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R7649

(−)-Riboflavin

Name: (−)-Riboflavin
Brand: SIAL

meets USP testing specifications

Synonym(s):

Vitamin G, Lactoflavin, Vitamin B₂

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About This Item

Empirical Formula (Hill Notation):

C₁₇H₂₀N₄O₆

CAS Number:

83-88-5

Molecular Weight:

376.36

NACRES:

NA.21

PubChem Substance ID:

24899397

eCl@ss:

34058005

UNSPSC Code:

12352205

EC Number:

201-507-1

MDL number:

MFCD00005022

Beilstein/REAXYS Number:

97825

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Properties

Quality Level

200

agency

USP/NF, meets USP testing specifications

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Articles

Riboflavin in Cell Culture

Riboflavin's impact on cell culture systems for manufacturing proteins and monoclonal antibodies discussed.

Evaluation of antibacterial efficacy of photo-activated riboflavin using ultraviolet light (UVA)

Makdoumi K, et al.

Graefe'S Archive For Clinical and Experimental Ophthalmology = Albrecht Von Graefes Archiv Fur Klinische Und Experimentelle Ophthalmologie, 248(2), 207-212 (2010)

Mechanical stretching elevates peptidyl arginine deiminase 2 expression in astrocytes

Algeciras ME, et al.

Current Eye Research, 33(11-12), 994-1001 (2008)

Photochemical eradication of methicillin-resistant Staphylococcus aureus by blue light activation of riboflavin