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R9504

Sigma-Aldrich

(−)-Riboflavina

BioReagent, suitable for cell culture, suitable for insect cell culture, ≥98%

Sinônimo(s):

Lactoflavina, Vitamina B2, Vitamina G

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About This Item

Fórmula empírica (Notação de Hill):
C17H20N4O6
Número CAS:
Peso molecular:
376.36
Beilstein:
97825
Número CE:
Número MDL:
Código UNSPSC:
12352205
eCl@ss:
34058005
ID de substância PubChem:
NACRES:
NA.75

fonte biológica

Eremothecium ashbyii

linha de produto

BioReagent

Ensaio

≥98%

forma

powder

peso molecular

Mw 376.36 g/mol

técnica(s)

cell culture | insect: suitable
cell culture | mammalian: suitable

cor

yellow to orange

pf

290 °C (dec.) (lit.)

solubilidade

0.1 M NaOH: 10 mg/mL, clear, yellow to orange

temperatura de armazenamento

room temp

cadeia de caracteres SMILES

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

chave InChI

AUNGANRZJHBGPY-SCRDCRAPSA-N

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Descrição geral

Riboflavin supports cell growth and metabolism, aiding researchers in R&D. In cell culture, it is often found as a key ingredient in media formulations. Cancer researchers study its impact on oxidative stress responses. Stem cell researchers value its role in maintaining pluripotency.


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.

Aplicação

(-)-Riboflavin has been used to administer intraperitoneally to experimental mice to study its protective role in stroke in middle cerebral artery occlusion. It has also been used with Krebs′ solution, to model ischemia-like conditions in vitro.

Ações bioquímicas/fisiológicas

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, having symptoms including cheilosis, angular stomatitis, glossitis, keratitis, and seborrhoeic dermatitis. 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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


Certificados de análise (COA)

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Chia-An Yen et al.
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Exposure to environmental stress is clinically established to influence male reproductive health, but the impact of normal cellular metabolism on sperm quality is less well-defined. Here we show that impaired mitochondrial proline catabolism, reduces energy-storing flavin adenine dinucleotide (FAD) levels
Riboflavin (vitamin B-2) and health
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American Journal of Clinical Nutrition, 77(6), 1352-1360 (2003)
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Riboflavin transporter deficiency (RTD) is a childhood-onset neurodegenerative disorder characterized by sensorineural deafness and motor neuron degeneration. Since riboflavin plays key functions in biological oxidation-reduction reactions, energy metabolism pathways involving flavoproteins are affected in RTD. We recently generated induced pluripotent
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Tumkiratiwong P, et al.
The Southeast Asian Journal of Tropical Medicine and Public Health, 34(3), 480-485 (2003)
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Journal of refractive surgery (Thorofare, N.J. : 1995), 29(12), 846-848 (2013-10-31)
To investigate the effect of high-fluence corneal collagen cross-linking (CXL) with riboflavin and ultraviolet-A in the management of progressive keratoconus. Preliminary results from a prospective cohort study. Seven eyes from 7 patients with progressive keratoconus subjected to CXL were included.

Artigos

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

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