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83-88-5 molecular structure
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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 and InChIs

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

Cite this record

CBID:26 http://www.chembase.cn/molecule-26.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
Vitamin B2
Riboflavina [INN-Spanish]
Riboflavine [INN-French]
Riboflavinum [INN-Latin]
Russupteridine Yellow III
Vitamin G
Vitamin Bi
Lactoflavin
Lactoflavine
Riboflavin
E101
(-)-Riboflavin
Riboflavin (B2)
(-)-Riboflavin
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)
CAS Number
83-88-5
83-88-5
EC Number
201-507-1
MDL Number
MFCD00005022
Beilstein Number
97825
PubChem SID
24899415
24899340
160963489
24871529
46507342
24899397
24899370
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 6.9699388  H Acceptors
H Donor LogD (pH = 5.5) -0.93084645 
LogD (pH = 7.4) -1.4706613  Log P -0.91654027 
Molar Refractivity 96.2684 cm3 Polarizability 35.49111 Å3
Polar Surface Area 155.05 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.05  LOG S -2.76 
Solubility (Water) 6.57e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
84.7 mg/L expand Show data source
DMSO expand Show data source
Water expand Show data source
Apperance
Orange crystals expand Show data source
Orange Solid expand Show data source
Melting Point
>269°C (dec.) expand Show data source
290 °C (dec.)(lit.) expand Show data source
Partition Coefficient
0.095 expand Show data source
Optical Rotation
[α]21/D -114.9°, c = 0.5 in 0.1 M NaOH in methanol: water expand Show data source
Hydrophobicity(logP)
-1.9 expand Show data source
pKa
9.888 expand Show data source
pKb
4.109 expand Show data source
Storage Condition
-20°C expand Show data source
Hygroscopic, Refrigerator, Under inert atmosphere expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
NFPA704
NFPA 704 diagram
1
1
0
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98% expand Show data source
≥98.0% (HPLC) expand Show data source
≥99% expand Show data source
98% expand Show data source
Grade
analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Packaging
ampule of 1000 mg expand Show data source
Suitability
acrylamide photopolymerization tested expand Show data source
meets USP testing specifications expand Show data source
passes test for lumiflavin expand Show data source
plant cell culture tested expand Show data source
suitable for cell culture expand Show data source
suitable for insect cell culture expand Show data source
Ignition Residue
≤0.1% (as SO4) expand Show data source
Cation Traces
Al: ≤5 mg/kg expand Show data source
Ba: ≤5 mg/kg expand Show data source
Bi: ≤5 mg/kg expand Show data source
Ca: ≤20 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤20 mg/kg expand Show data source
Li: ≤5 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Mo: ≤5 mg/kg expand Show data source
Na: ≤20 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Sr: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Foreign Activity
Protease, none detected expand Show data source
Loss on Drying
≤1.5% loss on drying expand Show data source
Feature
standard type water soluble vitamin expand Show data source
Pharmacopeia Traceability
traceable to PhEur R060000 expand Show data source
traceable to USP 1603006 expand Show data source
Empirical Formula (Hill Notation)
C17H20N4O6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich Selleck Chemicals Selleck Chemicals TRC TRC
DrugBank - DB00140 external link
Item Information
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
Sigma Aldrich - 47861 external link
General description
Standard for Supelco MIP SPE cartridges. For more information request Supelco Literature T407075, T706022
Sigma Aldrich - 95170 external link
Other Notes
Review: Flavin Coenzymes: At the crossroads of biological redox chemistry1
Sigma Aldrich - R0508 external link
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 external link
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 - R9881 external link
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.
Selleck Chemicals - S2540 external link
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]
Toronto Research Chemicals - R414995 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
  • • 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
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PATENTS

PATENTS

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