Isomalathion | CAS#3344-12-5 | insecticide

MedKoo Cat#: 146153 | Name: Isomalathion

Description:

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

Isomalathion is a synthetic organophosphate insecticide that functions by inhibiting the enzyme acetylcholinesterase, which is crucial for nerve function. By blocking the breakdown of acetylcholine at nerve synapses, it leads to continuous nerve signal transmission, resulting in paralysis and death of the target pest. Isomalathion is primarily used in agriculture to control a variety of insect pests on crops. Its mechanism of action makes it effective in pest management, although its toxicity to humans and animals requires careful handling and use.

Chemical Structure

Isomalathion

CAS#3344-12-5

Theoretical Analysis

MedKoo Cat#: 146153

Name: Isomalathion

CAS#: 3344-12-5

Chemical Formula: C10H19O6PS2

Exact Mass: 330.0361

Molecular Weight: 330.35

Elemental Analysis: C, 36.36; H, 5.80; O, 29.06; P, 9.38; S, 19.41

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Isomalathion;

IUPAC/Chemical Name

diethyl 2-((methoxy(methylthio)phosphoryl)thio)succinate

InChi Key

LPQDGVLVYVULMX-UHFFFAOYSA-N

InChi Code

1S/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(13,14-3)18-4/h8H,5-7H2,1-4H3

SMILES Code

CCOC(=O)CC(SP(=O)(OC)SC)C(=O)OCC

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 330.35 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.

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: Josse R, Sharanek A, Savary CC, Guillouzo A. Impact of isomalathion on malathion cytotoxicity and genotoxicity in human HepaRG cells. Chem Biol Interact. 2014 Feb 25;209:68-76. doi: 10.1016/j.cbi.2013.12.002. Epub 2013 Dec 12. PMID: 24333466. 2: Berkman CE, Quinn DA, Thompson CM. Interaction of acetylcholinesterase with the enantiomers of malaoxon and isomalathion. Chem Res Toxicol. 1993 Sep- Oct;6(5):724-30. doi: 10.1021/tx00035a019. PMID: 8292752. 3: Sun JQ, Tao NE, Zhang AP, Qi H. Effects of cyclodextrin on the stereoselectivity inhibition of acetylcholinesterase by isomalathion. J Environ Sci Health B. 2018;53(9):580-586. doi: 10.1080/03601234.2018.1473963. Epub 2018 May 29. PMID: 29842826. 4: Doorn JA, Talley TT, Thompson CM, Richardson RJ. Probing the active sites of butyrylcholinesterase and cholesterol esterase with isomalathion: conserved stereoselective inactivation of serine hydrolases structurally related to acetylcholinesterase. Chem Res Toxicol. 2001 Jul;14(7):807-13. doi: 10.1021/tx015501s. PMID: 11453726. 5: Doorn JA, Thompson CM, Christner RB, Richardson RJ. Stereoselective inactivation of Torpedo californica acetylcholinesterase by isomalathion: inhibitory reactions with (1R)- and (1S)-isomers proceed by different mechanisms. Chem Res Toxicol. 2003 Aug;16(8):958-65. doi: 10.1021/tx030026e. PMID: 12924923. 6: Jianmongkol S, Marable BR, Berkman CE, Talley TT, Thompson CM, Richardson RJ. Kinetic evidence for different mechanisms of acetylcholinesterase inhibition by (1R)- and (1S)-stereoisomers of isomalathion. Toxicol Appl Pharmacol. 1999 Feb 15;155(1):43-53. doi: 10.1006/taap.1998.8608. PMID: 10036217. 7: Zhang A, Sun J, Lin C, Hu X, Liu W. Enantioselective interaction of acid α-naphthyl acetate esterase with chiral organophosphorus insecticides. J Agric Food Chem. 2014 Feb 19;62(7):1477-81. doi: 10.1021/jf404959v. Epub 2014 Feb 5. PMID: 24475784. 8: Bavcon Kralj M, Cernigoj U, Franko M, Trebse P. Comparison of photocatalysis and photolysis of malathion, isomalathion, malaoxon, and commercial malathion-- products and toxicity studies. Water Res. 2007 Nov;41(19):4504-14. doi: 10.1016/j.watres.2007.06.016. Epub 2007 Jun 15. PMID: 17624398. 9: Berkman CE, Ryu S, Quinn DA, Thompson CM. Kinetics of the postinhibitory reactions of acetylcholinesterase poisoned by chiral isomalathion: a surprising nonreactivation induced by the RP stereoisomers. Chem Res Toxicol. 1993 Jan- Feb;6(1):28-32. doi: 10.1021/tx00031a004. PMID: 8448346. 10: Berkman CE, Thompson CM, Perrin SR. Synthesis, absolute configuration, and analysis of malathion, malaoxon, and isomalathion enantiomers. Chem Res Toxicol. 1993 Sep-Oct;6(5):718-23. doi: 10.1021/tx00035a018. Erratum in: Chem Res Toxicol 1994 Mar-Apr;7(2):275. PMID: 8292751. 11: Zhang A, Lai W, Sun J, Hu G, Liu W. Probing the chiral separation mechanism and the absolute configuration of malathion, malaoxon and isomalathion enantiomers by chiral high performance liquid chromatography coupled with chiral detector-binding energy computations. J Chromatogr A. 2013 Mar 15;1281:26-31. doi: 10.1016/j.chroma.2013.01.016. Epub 2013 Jan 18. PMID: 23398995. 12: Błasiak J, Jałoszynski P, Trzeciak A, Szyfter K. In vitro studies on the genotoxicity of the organophosphorus insecticide malathion and its two analogues. Mutat Res. 1999 Sep 30;445(2):275-83. doi: 10.1016/s1383-5718(99)00132-1. PMID: 10575436. 13: Jianmongkol S, Berkman CE, Thompson CM, Richardson RJ. Relative potencies of the four stereoisomers of isomalathion for inhibition of hen brain acetylcholinesterase and neurotoxic esterase in vitro. Toxicol Appl Pharmacol. 1996 Aug;139(2):342-8. doi: 10.1006/taap.1996.0174. PMID: 8806851. 14: Bastos PL, Bastos AFTL, Gurgel ADM, Gurgel IGD. Carcinogenicity and mutagenicity of malathion and its two analogues: a systematic review. Cien Saude Colet. 2020 Aug 5;25(8):3273-3298. Portuguese, English. doi: 10.1590/1413-81232020258.10672018. PMID: 32785560. 15: Doorn JA, Schall M, Gage DA, Talley TT, Thompson CM, Richardson RJ. Identification of butyrylcholinesterase adducts after inhibition with isomalathion using mass spectrometry: difference in mechanism between (1R)- and (1S)-stereoisomers. Toxicol Appl Pharmacol. 2001 Oct 15;176(2):73-80. doi: 10.1006/taap.2001.9279. PMID: 11601883. 16: Doorn JA, Gage DA, Schall M, Talley TT, Thompson CM, Richardson RJ. Inhibition of acetylcholinesterase by (1S,3S)-isomalathion proceeds with loss of thiomethyl: kinetic and mass spectral evidence for an unexpected primary leaving group. Chem Res Toxicol. 2000 Dec;13(12):1313-20. doi: 10.1021/tx000184v. PMID: 11123973. 17: Li H, Schopfer LM, Nachon F, Froment MT, Masson P, Lockridge O. Aging pathways for organophosphate-inhibited human butyrylcholinesterase, including novel pathways for isomalathion, resolved by mass spectrometry. Toxicol Sci. 2007 Nov;100(1):136-45. doi: 10.1093/toxsci/kfm215. Epub 2007 Aug 13. PMID: 17698511. 18: Buratti FM, Testai E. Malathion detoxification by human hepatic carboxylesterases and its inhibition by isomalathion and other pesticides. J Biochem Mol Toxicol. 2005;19(6):406-14. doi: 10.1002/jbt.20106. PMID: 16421896. 19: Aldridge WN, Miles JW, Mount DL, Verschoyle RD. The toxicological properties of impurities in malathion. Arch Toxicol. 1979 Jun 8;42(2):95-106. doi: 10.1007/BF00316489. PMID: 755464. 20: Reiner E, Radić Z. An enzyme test for determining isomalathion impurities in water-dispersible powders of malathion. Bull World Health Organ. 1986;64(3):397-401. PMID: 3490319; PMCID: PMC2490876.