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103217

Sigma-Aldrich

Lumichrome

Synonym(s):

7,8-Dimethylalloxazine

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About This Item

Empirical Formula (Hill Notation):
C12H10N4O2
CAS Number:
1086-80-2
Molecular Weight:
242.23
EC Number:
214-120-8
MDL number:
MFCD00005021
UNSPSC Code:
12171500
PubChem Substance ID:
24846599
NACRES:
NA.47

form

powder, crystals or chunks

mp

>300 °C (lit.)

λmax

350 nm
392 nm (2nd)

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

Cc1cc2nc3NC(=O)NC(=O)c3nc2cc1C

InChI

1S/C12H10N4O2/c1-5-3-7-8(4-6(5)2)14-10-9(13-7)11(17)16-12(18)15-10/h3-4H,1-2H3,(H2,14,15,16,17,18)

InChI key

ZJTJUVIJVLLGSP-UHFFFAOYSA-N

Related Categories

General description

Lumichrome (7,8-Dimethylalloxazine) is a natural metabolite of riboflavin. It is a flourescent photoproduct of riboflavin degradation. It is known to be an effective photosensitizer and a fluorescent dye.

Application

Lumichrome is suitable as a fluorescence probe, metal ion sensor, and may be used for the inactivation of biological contaminants. Its applications are also seen in memory and semiconductor devices.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000387410
0000373839
0000358933
0000358934
0000373839

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Carlo I G Tuberoso et al.
Journal of agricultural and food chemistry, 59(1), 364-369 (2010-12-04)
HPLC-DAD-MS/MS chromatograms of thistle (Galactites tomentosa Moench) unifloral honeys, previously selected by sensory evaluation and melissopalynological analysis, showed high levels of two compounds. One was characterized as phenyllactic acid, a common acid found in honeys, but the other compound was
N Shaemningwar Moyon et al.
The journal of physical chemistry. A, 115(12), 2456-2464 (2011-03-11)
Fluorescence solvatochromism of lumichrome (LC) was studied by steady-state and time-resolved fluorescence spectroscopy. The excited-state properties of LC do not show any correlation with solvent polarity, however, reasonably good correlation with solvent E(T)(30) parameter was observed. A quantitative estimation of
Carlo Ignazio Giovanni Tuberoso et al.
Food chemistry, 135(3), 1985-1990 (2012-09-08)
Riboflavin (vitamin B(2)) and its metabolite lumichrome were quantified in 117 samples from 11 unifloral honeys types (Arbutus unedo L., Asphodelus microcarpus Salzm. et Viv., Citrus spp., Eucalyptus spp., Hedysarum coronarium L., Castanea sativa L. honeydew, Mentha spp., Paliurus spina-christi.
Xiancheng Zeng et al.
The Journal of chemical physics, 130(16), 164111-164111 (2009-05-02)
A quantum mechanical/molecular mechanical minimum free energy path (QM/MM-MFEP) method was developed to calculate the redox free energies of large systems in solution with greatly enhanced efficiency for conformation sampling. The QM/MM-MFEP method describes the thermodynamics of a system on
Iqbal Ahmad et al.
International journal of pharmaceutics, 280(1-2), 199-208 (2004-07-22)
The kinetics of photolysis of aqueous riboflavin solutions on UV and visible irradiation has been studied in the pH range 1-12 using a specific multicomponent spectrophotometric method for the simultaneous determination of riboflavin and its major photoproducts (formylmethylflavin, lumichrome and
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