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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:31 UTC

Update Date

2023-02-21 17:19:59 UTC

HMDB ID

HMDB0031188

Secondary Accession Numbers

HMDB31188

Metabolite Identification

Common Name

Ethanethioic acid

Description

Ethanethioic acid, also known as thioacetic acid or thioacetate, belongs to the class of organic compounds known as carbothioic s-acids. These are organic acids with the general formula RCS-OH (R=H, organic group). Based on a literature review a significant number of articles have been published on Ethanethioic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Acetyl mercaptan	ChEBI
CH3COSH	ChEBI
Thioacetic acid	ChEBI
Thioacetic S-acid	ChEBI
Thioacetate	Generator
Ethanethioate	Generator
Ethanethioic O-acid	HMDB
Ethanethiolic acid	HMDB
Methanecarbothiolic acid	HMDB
Schiff'S reagent	HMDB
Thiacetic acid	HMDB
Thio-acetic acid	HMDB
Thioacetate esters	HMDB
Thiolacetic acid	HMDB
Thiolacetic acid?	HMDB
Thionoacetic acid	HMDB
Thioacetic acid, potassium salt	HMDB
Thioacetic acid, sodium salt	HMDB

Chemical Formula

C₂H₄OS

Average Molecular Weight

76.118

Monoisotopic Molecular Weight

75.99828544

IUPAC Name

ethanethioic S-acid

Traditional Name

schiff reagent

CAS Registry Number

507-09-5

SMILES

CC(S)=O

InChI Identifier

InChI=1S/C2H4OS/c1-2(3)4/h1H3,(H,3,4)

InChI Key

DUYAAUVXQSMXQP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbothioic s-acids. These are organic acids with the general formula RCS-OH (R=H, organic group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carbothioic S-acids

Sub Class

Not Available

Direct Parent

Carbothioic S-acids

Alternative Parents

Substituents

Carbothioic s-acid
Carbodithioic acid
Thiocarboxylic acid or derivatives
Carboxylic acid derivative
Alkylthiol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

thioacetic acid (CHEBI:16555 )

Ontology

Endogenous (HMDB: HMDB0031188)

Exogenous

Food

Food (HMDB: HMDB0031188)

Exogenous (HMDB: HMDB0031188)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	17 °C	Not Available
Boiling Point	88.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	101600 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.528 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.2 g/L	ALOGPS
logP	0.78	ALOGPS
logP	0.29	ChemAxon
logS	-0.65	ALOGPS
pKa (Strongest Acidic)	0.62	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	19.06 m³·mol⁻¹	ChemAxon
Polarizability	7.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	112.381	31661259
DarkChem	[M-H]-	105.095	31661259
DeepCCS	[M+H]+	122.613	30932474
DeepCCS	[M-H]-	120.779	30932474
DeepCCS	[M-2H]-	156.174	30932474
DeepCCS	[M+Na]+	130.127	30932474
AllCCS	[M+H]+	124.0	32859911
AllCCS	[M+H-H2O]+	119.6	32859911
AllCCS	[M+NH4]+	128.1	32859911
AllCCS	[M+Na]+	129.3	32859911
AllCCS	[M-H]-	148.1	32859911
AllCCS	[M+Na-2H]-	155.0	32859911
AllCCS	[M+HCOO]-	162.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethanethioic acid	CC(S)=O	1099.2	Standard polar	33892256
Ethanethioic acid	CC(S)=O	651.2	Standard non polar	33892256
Ethanethioic acid	CC(S)=O	655.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethanethioic acid,1TMS,isomer #1	CC(=O)S[Si](C)(C)C	860.7	Semi standard non polar	33892256
Ethanethioic acid,1TMS,isomer #1	CC(=O)S[Si](C)(C)C	868.8	Standard non polar	33892256
Ethanethioic acid,1TBDMS,isomer #1	CC(=O)S[Si](C)(C)C(C)(C)C	1101.6	Semi standard non polar	33892256
Ethanethioic acid,1TBDMS,isomer #1	CC(=O)S[Si](C)(C)C(C)(C)C	1123.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethanethioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-06248445f56db7f10761	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethanethioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethanethioic acid 10V, Positive-QTOF	splash10-004i-9000000000-9edb1da91d26c472db74	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethanethioic acid 20V, Positive-QTOF	splash10-004i-9000000000-d7b964960a1c1e4be5c1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethanethioic acid 40V, Positive-QTOF	splash10-0006-9000000000-2aed74d00cb791bf0dcc	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethanethioic acid 10V, Negative-QTOF	splash10-00dl-9000000000-3cb2ccfaeee23177c1c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethanethioic acid 20V, Negative-QTOF	splash10-00di-9000000000-bdd638bc137bd61d2bc8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethanethioic acid 40V, Negative-QTOF	splash10-0596-9000000000-5bd7f1b88de4d4ef9be8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethanethioic acid 10V, Positive-QTOF	splash10-004l-9000000000-5f6f7fef7d8c01427470	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethanethioic acid 20V, Positive-QTOF	splash10-052f-9000000000-01257c437988da882c19	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethanethioic acid 40V, Positive-QTOF	splash10-052f-9000000000-9633f3baf3f013462f5e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethanethioic acid 10V, Negative-QTOF	splash10-006x-9000000000-b061934dee6f4e2506c9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethanethioic acid 20V, Negative-QTOF	splash10-00dl-9000000000-d222edf5c2b479bd176d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethanethioic acid 40V, Negative-QTOF	splash10-00di-9000000000-537abdbe4f5b71b09ed6	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003208

KNApSAcK ID

Not Available

Chemspider ID

10052

KEGG Compound ID

C01857

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10484

PDB ID

Not Available

ChEBI ID

16555

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1107971

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Yang W, Du DM: Squaramide-catalysed enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to alpha,beta-disubstituted nitroalkenes. Org Biomol Chem. 2012 Sep 14;10(34):6876-84. doi: 10.1039/c2ob26068a. Epub 2012 Jul 31. [PubMed:22847715 ]
Piro B, Zhang QD, Reisberg S, Noel V, Dang LA, Duc HT, Pham MC: Direct and rapid electrochemical immunosensing system based on a conducting polymer. Talanta. 2010 Jul 15;82(2):608-12. doi: 10.1016/j.talanta.2010.05.015. Epub 2010 May 19. [PubMed:20602943 ]
Liu M, Deng J, Lai C, Chen Q, Zhao Q, Zhang Y, Li H, Yao S: Synthesis, characterization of conjugated oligo-phenylene-ethynylenes and their supramolecular interaction with beta-cyclodextrin for salicylaldehyde detection. Talanta. 2012 Oct 15;100:229-38. doi: 10.1016/j.talanta.2012.08.008. Epub 2012 Aug 17. [PubMed:23141331 ]
Chauhan HP, Bhatiya S: Synthesis, spectroscopic, thermal and antimicrobial studies of toluene-3,4-dithiolatoarsenic(III) derivatives with some oxygen and sulphur donor ligands. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Nov;97:1133-9. doi: 10.1016/j.saa.2012.07.086. Epub 2012 Aug 3. [PubMed:22940048 ]
Inoue K, Asai N, Mizuo H, Fukuda K, Kusano K, Yoshimura T: Unique metabolic pathway of [(14)C]lenvatinib after oral administration to male cynomolgus monkey. Drug Metab Dispos. 2012 Apr;40(4):662-70. doi: 10.1124/dmd.111.043281. Epub 2011 Dec 29. [PubMed:22207053 ]
Robertson F, Wu J: Convenient synthesis of allylic thioethers from phosphorothioate esters and alcohols. Org Lett. 2010 Jun 4;12(11):2668-71. doi: 10.1021/ol1009202. [PubMed:20441179 ]
Fischer JA, Zoldan VC, Benitez G, Rubert AA, Ramirez EA, Carro P, Salvarezza RC, Pasa AA, Vela ME: Sulfidization of Au(111) from thioacetic acid: an experimental and theoretical study. Langmuir. 2012 Oct 30;28(43):15278-85. doi: 10.1021/la303059u. Epub 2012 Oct 18. [PubMed:23002810 ]
Bendena WG, Zhang J, Burtenshaw SM, Tobe SS: Evidence for differential biosynthesis of juvenile hormone (and related) sesquiterpenoids in Drosophila melanogaster. Gen Comp Endocrinol. 2011 May 15;172(1):56-61. doi: 10.1016/j.ygcen.2011.02.014. Epub 2011 Feb 24. [PubMed:21354154 ]
Cimadevilla F, Garcia ME, Garcia-Vivo D, Ruiz MA, Graiff C, Tiripicchio A: Reactions of the tetrafluoroborate complex [Mo2Cp2(kappa(2)-F2BF2)(mu-PPh2)2(CO)]BF4 with mono- and bidentate ligands having E-H bonds (E = O, S, Se, N, P). Inorg Chem. 2012 Jul 2;51(13):7284-95. doi: 10.1021/ic300626y. Epub 2012 Jun 20. [PubMed:22715993 ]
Hintermann L, Turockin A: Reversible generation of metastable enols in the 1,4-addition of thioacetic acid to alpha,beta-unsaturated carbonyl compounds. J Org Chem. 2012 Dec 21;77(24):11345-8. doi: 10.1021/jo3021709. Epub 2012 Dec 3. [PubMed:23164060 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Ethanethioic acid (HMDB0031188)

MOL for HMDB0031188 (Ethanethioic acid)

3D MOL for HMDB0031188 (Ethanethioic acid)

3D SDF for HMDB0031188 (Ethanethioic acid)

3D-SDF for HMDB0031188 (Ethanethioic acid)

PDB for HMDB0031188 (Ethanethioic acid)

3D PDB for HMDB0031188 (Ethanethioic acid)

SMILES for HMDB0031188 (Ethanethioic acid)

INCHI for HMDB0031188 (Ethanethioic acid)

Structure for HMDB0031188 (Ethanethioic acid)

3D Structure for HMDB0031188 (Ethanethioic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra