R9504

Sigma-Aldrich

(−)-Riboflavin

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

Synonym(s):
Vitamin G, Vitamin B2, Lactoflavin
Empirical Formula (Hill Notation):
C17H20N4O6
CAS Number:
Molecular Weight:
376.36
Beilstein/REAXYS Number:
97825
EC Number:
MDL number:
eCl@ss:
34058005
PubChem Substance ID:
NACRES:
NA.75
Pricing and availability is not currently available.

Quality Level

biological source

Eremothecium ashbyii

product line

BioReagent

assay

≥98%

form

powder

mol wt

Mw 376.36 g/mol

application(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 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.

Packaging

25, 100 g in glass bottle

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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Ulises Alvarado et al.
Foods (Basel, Switzerland), 9(1) (2019-12-22)
The front-face fluorescence spectroscopy technique was used to establish a rapid prediction model of riboflavin concentration in milk without prior sample preparation. The prediction model developed was then compared with two conventional high performance liquid chromatography (HPLC)-based quantification methods. The...
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)
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...
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
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.
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