Syringaldazine
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MedKoo CAT#: 585190

CAS#: 14414-32-5

Description: Syringaldazine is a chromogenic agent used for detection of laccase in sporophores of wood rotting fungi.


Chemical Structure

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Syringaldazine
CAS# 14414-32-5

Theoretical Analysis

MedKoo Cat#: 585190
Name: Syringaldazine
CAS#: 14414-32-5
Chemical Formula: C18H20N2O6
Exact Mass: 360.1321
Molecular Weight: 360.366
Elemental Analysis: C, 59.99; H, 5.59; N, 7.77; O, 26.64

Price and Availability

Size Price Availability Quantity
1.0g USD 265.0 2 Weeks
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Synonym: Syringaldazine

IUPAC/Chemical Name: Benzaldehyde, 4-hydroxy-3,5-dimethoxy-, 2-((4-hydroxy-3,5-dimethoxyphenyl)methylene)hydrazone

InChi Key: YARKTHNUMGKMGS-LQGKIZFRSA-N

InChi Code: 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+

SMILES Code: COC1=C(O)C(OC)=CC(/C=N/N=C/C2=CC(OC)=C(O)C(OC)=C2)=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 360.366 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Ulyanova Y, Babanova S, Pinchon E, Matanovic I, Singhal S, Atanassov P. Effect of enzymatic orientation through the use of syringaldazine molecules on multiple multi-copper oxidase enzymes. Phys Chem Chem Phys. 2014 Jul 14;16(26):13367-75. doi: 10.1039/c4cp01296h. PubMed PMID: 24875125.

2: Christensen JH, Overney S, Rohde A, Diaz WA, Bauw G, Simon P, Van Montagu M, Boerjan W. The syringaldazine-oxidizing peroxidase PXP 3-4 from poplar xylem: cDNA isolation, characterization and expression. Plant Mol Biol. 2001 Nov;47(5):581-93. PubMed PMID: 11725944.

3: Holm KA, Nielsen DM, Eriksen J. Automated colorimetric determination of recombinant fungal laccase activity in fermentation sarples using syringaldazine as chromogenic substrate. J Automat Chem. 1998;20(6):199-203. doi: 10.1155/S1463924698000261. PubMed PMID: 18924836; PubMed Central PMCID: PMC2548160.

4: Rajendiran N, Balasubramanian T. Dual fluorescence of syringaldazine. Spectrochim Acta A Mol Biomol Spectrosc. 2007 Nov;68(3):894-904. Epub 2007 Jan 13. PubMed PMID: 17317290.

5: Grison R, Pilet PE. Properties of syringaldazine oxidase/peroxidase in maize roots. J Plant Physiol. 1985 Mar;118(3):201-8. doi: 10.1016/S0176-1617(85)80221-2. Epub 2012 Jan 2. PubMed PMID: 23196004.

6: Harkin JM, Larsen MJ, Obst JR. Use of syringaldazine for detection of laccase in sporophores of wood rotting fungi. Mycologia. 1974 May-Jun;66(3):469-76. PubMed PMID: 4210374.

7: Michalak M, Kurel M, Jedraszko J, Toczydlowska D, Wittstock G, Opallo M, Nogala W. Voltammetric pH Nanosensor. Anal Chem. 2015 Dec 1;87(23):11641-5. doi: 10.1021/acs.analchem.5b03482. Epub 2015 Nov 10. PubMed PMID: 26516786.

8: Ike PT, Moreira AC, de Almeida FG, Ferreira D, Birolli WG, Porto AL, Souza DH. Functional characterization of a yellow laccase from Leucoagaricus gongylophorus. Springerplus. 2015 Oct 30;4:654. doi: 10.1186/s40064-015-1464-y. eCollection 2015. PubMed PMID: 26543788; PubMed Central PMCID: PMC4628026.

9: Li Q, Wang X, Korzhev M, Schröder HC, Link T, Tahir MN, Diehl-Seifert B, Müller WE. Potential biological role of laccase from the sponge Suberites domuncula as an antibacterial defense component. Biochim Biophys Acta. 2015 Jan;1850(1):118-28. doi: 10.1016/j.bbagen.2014.10.007. Epub 2014 Oct 16. PubMed PMID: 25459515.

10: Fernández-Fernández M, Sanromán MÁ, Moldes D. Recent developments and applications of immobilized laccase. Biotechnol Adv. 2013 Dec;31(8):1808-25. doi: 10.1016/j.biotechadv.2012.02.013. Epub 2012 Feb 28. Review. PubMed PMID: 22398306.

11: Prasetyo EN, Knes O, Nyanhongo GS, Guebitz GM. Developing SyrinOX total antioxidant capacity assay for measuring antioxidants in humans. Int J Exp Pathol. 2013 Feb;94(1):25-33. doi: 10.1111/iep.12001. Epub 2012 Nov 30. PubMed PMID: 23198957; PubMed Central PMCID: PMC3575870.

12: Ricklefs E, Winkler N, Koschorreck K, Urlacher VB. Expanding the laccase-toolbox: a laccase from Corynebacterium glutamicum with phenol coupling and cuprous oxidase activity. J Biotechnol. 2014 Dec 10;191:46-53. doi: 10.1016/j.jbiotec.2014.05.031. Epub 2014 Jun 6. PubMed PMID: 24910971.

13: Liu Y, Cusano AM, Wallace EC, Mekmouche Y, Ullah S, Robert V, Tron T. Characterization of C-terminally engineered laccases. Int J Biol Macromol. 2014 Aug;69:435-41. doi: 10.1016/j.ijbiomac.2014.05.053. Epub 2014 May 27. PubMed PMID: 24877646.

14: Nicolini C, Bruzzese D, Cambria MT, Bragazzi NL, Pechkova E. Recombinant laccase: I. Enzyme cloning and characterization. J Cell Biochem. 2013 Mar;114(3):599-605. doi: 10.1002/jcb.24397. PubMed PMID: 22991171.

15: Eichlerová I, Šnajdr J, Baldrian P. Laccase activity in soils: considerations for the measurement of enzyme activity. Chemosphere. 2012 Aug;88(10):1154-60. doi: 10.1016/j.chemosphere.2012.03.019. Epub 2012 Apr 2. PubMed PMID: 22475148.

16: Skoronski E, Fernandes M, Magalhães Mde L, da Silva GF, João JJ, Soares CH, Júnior AF. Substrate specificity and enzyme recycling using chitosan immobilized laccase. Molecules. 2014 Oct 17;19(10):16794-809. doi: 10.3390/molecules191016794. PubMed PMID: 25329872; PubMed Central PMCID: PMC6270992.

17: Jelali N, Donnini S, Dell'Orto M, Abdelly C, Gharsalli M, Zocchi G. Root antioxidant responses of two Pisum sativum cultivars to direct and induced Fe deficiency. Plant Biol (Stuttg). 2014 May;16(3):607-14. doi: 10.1111/plb.12093. Epub 2013 Aug 19. PubMed PMID: 23957505.

18: Shigeto J, Nagano M, Fujita K, Tsutsumi Y. Catalytic profile of Arabidopsis peroxidases, AtPrx-2, 25 and 71, contributing to stem lignification. PLoS One. 2014 Aug 19;9(8):e105332. doi: 10.1371/journal.pone.0105332. eCollection 2014. PubMed PMID: 25137070; PubMed Central PMCID: PMC4138150.

19: Kitajima S, Imamura T, Iibushi J, Ikenaga M, Tachibana Y, Andoh N, Oyabu H, Hirooka K, Shiina T, Ishizaki Y. Ferritin 2 domain-containing protein found in lacquer tree (Toxicodendron vernicifluum) sap has negative effects on laccase and peroxidase reactions. Biosci Biotechnol Biochem. 2017 Jun;81(6):1165-1175. doi: 10.1080/09168451.2017.1289814. Epub 2017 Feb 10. PubMed PMID: 28485213.

20: Kuznetsova YA, Romakh VB. Syringaldazine. New attractive electron donor of prostaglandin H synthase. Appl Biochem Biotechnol. 1996 Oct-Nov;61(1-2):205-9. PubMed PMID: 9100356.