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R4500

Sigma-Aldrich

(−)-Riboflavin

from Eremothecium ashbyii, ≥98%

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Synonym(s):
Lactoflavin, Vitamin B2, Vitamin G
Empirical Formula (Hill Notation):
C17H20N4O6
CAS Number:
83-88-5
Molecular Weight:
376.36
Beilstein:
97825
EC Number:
201-507-1
MDL number:
MFCD00005022
eCl@ss:
34058005
PubChem Substance ID:
57654591
NACRES:
NA.79

biological source

Eremothecium ashbyii

Quality Level

200

Assay

≥98%

form

powder

color

yellow to orange

mp

290 °C (dec.) (lit.)

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 belongs to the vitamin-B family and contains a pentose side chain ribitol.

Application

Riboflavin has been used:
  • to check the role of riboflavin diet in rats
  • as a supplement in HECM-6 medium (hamster embryo culture medium)
  • as a supplement in the bacterial basal media

Biochem/physiol Actions

Riboflavin is a key component of the redox cofactors flavin adenine dinucleotide (FAD) and flavin mononucleotide (FMN) that are used by a wide variety of flavoprotein oxidoreductases, dehydrogenase(s), decarboxylase(s) and electron transporters. Riboflavin is involved in various cellular processes, including β oxidation in lipid metabolism, glucose metabolism, protection from cellular oxidative injury, DNA and RNA metabolism, gluconeogenesis, erythropoiesis and generation of corticosteroids. Riboflavin deficiency causes ariboflavinosis with symptoms such as sore throat, hyperemia, edema of oral and mucous membranes, cheilosis and glossitis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Catherine Burgess et al.
Applied and environmental microbiology, 70(10), 5769-5777 (2004-10-07)
This study describes the genetic analysis of the riboflavin (vitamin B(2)) biosynthetic (rib) operon in the lactic acid bacterium Lactococcus lactis subsp. cremoris strain NZ9000. Functional analysis of the genes of the L. lactis rib operon was performed by using
S H McKiernan et al.
Human reproduction (Oxford, England), 15(1), 157-164 (1999-12-28)
The effects of water-soluble vitamins, singly or in combinations, on development of hamster 1-cell embryos were examined in a protein-free, chemically defined culture medium, HECM-6. Pantothenate significantly stimulated blastocyst development compared to the vitamin-free control and to every other single
The response of young and adult rats to the riboflavin supplementation.
Franca CF
Brazilian Archives of Biology and Technology, 53, 855-860 (2010)
Stargrove MB, et al.
Herb, Nutrient, and Drug Interactions: Clinical Implications and Therapeutic Strategies (2008)
Ana Rita da Silva Ferreira et al.
Biomolecules, 11(1) (2021-01-02)
Mucositis is a common side-effect of chemotherapy treatment, inducing alterations in the composition of the gut microbiota. Redox active compounds, such as vitamins B2 and C, have been shown to reduce inflammation and enhance the growth of anaerobic bacteria in
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