R9504

(−)-Riboflavin

BioReagent, suitable for cell culture, suitable for insect cell culture, ≥98%

• Synonym(s): Lactoflavin, Vitamin B₂, Vitamin G
• Empirical Formula (Hill Notation): C₁₇H₂₀N₄O₆
• CAS Number: 83-88-5
• Molecular Weight: 376.36
• Beilstein/REAXYS Number: 97825
• EC Number: 201-507-1
• MDL number: MFCD00005022
• UNSPSC Code: 12352205
• eCl@ss: 34058005
• PubChem Substance ID: 24899415
• NACRES: NA.75

Properties

• biological source: Eremothecium ashbyii
• product line: BioReagent
• assay: ≥98%
• form: powder
• mol wt: M_w 376.36 g/mol
• technique(s): cell culture | insect: suitable; cell culture | mammalian: suitable
• color: yellow to orange
• mp: 290 °C (dec.) (lit.)
• solubility: 0.1 M NaOH: 10 mg/mL, clear, yellow to orange
• storage temp.: room temp
• SMILES string: CC1=C(C)C=C(N(C[C@H](O)[C@@H]([C@H](O)CO)O)C(C2=N3)=NC(NC2=O)=O)C3=C1
• 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
• InChI key: AUNGANRZJHBGPY-SCRDCRAPSA-N

Description

General description

Riboflavin supports cell growth and metabolism, aiding researchers in R&D. In cell culture, it is often found as a key ingredient in media formulations. Cancer researchers study its impact on oxidative stress responses. Stem cell researchers value its role in maintaining pluripotency.


Riboflavin is an essential vitamin soluble in water. Milk and eggs are found to be its major sources. Riboflavin is usually bound to enzymes in all tissues. During riboflavin localization in plasma, it is bound to albumin and specific immunoglobulins.

Application

(-)-Riboflavin has been used to administer intraperitoneally to experimental mice to study its protective role in stroke in middle cerebral artery occlusion. It has also been used with Krebs′ solution, to model ischemia-like conditions in vitro.

Biochem/physiol Actions

Riboflavin serves as a precursor for the active enzyme cofactors riboflavin 5′-monophosphate (also called flavin mononucleotide or FMN) and flavin adenine dinucleotide (FAD). Riboflavin deficiency in the diet results in a well-defined syndrome known as ariboflavinosis, having symptoms including cheilosis, angular stomatitis, glossitis, keratitis, and seborrhoeic dermatitis. Riboflavin exhibits protective effects against tumor development and cardiovascular disease. Its deficiency often affects metabolism involving redox reactions. Riboflavin is found essential for iron absorption, gastrointestinal development, neurogenesis, corneal vascularization and corneal opacity.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)