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Merck
CN

36142

Malaoxon

PESTANAL®, analytical standard

Synonym(s):

Diethyl 2-[(dimethoxyphosphoryl)sulfanyl]succinate

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About This Item

Empirical Formula (Hill Notation):
C10H19O7PS
CAS Number:
1634-78-2
Molecular Weight:
314.29
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329755290
MDL number:
MFCD00055461
Beilstein/REAXYS Number:
1804523

Key Documents

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InChI

1S/C10H19O7PS/c1-5-16-9(11)7-8(10(12)17-6-2)19-18(13,14-3)15-4/h8H,5-7H2,1-4H3

SMILES string

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

InChI key

WSORODGWGUUOBO-UHFFFAOYSA-N

grade

analytical standard

product line

PESTANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

application(s)

agriculture
environmental

format

neat

storage temp.

2-8°C

Quality Level

100

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General description

Malaoxon is one of the major metabolites of malathion and a widely used insecticide in agriculture. Its mode of action includes DNA damage in human lymphocytes by the mechanism of oxidative action.

Application

Malaoxon may be used as a reference standard for the determination of malaoxon in plasma and urine samples of rat by high-performance liquid chromatography.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

Legal Information

PESTANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

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Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 2 - Carc. 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

>212.0 °F - closed cup

flash_point_c

> 100 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL8667
BCCK0635
BCCH6956
BCCF6826
BCCD0439

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Simultaneous determination of malathion, permethrin, DEET (N, N-diethyl-m-toluamide), and their metabolites in rat plasma and urine using high performance liquid chromatography.
Abu-Qare AW, et al.
Journal of Pharmaceutical and Biomedical Analysis, 26(2), 291-299 (2001)
Genotoxicity of Malaoxon: Induction of oxidized and methylated bases and protective effect of alpha-Tocopherol.
Blasiak J and Stankowska D
Pesticide Biochemistry and Physiology, 71(2), 88-96 (2001)
S Padilla et al.
Journal of toxicology and environmental health. Part A, 67(18), 1477-1489 (2004-09-17)
Some, but not all, organophosphorus pesticides are more acutely toxic to the young as compared to adults. We have developed an in vitro assay that measures the detoxification potential (via carboxylesterase and A-esterases) of tissues. Previous results using this in
Franca M Buratti et al.
Drug metabolism and disposition: the biological fate of chemicals, 33(3), 295-302 (2004-11-24)
Among organophosphorothioate (OPT) pesticides, malathion is considered relatively safe for use in mammals. Its rapid degradation by carboxylesterases competes with the cytochrome P450 (P450)-catalyzed formation of malaoxon, the toxic metabolite. However, impurities in commercial formulations are potent inhibitors of carboxylesterase
Olajire A Gbaye et al.
Pest management science, 68(9), 1265-1271 (2012-05-19)
Bruchid beetles, Callosobruchus species, are serious pests of economically important grain legumes; their activity in stores is often controlled by the use of synthetic insecticides. Esterases are known to be involved in insecticide resistance in insects. However, there is a
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