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Merck
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Key Documents

R9504

Sigma-Aldrich

(−)-Riboflavine

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

Synonyme(s) :

Lactoflavin, Vitamin B2, Vitamin G

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About This Item

Formule empirique (notation de Hill):
C17H20N4O6
Numéro CAS:
Poids moléculaire :
376.36
Numéro Beilstein :
97825
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352205
eCl@ss :
34058005
ID de substance PubChem :
Nomenclature NACRES :
NA.75

Source biologique

Eremothecium ashbyii

Niveau de qualité

Gamme de produits

BioReagent

Pureté

≥98%

Forme

powder

Poids mol.

Mw 376.36 g/mol

Technique(s)

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

Couleur

yellow to orange

Pf

290 °C (dec.) (lit.)

Solubilité

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

Température de stockage

room temp

Chaîne 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

Clé InChI

AUNGANRZJHBGPY-SCRDCRAPSA-N

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Description générale

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.

Application

(-)-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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Chia-An Yen et al.
eLife, 9 (2020-02-06)
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
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)
Riboflavin (vitamin B-2) and health
Powers Hilary J
American Journal of Clinical Nutrition, 77(6), 1352-1360 (2003)
Fiorella Colasuonno et al.
Antioxidants (Basel, Switzerland), 9(12) (2020-12-16)
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
Ying-Xin Zou et al.
CNS neuroscience & therapeutics, 18(10), 834-840 (2012-08-29)
To explore risk factors for stroke independent of hypertension and the relationship between riboflavin kinase (RFK) and stroke. Gene expression profiling in the brains of spontaneously hypertensive rats (SHR) and stroke-prone spontaneously hypertensive rats (SHRSP) was comparatively analyzed by gene

Articles

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

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