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MedKoo Cat#: 526501 | Name: Triadimenol
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Description:

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

Triadimenol is a flammable white to gray solid with phenolartigem odor which is practically insoluble in water. It decomposes when heated above 150 ° C. The compound is present in several isomeric front forms, the technical product to 78 to 88% of the diastereoisomer A is (RS + SR). The compound is stable to hydrolysis at pH values ​​of 4, 7 and 9 and is subject to a small extent of photolysis. Triadimenol is a systemic fungicide with a broad spectrum. It inhibits the ergosterol - and gibberellin - biosynthesis , and thus the rate of cell division.

Chemical Structure

Triadimenol
Triadimenol
CAS#55219-65-3

Theoretical Analysis

MedKoo Cat#: 526501

Name: Triadimenol

CAS#: 55219-65-3

Chemical Formula: C14H18ClN3O2

Exact Mass: 295.1088

Molecular Weight: 295.77

Elemental Analysis: C, 56.85; H, 6.13; Cl, 11.99; N, 14.21; O, 10.82

Price and Availability

Size Price Availability Quantity
2g USD 150.00
5g USD 250.00
10g USD 450.00
25g USD 750.00
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Related CAS #
No Data
Synonym
UK 199; UK-199; UK199; Triadimenol; Baytan; Spinnaker; Summit
IUPAC/Chemical Name
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
InChi Key
BAZVSMNPJJMILC-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H18ClN3O2/c1-14(2,3)12(19)13(18-9-16-8-17-18)20-11-6-4-10(15)5-7-11/h4-9,12-13,19H,1-3H3
SMILES Code
CC(C)(C)C(O)C(OC1=CC=C(Cl)C=C1)N2N=CN=C2
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, not in water
Shelf Life
>2 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 295.77 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: Chu SH, Liao PH, Chen PJ. Developmental exposures to an azole fungicide triadimenol at environmentally relevant concentrations cause reproductive dysfunction in females of medaka fish. Chemosphere. 2016 Jun;152:181-9. doi: 10.1016/j.chemosphere.2016.02.078. Epub 2016 Mar 9. PubMed PMID: 26971170. 2: Yao Z, Li X, Miao Y, Lin M, Xu M, Wang Q, Zhang H. Simultaneous enantioselective determination of triadimefon and its metabolite triadimenol in edible vegetable oil by gel permeation chromatography and ultraperformance convergence chromatography/tandem mass spectrometry. Anal Bioanal Chem. 2015 Nov;407(29):8849-59. doi: 10.1007/s00216-015-9046-y. Epub 2015 Sep 28. PubMed PMID: 26416018. 3: Wang Y, Yu D, Xu P, Guo B, Zhang Y, Li J, Wang H. Stereoselective metabolism, distribution, and bioaccumulation brof triadimefon and triadimenol in lizards. Ecotoxicol Environ Saf. 2014 Sep;107:276-83. doi: 10.1016/j.ecoenv.2014.06.021. Epub 2014 Jul 8. PubMed PMID: 25011125. 4: Li W, Zhao L, Zhang H, Chen X, Chen S, Zhu Z, Hong Z, Chai Y. Enantioseparation of new triadimenol antifungal active compounds by electrokinetic chromatography and molecular modeling study of chiral recognition mechanisms. Electrophoresis. 2014 Oct;35(19):2855-62. doi: 10.1002/elps.201300607. Epub 2014 Mar 26. PubMed PMID: 24615979. 5: Li Y, Dong F, Liu X, Xu J, Han Y, Zheng Y. Chiral fungicide triadimefon and triadimenol: Stereoselective transformation in greenhouse crops and soil, and toxicity to Daphnia magna. J Hazard Mater. 2014 Jan 30;265:115-23. doi: 10.1016/j.jhazmat.2013.11.055. Epub 2013 Dec 1. PubMed PMID: 24342051. 6: Liang H, Li L, Qiu J, Li W, Yang S, Zhou Z, Qiu L. Stereoselective transformation of triadimefon to metabolite triadimenol in wheat and soil under field conditions. J Hazard Mater. 2013 Sep 15;260:929-36. doi: 10.1016/j.jhazmat.2013.06.046. Epub 2013 Jun 27. PubMed PMID: 23876258. 7: Li Z, Li Q, Zhao J, Wang W. Stereoselective degradation and microbial epimerization of triadimenol in soils. Chirality. 2013 Jun;25(6):355-60. doi: 10.1002/chir.22175. Epub 2013 May 9. PubMed PMID: 23661341. 8: Zhang Y, Zhang G, Fu P, Ma Y, Zhou J. Study on the interaction of triadimenol with calf thymus DNA by multispectroscopic methods and molecular modeling. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Oct;96:1012-9. doi: 10.1016/j.saa.2012.08.002. Epub 2012 Aug 16. PubMed PMID: 22944149. 9: Li W, Tan G, Zhao L, Chen X, Zhang X, Zhu Z, Chai Y. Computer-aided molecular modeling study of enantioseparation of iodiconazole and structurally related triadimenol analogues by capillary electrophoresis: chiral recognition mechanism and mathematical model for predicting chiral separation. Anal Chim Acta. 2012 Mar 9;718:138-47. doi: 10.1016/j.aca.2012.01.007. Epub 2012 Jan 12. PubMed PMID: 22305909. 10: Liang H, Qiu J, Li L, Li W, Zhou Z, Liu F, Qiu L. Stereoselective separation and determination of triadimefon and triadimenol in wheat, straw, and soil by liquid chromatography-tandem mass spectrometry. J Sep Sci. 2012 Jan;35(1):166-73. doi: 10.1002/jssc.201100365. Epub 2011 Nov 21. PubMed PMID: 22102610. 11: Crowell SR, Henderson WM, Kenneke JF, Fisher JW. Development and application of a physiologically based pharmacokinetic model for triadimefon and its metabolite triadimenol in rats and humans. Toxicol Lett. 2011 Aug 28;205(2):154-62. doi: 10.1016/j.toxlet.2011.05.1036. Epub 2011 May 27. PubMed PMID: 21641977. 12: Garrison AW, Avants JK, Jones WJ. Microbial transformation of triadimefon to triadimenol in soils: selective production rates of triadimenol stereoisomers affect exposure and risk. Environ Sci Technol. 2011 Mar 15;45(6):2186-93. doi: 10.1021/es103430s. Epub 2011 Feb 22. PubMed PMID: 21341686. 13: Zhang G, Sun Q, Hou Y, Hong Z, Zhang J, Zhao L, Zhang H, Chai Y. New mathematic model for predicting chiral separation using molecular docking: mechanism of chiral recognition of triadimenol analogues. J Sep Sci. 2009 Jul;32(14):2401-7. doi: 10.1002/jssc.200900012. PubMed PMID: 19557809. 14: Dong F, Liu X, Zheng Y, Cao Q, Li C. Stereoselective degradation of fungicide triadimenol in cucumber plants. Chirality. 2010 Feb;22(2):292-8. doi: 10.1002/chir.20715. PubMed PMID: 19496157. 15: Shen W, Lin H, Zhao Z, Ding T, Xu J, Shen C. [Determination of triadimenol residue in foods with dispersive solid phase extraction cleanup by gas chromatography-negative chemical ionization mass spectrometry]. Se Pu. 2008 Jul;26(4):515-8. Chinese. PubMed PMID: 18959253. 16: Kenneke JF, Mazur CS, Ritger SE, Sack TJ. Mechanistic investigation of the noncytochrome P450-mediated metabolism of triadimefon to triadimenol in hepatic microsomes. Chem Res Toxicol. 2008 Oct;21(10):1997-2004. doi: 10.1021/tx800211t. Epub 2008 Sep 3. PubMed PMID: 18763812. 17: Du F, Luo X, Jiang G, Hou S, Liu G, Ren L, Zhang L, Huang Q, Jie N. Determination of triadimenol based on the quenching effect on resonance light scattering from the triadimenol-deoxyribonucleic acid-hydrochloric acid system. Anal Bioanal Chem. 2007 May;388(2):489-93. Epub 2007 Mar 22. PubMed PMID: 17377777. 18: Groppelli S, Pennati R, De Bernardi F, Menegola E, Giavini E, Sotgia C. Teratogenic effects of two antifungal triazoles, triadimefon and triadimenol, on Xenopus laevis development: craniofacial defects. Aquat Toxicol. 2005 Jul 30;73(4):370-81. PubMed PMID: 15992940. 19: Jie N, Hou S, Du F, Zhang C, Qin G. The determination of deoxyribonucleic acids with triadimenol based on the enhancement of resonance light scattering. Nucleosides Nucleotides Nucleic Acids. 2004;23(4):725-34. PubMed PMID: 15200034. 20: Iesce MR, Graziano ML, Cermola F, Montella S, di Gioia L, Stasio C. Effects of sensitizers on the photodegradation of the systemic fungicide triadimenol. Chemosphere. 2003 Apr;51(2):163-6. PubMed PMID: 12586149.