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R9504

Sigma-Aldrich

(−)-Riboflavin

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

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Synonym(s):
Lactoflavin, Vitamin B2, Vitamin G
Empirical Formula (Hill Notation):
C17H20N4O6
CAS Number:
Molecular Weight:
376.36
Beilstein:
97825
EC Number:
MDL number:
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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This Item
R7649R4500PHR1054
(−)-Riboflavin BioReagent, suitable for cell culture, suitable for insect cell culture, ≥98%

Sigma-Aldrich

R9504

(−)-Riboflavin

(−)-Riboflavin meets USP testing specifications

Sigma-Aldrich

R7649

(−)-Riboflavin

(−)-Riboflavin from Eremothecium ashbyii, ≥98%

Sigma-Aldrich

R4500

(−)-Riboflavin

Riboflavin Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1054

Riboflavin

assay

≥98%

assay

98.0-102.0% dry basis

assay

≥98%

assay

-

form

powder

form

powder

form

powder

form

-

technique(s)

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

technique(s)

-

technique(s)

-

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

color

yellow to orange

color

dark yellow

color

yellow to orange

color

-

mp

290 °C (dec.) (lit.)

mp

290 °C (dec.) (lit.)

mp

290 °C (dec.) (lit.)

mp

290 °C (dec.) (lit.)

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Customers Also Viewed

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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