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SML1583

Roseoflavin

Name: Roseoflavin
Brand: SIGMA

≥95% (HPLC), Riboflavin antagonist, powder

Synonym(s):

8-Demethyl-8-(dimethylamino)-riboflavin, 8-Dimethylaminoriboflavin

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About This Item

Empirical Formula (Hill Notation):

C₁₈H₂₃N₅O₆

CAS Number:

51093-55-1

Molecular Weight:

405.41

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥95% (HPLC)

Form:

powder

Storage condition:

protect from light

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Properties

Product Name

Roseoflavin, ≥95% (HPLC)

Quality Segment

100

assay

≥95% (HPLC)

form

powder

storage condition

protect from light

color

faint red to very dark brown-red

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

[n]1(c2n[c]([nH][c](c2nc3c1cc(c(c3)C)N(C)C)=O)=O)CC(O)C(O)C(O)CO

InChI

1S/C18H23N5O6/c1-8-4-9-11(5-10(8)22(2)3)23(6-12(25)15(27)13(26)7-24)16-14(19-9)17(28)21-18(29)20-16/h4-5,12-13,15,24-27H,6-7H2,1-3H3,(H,21,28,29)

InChI key

IGQLDUYTWDABFK-UHFFFAOYSA-N

Description

Biochem/physiol Actions

Roseoflavin is an analog of flavin mononucleotide (FMN) and riboflavin with antimicrobial activity.

Roseoflavin is an analog of flavin mononucleotide (FMN) and riboflavin with antimicrobial activity. Roseoflavin is converted to the flavin mononucleotide (FMN) analog roseoflavin mononucleotide (RoFMN) by flavokinase and to the flavin adenine dinucleotide (FAD) analog roseoflavin adenine dinucleotide (RoFAD) by FAD synthetase, and acts as a riboflavin antagonist. Roseoflavin is an inhibitor of bacterial riboflavin riboswitches, cis regulatory elements present in non-coding RNA that specifically bind to natural ligands to regulate gene expression. Roseoflavin, converted to RoFMN, blocks the flavin mononucleotide riboswitch-mediated expression of the ribB gene, which is required for riboflavin biosynthesis.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

0000544864

0000544862