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R9504

Sigma-Aldrich

(−)-Riboflavin

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

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
Beilstein:
97825
EC Number:
MDL number:
UNSPSC Code:
12352205
eCl@ss:
34058005
PubChem Substance ID:
NACRES:
NA.75

biological source

Eremothecium ashbyii

Quality Level

product line

BioReagent

Assay

≥98%

form

powder

mol wt

Mw 376.36 g/mol

technique(s)

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

color

yellow to orange

mp

290 °C (dec.) (lit.)

solubility

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

storage temp.

room temp

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

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General description

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.

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, 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.

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Riboflavin (vitamin B-2) and health
Powers Hilary J
American Journal of Clinical Nutrition, 77(6), 1352-1360 (2003)
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
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
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)
Zisis Gatzioufas et al.
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.

Articles

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

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