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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 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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

103217-BULK:
103217-5G:
103217-VAR:
103217-1G:

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Certificates of Analysis (COA)

Lot/Batch Number
0000387410
0000373839
0000358934
0000358933
0000373839

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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
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 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
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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