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177539

Sigma-Aldrich

Syringaldazine

98%

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:
329751558
NACRES:
NA.83

Quality Level

100

assay

98%

form

powder or crystals

mp

209-210 °C (lit.)

solubility

DMF: 5%, clear to 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 measure the enzymatic activity of recombinant laccase.

Biochem/physiol Actions

Syringaldazine (4-Hydroxy-3, 5-dimethoxybenzaldehyde azine) is a nonautooxidizable laccase-specific compound. It acts as a substrate for laccase and peroxidase in the presence of hydrogen peroxide (H2O2). Syringaldazine also acts as an electron donor in the prostaglandin H synthase (PGHS) reaction.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H228

pcodes

P210

Hazard Classifications

Flam. Sol. 2

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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S Molinari
Journal of nematology, 23(2), 254-258 (1991-04-01)
Isoperoxidases were detected in resistant Rossol and susceptible Roma VF tomato roots uninfected and infected by Meloidogyne incognita. Syringaldazine, guaiacol, p-phenylenediamine-pyrocatechol (PPD-PC), and indoleacetic acid (IAA) were used as substrates, and the corresponding peroxidative activities were detected either in cytoplasmic
W Bao et al.
Science (New York, N.Y.), 260(5108), 672-674 (1993-04-30)
Peroxidase has been thought to be the only enzyme that oxidizes monolignol precursors to initiate lignin formation in plants. A laccase was purified from cell walls of differentiating xylem of loblolly pine and shown to coincide in time and place
Use of syringaldazine for detection of laccase in sporophores of wood rotting fungi.
J M Harkin et al.
Mycologia, 66(3), 469-476 (1974-05-01)
Y A Kuznetsova et al.
Applied biochemistry and biotechnology, 61(1-2), 205-209 (1996-10-01)
The prostaglandin H synthase (PGHS) reaction has been studied with syringaldazine as the electron donor. Kinetic parameters of the reaction agreed with those for commonly used electron donors. The sensitivity of the PGHS activity detection in the presence of syringaldazine
C L Wabner et al.
The Journal of urology, 149(6), 1405-1408 (1993-06-01)
The value of orange juice consumption in kidney stone prevention was examined in 8 healthy men and 3 men with documented hypocitraturic nephrolithiasis. They underwent 3 phases of a metabolic study, a placebo phase and 2 treatment phases in which
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