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: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-diethyl 2-{[dimethoxy(sulfanylidene)-$l^{5}-phosphanyl]sulfanyl}butanedioate; 1,4-diethyl 2-{[dimethoxy(sulfanylidene)-λ^5-phosphanyl]sulfanyl}butanedioate
• IUPAC Traditional name: malathion; paladin; 1,4-diethyl 2-{[dimethoxy(sulfanylidene)-λ^5-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

Database IDs

• CAS Number: 121-75-5
• EC Number: 204-497-7
• MDL Number: MFCD00036233
• Beilstein Number: 1804525
• PubChem SID: 24862222; 24869494; 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

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.8572832
• LogD (pH = 7.4): 1.8572832
• Log P: 1.8572832
• Molar Refractivity: 78.1823 cm^3
• Polarizability: 31.96836 Å^3
• Polar Surface Area: 71.06 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.67
• LOG S: -3.3
• Solubility (Water): 1.65e-01 g/l

PROPERTIES

Physical Property

• Solubility: 143 mg/L; 145 mg/L at 20 °C in water; Chloroform; Ethyl Acetate; Soluble in ethanol and acetone; very soluble in ethyl ether
• Apperance: Clear colorless liquid; Light Yellow Oil
• Melting Point: 2.9°C; 2.9 °C
• Boiling Point: 156°C; 156-157 °C at 0.7 mmHg; 156-157°C
• Flash Point: -.4 °F; -18 °C
• Density: 1.23 g/cm^3; 1.23 g/ml
• Partition Coefficient: 2.36 (octanol/water)
• Hydrophobicity(logP): 2

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• RTECS: WM8400000
• European Hazard Symbols: Flammable (F); Nature polluting (N); Harmful (Xn)
• UN Number: 1145; 3082
• German water hazard class: 2; 3
• Hazard Class: 3; 9
• Packing Group: 2; 3
• Risk Statements: 11-38-50/53-65-67; 22-43-50/53
• Safety Statements: 16-61-62; 24-37-46-60-61
• GHS Pictograms: GHS02; GHS07; GHS08; GHS09
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H225-H304-H315-H336-H410; H302-H317-H410
• GHS Precautionary statements: P210-P261-P273-P301 + P310-P331-P501; P273-P280-P501
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1145 3/PG 2; UN 3082 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: 96%
• Concentration: 100 ng/μL in cyclohexane
• Grade: analytical standard; certified reference material; PESTANAL®, analytical standard; TraceCERT®
• Packaging: ampule of 500 mg
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C10H19O6PS2

DETAILS

MP Biomedicals - 05224056

MP Biomedicals Rare Chemical collection

DrugBank - DB00772

• 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

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Sigma Aldrich - 31558

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Sigma Aldrich - 91481

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Sigma Aldrich - PS86

Frequently Asked Questions
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Toronto Research Chemicals - M111000

Used as an insecticide.

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