Record Information
Version1.0
Creation Date2009-06-19 21:58:30 UTC
Update Date2026-04-04 18:35:36 UTC
Accession NumberCHEM001070
Identification
Common NameBis(tributyltin) oxide
ClassSmall Molecule
DescriptionBis(tributyltin) oxide is an organotin compound. Tributyltins are the main active ingredients in certain biocides used to control a broad spectrum of organisms, and are also used in wood preservation, marine paints (as antifouling pesticides), and textiles and industrial water systems (as antifungal agents). They also considered moderately to highly persistent organic pollutants and are especially hazardous to marine ecosystems. The main toxic component of tributyltins is tin. Tin is a chemical element with the symbol Sn and atomic number 50. It is a natural component of the earth's crust and is obtained chiefly from the mineral cassiterite, where it occurs as tin dioxide. (3, 5, 4)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organometallic
  • Pesticide
  • Pollutant
  • Synthetic Compound
  • Tin Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H56OSn2
Average Molecular Mass598.131 g/mol
Monoisotopic Mass600.238 g/mol
CAS Registry Number56-35-9
IUPAC Nametributyltin oxide
Traditional Nametributyltin oxide
SMILESO.[Sn].[Sn].[CH2]CCC.[CH2]CCC.[CH2]CCC.[CH2]CCC.[CH2]CCC.[CH2]CCC
InChI IdentifierInChI=1S/6C4H9.H2O.2Sn/c6*1-3-4-2;;;/h6*1,3-4H2,2H3;1H2;;
InChI KeyXWWXHBDNGBFEMZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic oxides
Sub ClassNot Available
Direct ParentOrganic oxides
Alternative Parents
Substituents
  • Organic oxide
  • Hydrocarbon derivative
  • Saturated hydrocarbon
  • Hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceYellow oil.
Experimental Properties
PropertyValue
Melting Point-45°C
Boiling PointNot Available
Solubility0.0195 mg/mL [BLUNDEN,SJ et al. (1984)]
Predicted Properties
PropertyValueSource
Water Solubility0.71 g/LALOGPS
logP2.81ALOGPS
logP2.11ChemAxon
logS-1.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity19.11 m³·mol⁻¹ChemAxon
Polarizability7.99 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-488e64a2ce30deb3e057Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000009000-488e64a2ce30deb3e057Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0000009000-488e64a2ce30deb3e057Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000009000-65c66cbea4fd2cd71497Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000009000-65c66cbea4fd2cd71497Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000009000-65c66cbea4fd2cd71497Spectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of ToxicityOrganotin compounds produce neurotoxic and immunotoxic effects. Organotins may directly activate glial cells contributing to neuronal cell degeneration by local release of pro-inflammatory cytokines, tumor necrosis factor-_, and/or interleukins. They may also induce apoptosis by direct action on neuronal cells. Organotin compounds stimulate the neuronal release of and/or decrease of neuronal cell uptake of neurotransmitters in brain tissue, including aspartate, GABA, glutamate, norepinephrine, and serotonin. This may be either a contributing factor to or result of the neuronal cell loss. The immunotoxic effects of organotins are characterized by thymic atrophy caused by the suppression of proliferation of immature thymocytes and apoptosis of mature thymocytes. Organotin compounds are believed to exert these effects by suppressing DNA and protein synthesis, inducing the expression of genes involved in apoptosis (such as nur77), and disrupting the regulation of intracellular calcium levels, giving rise to the uncontrolled production of reactive oxygen species, release of cytochrome c to the cytosol, and the proteolytic and nucleolytic cascade of apoptosis. The suppression of proliferation of immature thymocytes further results in the suppression of T-cell-mediated immune responses. Organotins are also endocrine disruptors and are believed to contribute to obesity by inappropriate receptor activation, leading to adipocyte differentiation. Inorganic tin triggers eryptosis, contributing to tin-induced anemia. (4, 1, 2)
MetabolismThough tin metal is very poorly absorbed, tin compounds may be absorbed via oral, inhalation, or dermal routes, with organotin compounds being much more readily absorbed than inorganic tin compounds. Tin may enter the bloodstream and bind to hemoglobin, where it is distributed and accumulates mainly in the kidney, liver, lung, and bone. Organotin compounds may undergo dealkylation, hydroxylation, dearylation, and oxidation catalyzed by cytochrome P-450 enzymes in the liver. The alkyl products of dealkylation are conjugated with glutathione and further metabolized to mercapturic acid derivatives. Tin and its metabolites are excreted mainly in the urine and feces. (4)
Toxicity ValuesLD50: 7210 ug/kg (Intraperitoneal, Rat) (6) LD50: 11 700 mg/kg (Subcutaneous, Rat) (6) LD50: 55 mg/kg (Oral, Mouse) (6) LD50: 6 mg/kg (Intravenous, Mouse) (6) LD50: 900 mg/kg (Dermal, Rabbit) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesTributyltins are the main active ingredients in certain biocides used to control a broad spectrum of organisms, and are also used in wood preservation, marine paints (as antifouling pesticides), and textiles and industrial water systems (as antifungal agents). (3)
Minimum Risk LevelNot Available
Health EffectsBreathing or swallowing, or skin contact with organotins, can interfere with the way the brain and nervous system work, causing death in severe cases. Organic tin compounds may also damage the immune and reproductive system. (3, 4)
SymptomsInorganic or organic tin compounds placed on the skin or in the eyes can produce skin and eye irritation. (4)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID6327573
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available