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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:52:24 UTC

Update Date

2023-02-21 17:25:52 UTC

HMDB ID

HMDB0037621

Secondary Accession Numbers

HMDB37621

Metabolite Identification

Common Name

4-Methyl-4-(methylthio)-2-pentanone

Description

4-Methyl-4-(methylthio)-2-pentanone belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 4-Methyl-4-(methylthio)-2-pentanone is a blackcurrant, fruity, and green tasting compound. Based on a literature review very few articles have been published on 4-Methyl-4-(methylthio)-2-pentanone.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-methylthio-4-Methyl-2-pentanone	HMDB
Corps cassis	HMDB
FEMA 3376	HMDB
4-Methyl-4-(methylsulphanyl)pentan-2-one	Generator

Chemical Formula

C₇H₁₄OS

Average Molecular Weight

146.25

Monoisotopic Molecular Weight

146.07653576

IUPAC Name

4-methyl-4-(methylsulfanyl)pentan-2-one

Traditional Name

4-methyl-4-(methylsulfanyl)pentan-2-one

CAS Registry Number

23550-40-5

SMILES

CSC(C)(C)CC(C)=O

InChI Identifier

InChI=1S/C7H14OS/c1-6(8)5-7(2,3)9-4/h5H2,1-4H3

InChI Key

DHANVOSHQILVNQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Dialkylthioether
Sulfenyl compound
Thioether
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0037621)
Cytoplasm (HMDB: HMDB0037621)

Source

Exogenous

Exogenous (HMDB: HMDB0037621)

Food

Food (HMDB: HMDB0037621)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037621)

Biological role

Nutrient (HMDB: HMDB0037621)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	78.00 °C. @ 15.00 mm Hg	The Good Scents Company Information System
Water Solubility	7241 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.403 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.47 g/L	ALOGPS
logP	2.3	ALOGPS
logP	1.65	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	19.46	ChemAxon
pKa (Strongest Basic)	-7.3	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	42.43 m³·mol⁻¹	ChemAxon
Polarizability	16.5 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]+	132.537	31661259
DarkChem	[M-H]-	129.273	31661259
DeepCCS	[M+H]+	136.913	30932474
DeepCCS	[M-H]-	133.919	30932474
DeepCCS	[M-2H]-	170.896	30932474
DeepCCS	[M+Na]+	145.923	30932474
AllCCS	[M+H]+	130.3	32859911
AllCCS	[M+H-H2O]+	126.5	32859911
AllCCS	[M+NH4]+	134.0	32859911
AllCCS	[M+Na]+	135.0	32859911
AllCCS	[M-H]-	137.6	32859911
AllCCS	[M+Na-2H]-	140.5	32859911
AllCCS	[M+HCOO]-	143.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.07 minutes	32390414
Predicted by Siyang on May 30, 2022	13.8261 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.43 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1950.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	501.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	168.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	308.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	116.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	504.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	543.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1072.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	401.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1078.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	350.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	390.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	431.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	15.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methyl-4-(methylthio)-2-pentanone	CSC(C)(C)CC(C)=O	1445.0	Standard polar	33892256
4-Methyl-4-(methylthio)-2-pentanone	CSC(C)(C)CC(C)=O	1038.6	Standard non polar	33892256
4-Methyl-4-(methylthio)-2-pentanone	CSC(C)(C)CC(C)=O	1068.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Methyl-4-(methylthio)-2-pentanone,1TMS,isomer #1	CSC(C)(C)C=C(C)O[Si](C)(C)C	1197.1	Semi standard non polar	33892256
4-Methyl-4-(methylthio)-2-pentanone,1TMS,isomer #1	CSC(C)(C)C=C(C)O[Si](C)(C)C	1269.0	Standard non polar	33892256
4-Methyl-4-(methylthio)-2-pentanone,1TMS,isomer #2	C=C(CC(C)(C)SC)O[Si](C)(C)C	1246.5	Semi standard non polar	33892256
4-Methyl-4-(methylthio)-2-pentanone,1TMS,isomer #2	C=C(CC(C)(C)SC)O[Si](C)(C)C	1269.3	Standard non polar	33892256
4-Methyl-4-(methylthio)-2-pentanone,1TBDMS,isomer #1	CSC(C)(C)C=C(C)O[Si](C)(C)C(C)(C)C	1429.0	Semi standard non polar	33892256
4-Methyl-4-(methylthio)-2-pentanone,1TBDMS,isomer #1	CSC(C)(C)C=C(C)O[Si](C)(C)C(C)(C)C	1498.6	Standard non polar	33892256
4-Methyl-4-(methylthio)-2-pentanone,1TBDMS,isomer #2	C=C(CC(C)(C)SC)O[Si](C)(C)C(C)(C)C	1478.1	Semi standard non polar	33892256
4-Methyl-4-(methylthio)-2-pentanone,1TBDMS,isomer #2	C=C(CC(C)(C)SC)O[Si](C)(C)C(C)(C)C	1480.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9100000000-b34b8474bf53fffecd40	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone 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 - 4-Methyl-4-(methylthio)-2-pentanone 10V, Positive-QTOF	splash10-002b-1900000000-1a53f4ffbb741ea98a2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone 20V, Positive-QTOF	splash10-002b-9700000000-23f4a0282bbdeaeeb68b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone 40V, Positive-QTOF	splash10-001i-9300000000-eed5b23d28d9fa8744fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone 10V, Negative-QTOF	splash10-0002-8900000000-525fb0956ba51b5414ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone 20V, Negative-QTOF	splash10-0002-9200000000-8443ef0c55d7f8d9e868	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone 40V, Negative-QTOF	splash10-0002-9000000000-533fdf5b3a1506ad5b11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone 10V, Negative-QTOF	splash10-0002-9000000000-eaad97dc8afa1825e036	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone 20V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone 40V, Negative-QTOF	splash10-0002-9000000000-e1d92d2a30bee517d754	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone 10V, Positive-QTOF	splash10-001a-9000000000-d167e314b06f58c2ab36	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone 20V, Positive-QTOF	splash10-000w-9000000000-5a55968a2d9930b7910e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methyl-4-(methylthio)-2-pentanone 40V, Positive-QTOF	splash10-0005-9000000000-2959651c50a7ed2d2bb2	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]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB016735

KNApSAcK ID

Not Available

Chemspider ID

3870667

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4682590

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036031

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 4-Methyl-4-(methylthio)-2-pentanone (HMDB0037621)

MOL for HMDB0037621 (4-Methyl-4-(methylthio)-2-pentanone)

3D MOL for HMDB0037621 (4-Methyl-4-(methylthio)-2-pentanone)

3D SDF for HMDB0037621 (4-Methyl-4-(methylthio)-2-pentanone)

3D-SDF for HMDB0037621 (4-Methyl-4-(methylthio)-2-pentanone)

PDB for HMDB0037621 (4-Methyl-4-(methylthio)-2-pentanone)

3D PDB for HMDB0037621 (4-Methyl-4-(methylthio)-2-pentanone)

SMILES for HMDB0037621 (4-Methyl-4-(methylthio)-2-pentanone)

INCHI for HMDB0037621 (4-Methyl-4-(methylthio)-2-pentanone)

Structure for HMDB0037621 (4-Methyl-4-(methylthio)-2-pentanone)

3D Structure for HMDB0037621 (4-Methyl-4-(methylthio)-2-pentanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra