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87787

Sigma-Aldrich

6-(4-Methoxyphenyl)-2-methyl-3,7-dihydroimidazo[1,2-a]pyrazin-3(7H)-one hydrochloride

suitable for chemiluminescence, ≥98.0% (HPLC)

Synonym(s):

2-Methyl-6-(4-methoxyphenyl)-3,7-dihydroimidazo[1,2-a]pyrazin-3(7H)-one hydrochloride, Cypridina Luciferin methoxy-analogue, MCLA

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About This Item

Empirical Formula (Hill Notation):
C14H13N3O2 · HCl
CAS Number:
Molecular Weight:
291.73
Beilstein/REAXYS Number:
5838857
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.32

description

luminescence test: Emmax465 nm, 0.1 M Tris pH 8.5; after addition of H2O2 (Chemiluminescence: in 0.1 M Tris pH 8.5; after addition of H2O2)

assay

≥98.0% (HPLC)

form

powder

solubility

DMSO: soluble
H2O: soluble

suitability

suitable for chemiluminescence

SMILES string

Cl[H].COc1ccc(cc1)C2=CN3C(=O)C(C)=NC3=CN2

InChI

1S/C14H13N3O2.ClH/c1-9-14(18)17-8-12(15-7-13(17)16-9)10-3-5-11(19-2)6-4-10;/h3-8,15H,1-2H3;1H

InChI key

KGMPQNFFCUDXSO-UHFFFAOYSA-N

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Generation of chemiluminescence by reaction with super oxide O2 or singlet oxygen. Used in research of leucocyte function[1][2][3].

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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A Takahashi et al.
FEBS letters, 261(2), 369-372 (1990-02-26)
To investigate O2- generation in in situ lungs of rats treated with drugs to induce experimental acute respiratory distress syndrome, phorbol myristate acetate (PMA) or endotoxin were injected into rats, who had been continuously infused with 2(methyl-6-[p-methoxyphenyl]-3,7-dihydroimidazo[1,2-alpha]pyraz in-3-one (MCLA) and
S Koga et al.
Archives of biochemistry and biophysics, 289(2), 223-229 (1991-09-01)
Heme compound, hematin or cytochrome c, catalyzes the decomposition of 13-hydroperoxy linoleic acid yielding both O2- and 1O2 under aerobic conditions. No 1O2 is produced when hydrogen peroxide and cumene hydroperoxide are used as substrates. In these experiments, both O2-
Taeko Mizutani et al.
Journal of oleo science, 65(12), 993-1001 (2016-11-11)
Sodium lauryl sulfate (SLS), a representative anionic surfactant, is well-known to induce rough skin following single or multiple topical applications. The mechanism by which SLS induces rough skin is thought to result from the disruption of skin moisture function consisting
Lucas J Beversdorf et al.
Water research, 140, 280-290 (2018-05-08)
Freshwater cyanobacterial blooms are becoming increasingly problematic in regions that rely on surface waters for drinking water production. Microcystins (MCs) are toxic peptides produced by multiple cyanobacterial genera with a global occurrence. Cyanobacteria also produce a variety of other toxic
Julia M Diaz et al.
Nature communications, 7, 13801-13801 (2016-12-08)
The reactive oxygen species superoxide (O2·-) is both beneficial and detrimental to life. Within corals, superoxide may contribute to pathogen resistance but also bleaching, the loss of essential algal symbionts. Yet, the role of superoxide in coral health and physiology

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