7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione

• ChemBase ID: 26
• Molecular Formular: C17H20N4O6
• Molecular Mass: 376.3639
• Monoisotopic Mass: 376.13828438
• SMILES: c12c(nc3c(cc(c(c3)C)C)n2C[C@@H]([C@@H]([C@@H](CO)O)O)O)c(=O)[nH]c(=O)n1
• Canonical SMILES: OC[C@H]([C@H]([C@H](Cn1c2cc(C)c(cc2nc2c1nc(=O)[nH]c2=O)C)O)O)O
• 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
• InChIKey: AUNGANRZJHBGPY-SCRDCRAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione
• IUPAC Traditional name: riboflavin
• Brand Name: Aqua-Flave; Beflavin; Beflavine; Bisulase; Dermadram; Fiboflavin; Flavaxin; Flavin; Flavin Bb; Flaxain; HSDB 817; Hyflavin; Hyre; Lactobene; Ovoflavin; Ribipca; Ribocrisina; Riboderm; Ribosyn; Ribotone; Ribovel; Vitaflavine; Vitasan B2
• Synonyms: E101; Vitamin B2; Riboflavina [INN-Spanish]; Riboflavine [INN-French]; Riboflavinum [INN-Latin]; Russupteridine Yellow III; Vitamin G; Vitamin Bi; Lactoflavin; Lactoflavine; Riboflavin; (-)-Riboflavin; (-)-Riboflavin; Riboflavin (B2); 1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol; 7,8-Dimethyl-10-ribitylisoalloxazine; Beflavin; Beflavine; Flavaxin; Lactobene; NSC 33298; Ribipca; Ribocrisina; Riboderm; Ribosyn; Ribotone; Ribovel; Ricrolin; Vitaflavine; Vitasan B2; (-)-Riboflavin; 乳黄素; 维生素 B2; 维生素 G; (-)-核黄素; (-)-核黄素; 核黄素 (B2)

Database IDs

• CAS Number: 83-88-5; 83-88-5
• EC Number: 201-507-1
• MDL Number: MFCD00005022
• Beilstein Number: 97825
• PubChem SID: 160963489; 24899415; 46507342; 24899397; 24899340; 24899370; 24871529
• PubChem CID: 493570
• CHEBI ID: 17015
• ATC CODE: A11HA04
• CHEMBL: 511565
• Chemspider ID: 431981
• DrugBank ID: DB00140
• KEGG ID: D00050
• MeSH Name: Riboflavin
• Unique Ingredient Identifier: TLM2976OFR
• Wikipedia Title: Riboflavin
• E Number: E101

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.9699388
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.93084645
• LogD (pH = 7.4): -1.4706613
• Log P: -0.91654027
• Molar Refractivity: 96.2684 cm^3
• Polarizability: 35.49111 Å^3
• Polar Surface Area: 155.05 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.05
• LOG S: -2.76
• Solubility (Water): 6.57e-01 g/l

PROPERTIES

Physical Property

• Solubility: 84.7 mg/L; DMSO; Water
• Apperance: Orange crystals; Orange Solid
• Melting Point: >269°C (dec.); 290 °C (dec.)(lit.)
• Partition Coefficient: 0.095
• Optical Rotation: [α]21/D -114.9°, c = 0.5 in 0.1 M NaOH in methanol: water
• Hydrophobicity(logP): -1.9
• pKa: 9.888
• pKb: 4.109

Safety Information

• Storage Condition: -20°C; Hygroscopic, Refrigerator, Under inert atmosphere
• German water hazard class: 1
• NFPA704:
  

  1

  1

  0
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%; ≥98.0% (HPLC); ≥99%; 98%
• Grade: analytical standard
• Salt Data: Free Base
• Packaging: ampule of 1000 mg
• Suitability: acrylamide photopolymerization tested; meets USP testing specifications; passes test for lumiflavin; plant cell culture tested; suitable for cell culture; suitable for insect cell culture
• Ignition Residue: ≤0.1% (as SO4)
• Cation Traces: Al: ≤5 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤20 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤20 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤20 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Foreign Activity: Protease, none detected
• Loss on Drying: ≤1.5% loss on drying
• Feature: standard type water soluble vitamin
• Pharmacopeia Traceability: traceable to PhEur R060000; traceable to USP 1603006
• Empirical Formula (Hill Notation): C17H20N4O6

DETAILS

DrugBank - DB00140

• Drug Groups: approved; nutraceutical
• Description: Nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. The richest natural source is yeast. It occurs in the free form 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. [PubChem]
• Indication: For the treatment of ariboflavinosis (vitamin B2 deficiency).
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Vitamin B2 is readily absorbed from the upper gastrointestinal tract.
• Half Life: 66-84 minutes
• Protein Binding: 60%
• References: Zempleni J, Galloway JR, McCormick DB: Pharmacokinetics of orally and intravenously administered riboflavin in healthy humans. Am J Clin Nutr. 1996 Jan;63(1):54-66. [Pubmed]
• External Links: Wikipedia; PDRhealth; Drugs.com

Selleck Chemicals - S2540

Research Area: Metabolic Disease
Biological Activity:
Riboflavin (vitamin B2) is an easily absorbed micronutrient with a key role in maintaining health in humans and other animals. Riboflavin (vitamin B2) is the central component of the cofactors FAD and FMN, and is therefore required by all flavoproteins. As such, riboflavin (vitamin B2) is required for a wide variety of cellular processes. Riboflavin (vitamin B2) plays a key role in energy metabolism, and for the metabolism of fats, ketone bodies, carbohydrates, and proteins. [1][2]

Sigma Aldrich - R9881

Caution
Riboflavin is a photo-sensitive component of cell culture media.
Other Notes
This product has been qualified for use in plant cell culture applications.
General description
Riboflavin is one of the essential water soluble vitamins. It is made by all plants and many microorganism, but not by higher animals. Riboflavin is the precursor for the active enzyme cofactors riboflavin 5′-monophosphate (also called flavinmononucleotide or FMN) and flavin adenine dinucleotide (FAD). Flavin nucleotides function as prosthetic groups of oxidation-reduction enzymes known as flavoproteins. These enzymes function in the oxidative degradation of pyruvate, fatty acids, and amino acids. The flavins are reversibly reduced by the action of flavoproteins to form FMNH2 and FADH2.

Sigma Aldrich - R0508

Application
Riboflavin is suitable as a photopolymerization reagent in PAGE by forming free radicals in aqueous solution in the presence of light. Riboflavin photodecomposes to leucoflavin. No free radicals are formed in the absence of oxygen but traces of oxygen allows for leucoflavin to reoxidize with free-radical generation. The catalysts TEMED or DMAPN are commonly added to speed up the free radical formation. The free radicals will cause acrylamide and bis-acrylamide to polymerize to form a gel matrix which can be used for sieving macromolecules. Riboflavin is commonly used in the stacking gel for non-denaturing PAGE because native proteins can be sensitive to persulfate ions from ammonium persulfate. Another advantage of riboflavin over ammonium persulfate is that it will not start polymerizing until the gel is illuminated.

Sigma Aldrich - R4500

Application
Enzyme cofactor
包装
1 kg in poly drum
500 g in poly drum
5, 25, 100 g in glass bottle
Biochem/physiol Actions
Riboflavin is a key component of the redox cofactors flavin adenine dinucleotide (FAD) and flavin mononucleotide (FMN) that are used by a wide variety of flavoprotein oxidoreductases, dehydrogenase(s), decarboxylase(s) and electron transporters.

Sigma Aldrich - 95170

Other Notes
Review: Flavin Coenzymes: At the crossroads of biological redox chemistry1

Sigma Aldrich - 47861

General description
Standard for Supelco MIP SPE cartridges. For more information request Supelco Literature T407075, T706022

Toronto Research Chemicals - R414995

Nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, leafy vegetables. Richest natural source is yeast. Minute amounts present in all plant and animal cells. Vitamin (enzyme cofactor).

REFERENCES

• Zempleni J, Galloway JR, McCormick DB: Pharmacokinetics of orally and intravenously administered riboflavin in healthy humans. Am J Clin Nutr. 1996 Jan;63(1):54-66. Pubmed
• Zempleni J et al. Am J Clin Nutr. 1996 Jan;63(1):54-66.
• Unna, K., et al.: J. Pharmacol. Exp. Ther., 76, 75 (1942)
• Rivlin, et al.: N. Engl. J. Med., 283, 463 (1942)
• Al-Shammary, F.J., et al.: Anal. Profiles Drug Subs., 19, 429 (1942)