ContaminantDB: Endosulfan sulfate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (42)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:00 UTC

Update Date

2026-03-31 18:20:20 UTC

Accession Number

CHEM000051

Identification

Common Name

Endosulfan sulfate

Class

Small Molecule

Description

Endosulfan sulfate is one of the primary metabolites of endosulfan. Endosulfan is a organochlorine insecticide and acaricide. It is used to control insects on food and non-food crops and also as a wood preservative. Due to its toxicity and tendency to bioaccumulate, the use of endosulfan is banned in many areas. (4)

Contaminant Sources

Clean Air Act Chemicals
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Ester
Food Toxin
Organic Compound
Organochloride
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
endoSulfan sulfuric acid	Generator
endoSulphan sulphate	Generator
endoSulphan sulphuric acid	Generator
endoSulfan sulphate	MeSH

Chemical Formula

C₉H₆Cl₆O₄S

Average Molecular Mass

422.925 g/mol

Monoisotopic Mass

419.812 g/mol

CAS Registry Number

1031-07-8

IUPAC Name

1,9,10,11,12,12-hexachloro-4,6-dioxa-5lambda6-thiatricyclo[7.2.1.0^{2,8}]dodec-10-ene-5,5-dione

Traditional Name

1,9,10,11,12,12-hexachloro-4,6-dioxa-5lambda6-thiatricyclo[7.2.1.0^{2,8}]dodec-10-ene-5,5-dione

SMILES

ClC1=C(Cl)C2(Cl)C3COS(=O)(=O)OCC3C1(Cl)C2(Cl)Cl

InChI Identifier

InChI=1S/C9H6Cl6O4S/c10-5-6(11)8(13)4-2-19-20(16,17)18-1-3(4)7(5,12)9(8,14)15/h3-4H,1-2H2

InChI Key

AAPVQEMYVNZIOO-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as sulfuric acid diesters. These are organic compounds containing the sulfuric acid diester functional group with the generic structure ROS(OR')(=O)=O, (R,R'=organyl group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Sulfuric acid esters

Direct Parent

Sulfuric acid diesters

Alternative Parents

Substituents

Sulfuric acid diester
Alkyl sulfate
Vinyl chloride
Vinyl halide
Organoheterocyclic compound
Haloalkene
Chloroalkene
Oxacycle
Alkyl chloride
Organic oxygen compound
Organic oxide
Alkyl halide
Organohalogen compound
Organochloride
Organooxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	181-182°C
Boiling Point	Not Available
Solubility	0.00048 mg/mL at 20 °C [SHIU,WY et al. (1990)]

Predicted Properties

Property	Value	Source
Water Solubility	0.0055 g/L	ALOGPS
logP	3.02	ALOGPS
logP	3.16	ChemAxon
logS	-4.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	78.42 m³·mol⁻¹	ChemAxon
Polarizability	32.64 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0002-9000000000-bcfc0ef54bb49abc2d99	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0002-9000000000-1d4eb1166470011ca45f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0002-9000000000-b427a7756f10c58e2353	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0002-9000000000-d24fe9db5cdc9ba634d0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0002-9000000000-897c73a04862ce32ab17	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000900000-26e3e675c4ae347bd21e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0009000000-4fd01200e6c319f6890f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ff9-3019000000-20d38c59f554d946135e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0001900000-1d7035bc1ff68ecff951	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-1009800000-800f704d9bb496d72468	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-2009100000-76b57f01be79557bc9e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000900000-f67404d0abf93a88ef2e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000900000-f67404d0abf93a88ef2e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0009600000-6e614cac5b1bd89c20c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000900000-abc9129ca251561f0bb6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0000900000-93029fc8eccef788adb9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-2000900000-bd75593ef06e70824c90	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0079-2393100000-82ea23da9fa65ba9ec63	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (5) ; inhalation (5) ; dermal (5)

Mechanism of Toxicity

Endosulfan sulfate antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions. Endosulfan sulfate also inhibits Na+ K+ ATPase and Ca2+ and Mg2+ ATPase which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the CNS. This results in hyperexcitation and generalized seizures. Endosulfan sulfate is also an endocrine disruptor and acts as an agonist at the progesterone receptor and estrogen receptors. (7, 4, 5, 1, 3)

Metabolism

Endosulfan and its metabolites, which include sulfate, diol, α-hydroxyether, lactone, and ether derivatives of endosulfan, are excreted in the urine and faeces. (5)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Endosulfan is used as an insecticide, acaricide, and in wood preservatives. (5)

Minimum Risk Level

Not Available

Health Effects

Endosulfan is a neurotoxin and damages the central nervous system, causing effects such as intermittent muscle twitching and myoclonic jerking. Endosulfan can also damage the kidneys, testes, and liver, and may possibly affect the body's ability to fight infection. It is also an endocrine disruptor and causes reproductive and developmental damage. (7, 4, 5)

Symptoms

Symptoms of endosulfan poisoning include hyperactivity, hyperreflexia, tremors, dizziness, headache, convulsions, lack of coordination, staggering, difficulty breathing, nausea and vomiting, diarrhea, and in severe cases, unconsciousness. (7, 4, 5)

Treatment

Treatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (6)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0251795

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Endosulfan

Chemspider ID

13338

ChEBI ID

Not Available

PubChem Compound ID

13940

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Endosulfan sulfate (CHEM000051)

Structure for CHEM000051: Endosulfan sulfate