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Merck

R7649

(−)-Riboflavin

meets USP testing specifications

Synonym(s):

Lactoflavin, Vitamin B2, Vitamin G

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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

Product Name

(−)-Riboflavin, meets USP testing specifications

InChI key

AUNGANRZJHBGPY-SCRDCRAPSA-N

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

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

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)

Quality Level

200

Related Categories

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.

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.

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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Certificates of Analysis (COA)

Lot/Batch Number
WXBF6279V
WXBF5798V
WXBF5223V
WXBF4481V
WXBF3135V

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Mechanical stretching elevates peptidyl arginine deiminase 2 expression in astrocytes
Algeciras ME, et al.
Current Eye Research, 33(11-12), 994-1001 (2008)
Graciely Gomes Correa et al.
Data in brief, 31, 105736-105736 (2020-06-09)
Modular and tuneable genetic tools for Metabolic Engineering fuels the development of chassis for the efficient production of biocompounds at industrial scale. We have constructed an autoinduction device for gene expression in Bacillus subtilis based on the LuxR/I quorum sensing
The efficiency of cross-linking methods in eradication of bacteria is influenced by the riboflavin concentration and the irradiation time of ultraviolet light
Backman A, et al.
Acta Ophthalmologica, 92(7), 656-661 (2014)
Photochemical eradication of methicillin-resistant Staphylococcus aureus by blue light activation of riboflavin
Makdoumi K, et al.
Acta Ophthalmologica, 95(5), 498-502 (2017)
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)
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Articles

Riboflavin in Cell Culture

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

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