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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:42:17 UTC

Update Date

2023-02-21 17:20:21 UTC

HMDB ID

HMDB0031317

Secondary Accession Numbers

HMDB31317

Metabolite Identification

Common Name

Bis(methylthio)methane

Description

Bis(methylthio)methane is found in animal foods. Bis(methylthio)methane is a odorous constituent of white truffle (Tuber magnatum); volatile component of some cheeses and boiled beef aroma. Also found in milk, fish oils, shitake mushroom, truffles, prawns and lobster. Bis(methylthio)methane is an important off-flavour component of foods. Bis(methylthio)methane is used in seasonings. It is used as a primary aromatic ingredient in truffle oil when combined in an olive oil base

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2, 4-Dithiapentane	HMDB
2,4-Dithiapentane	HMDB
2,4-Dithiopentane	HMDB
Bis(methylmercapto)methane	HMDB
Bis(methylsulfanyl)methane	HMDB
Bis(methylthio)-methane	HMDB
Bis(methylthio)methan	HMDB
Bismethylmercaptomethane	HMDB
Bis[methylmercapto]methane	HMDB
CH3Sch2Sch3	HMDB
Dimethylthiomethane	HMDB
Formaldehyde dimethyl mercaptal	HMDB
Formaldehyde dimethylmercaptal	HMDB
Methylenebis(methyl sulfide)	HMDB
Methylenebis[methyl sulfide]	HMDB
Thioformaldehyde dimethylacetal	HMDB
Thioformaldehyde dimethylthioacetal	HMDB
Bis(methylsulphanyl)methane	Generator
Bis(methylthio)methane	MeSH

Chemical Formula

C₃H₈S₂

Average Molecular Weight

108.226

Monoisotopic Molecular Weight

108.006741636

IUPAC Name

bis(methylsulfanyl)methane

Traditional Name

2,4-dithiapentane

CAS Registry Number

1618-26-4

SMILES

CSCSC

InChI Identifier

InChI=1S/C3H8S2/c1-4-3-5-2/h3H2,1-2H3

InChI Key

LOCDPORVFVOGCR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dithioacetals. Dithioacetals are compounds containing a dithioacetal functional group with the general structure R2C(SR')2.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioacetals

Sub Class

Dithioacetals

Direct Parent

Dithioacetals

Alternative Parents

Substituents

Thioacetal
Dialkylthioether
Sulfenyl compound
Thioether
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031317)
Cytoplasm (HMDB: HMDB0031317)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0031317)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031317)

Source

Endogenous

Endogenous (HMDB: HMDB0031317)

Plant

Plant (HMDB: HMDB0031317)

Animal

Animal (HMDB: HMDB0031317)

Exogenous

Food

Food (HMDB: HMDB0031317)

Fishes (FooDB: FOOD00865)

Crustacean

Crustaceans (FooDB: FOOD00862)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	147.00 to 148.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	1.245 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.72 g/L	ALOGPS
logP	1.21	ALOGPS
logP	1.82	ChemAxon
logS	-1.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	31.01 m³·mol⁻¹	ChemAxon
Polarizability	12.35 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]+	120.011	31661259
DarkChem	[M-H]-	114.413	31661259
DeepCCS	[M+H]+	124.966	30932474
DeepCCS	[M-H]-	123.081	30932474
DeepCCS	[M-2H]-	158.468	30932474
DeepCCS	[M+Na]+	132.453	30932474
AllCCS	[M+H]+	122.5	32859911
AllCCS	[M+H-H2O]+	118.5	32859911
AllCCS	[M+NH4]+	126.2	32859911
AllCCS	[M+Na]+	127.3	32859911
AllCCS	[M-H]-	144.5	32859911
AllCCS	[M+Na-2H]-	150.1	32859911
AllCCS	[M+HCOO]-	156.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bis(methylthio)methane	CSCSC	1224.7	Standard polar	33892256
Bis(methylthio)methane	CSCSC	828.3	Standard non polar	33892256
Bis(methylthio)methane	CSCSC	890.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bis(methylthio)methane GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fs-9200000000-7c75cafa0c32de95f9ba	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bis(methylthio)methane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bis(methylthio)methane 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 - Bis(methylthio)methane 10V, Positive-QTOF	splash10-0a4i-0900000000-c2a561a16dae256f0727	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(methylthio)methane 20V, Positive-QTOF	splash10-0a4i-6900000000-9f7ee5de77bd84846ef4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(methylthio)methane 40V, Positive-QTOF	splash10-0005-9100000000-7130a435522e48160737	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(methylthio)methane 10V, Negative-QTOF	splash10-0bt9-9700000000-2ef2159161a621d07dcd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(methylthio)methane 20V, Negative-QTOF	splash10-0a4l-7900000000-c498cad93f54c3487803	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(methylthio)methane 40V, Negative-QTOF	splash10-052f-9300000000-15c0cea41425a67983f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(methylthio)methane 10V, Positive-QTOF	splash10-0a4i-3900000000-60f48964fc797e9375b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(methylthio)methane 20V, Positive-QTOF	splash10-03dj-9000000000-1b9d1acf156faebdaeeb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(methylthio)methane 40V, Positive-QTOF	splash10-0002-9000000000-e8302e7ce3d65e4d9ffc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(methylthio)methane 10V, Negative-QTOF	splash10-0a4i-0900000000-b6cb82ca66d1c0b0f111	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(methylthio)methane 20V, Negative-QTOF	splash10-052b-9800000000-aba0e01bf603968edfcd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(methylthio)methane 40V, Negative-QTOF	splash10-0007-9000000000-2f8b357b6dff857b0362	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24811995	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn's disease	24811995	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]

Associated OMIM IDs

266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003375

KNApSAcK ID

C00054008

Chemspider ID

14639

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,4-Dithiapentane

METLIN ID

Not Available

PubChem Compound

15380

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1057521

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Trost BM, Nubling C: An asymmetric approach to 2-deoxynucleosides via organosulfur building blocks as chemical chameleons. Carbohydr Res. 1990 Jul 15;202:1-12. [PubMed:2224884 ]
Gereben O, Pusztai L: Molecular conformations and the liquid structure in bis(methylthio)methane and diethyl sulfide: diffraction experiments vs molecular dynamics simulations. J Phys Chem B. 2012 Aug 2;116(30):9114-21. doi: 10.1021/jp3040117. Epub 2012 Jul 13. [PubMed:22746696 ]
Awaleh MO, Baril-Robert F, Reber C, Badia A, Brosse F: Gold(I)-dithioether supramolecular polymers: synthesis, characterization, and luminescence. Inorg Chem. 2008 Apr 21;47(8):2964-74. doi: 10.1021/ic701275k. [PubMed:18366159 ]
Awaleh MO, Badia A, Brisse F: One-dimensional coordination polymers incorporating silver(I) perfluorocarboxylate cuboctahedral clusters and the bis(methylthio)methane ligand. Inorg Chem. 2007 Apr 16;46(8):3185-91. Epub 2007 Mar 16. [PubMed:17361998 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Bis(methylthio)methane (HMDB0031317)

MOL for HMDB0031317 (Bis(methylthio)methane)

3D MOL for HMDB0031317 (Bis(methylthio)methane)

3D SDF for HMDB0031317 (Bis(methylthio)methane)

3D-SDF for HMDB0031317 (Bis(methylthio)methane)

PDB for HMDB0031317 (Bis(methylthio)methane)

3D PDB for HMDB0031317 (Bis(methylthio)methane)

SMILES for HMDB0031317 (Bis(methylthio)methane)

INCHI for HMDB0031317 (Bis(methylthio)methane)

Structure for HMDB0031317 (Bis(methylthio)methane)

3D Structure for HMDB0031317 (Bis(methylthio)methane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra