R7649

(−)-Riboflavin

meets USP testing specifications

• Synonym(s): Lactoflavin, Vitamin B₂, Vitamin G
• Empirical Formula (Hill Notation): C₁₇H₂₀N₄O₆
• CAS Number: 83-88-5
• Molecular Weight: 376.36
• Beilstein: 97825
• EC Number: 201-507-1
• MDL number: MFCD00005022
• eCl@ss: 34058005
• PubChem Substance ID: 24899397
• NACRES: NA.21

Properties

• Agency: USP/NF; meets USP testing specifications
• Quality Level: 200
• Assay: 98.0-102.0% dry basis
• form: powder
• color: dark yellow
• mp: 290 °C (dec.) (lit.)
• application(s): pharmaceutical (small molecule)
• 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 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 study its antimicrobial effect in vitro, through ultraviolet light A (UVA) activation.It has also been used collagen coated surface of the polyethylene membrane for cross-linking astrocytes.

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, 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 Code: 11 - Combustible Solids
• WGK: WGK 1
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves