MedKoo Cat#: 146239 | Name: Coroxon

Description:

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

​Coroxon is the active metabolite of the organophosphate insecticide coumaphos, primarily used to control the Varroa destructor mite in beekeeping. It is formed when coumaphos undergoes activation via cytochrome P450 enzymes, resulting in a potent acetylcholinesterase inhibitor that disrupts neural function in the mite. In susceptible mites, coroxon is produced efficiently, leading to high toxicity; however, resistant mites exhibit reduced coroxon formation due to impaired P450 activation, significantly diminishing coumaphos efficacy . This mechanism underscores the importance of metabolic activation in determining the insecticidal potency of organophosphate compounds.​

Chemical Structure

Coroxon
Coroxon
CAS#321-54-0

Theoretical Analysis

MedKoo Cat#: 146239

Name: Coroxon

CAS#: 321-54-0

Chemical Formula: C14H16ClO6P

Exact Mass: 346.0373

Molecular Weight: 346.70

Elemental Analysis: C, 48.50; H, 4.65; Cl, 10.22; O, 27.69; P, 8.93

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.
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Related CAS #
No Data
Synonym
Coroxon;
IUPAC/Chemical Name
3-chloro-4-methyl-2-oxo-2H-chromen-7-yl diethyl phosphate
InChi Key
FDYMERLIFOUIRZ-UHFFFAOYSA-N
InChi Code
1S/C14H16ClO6P/c1-4-18-22(17,19-5-2)21-10-6-7-11-9(3)13(15)14(16)20-12(11)8-10/h6-8H,4-5H2,1-3H3
SMILES Code
CCOP(=O)(OCC)OC1=CC2=C(C=C1)C(C)=C(Cl)C(=O)O2
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

Preparing Stock Solutions

The following data is based on the product molecular weight 346.70 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: Santillan JY, Muzlera A, Molina M, Lewkowicz ES, Iribarren AM. Microbial degradation of organophosphorus pesticides using whole cells and enzyme extracts. Biodegradation. 2020 Dec;31(4-6):423-433. doi: 10.1007/s10532-020-09918-7. Epub 2020 Nov 7. PMID: 33159614. 2: Vlogiannitis S, Mavridis K, Dermauw W, Snoeck S, Katsavou E, Morou E, Harizanis P, Swevers L, Hemingway J, Feyereisen R, Van Leeuwen T, Vontas J. Reduced proinsecticide activation by cytochrome P450 confers coumaphos resistance in the major bee parasite Varroa destructor. Proc Natl Acad Sci U S A. 2021 Feb 9;118(6):e2020380118. doi: 10.1073/pnas.2020380118. PMID: 33547243; PMCID: PMC8017976. 3: Horne I, Harcourt RL, Sutherland TD, Russell RJ, Oakeshott JG. Isolation of a Pseudomonas monteilli strain with a novel phosphotriesterase. FEMS Microbiol Lett. 2002 Jan 2;206(1):51-5. doi: 10.1111/j.1574-6968.2002.tb10985.x. PMID: 11786256. 4: Gifkins MR, Jacobson RA. Crystal and molecular structure of organophosphorus insecticides. II. Coroxon. J Agric Food Chem. 1976 Mar-Apr;24(2):232-6. doi: 10.1021/jf60204a065. PMID: 1254802. 5: Stone BF, Nolan J, Schuntner CA. Biochemical genetics of resistance to organophosphorus acaricides in three strains of the cattle tick, Boophilus microplus. Aust J Biol Sci. 1976 Jul;29(3):265-79. doi: 10.1071/bi9760265. PMID: 985226. 6: Horne I, Sutherland TD, Oakeshott JG, Russell RJ. Cloning and expression of the phosphotriesterase gene hocA from Pseudomonas monteilii C11. Microbiology (Reading). 2002 Sep;148(Pt 9):2687-2695. doi: 10.1099/00221287-148-9-2687. PMID: 12213915. 7: Temeyer KB, Schlechte KG, Gross AD, Lohmeyer KH. Identification, Baculoviral Expression, and Biochemical Characterization of a Novel Cholinesterase of Amblyomma americanum (Acari: Ixodidae). Int J Mol Sci. 2023 Apr 22;24(9):7681. doi: 10.3390/ijms24097681. PMID: 37175388; PMCID: PMC10178864. 8: Temeyer KB, Chen AC. Acetylcholinesterase of Stomoxys calcitrans (L.) (Diptera: Muscidae): cDNA sequence, baculovirus expression, and biochemical properties. Vet Parasitol. 2012 Feb 28;184(1):92-5. doi: 10.1016/j.vetpar.2011.08.007. Epub 2011 Aug 10. PMID: 21872994. 9: Santillan JY, Rojas NL, Ghiringhelli PD, Nóbile ML, Lewkowicz ES, Iribarren AM. Organophosphorus compounds biodegradation by novel bacterial isolates and their potential application in bioremediation of contaminated water. Bioresour Technol. 2020 Dec;317:124003. doi: 10.1016/j.biortech.2020.124003. Epub 2020 Aug 11. PMID: 32810733. 10: Horne I, Sutherland TD, Harcourt RL, Russell RJ, Oakeshott JG. Identification of an opd (organophosphate degradation) gene in an Agrobacterium isolate. Appl Environ Microbiol. 2002 Jul;68(7):3371-6. doi: 10.1128/AEM.68.7.3371-3376.2002. PMID: 12089017; PMCID: PMC126808. 11: Zakrevsky JG, Mallet VN. Determination of coumaphos and its oxygen analog in eggs by in situ fluorometry. J Assoc Off Anal Chem. 1975 May;58(3):554-6. PMID: 1141186. 12: Wright FC, Ahrens EH. Effect of selection pressure on the cholinesterase of Boophilus microplus (Acari: Ixodidae) resistant to coumaphos. J Econ Entomol. 1989 Apr;82(2):524-9. doi: 10.1093/jee/82.2.524. PMID: 2708629. 13: Miller RJ, Li AY, Tijerina M, Davey RB, George JE. Differential response to diazinon and coumaphos in a strain of Boophilus microplus (Acari: Ixodidae) collected in Mexico. J Med Entomol. 2008 Sep;45(5):905-11. doi: 10.1603/0022-2585(2008)45[905:drtdac]2.0.co;2. PMID: 18826034. 14: Mackness MI, Walker CH. Multiple forms of sheep serum A-esterase activity associated with the high-density lipoprotein. Biochem J. 1988 Mar 1;250(2):539-45. doi: 10.1042/bj2500539. PMID: 2451511; PMCID: PMC1148889.