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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:
Molecular Weight:
376.36
NACRES:
NA.21
PubChem Substance ID:
eCl@ss:
34058005
UNSPSC Code:
12352205
EC Number:
201-507-1
MDL number:
Beilstein/REAXYS Number:
97825
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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
1 of 4
This Item | R0600000 | 1603006 | R9504 |
|---|---|---|---|
| assay 98.0-102.0% dry basis | assay - | assay - | assay ≥98% |
| form powder | form solid | form - | form powder |
| application(s) pharmaceutical (small molecule) | application(s) pharmaceutical (small molecule) | application(s) pharmaceutical (small molecule) | application(s) - |
| mp 290 °C (dec.) (lit.) | mp 290 °C (dec.) (lit.) | mp 290 °C (dec.) (lit.) | mp 290 °C (dec.) (lit.) |
| color dark yellow | color - | color - | color yellow to orange |
| Quality Level 200 | Quality Level - | Quality Level - | Quality Level 200 |
Application
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).[5] Riboflavin deficiency in the diet results in a well-defined syndrome known as ariboflavinosis,[6] 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.[5]
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.[5]
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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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)
Articles
Riboflavin's impact on cell culture systems for manufacturing proteins and monoclonal antibodies discussed.
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Is this of animal origin
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Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf
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