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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:41 UTC

Update Date

2023-02-21 17:20:28 UTC

HMDB ID

HMDB0031370

Secondary Accession Numbers

HMDB31370

Metabolite Identification

Common Name

2-[(Methylthio)methyl]-2-butenal

Description

2-[(Methylthio)methyl]-2-butenal belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position. 2-[(Methylthio)methyl]-2-butenal is a burnt, cabbage, and cooked tasting compound. 2-[(Methylthio)methyl]-2-butenal has been detected, but not quantified in, several different foods, such as mushrooms, oyster mushrooms (Pleurotus ostreatus), potatos (Solanum tuberosum), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 2-[(methylthio)methyl]-2-butenal a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-[(Methylthio)methyl]-2-butenal.

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-((methylthio)Methyl)-2-butenal	HMDB
2-(methylmercapto)Methyl-2-butenal	HMDB
2-(methylthio)Methyl-2-butenal	HMDB
2-Ethylidene methional	HMDB
FEMA 3601	HMDB
(2E)-2-[(Methylsulphanyl)methyl]but-2-enal	Generator

Chemical Formula

C₆H₁₀OS

Average Molecular Weight

130.208

Monoisotopic Molecular Weight

130.045235632

IUPAC Name

(2E)-2-[(methylsulfanyl)methyl]but-2-enal

Traditional Name

(2E)-2-[(methylsulfanyl)methyl]but-2-enal

CAS Registry Number

40878-72-6

SMILES

CSC\C(=C\C)C=O

InChI Identifier

InChI=1S/C6H10OS/c1-3-6(4-7)5-8-2/h3-4H,5H2,1-2H3/b6-3+

InChI Key

IBSLHWQWKUNIJE-ZZXKWVIFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enals

Alternative Parents

Substituents

Enal
Dialkylthioether
Sulfenyl compound
Thioether
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031370)

Source

Endogenous

Endogenous (HMDB: HMDB0031370)

Plant

Plant (HMDB: HMDB0031370)
Coffea (HMDB: HMDB0031370)

Exogenous

Food

Food (HMDB: HMDB0031370)

Vegetable

Mushroom

Tuber

Potato (FooDB: FOOD00175)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Exogenous (HMDB: HMDB0031370)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0031370)

Role

Biological role

Energy source (HMDB: HMDB0031370)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031370)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	77.00 °C. @ 5.00 mm Hg	The Good Scents Company Information System
Water Solubility	8089 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.368 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.56 g/L	ALOGPS
logP	1.89	ALOGPS
logP	1.51	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	38.85 m³·mol⁻¹	ChemAxon
Polarizability	14.41 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]+	128.841	31661259
DarkChem	[M-H]-	124.185	31661259
DeepCCS	[M+H]+	130.452	30932474
DeepCCS	[M-H]-	128.182	30932474
DeepCCS	[M-2H]-	164.539	30932474
DeepCCS	[M+Na]+	139.151	30932474
AllCCS	[M+H]+	128.6	32859911
AllCCS	[M+H-H2O]+	124.5	32859911
AllCCS	[M+NH4]+	132.5	32859911
AllCCS	[M+Na]+	133.6	32859911
AllCCS	[M-H]-	132.7	32859911
AllCCS	[M+Na-2H]-	135.9	32859911
AllCCS	[M+HCOO]-	139.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-[(Methylthio)methyl]-2-butenal	CSC\C(=C\C)C=O	1664.8	Standard polar	33892256
2-[(Methylthio)methyl]-2-butenal	CSC\C(=C\C)C=O	1080.2	Standard non polar	33892256
2-[(Methylthio)methyl]-2-butenal	CSC\C(=C\C)C=O	1096.7	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 - 2-[(Methylthio)methyl]-2-butenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ls-9200000000-369f53e9d82267b87170	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-[(Methylthio)methyl]-2-butenal 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 - 2-[(Methylthio)methyl]-2-butenal 10V, Positive-QTOF	splash10-001i-3900000000-ad7cf424fb8a72c9ee9b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(Methylthio)methyl]-2-butenal 20V, Positive-QTOF	splash10-001i-9400000000-f19de4d3e8f84be1fbd6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(Methylthio)methyl]-2-butenal 40V, Positive-QTOF	splash10-0udi-9100000000-a59c4ae26c5c5b9c342e	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(Methylthio)methyl]-2-butenal 10V, Negative-QTOF	splash10-0002-9000000000-f9187d0a5e734095ebf7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(Methylthio)methyl]-2-butenal 20V, Negative-QTOF	splash10-000t-9100000000-29cd1035b5d7f45663e3	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(Methylthio)methyl]-2-butenal 40V, Negative-QTOF	splash10-0002-9000000000-e6df13e02bcf6b22267e	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(Methylthio)methyl]-2-butenal 10V, Positive-QTOF	splash10-03di-9000000000-c48dde0b891b164d09cd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(Methylthio)methyl]-2-butenal 20V, Positive-QTOF	splash10-0bt9-9000000000-767dd559aa40a6c0f34a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(Methylthio)methyl]-2-butenal 40V, Positive-QTOF	splash10-03dj-9000000000-bbf87851eca2300153cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(Methylthio)methyl]-2-butenal 10V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(Methylthio)methyl]-2-butenal 20V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(Methylthio)methyl]-2-butenal 40V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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
Membrane

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

FDB003437

KNApSAcK ID

Not Available

Chemspider ID

30776898

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57501028

PDB ID

Not Available

ChEBI ID

172409

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1037021

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-[(Methylthio)methyl]-2-butenal (HMDB0031370)

MOL for HMDB0031370 (2-[(Methylthio)methyl]-2-butenal)

3D MOL for HMDB0031370 (2-[(Methylthio)methyl]-2-butenal)

3D SDF for HMDB0031370 (2-[(Methylthio)methyl]-2-butenal)

3D-SDF for HMDB0031370 (2-[(Methylthio)methyl]-2-butenal)

PDB for HMDB0031370 (2-[(Methylthio)methyl]-2-butenal)

3D PDB for HMDB0031370 (2-[(Methylthio)methyl]-2-butenal)

SMILES for HMDB0031370 (2-[(Methylthio)methyl]-2-butenal)

INCHI for HMDB0031370 (2-[(Methylthio)methyl]-2-butenal)

Structure for HMDB0031370 (2-[(Methylthio)methyl]-2-butenal)

3D Structure for HMDB0031370 (2-[(Methylthio)methyl]-2-butenal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra