SynCED: Tributyltin

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:08 UTC

Update Date

2026-05-14 18:58:47 UTC

Accession Number

CHEM000124

Identification

Common Name

Tributyltin

Class

Small Molecule

Description

Tributyltin 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

STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Industrial/Workplace Toxin
Lachrymator
Organic Compound
Organometallic
Pesticide
Pollutant
Synthetic Compound
Tin Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
[sn(Bu)3H]	ChEBI
SnBu3h	ChEBI
TBT	ChEBI
Tri-N-butyltin	ChEBI
Tri-N-butyltin hydride	ChEBI
Tributyltin	ChEBI
Tributyltin hydride	MeSH
Tributyltin tetrafluoroborate	MeSH
Tri-N-butyl tin maleate	MeSH
Tributyltin chloride	MeSH
Tributyltin ion (1+)	MeSH
Tributyltin fluoride	MeSH
TBTC Chloride	MeSH
Tributyltin acetate	MeSH
Tributyltin-D27	MeSH

Chemical Formula

C₁₂H₂₇Sn

Average Molecular Mass

290.050 g/mol

Monoisotopic Mass

291.113 g/mol

CAS Registry Number

688-73-3

IUPAC Name

tributylstannyl

Traditional Name

tributylstannanyl

SMILES

CCCC[Sn](CCCC)CCCC

InChI Identifier

InChI=1S/3C4H9.Sn.H/c3*1-3-4-2;;/h3*1,3-4H2,2H3;;

InChI Key

DBGVGMSCBYYSLD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trialkyltins. These are triorganotin compounds where the tin atom is linked to exactly three alkyl groups.

Kingdom

Organic compounds

Super Class

Organometallic compounds

Class

Organo-post-transition metal compounds

Sub Class

Organotin compounds

Direct Parent

Trialkyltins

Alternative Parents

Substituents

Trialkyltin
Hydrocarbon derivative
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organotin compound (CHEBI:27086 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Actin Cytoskeleton
Actin Filament
Cell junction
Cell surface
Cytoskeleton
Cytosol
Endoplasmic reticulum
Extracellular
Extracellular matrix
Golgi apparatus
Lysosome
Membrane
Microsome
Mitochondrial Membrane
Mitochondrion
Nuclear Membrane
Peroxisome
Plasma Membrane
Sarcoplasmic Reticulum
Secretory Granule
Secretory vesicle
Soluble Fraction
Synaptic Vesicle
Zymogen Granule

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Apoptosis	Not Available	map04210
Oxidative phosphorylation	Not Available	map00190
Steroid Biosynthesis	SMP00023	map00100
Osteoclast differentiation	Not Available	map04380
Nucleotide Excision Repair	SMP00478	map03420
Steroid hormone biosynthesis	Not Available	map00140
Cell cycle	Not Available	map04110
Base excision repair	Not Available	map03410
Rna degradation	Not Available	map03018
Proteasome	Not Available	Not Available
Penicillins	Not Available	Not Available
Gastric acid secretion	Not Available	map04971
Fatty acid Metabolism	SMP00051	map00071
Eicosanoids	Not Available	Not Available
Degradation Of Aromatic Compounds	Not Available	Not Available
Abc transporters	Not Available	map02010

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	80 °C at 4.00E-01 mm Hg
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.088 g/L	ALOGPS
logP	6.17	ALOGPS
logP	3.53	ChemAxon
logS	-3.5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	58.42 m³·mol⁻¹	ChemAxon
Polarizability	27.18 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Oral (4) ; inhalation (4) ; dermal(4)

Mechanism of Toxicity

Organotin 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-alpha, 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)

Metabolism

Organotin compounds are readily absorbed via oral, inhalation, or dermal routes. 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. Dealkylation of butyltin compounds produces di- and monobutyltin compounds, while oxidation of butyltin compounds produces the 3-hydroxybutyl, 4-hydroxybutyl, 3-oxobutyl, and 3-carboxy metabolites. 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 Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

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). (3)

Minimum Risk Level

Not Available

Health Effects

Breathing 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)

Symptoms

Inorganic or organic tin compounds placed on the skin or in the eyes can produce skin and eye irritation. (4)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB08601

HMDB ID

Not Available

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

Not Available

Chemspider ID

Not Available

ChEBI ID

27086

PubChem Compound ID

5948

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Tributyltin (CHEM000124)

Structure for CHEM000124: Tributyltin