3-{[dimethoxy(sulfanylidene)-λ5-phosphanyl]sulfanyl}-4-(2H5)ethoxy-4-oxobutanoic acid

• ChemBase ID: 172480
• Molecular Formular: C8H15O6PS2
• Molecular Mass: 302.304861
• Monoisotopic Mass: 302.00476683
• SMILES: C(C(=O)OCC)(CC(=O)O)SP(=S)(OC)OC
• Canonical SMILES: CCOC(=O)C(SP(=S)(OC)OC)CC(=O)O
• InChI: InChI=1S/C8H15O6PS2/c1-4-14-8(11)6(5-7(9)10)17-15(16,12-2)13-3/h6H,4-5H2,1-3H3,(H,9,10)
• InChIKey: FARGSBYVTRDSKX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[dimethoxy(sulfanylidene)-λ^5-phosphanyl]sulfanyl}-4-(^2H₅)ethoxy-4-oxobutanoic acid
• IUPAC Traditional name: 3-{[dimethoxy(sulfanylidene)-λ^5-phosphanyl]sulfanyl}-4-(^2H₅)ethoxy-4-oxobutanoic acid
• Synonyms: 2-[(Dimethoxyphosphinothioyl)thio]butanedioic Acid 1-Ethyl EsterMalathion β-Monocarboxylic Acid; O,O-Dimethyl S-(1-Carbethoxy-2-carboxy)ethyl Phosphorodithioate; S-[2-Carboxy-1-(ethoxycarbonyl)ethyl]O,O-di-methyl Phosphorodithioate; Malathion Monoacid; Malathion β-Monoacid-d5

Database IDs

• PubChem SID: 164228390
• PubChem CID: 71749877

CALCULATED PROPERTIES

• Acid pKa: 4.354087
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.18048255
• LogD (pH = 7.4): -1.5683831
• Log P: 1.3545812
• Molar Refractivity: 68.6646 cm^3
• Polarizability: 28.085081 Å^3
• Polar Surface Area: 82.06 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M111022

A labelled major biodegradation product of Malathion (M111000). Malathion metabolite.

REFERENCES

• Kim, Y. et al.: Chemosphere, 60, 1349 (2005)
• Yoshii, K. et al.: J. Health Sci., 54, 535 (2005)
• Hayasaka, M. et al.: Jap. J. Forensic Toxicol., 12, 15 (2005)