R4500

(−)-Riboflavin

from Eremothecium ashbyii, ≥98%

• 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
• UNSPSC Code: 12352205
• eCl@ss: 34058005
• PubChem Substance ID: 57654591
• NACRES: NA.79

Properties

• biological source: Eremothecium ashbyii
• Assay: ≥98%
• form: powder
• color: yellow to orange
• mp: 290 °C (dec.) (lit.)
• 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 belongs to the vitamin-B family and contains a pentose side chain ribitol.

Application

Riboflavin has been used:

• to check the role of riboflavin diet in rats
• as a supplement in HECM-6 medium (hamster embryo culture medium)
• as a supplement in the bacterial basal media

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. Riboflavin is involved in various cellular processes, including β oxidation in lipid metabolism, glucose metabolism, protection from cellular oxidative injury, DNA and RNA metabolism, gluconeogenesis, erythropoiesis and generation of corticosteroids. Riboflavin deficiency causes ariboflavinosis with symptoms such as sore throat, hyperemia, edema of oral and mucous membranes, cheilosis and glossitis.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves