent riboflavin deficiency and to treat ariboflavinosis. Whenever possible, poor dietary habits should be corrected, and many clinicians recommend administration of multivitamin preparations containing riboflavin in patients with vitamin deficiencies since poor dietary habits often result in concurrent deficiencies.
Riboflavin may be useful in treating microcytic anemia that occurs in patients with a familial metabolic disease associated with splenomegaly and glutathione reductase deficiency.
Although riboflavin has not been shown by well-controlled trials to have any therapeutic value, the drug also has been used for the management of acne, congenital methemoglobinemia, muscle cramps, and burning feet syndrome.
People undergoing hemodialysis or peritioneal dialysis and those with severe malabsorption are likely to require extra riboflavin. Women who are carrying more than one fetus or breastfeeding more than one infant are also likely to require more riboflavin. It is possible that individuals who are ordinarily extremely physically active may also have increased needs for riboflavin.
Milder forms of glutaric aciduria type II may respond to riboflavin. Treatment with riboflavin 50 mg daily resulted in progressive improvement in a 4 year old boy, with full recovery after 1 year. His brother, who had sustained permanent brain damage after epileptic seizures, showed moderate clinical improvement with riboflavin therapy. In an adult patient with a history of recurrent pancreatitis and exercise intolerance, treatment with riboflavin 120 mg daily and levocarnitine resulted in no further episodes, although abnormal concentrations of amino acids were still apparent in her urine.
/Experimental Therapy/ ... The only existing countermeasures for botulinum neurotoxin (BoNT) intoxication involve vaccinations that are only effective prior to entry of the toxin into neuronal cells. Herein, /the authors/ disclose the ability of the micronutrient riboflavin (vitamin B(2)) to photooxidatively inactivate BoNT in cell-based assays without the need for toxin and riboflavin pre-exposure. In total, this study suggests that botulism neurotoxicity may be blunted with photodynamic therapy technology. [Eubanks LM et al; FEBS Lett 579 (24): 5361-4 (2005). Available from, as of March 15, 2010:]
【Biomedical Effects and Toxicity】
Riboflavin is readily absorbed from the upper GI tract; however, absorption of the drug involves active transport mechanisms and the extent of GI absorption is limited by the duration of contact of the drug with the specialized segment of mucosa where absorption occurs. Riboflavin 5-phosphate is rapidly and almost completely dephosphorylated in the GI lumen before absorption occurs. The extent of GI absorption of riboflavin is increased when the drug is administered with food and is decreased in patients with hepatitis, cirrhosis, biliary obstruction, or in those receiving probenecid.
Primary absorption of riboflavin occurs in the small intestine via a rapid, saturable transport system. A small amount is absorbed in the large intestine. 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. At low intake levels, most absorption of riboflavin occurs via an active or facilitated transport system. At higher levels of intake, riboflavin can be absorbed by passive diffusion.
In the plasma, a large portion of riboflavin associates with other proteins, mainly immunoglobulins, for transport. Pregnancy increases the level of carrier proteins available for riboflavin, which results in a higher rate of riboflavin uptake at the maternal surface of the placenta.
In the stomach, gastric acidification releases most of the coenzyme forms of riboflavin (flavin-adenine dinucleotide (FAD) and flavin mononucleotide (FMN)) from the protein. The noncovalently bound coenzymes are then hydrolyzed to riboflavin by nonspecific pyrophosphatases and phosphatases in the upper gut. Primary absorption of riboflavin occurs in the proximal small intestine via a rapid, saturable transport system. 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. A small amount of riboflavin circulates via the enterohepatic system. At low intake levels most absorption of riboflavin is via an active or facilitated transport system.
Riboflavin (RF), a water-soluble vitamin, is essential for normal cellular functions, growth, and development. Normal RF body homeostasis depends on intestinal absorption and recovery of the filtered vitamin in renal tubules. The mechanism and cellular regulation of the RF renal reabsorption process, especially in the human situation, are poorly understood. The aim of this study was therefore to address these issues, using a recently established human normal renal epithelial cell line, HK-2, as a model. Uptake of RF by HK-2 cells was found to be 1) linear with time for 5 min of incubation and occurring with minimal metabolic alterations, 2) temperature dependent, 3) Na+ independent, 4) saturable as a function of concentration [apparent Michaelis constant (K(m)) of 0.67 +/- 0.21 microM and maximal velocity (Vmax) of 10.05 +/- 0.87 pmol.mg protein-1.3 min-1], 5) inhibited by structural analogs and anion transport inhibitors, and 6) energy dependent. Protein kinase C-, protein kinase A-, and protein tyrosine kinase-mediated pathways were found to have no role in regulating RF uptake. On the other hand, a Ca2+/calmodulin-mediated pathway appeared to play a role in the regulation of RF uptake by HK-2 cells via an effect on the Vmax, as well as on the apparent K(m) of the RF uptake process. The uptake process of RF was also found to be adaptively regulated by the level of the substrate in the growth medium, with the effect being mediated through changes in the apparent K(m) and the Vmax of the uptake process. These results demonstrate that RF uptake by the human-derived renal epithelial cell line HK-2 is via a carrier-mediated system that is temperature and energy dependent and appears to be under the regulation of a Ca2+/calmodulin-mediated pathways and substrate level in the growth medium. [Kumar CK et al; Am J Physiol 274 (1 Pt 2): F104-10 (1998). Available from, as of March 15, 2010:] PubMed Abstract
A small amount of riboflavin is absorbed in the large intestine.
This study ... examined riboflavin (RF) uptake by the human-derived cultured Caco-2 intestinal epithelial cells. RF uptake was Na+ and pH independent and occurred without metabolic alterations of the transported RF. Initial rate of RF uptake was temperature dependent and saturable as a function of concentration at 37 degrees C but not at 4 degrees C (apparent Michaelis constant = 0.30 +/- 0.03 microM, maximal velocity = 209.90 +/- 24.40 pmol.mg protein-1.3 min-1). Unlabeled RF, lumiflavine, 8-amino-riboflavine, isoriboflavine, and lumichrome in the incubation solution caused significant inhibition of RF uptake. RF uptake was also energy dependent and was sensitive to the inhibitory effect of sulfhydryl group reagents. The membrane transport inhibitor amiloride, but not 4,4'-diisothiocyanostilbene-2,2'-disulfonic acid, 4-acetamide-4'-isothiocyanostilbene-2,2'-disulfonic acid, furosemide, or probenecid, inhibited RF uptake in a competitive (inhibitory constant = 0.48 mM) and reversible manner. Growing Caco-2 monolayers in a RF-deficient and oversupplemented media caused significant up- and downregulation of RF uptake, respectively. These results demonstrate the existence of a carrier-mediated system for RF uptake by Caco-2 cells and provide new information regarding amiloride sensitivity, involvement of sulfhydryl groups, and up- and downregulation by the substrate level and clarify the controversy regarding the role of Na+ in the uptake process. [Said HM, MA TY; Am J Physiol 266 (1 Pt 1): G15-21 (1994). Available from, as of March 15, 2010:] PubMed Abstract
In plasma some riboflavin is complexed with albumin; however, a large portion of riboflavin associates with other proteins, mainly immunoglobulins, for transport. Pregnancy increases the level of carrier proteins available for riboflavin. This results in a higher rate of riboflavin uptake at the maternal surface of the placenta.
At physiological concentrations the uptake of riboflavin into the cells of organs such as the liver is facilitated and may require specific carriers. At higher levels of intake, riboflavin can be absorbed by diffusion.
When riboflavin is absorbed in excess, very little is stored in the body tissues. The excess is excreted, primarily in the urine. A wide variety of flavin-related products have been identified in the urine of humans. In healthy adults consuming well-balanced diets, riboflavin accounts for 60 to 70 percent of the excreted urinary flavins.
Urinary excretion of riboflavin varies with intake, metabolic events, and age. In newborns, urinary excretion is slow; however, the cumulative amount excreted is similar to the amount excreted by older infants.
A markedly increased excretion of riboflavin has been noted at intakes exceeding 0.8 to 0.9 mg/day for women and 1.0 to 1.1 mg/day for men. A similar break in the riboflavin excretion curve for young women had also been observed earlier. Studying an elderly population, pointed to approximately 1.0 mg/day as the intake at which the excretion of excess vitamin became apparent.
The urinary riboflavin and flavin metabolite contents /were determined/ before and after the ingestion of a 1.7-mg riboflavin supplement. Mean dietary intake of the group, obtained from three 1-day dietary records for each subject, was at least 1.7 mg in addition to the supplement. These investigators found that most of the 1.7 mg of the supplemental riboflavin appeared in the urine without being metabolized.
In healthy elderly women aged 70 years or older, doubling the estimated riboflavin intake by means of a supplement containing 1.7 mg of riboflavin doubled the urinary riboflavin excretion in the supplemented group compared to the unsupplemented group, from 4.36 to 9.06 umol/g (1.64 to 3.41 mg/g) creatinine.
No adverse effects associated with riboflavin consumption from food or supplements have been reported. ... The apparent lack of harm resulting from high oral doses of riboflavin may be due to its limited solubility and limited capacity for absorption in the human gastrointestinal tract; /and/ its rapid excretion in the urine.

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