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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

technique(s)

titration: suitable

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

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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 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

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Certificates of Analysis (COA)

Lot/Batch Number
0000387410
0000373839
0000358934
0000358933
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
Dorota Prukała et al.
The journal of physical chemistry. A, 116(28), 7474-7490 (2012-06-27)
Lumichrome photophysical properties at different pH were characterized by UV-vis spectroscopy and steady-state and time-resolved fluorescence techniques, in four forms of protonation/deprotonation: neutral form, two monoanions, and dianion. The excited-state lifetimes of these forms of lumichrome were measured and discussed.
Wajahatullah Khan et al.
Journal of plant physiology, 165(13), 1342-1351 (2008-01-15)
The foliar application of Nod factor [Nod Bj V (C(18:1), MeFuc)] enhanced (P<0.05) the photosynthetic rate of corn; the increases were 36%, 23% and 12% for 10(-6), 10(-8) and 10(-10)M treated plants, respectively. Similarly, lumichrome at 10(-5) and 10(-6)M stimulated
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
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