Malaoxon

Structural formula
General
Surname	Malaoxon
other names	Diethyl 2 - [(dimethoxyphosphoryl) thio] succinate; Liromat; Malathion oxon;
Molecular formula	C 10 H 19 O 7 PS
Brief description	light yellow liquid
External identifiers / databases
EC number	634-923-0
ECHA InfoCard	100.162.859
PubChem	15415
ChemSpider	14674
Wikidata	Q3270235
properties
Molar mass	314.29 g · mol -1
Physical state	liquid
density	1.231 g cm −3 (at 20 ° C)
Melting point	<20 ° C
boiling point	114 ° C
safety instructions
H and P phrases	H: 301-310-351-411
	P: 201-262-273-280-301 + 310 + 330-302 + 352 + 310
Toxicological data	158 mg kg −1 ( LD 50 , rat , oral ) ; 119 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Malaoxon is a chemical compound from the group of thiophosphoric acid esters . It is a breakdown product of the dithiophosphoric acid ester malathion .

Emergence

Malaoxon is produced by oxidative desulfurization of malathion. This can be done by mixed-functional oxygenases (for example cytochrome P450 ) in mammals and insects , peroxidases in plants, or photooxidatively by sunlight.

toxicology

As with all phosphoric acid esters, the effect of Malaoxon is based on the irreversible inhibition of the enzyme acetylcholinesterase . This has the effect that the transmission of stimuli to the central nervous system is impaired, which can lead to paralysis, respiratory failure and ultimately death.

The effects of malathion and malaoxon are very dependent on the organism. This selectivity is based on the different enzyme equipment of mammals and insects. While in the former malathion is only converted very slowly into the more toxic malaoxon, this happens much faster in insects. The detoxification of the malaoxon can take place very quickly in mammals, but only very slowly in insects. This is sufficient for an insecticidal effect, while malathion is comparatively less toxic to mammals.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ data sheet Malaoxon at Sigma-Aldrich , accessed on October 01, 2019 ( PDF ).
^ Sigmund F. Zakrzewski: Environmental Toxicology . Oxford University Press, 2002, ISBN 978-0-19-803376-9 ( limited preview in Google Book Search [accessed October 2, 2019]).
↑ Entry on malathion in the GESTIS substance database of the IFA , accessed on October 2nd, 2019(JavaScript required) .
^ National Cancer Institute Carcinogenesis Technical Report Series . United States Department of Health, Education, and Welfare, Public Health Service, National Institutes of Health, 1979 ( limited preview in Google Book Search [accessed October 2, 2019]).
↑ Brown, Thomas M .: Principles of Toxicology. 3rd ed. CRC Press, Bosa Roca 2015, ISBN 978-1-4665-0343-4 ( limited preview in Google Book Search [accessed October 21, 2019]).
^ Adrien Albert: The Selectivity of Drugs . Springer Science & Business Media, 2012, ISBN 978-94-009-5734-3 ( limited preview in Google Book Search [accessed October 2, 2019]).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ data sheet Malaoxon at Sigma-Aldrich , accessed on October 01, 2019 ( PDF ).

[2] Sigmund F. Zakrzewski: Environmental Toxicology . Oxford University Press, 2002, ISBN 978-0-19-803376-9 ( limited preview in Google Book Search [accessed October 2, 2019]).

[GESTIS-3] Entry on malathion in the GESTIS substance database of the IFA , accessed on October 2nd, 2019(JavaScript required) .

[4] National Cancer Institute Carcinogenesis Technical Report Series . United States Department of Health, Education, and Welfare, Public Health Service, National Institutes of Health, 1979 ( limited preview in Google Book Search [accessed October 2, 2019]).

[5] Brown, Thomas M .: Principles of Toxicology. 3rd ed. CRC Press, Bosa Roca 2015, ISBN 978-1-4665-0343-4 ( limited preview in Google Book Search [accessed October 21, 2019]).

[6] Adrien Albert: The Selectivity of Drugs . Springer Science & Business Media, 2012, ISBN 978-94-009-5734-3 ( limited preview in Google Book Search [accessed October 2, 2019]).