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S7896

Sigma-Aldrich

Syringaldazine

indicator for laccase and peroxidase activity, ≥98% (TLC), powder or crystals

Synonym(s):

4-Hydroxy-3,5-dimethoxybenzaldehyde azine

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About This Item

Linear Formula:
[HOC6H2(OCH3)2CH=N-]2
CAS Number:
14414-32-5
Molecular Weight:
360.36
EC Number:
238-390-1
MDL number:
MFCD00008363
UNSPSC Code:
12352204
PubChem Substance ID:
24899766
NACRES:
NA.83

product name

Syringaldazine, indicator for laccase and peroxidase activity

assay

≥98% (TLC)

form

powder or crystals

mp

209-210 °C (lit.)

solubility

DMF: soluble, slightly hazy

storage temp.

2-8°C

SMILES string

COc1cc(\C=N\N=C\c2cc(OC)c(O)c(OC)c2)cc(OC)c1O

InChI

1S/C18H20N2O6/c1-23-13-5-11(6-14(24-2)17(13)21)9-19-20-10-12-7-15(25-3)18(22)16(8-12)26-4/h5-10,21-22H,1-4H3/b19-9+,20-10+

InChI key

YARKTHNUMGKMGS-LQGKIZFRSA-N

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Application

Syringaldazine has been used as a substrate to determine the enzymatic activity of the cuticular laccase.

Biochem/physiol Actions

Syringaldazine is a dimer of two molecules of 2,6-dimethoxyphenol linked by an azide bridge. It is a phenolic non-autooxidizable laccase-specific compound, that facilitates the detection of fungal laccase in some varieties of fungi. In addition, it also acts as an indicator for peroxidase activity in fungi.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H228

pcodes

P210

Hazard Classifications

Flam. Sol. 2

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Quantitative estimation of laccase forms in some white-rot fungi using syringaldazine as a substrate
Leonowicz A and Grzywnowicz K
Enzyme and Microbial Technology, 3(1), 55-58 (1981)
Use of syringaldazine for detection of laccase in sporophores of wood rotting fungi
Harkin JM, et al.
Mycologia, 66(3), 469-476 (1974)
Aptitude of Oxidative Enzymes for Treatment of Wastewater Pollutants: A Laccase Perspective
Unuofin JO, et al.
Molecules (Basel), 24(11), 2064-2064 (2019)
J M Harkin et al.
Science (New York, N.Y.), 180(4083), 296-298 (1973-04-20)
Syringaldazine did not turn purple on cross sections of tree branches or saplings or on cambial tissue cultures unless hydrogen peroxide was added; this indicated the absence of laccase but presence of peroxidase in lignifying cells. Peroxidase, therefore, apparently is
Characterization of endogenous and recombinant forms of laccase-2, a multicopper oxidase from the tobacco hornworm, Manduca sexta
Dittmer NT, et al.
Insect Biochemistry and Molecular Biology, 39(9), 596-606 (2009)
View All Related Papers

Protocols

Enzymatic Assay: Laccase (EC 1.10.3.2)

Laccase, a biocatalyst, oxidizes aromatic compounds with molecular oxygen reduction, making it useful in various applications.

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