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Safety Information

R7649

Sigma-Aldrich

(−)-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
Beilstein:
97825
EC Number:
201-507-1
MDL number:
MFCD00005022
UNSPSC Code:
12352205
eCl@ss:
34058005
PubChem Substance ID:
24899397
NACRES:
NA.21

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

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.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

R7649-25G:
R7649-500G:
R7649-1KG:
R7649-VAR:
R7649-BULK:
R7649-100G:

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD6038V
WXBD4613V
WXBD2883V
WXBD1472V
WXBC9615V

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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
Makdoumi K, et al.
Acta Ophthalmologica, 95(5), 498-502 (2017)
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)
Antioxidant enzyme levels in the erythrocytes of riboflavin-deficient and Trichinella spiralis-infected rats
Tumkiratiwong P, et al.
The Southeast Asian Journal of Tropical Medicine and Public Health, 34(3), 480-485 (2003)
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Articles

Riboflavin in Cell Culture

How riboflavin and othercell culture components affect the performance of serum-free, protein-free cell culture systems used for biomanufacturing heterologous proteins including monoclonal antibodies. The page introduces the in vitro chemistry and biochemistry of riboflavin.

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