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103217

Sigma-Aldrich

Lumichrome

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Synonym(s):
7,8-Dimethylalloxazine
Empirical Formula (Hill Notation):
C12H10N4O2
CAS Number:
Molecular Weight:
242.23
EC Number:
MDL number:
PubChem Substance ID:
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

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Amit Tyagi et al.
Photochemistry and photobiology, 87(3), 524-533 (2010-11-26)
The spectroscopic behavior of lumichrome (7,8-dimethyl-alloxazine, LC) in aqueous solutions in a pH range from -1.08 to 14.6 is studied. Absorption spectra, fluorescence quantum distributions, quantum yields, and lifetimes are determined. The ionization stage of ground-state LC changes with rising
Tamutenda Chidawanyika et al.
mBio, 11(4) (2020-08-14)
Extracellular hydrogen peroxide can induce oxidative stress, which can cause cell death if unresolved. However, the cellular mediators of H2O2-induced cell death are unknown. We determined that H2O2-induced cytotoxicity is an iron-dependent process in HAP1 cells and conducted a CRISPR/Cas9-based
Maria Marchena et al.
The journal of physical chemistry. B, 115(10), 2424-2435 (2011-02-22)
We report on photophysical studies of lumichrome (Lc) in water at different pHs, and interacting with the human serum albumin (HSA) protein and β-cyclodextrin (β-CD) in neutral aqueous solutions. We used steady-state and picosecond time-resolved emission spectroscopy to investigate the
Sathish Rajamani et al.
Molecular plant-microbe interactions : MPMI, 21(9), 1184-1192 (2008-08-15)
Many bacteria use quorum sensing (QS) as an intercellular signaling mechanism to regulate gene expression in local populations. Plant and algal hosts, in turn, secrete compounds that mimic bacterial QS signals, allowing these hosts to manipulate QS-regulated gene expression in
Partha Bairi et al.
The journal of physical chemistry. B, 114(35), 11454-11461 (2010-08-19)
Lumichrome (L) and melamine (M) produce thermoreversible hydrogels in LM31 and LM11 compositions, but LM13 composition does not produce hydrogel (the numbers indicate the respective molar ratio of the components). The formation of thermoreversible gels is confirmed from morphology, DSC

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