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MedKoo Cat#: 596287 | Name: Ioxynil

Description:

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

Ioxynil is a herbicide. Ioxynil is a plant protection active substance and a chemical compound from the group of substituted phenols, nitriles and organic iodine compounds .

Chemical Structure

Ioxynil
Ioxynil
CAS#1689-83-4

Theoretical Analysis

MedKoo Cat#: 596287

Name: Ioxynil

CAS#: 1689-83-4

Chemical Formula: C7H3I2NO

Exact Mass: 370.8304

Molecular Weight: 370.92

Elemental Analysis: C, 22.67; H, 0.82; I, 68.43; N, 3.78; O, 4.31

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Synonym
Ioxynil; Bantrol; Iotox; Trevespan; BRN 2364041; CA 69-15;
IUPAC/Chemical Name
4-hydroxy-3,5-diiodobenzonitrile
InChi Key
NRXQIUSYPAHGNM-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H3I2NO/c8-5-1-4(3-10)2-6(9)7(5)11/h1-2,11H
SMILES Code
N#CC1=CC(I)=C(O)C(I)=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
>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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Ioxynil is a herbicide.
In vitro activity:
TBD
In vivo activity:
Exposure of zebrafish embryos to IOX (ioxynil) and DES (0.1 μM) increased heart beat frequency and reduced ventricle volume and aorta diameter. The transcriptome of endothelial cells from blood vessels of hypertrophic, dilated and arrhythmogenic right ventricular cardiomyopathy was significantly changed and compound-specific toxic effects were found in IOX and DES exposed embryos. Both DES and IOX directly affected vascular and heart development and this indirectly impaired thyroid gland development in zebrafish. Reference: Environ Int. 2019 Mar;124:511-520. https://pubmed.ncbi.nlm.nih.gov/30685453/

Preparing Stock Solutions

The following data is based on the product molecular weight 370.92 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
Formulation protocol:
1. Li YF, Canário AVM, Power DM, Campinho MA. Ioxynil and diethylstilbestrol disrupt vascular and heart development in zebrafish. Environ Int. 2019 Mar;124:511-520. doi: 10.1016/j.envint.2019.01.009. Epub 2019 Jan 25. PMID: 30685453.
In vitro protocol:
TBD
In vivo protocol:
1. Li YF, Canário AVM, Power DM, Campinho MA. Ioxynil and diethylstilbestrol disrupt vascular and heart development in zebrafish. Environ Int. 2019 Mar;124:511-520. doi: 10.1016/j.envint.2019.01.009. Epub 2019 Jan 25. PMID: 30685453.
1: Vicario N, Calabrese G, Zappalà A, Parenti C, Forte S, Graziano ACE, Vanella L, Pellitteri R, Cardile V, Parenti R. Inhibition of Cx43 mediates protective effects on hypoxic/reoxygenated human neuroblastoma cells. J Cell Mol Med. 2017 Oct;21(10):2563-2572. doi: 10.1111/jcmm.13177. Epub 2017 May 9. PubMed PMID: 28488330; PubMed Central PMCID: PMC5618696. 2: Guibal R, Buzier R, Charriau A, Lissalde S, Guibaud G. Passive sampling of anionic pesticides using the Diffusive Gradients in Thin films technique (DGT). Anal Chim Acta. 2017 May 8;966:1-10. doi: 10.1016/j.aca.2017.02.007. Epub 2017 Feb 20. PubMed PMID: 28372722. 3: Yotsova EK, Stefanov MA, Dobrikova AG, Apostolova EL. Different sensitivities of photosystem II in green algae and cyanobacteria to phenylurea and phenol-type herbicides: effect on electron donor side. Z Naturforsch C. 2017 Jul 14;72(7-8):315-324. doi: 10.1515/znc-2016-0089. PubMed PMID: 28258977. 4: Halwachs S, Schäfer I, Kneuer C, Seibel P, Honscha W. Assessment of ABCG2-mediated transport of pesticides across the rabbit placenta barrier using a novel MDCKII in vitro model. Toxicol Appl Pharmacol. 2016 Aug 15;305:66-74. doi: 10.1016/j.taap.2016.06.007. Epub 2016 Jun 8. PubMed PMID: 27288731. 5: Bettiol C, De Vettori S, Minervini G, Zuccon E, Marchetto D, Ghirardini AV, Argese E. Assessment of phenolic herbicide toxicity and mode of action by different assays. Environ Sci Pollut Res Int. 2016 Apr;23(8):7398-408. doi: 10.1007/s11356-015-5958-5. Epub 2015 Dec 23. PubMed PMID: 26695414. 6: Lovecka P, Thimova M, Grznarova P, Lipov J, Knejzlik Z, Stiborova H, Nindhia TG, Demnerova K, Ruml T. Study of Cytotoxic Effects of Benzonitrile Pesticides. Biomed Res Int. 2015;2015:381264. doi: 10.1155/2015/381264. Epub 2015 Aug 3. PubMed PMID: 26339609; PubMed Central PMCID: PMC4538370. 7: Raeppel C, Fabritius M, Nief M, Appenzeller BM, Briand O, Tuduri L, Millet M. Analysis of airborne pesticides from different chemical classes adsorbed on Radiello® Tenax® passive tubes by thermal-desorption-GC/MS. Environ Sci Pollut Res Int. 2015 Feb;22(4):2726-34. doi: 10.1007/s11356-014-3534-z. Epub 2014 Sep 11. PubMed PMID: 25205153. 8: Otsuka S, Ishihara A, Yamauchi K. Ioxynil and tetrabromobisphenol A suppress thyroid-hormone-induced activation of transcriptional elongation mediated by histone modifications and RNA polymerase II phosphorylation. Toxicol Sci. 2014 Apr;138(2):290-9. doi: 10.1093/toxsci/kfu012. Epub 2014 Jan 21. PubMed PMID: 24449421. 9: Frková Z, Badawi N, Johansen A, Schultz-Jensen N, Bester K, Sørensen SR, Karlson UG. Degradation of three benzonitrile herbicides by Aminobacter MSH1 versus soil microbial communities: pathways and kinetics. Pest Manag Sci. 2014 Aug;70(8):1291-8. doi: 10.1002/ps.3697. Epub 2014 Jan 13. PubMed PMID: 24302680. 10: Campinho MA, Power DM. Waterborne exposure of zebrafish embryos to micromole concentrations of ioxynil and diethylstilbestrol disrupts thyrocyte development. Aquat Toxicol. 2013 Sep 15;140-141:279-87. doi: 10.1016/j.aquatox.2013.06.014. Epub 2013 Jun 22. PubMed PMID: 23851054. 11: Detzel C, Maas R, Tubeleviciute A, Jose J. Autodisplay of nitrilase from Klebsiella pneumoniae and whole-cell degradation of oxynil herbicides and related compounds. Appl Microbiol Biotechnol. 2013 Jun;97(11):4887-96. doi: 10.1007/s00253-012-4401-9. Epub 2012 Sep 18. PubMed PMID: 22987202. 12: Veselá AB, Pelantová H, Sulc M, Macková M, Lovecká P, Thimová M, Pasquarelli F, Pičmanová M, Pátek M, Bhalla TC, Martínková L. Biotransformation of benzonitrile herbicides via the nitrile hydratase-amidase pathway in rhodococci. J Ind Microbiol Biotechnol. 2012 Dec;39(12):1811-9. doi: 10.1007/s10295-012-1184-z. Epub 2012 Aug 26. PubMed PMID: 22922990. 13: Akiyoshi S, Sai G, Yamauchi K. Species-dependent effects of the phenolic herbicide ioxynil with potential thyroid hormone disrupting activity: modulation of its cellular uptake and activity by interaction with serum thyroid hormone-binding proteins. J Environ Sci (China). 2012;24(5):949-55. PubMed PMID: 22893975. 14: Hu JY, Dong BZ, Zhen ZH. Residue determination and dissipation of ioxynil octanoate in maize and soil. J Environ Sci Health B. 2012;47(5):385-9. doi: 10.1080/03601234.2012.648533. PubMed PMID: 22424062. 15: Raeppel C, Nief M, Fabritius M, Racault L, Appenzeller BM, Millet M. Simultaneous analysis of pesticides from different chemical classes by using a derivatisation step and gas chromatography-mass spectrometry. J Chromatogr A. 2011 Nov 4;1218(44):8123-9. doi: 10.1016/j.chroma.2011.08.098. Epub 2011 Sep 10. PubMed PMID: 21962330. 16: Budai P, Lehel J, Tavaszi J, Kormos E. HET-CAM test for determining the possible eye irritancy of pesticides. Acta Vet Hung. 2010 Sep;58(3):369-77. doi: 10.1556/AVet.58.2010.3.9. PubMed PMID: 20713327. 17: Takahashi R, Hasegawa K, Takano A, Noguchi T. Structures and binding sites of phenolic herbicides in the Q(B) pocket of photosystem II. Biochemistry. 2010 Jul 6;49(26):5445-54. doi: 10.1021/bi100639q. PubMed PMID: 20518513. 18: Leithe E, Kjenseth A, Bruun J, Sirnes S, Rivedal E. Inhibition of connexin 43 gap junction channels by the endocrine disruptor ioxynil. Toxicol Appl Pharmacol. 2010 Aug 15;247(1):10-7. doi: 10.1016/j.taap.2010.05.006. Epub 2010 May 25. PubMed PMID: 20510257. 19: Veselá AB, Franc M, Pelantová H, Kubác D, Vejvoda V, Sulc M, Bhalla TC, Macková M, Lovecká P, Janů P, Demnerová K, Martínková L. Hydrolysis of benzonitrile herbicides by soil actinobacteria and metabolite toxicity. Biodegradation. 2010 Sep;21(5):761-70. doi: 10.1007/s10532-010-9341-4. Epub 2010 Mar 4. Erratum in: Biodegradation. 2011 Nov;22(6):1255. PubMed PMID: 20204468. 20: Shimmen T. Unique cellular effect of the herbicide bromoxynil revealed by electrophysiological studies using characean cells. J Plant Res. 2010 Sep;123(5):715-22. doi: 10.1007/s10265-009-0297-6. Epub 2010 Jan 23. PubMed PMID: 20094899.