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MedKoo Cat#: 463203 | Name: Tridemorph

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tridemorph is a sterol biosynthetic inhibitor. It is a fungicide used to control Erysiphe graminis. It was developed by BASF in the 1960s who use the trade name Calixin. The World Health Organization has categorized it as a Class II "moderately hazardous" pesticide because it is believed harmful if swallowed and can cause irritation to skin and eyes.

Chemical Structure

Tridemorph
Tridemorph
CAS#24602-86-6

Theoretical Analysis

MedKoo Cat#: 463203

Name: Tridemorph

CAS#: 24602-86-6

Chemical Formula: C19H39NO

Exact Mass: 297.3032

Molecular Weight: 297.53

Elemental Analysis: C, 76.70; H, 13.21; N, 4.71; O, 5.38

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Synonym
Tridemorph; Kalinin; NSC 232676; NSC232676; NSC-232676; Kalixin; Calixine;
IUPAC/Chemical Name
2,6-dimethyl-4-tridecylmorpholine
InChi Key
YTOPFCCWCSOHFV-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H39NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-20-16-18(2)21-19(3)17-20/h18-19H,4-17H2,1-3H3
SMILES Code
CCCCCCCCCCCCCN1CC(OC(C1)C)C
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 297.53 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
1: Wang S, Sun H, Liu Y. Residual behavior and risk assessment of tridemorph in banana conditions. Food Chem. 2018 Apr 1;244:71-74. doi: 10.1016/j.foodchem.2017.09.124. Epub 2017 Sep 27. PMID: 29120807. 2: Ruan R, Wang M, Liu X, Sun X, Chung KR, Li H. Functional analysis of two sterol regulatory element binding proteins in Penicillium digitatum. PLoS One. 2017 May 3;12(5):e0176485. doi: 10.1371/journal.pone.0176485. PMID: 28467453; PMCID: PMC5415137. 3: Hernández A, Herrera-Palau R, Madroñal JM, Albi T, López-Lluch G, Perez- Castiñeira JR, Navas P, Valverde F, Serrano A. Vacuolar H(+)-Pyrophosphatase AVP1 is Involved in Amine Fungicide Tolerance in Arabidopsis thaliana and Provides Tridemorph Resistance in Yeast. Front Plant Sci. 2016 Feb 9;7:85. doi: 10.3389/fpls.2016.00085. PMID: 26904057; PMCID: PMC4746327. 4: Deng S, Wei T, Tan K, Hu M, Li F, Zhai Y, Ye S, Xiao Y, Hou L, Pei Y, Luo M. Phytosterol content and the campesterol:sitosterol ratio influence cotton fiber development: role of phytosterols in cell elongation. Sci China Life Sci. 2016 Feb;59(2):183-93. doi: 10.1007/s11427-015-4992-3. Epub 2016 Jan 23. PMID: 26803301. 5: Jia W, Chu X, Zhang F. Multiresidue pesticide analysis in nutraceuticals from green tea extracts by comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry. J Chromatogr A. 2015 May 22;1395:160-6. doi: 10.1016/j.chroma.2015.03.071. Epub 2015 Apr 1. PMID: 25865796. 6: Gilbert-López B, García-Reyes JF, Molina-Díaz A. Determination of fungicide residues in baby food by liquid chromatography-ion trap tandem mass spectrometry. Food Chem. 2012 Nov 15;135(2):780-6. doi: 10.1016/j.foodchem.2012.04.059. Epub 2012 May 2. PMID: 22868159. 7: Chen FP, Fan JR, Zhou T, Liu XL, Liu JL, Schnabel G. Baseline Sensitivity of Monilinia fructicola from China to the DMI Fungicide SYP-Z048 and Analysis of DMI-Resistant Mutants. Plant Dis. 2012 Mar;96(3):416-422. doi: 10.1094/PDIS-06-11-0495. PMID: 30727143. 8: Ebrahimi M, Es'haghi Z, Samadi F, Hosseini MS. Ionic liquid mediated sol-gel sorbents for hollow fiber solid-phase microextraction of pesticide residues in water and hair samples. J Chromatogr A. 2011 Nov 18;1218(46):8313-21. doi: 10.1016/j.chroma.2011.09.058. Epub 2011 Sep 29. PMID: 21993517. 9: Liu X, Fu J, Yun Y, Yin Y, Ma Z. A sterol C-14 reductase encoded by FgERG24B is responsible for the intrinsic resistance of Fusarium graminearum to amine fungicides. Microbiology (Reading). 2011 Jun;157(Pt 6):1665-1675. doi: 10.1099/mic.0.045690-0. Epub 2011 Mar 24. PMID: 21436218. 10: Karthika C, Muraleedharan NN. Contribution of leaf growth on the disappearance of fungicides used on tea under South Indian agroclimatic conditions. J Zhejiang Univ Sci B. 2009 Jun;10(6):422-6. doi: 10.1631/jzus.B0920026. PMID: 19489107; PMCID: PMC2689554. 11: Gilbert-López B, García-Reyes JF, Ortega-Barrales P, Molina-Díaz A, Fernández-Alba AR. Analyses of pesticide residues in fruit-based baby food by liquid chromatography/electrospray ionization time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(13):2059-71. doi: 10.1002/rcm.3062. PMID: 17551990. 12: Tian X, Jaber JJ, Rychnovsky SD. Synthesis and structure revision of calyxin natural products. J Org Chem. 2006 Apr 14;71(8):3176-83. doi: 10.1021/jo060094g. PMID: 16599616. 13: Hankins EG, Gillespie JR, Aikenhead K, Buckner FS. Upregulation of sterol C14-demethylase expression in Trypanosoma cruzi treated with sterol biosynthesis inhibitors. Mol Biochem Parasitol. 2005 Nov;144(1):68-75. doi: 10.1016/j.molbiopara.2005.08.002. PMID: 16165233. 14: Penagos H, Ruepert C, Partanen T, Wesseling C. Pesticide patch test series for the assessment of allergic contact dermatitis among banana plantation workers in panama. Dermatitis. 2004 Sep;15(3):137-45. doi: 10.2310/6620.2004.04014. PMID: 15724348. 15: Valachovic M, Wilcox LI, Sturley SL, Bard M. A mutation in sphingolipid synthesis suppresses defects in yeast ergosterol metabolism. Lipids. 2004 Aug;39(8):747-52. doi: 10.1007/s11745-004-1291-6. PMID: 15638242. 16: Zamora T, Pozo OJ, López FJ, Hernández F. Determination of tridemorph and other fungicide residues in fruit samples by liquid chromatography-electrospray tandem mass spectrometry. J Chromatogr A. 2004 Aug 6;1045(1-2):137-43. doi: 10.1016/j.chroma.2004.06.041. PMID: 15378888. 17: Matamoros D, Vanrolleghem PA. Pesticide assessment of the banana sector in an Ecuadorian watershed. Meded Rijksuniv Gent Fak Landbouwkd Toegep Biol Wet. 2001;66(2b):863-72. PMID: 12425113. 18: Nes WD, Zhou W, Dennis AL, Li H, Jia Z, Keith RA, Piser TM, Furlong ST. Purification, characterization and catalytic properties of human sterol 8-isomerase. Biochem J. 2002 Nov 1;367(Pt 3):587-99. doi: 10.1042/BJ20020551. PMID: 12133002; PMCID: PMC1222918. 19: Oros G, Ujváry I, Nachman RJ. Antimicrobial activity of o-carboranylalanine. Amino Acids. 1999;17(4):357-68. doi: 10.1007/BF01361661. PMID: 10707765. 20: Moebius FF, Reiter RJ, Bermoser K, Glossmann H, Cho SY, Paik YK. Pharmacological analysis of sterol delta8-delta7 isomerase proteins with [3H]ifenprodil. Mol Pharmacol. 1998 Sep;54(3):591-8. doi: 10.1124/mol.54.3.591. PMID: 9730919.