Record Information
Version1.0
Creation Date2009-06-19 21:58:40 UTC
Update Date2026-04-05 16:04:20 UTC
Accession NumberCHEM001182
Identification
Common NameThiomersal
ClassSmall Molecule
DescriptionThiomersal is an organomercuric compound. It is used mainly as an antiseptic and antifungal agent. Thiomersal was developed and registered under the trade name Merthiolate in 1928 by the pharmaceutical corporation Eli Lilly and Company and has been used as a preservative in vaccines, immunoglobulin preparations, skin test antigens, antivenins, ophthalmic and nasal products, and tattoo inks. Mercury is a heavy, silvery d-block metal and one of six elements that are liquid at or near room temperature and pressure. It is a naturally occuring substance, and combines with other elements such as chlorine, sulfur, or oxygen to form inorganic mercury compounds (salts). Mercury also combines with carbon to make organic mercury compounds. (6, 12)
Contaminant Sources
  • EAFUS Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Drug
  • Ester
  • Mercury Compound
  • Organic Compound
  • Organometallic
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
[(O-Carboxyphenyl)thio]ethylmercury sodium saltChEBI
Ethyl(2-mercaptobenzoato-S)mercury sodium saltChEBI
Ethylmercurithiosalicylate sodiumChEBI
Ethylmercurithiosalicylic acid sodium saltChEBI
MercurothiolateChEBI
MerthiolateChEBI
O-(Ethylmercurithio)benzoic acid sodium saltChEBI
Sodium ethylmercurithiosalicylateChEBI
Sodium merthiolateChEBI
ThiomersalChEBI
ThiomersalateChEBI
ThiomersalumChEBI
TiomersalChEBI
Ethylmercurithiosalicylic acid sodiumGenerator
Ethylmercurithiosalicylate sodium saltGenerator
Mercurothiolic acidGenerator
Merthiolic acidGenerator
O-(Ethylmercurithio)benzoate sodium saltGenerator
Sodium ethylmercurithiosalicylic acidGenerator
Sodium merthiolic acidGenerator
Thiomersalic acidGenerator
Chemical FormulaC9H9HgNaO2S
Average Molecular Mass404.810 g/mol
Monoisotopic Mass405.993 g/mol
CAS Registry Number54-64-8
IUPAC Nameethyl({2-[(sodiooxy)carbonyl]phenyl}sulfanyl)mercury
Traditional Nameethyl({2-[(sodiooxy)carbonyl]phenyl}sulfanyl)mercury
SMILESCC[Hg]SC1=CC=CC=C1C(=O)O[Na]
InChI IdentifierInChI=1S/C7H6O2S.C2H5.Hg.Na/c8-7(9)5-3-1-2-4-6(5)10;1-2;;/h1-4,10H,(H,8,9);1H2,2H3;;/q;;2*+1/p-2
InChI KeyRTKIYNMVFMVABJ-UHFFFAOYSA-L
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-sulfanylbenzoic acids. These are benzoic acids which bear a sulfanyl group (R-SH) attached to the benzene ring at positions 1 and 2, respectively.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentO-sulfanylbenzoic acids
Alternative Parents
Substituents
  • O-sulfanylbenzoic acid
  • Benzoic acid
  • Benzoyl
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organometallic compound
  • Organomercurial-compound
  • Organic transition metal moeity
  • Organic salt
  • Alkyl mercury compound
  • Hydrocarbon derivative
  • Organic oxide
  • Transition metal alkyl
  • Aromatic homomonocyclic compound
Molecular FrameworkNot Available
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceIvory crystals.
Experimental Properties
PropertyValue
Melting Point232-233°C
Boiling PointNot Available
Solubility500 mg/mL [MERCK INDEX (1996); approx.]
Predicted Properties
PropertyValueSource
Water Solubility6.17 g/LALOGPS
logP2.58ALOGPS
logP3.26ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity48.06 m³·mol⁻¹ChemAxon
Polarizability22.45 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aor-0017900000-28fd51bd05600301a86eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-0009200000-01134517a64b96210af2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0imr-9154000000-b265c8e1bf065d1eba7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-0425900000-8c4053d922a1312f9424Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-0329300000-5addb900ba52c53e310eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-1192000000-c80f13c39d08143d58ffSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (8) ; inhalation (8) ; dermal (8)
Mechanism of ToxicityHigh-affinity binding of the divalent mercuric ion to thiol or sulfhydryl groups of proteins is believed to be the major mechanism for the activity of mercury. Through alterations in intracellular thiol status, mercury can promote oxidative stress, lipid peroxidation, mitochondrial dysfunction, and changes in heme metabolism. Mercury is known to bind to microsomal and mitochondrial enzymes, resulting in cell injury and death. For example, mercury is known to inhibit aquaporins, halting water flow across the cell membrane. It also inhibits the protein LCK, which causes decreased T-cell signalling and immune system depression. Mercury is also believed to inhibit neuronal excitability by acting on the postsynaptic neuronal membrane. It also affects the nervous system by inhibiting protein kinase C and alkaline phosphatase, which impairs brain microvascular formation and function, as well as alters the blood-brain barrier. Organic mercury exerts developmental effects by binding to tubulin, preventing microtubule assembly and causing mitotic inhibition. Mercury also produces an autoimmune response, likely by modification of major histocompatibility complex (MHC) class II molecules, self peptides, T-cell receptors, or cell-surface adhesion molecules. (8, 3, 4, 5)
MetabolismOrganic mercury is absorbed mainly by the gastrointestinal tract, then distributed throughout the body via the bloodstream. Organic mercury complexes with free cysteine and the cysteine and sulfhydryl groups on proteins such as haemoglobin. These complexes are able to mimic methionine and thus be transported throughout the body, including through the blood-brain barrier and placenta. Organic mercury is metabolized into inorganic mercury, which is eventually excreted in the urine and faeces. (13)
Toxicity ValuesLD50: 91 mg/kg (Oral, Mouse) (14) LD50: 98 mg/kg (Subcutaneous, Rat) (14)
Lethal Dose100 mg for an adult human (average for organic mercurials). (15)
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (11)
Uses/SourcesThiomersal is used as an antiseptic and antifungal agent. (12)
Minimum Risk LevelChronic Inhalation: 0.0002 mg/m3 (10)
Health EffectsMercury mainly affects the nervous system. Exposure to high levels of metallic, inorganic, or organic mercury can permanently damage the brain, kidneys, and developing fetus. Effects on brain functioning may result in irritability, shyness, tremors, changes in vision or hearing, and memory problems. Acrodynia, a type of mercury poisoning in children, is characterized by pain and pink discoloration of the hands and feet. Mercury poisoning can also cause Hunter-Russell syndrome and Minamata disease. (8)
SymptomsCommon symptoms include peripheral neuropathy (presenting as paresthesia or itching, burning or pain), skin discoloration (pink cheeks, fingertips and toes), edema (swelling), and desquamation (dead skin peels off in layers). (1)
TreatmentMercury poisoning is treated by immediate decontamination and chelation therapy using DMSA, DMPS, DPCN, or dimercaprol. (2)
Concentrations
Not Available
DrugBank IDDB11590
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 LinkThiomersal
Chemspider IDNot Available
ChEBI ID9546
PubChem Compound ID5908
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18837732
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21616561
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21785120
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22015977
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22366633
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22658806
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22811707
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23145070
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23223227
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23282150
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23401210
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23554557
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23843785
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23949514
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23965928
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23992327
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=25042713