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121-75-5 molecular structure
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1,4-diethyl 2-{[dimethoxy(sulfanylidene)-$l^{5}-phosphanyl]sulfanyl}butanedioate

ChemBase ID: 652
Molecular Formular: C10H19O6PS2
Molecular Mass: 330.358021
Monoisotopic Mass: 330.03606696
SMILES and InChIs

SMILES:
S(P(=S)(OC)OC)C(CC(=O)OCC)C(=O)OCC
Canonical SMILES:
CCOC(=O)CC(C(=O)OCC)SP(=S)(OC)OC
InChI:
InChI=1S/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(18,13-3)14-4/h8H,5-7H2,1-4H3
InChIKey:
JXSJBGJIGXNWCI-UHFFFAOYSA-N

Cite this record

CBID:652 http://www.chembase.cn/molecule-652.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1,4-diethyl 2-{[dimethoxy(sulfanylidene)-$l^{5}-phosphanyl]sulfanyl}butanedioate
1,4-diethyl 2-{[dimethoxy(sulfanylidene)-λ5-phosphanyl]sulfanyl}butanedioate
IUPAC Traditional name
malathion
paladin
1,4-diethyl 2-{[dimethoxy(sulfanylidene)-λ5-phosphanyl]sulfanyl}butanedioate
Brand Name
Calmathion
Carbethoxy malathion
Carbetovur
Carbetox
Celthion
Chemathion
Cimexan
Cleensheen
Cythion
Derbac-M
Detmol MA
Emmatos
Emmatos extra
Ethiolacar
Etiol
Extermathion
Fog 3
Formal
Forthion
Fosfothion
Fosfotion
Fosfotion 550
Fyfanon
Hilthion
Hilthion 25WDP
Karbofos
Kop-Thionkypfosmalacide
Kop-thion
Kypfos
Latka 4049
Lice Rid
Malacide
Malafor
Malagran
Malakill
Malamar
Malamar 50
Malaphele
Malaphos
Malasol
Malaspray
Malathion 60
Malathion E50
Malathion LV Concentrate
Malathiozoo
Malathon
Malation
Malatol
Malatox
Malmed
Malphos
Maltox
Maltox MLT
Moscarda
OMS 1
Organoderm
Ortho Malathion
Ovide
Phosphothion
Prioderm
Sadofos
Sadofos 30
Sadophos
Siptox I
Staeubol-Puder
Suleo-M
Sumitox
TAK
Taskil
Vegfru malatox
Vetiol
Zithiol
Synonyms
Compound 4049
Experimental insecticide 4049
Malathione
Mercaptosuccinic acid diethyl ester
MLT
Carbophos
Carbofos
Maldison
Mercaptothion
Mercaptotion
Oleophosphothion
Insecticide no. 4049
malathion
Malathion
Malathion
Malathion solution
[(Dimethoxyphosphinothioyl)thio]butanedioic Acid Diethyl Ester
2-(dimethoxyphosphinothioylthio) butanedioic acid diethyl ester
Ortho malathion
马拉硫磷
马拉硫磷 溶液
CAS Number
121-75-5
EC Number
204-497-7
MDL Number
MFCD00036233
Beilstein Number
1804525
PubChem SID
24869494
24862222
160964115
24899302
46505287
PubChem CID
4004
CHEBI ID
6651
ATC CODE
P03AX03
QP53AF12
CHEMBL
1200468
Chemspider ID
3864
DrugBank ID
DB00772
KEGG ID
D00534
Unique Ingredient Identifier
U5N7SU872W
Wikipedia Title
Malathion

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.8572832  LogD (pH = 7.4) 1.8572832 
Log P 1.8572832  Molar Refractivity 78.1823 cm3
Polarizability 31.96836 Å3 Polar Surface Area 71.06 Å2
Rotatable Bonds 11  Lipinski's Rule of Five true 
Log P 2.67  LOG S -3.3 
Solubility (Water) 1.65e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
143 mg/L expand Show data source
145 mg/L at 20 °C in water expand Show data source
Chloroform expand Show data source
Ethyl Acetate expand Show data source
Soluble in ethanol and acetone; very soluble in ethyl ether expand Show data source
Apperance
Clear colorless liquid expand Show data source
Light Yellow Oil expand Show data source
Melting Point
2.9°C expand Show data source
2.9 °C expand Show data source
Boiling Point
156°C expand Show data source
156-157 °C at 0.7 mmHg expand Show data source
156-157°C expand Show data source
Flash Point
-.4 °F expand Show data source
-18 °C expand Show data source
Density
1.23 g/cm3 expand Show data source
1.23 g/ml expand Show data source
Partition Coefficient
2.36 (octanol/water) expand Show data source
Hydrophobicity(logP)
2 expand Show data source
Storage Condition
-20°C Freezer, Under Inert Atmosphere expand Show data source
RTECS
WM8400000 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Nature polluting Nature polluting (N) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
1145 expand Show data source
3082 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
3 expand Show data source
Hazard Class
3 expand Show data source
9 expand Show data source
Packing Group
2 expand Show data source
3 expand Show data source
Risk Statements
11-38-50/53-65-67 expand Show data source
22-43-50/53 expand Show data source
Safety Statements
16-61-62 expand Show data source
24-37-46-60-61 expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS07 expand Show data source
GHS08 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Danger expand Show data source
Warning expand Show data source
GHS Hazard statements
H225-H304-H315-H336-H410 expand Show data source
H302-H317-H410 expand Show data source
GHS Precautionary statements
P210-P261-P273-P301 + P310-P331-P501 expand Show data source
P273-P280-P501 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 1145 3/PG 2 expand Show data source
UN 3082 9/PG 3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
96% expand Show data source
Concentration
100 ng/μL in cyclohexane expand Show data source
Grade
analytical standard expand Show data source
certified reference material expand Show data source
PESTANAL®, analytical standard expand Show data source
TraceCERT® expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Packaging
ampule of 500 mg expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Empirical Formula (Hill Notation)
C10H19O6PS2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 05224056 external link
MP Biomedicals Rare Chemical collection
DrugBank - DB00772 external link
Item Information
Drug Groups approved; investigational
Description A wide spectrum aliphatic organophosphate insecticide widely used for both domestic and commercial agricultural purposes. [PubChem]
Indication For patients infected with Pediculus humanus capitis (head lice and their ova) of the scalp hair.
Pharmacology Malathion is an organophosphate insecticide commonly used to control mosquitos and other flying insects. Pharmaceutically, malathion is used to eliminate head lice. The principal toxicological effect of malathion is cholinesterase inhibition, due primarily to malaoxon and to phosphorus thionate impurities.
Toxicity Malathion is slightly toxic via the oral route, with reported oral LD50 values of 1000 mg/kg to greater than 10,000 mg/kg in the rat. It is also slightly toxic via the dermal route, with reported dermal LD50 values of greater than 4000 mg/kg in rats. Moderate poisoning can result in chest tightness, difficulty breathing, bradycardia, tachycardia, tremor/ataxia, blurred vision, and confusion. Severe, life-threatening signs include coma, seizures, respiratory arrest, and paralysis. Malathion may also be irritating to the skin and eyes.
Affected Organisms
Head lice
Biotransformation The major metabolites of malathion are the diacid and monoacid metabolites, namely, malathion dicarboxylic acid (DCA) and malathion monocarboxylic acid (MCA). Malaoxon, the active cholinesterase-inhibiting metabolite of malathion, is a minor metabolite. Both malathion and malaoxon are detoxified by carboxyesterases leading to polar, water-soluble compounds that are excreted.
Absorption Malathion in an acetone vehicle has been reported to be absorbed through normal human skin only to the extent of 8% of the applied dose. Absorption may be increased when malathion is applied to damaged skin. Malathion is rapidly and effectively absorbed by practically all routes including the gastrointestinal tract, skin, mucous membranes, and lungs. However, it is readily excreted in the urine, and does not accumulate in organs or tissues.
Half Life 8-24 hours
References
Baker EL Jr, Warren M, Zack M, Dobbin RD, Miles JW, Miller S, Alderman L, Teeters WR: Epidemic malathion poisoning in Pakistan malaria workers. Lancet. 1978 Jan 7;1(8054):31-4. [Pubmed]
Bonner MR, Coble J, Blair A, Beane Freeman LE, Hoppin JA, Sandler DP, Alavanja MC: Malathion exposure and the incidence of cancer in the agricultural health study. Am J Epidemiol. 2007 Nov 1;166(9):1023-34. Epub 2007 Aug 23. [Pubmed]
Edwards JW, Lee SG, Heath LM, Pisaniello DL: Worker exposure and a risk assessment of malathion and fenthion used in the control of Mediterranean fruit fly in South Australia. Environ Res. 2007 Jan;103(1):38-45. Epub 2006 Aug 17. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - 36143 external link
Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH
Sigma Aldrich - 31558 external link
Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH
Sigma Aldrich - 91481 external link
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - PS86 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Toronto Research Chemicals - M111000 external link
Used as an insecticide.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Baker EL Jr, Warren M, Zack M, Dobbin RD, Miles JW, Miller S, Alderman L, Teeters WR: Epidemic malathion poisoning in Pakistan malaria workers. Lancet. 1978 Jan 7;1(8054):31-4. Pubmed
  • • Bonner MR, Coble J, Blair A, Beane Freeman LE, Hoppin JA, Sandler DP, Alavanja MC: Malathion exposure and the incidence of cancer in the agricultural health study. Am J Epidemiol. 2007 Nov 1;166(9):1023-34. Epub 2007 Aug 23. Pubmed
  • • Edwards JW, Lee SG, Heath LM, Pisaniello DL: Worker exposure and a risk assessment of malathion and fenthion used in the control of Mediterranean fruit fly in South Australia. Environ Res. 2007 Jan;103(1):38-45. Epub 2006 Aug 17. Pubmed
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PATENTS

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