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177539

Sigma-Aldrich

Syringaldazine

98%, 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:
329751558
NACRES:
NA.83

product name

Syringaldazine, 98%

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

Signal Word

Warning

Hazard Statements

H228

Precautionary Statements

P210

Hazard Classifications

Flam. Sol. 2

Storage Class Code

4.1B - Flammable solid hazardous materials

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCK2256
BCCH9948
BCCG4241
STBJ7683
STBJ3050

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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
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
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