L4879
Lumiflavine
powder
Synonym(s):
7,8,10-Trimethylbenzo[g]pteridine-2,4(3H,10H)-dione, 7,8,10-Trimethylisoalloxazine
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About This Item
Empirical Formula (Hill Notation):
C13H12N4O2
CAS Number:
Molecular Weight:
256.26
Beilstein:
269756
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
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![10-Ethyl-3,7,8-trimethyl-benzo[g]pteridine-2,4(3H,10H)-dione ≥95%](/deepweb/assets/sigmaaldrich/product/structures/610/004/664b92ed-0ce1-4e66-9f3e-d1cc53f1bc9a/640/664b92ed-0ce1-4e66-9f3e-d1cc53f1bc9a.png)
form
powder
storage temp.
−20°C
SMILES string
CN1c2cc(C)c(C)cc2N=C3C(=O)NC(=O)N=C13
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Biochem/physiol Actions
Lumiflavine (Lumiflavin) is produced by the photolysis of vitamin B2 (Riboflavin). Lumiflavine, a riboflavin uptake inhibitor, is used to study riboflavin uptake in intestinal epithelial (Caco-2) and other epithelial cells.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Muta. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Michael A North et al.
The journal of physical chemistry. B, 114(46), 14907-14915 (2010-10-22)
The energetics of electrochemical changes have been investigated for several substituted flavins with the M06-L density functional. The reduction potentials for one- and two-electron reductions of these molecules have been determined and the results are consistent with experimental findings with
Valeria Bafunno et al.
The Journal of biological chemistry, 279(1), 95-102 (2003-10-14)
We have studied the functional steps by which Saccharomyces cerevisiae mitochondria can synthesize FAD from cytosolic riboflavin (Rf). Riboflavin uptake into mitochondria took place via a mechanism that is consistent with the existence of (at least two) carrier systems. FAD
Vincent Sichula et al.
The journal of physical chemistry. B, 114(29), 9452-9461 (2010-07-06)
We investigated the oxidation behavior of 5-ethyl-4a-hydroxy-3-methyl-4a,5-dihydrolumiflavin (pseudobase Et-FlOH) in acetonitrile with the aim of determining if the two-electron oxidized Et-FlOH(2+) undergoes a release of hydroxyl cation and the production of 5-ethyl-3methyllumiflavinium cation (Et-Fl(+)). The focus of this work is
Hamid M Said et al.
The Journal of physiology, 566(Pt 2), 369-377 (2005-05-10)
In mammalian cells (including those of the ocular system), the water-soluble vitamin B2 (riboflavin, RF) assumes an essential role in a variety of metabolic reactions and is critical for normal cellular functions, growth and development. Cells of the human retinal
N B Sankaran et al.
The journal of physical chemistry. B, 113(5), 1522-1529 (2009-01-30)
The binding behavior of lumiflavin, a biologically vital ligand, with DNA duplexes containing an abasic (AP) site and various target nucleobases opposite the AP site is studied. Lumiflavin binds selectively to thymine (T) opposite the AP site in a DNA
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