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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:48 UTC
Update Date2021-10-13 06:16:16 UTC
HMDB IDHMDB0031519
Secondary Accession Numbers
  • HMDB31519
Metabolite Identification
Common Name4-Mercapto-4-methyl-2-pentanone
Description4-Mercapto-4-methyl-2-pentanone, also known as 4-sulfanyl-4-methylpentan-2-one or 4-methyl-4-sulfanyl-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. Thus, 4-mercapto-4-methyl-2-pentanone is considered to be an oxygenated hydrocarbon. 4-Mercapto-4-methyl-2-pentanone is a blackcurrant, box tree, and cat-urine tasting compound. 4-Mercapto-4-methyl-2-pentanone has been detected, but not quantified in, alcoholic beverages and grape wine. This could make 4-mercapto-4-methyl-2-pentanone a potential biomarker for the consumption of these foods. 4-Mercapto-4-methyl-2-pentanone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-Mercapto-4-methyl-2-pentanone.
Structure
Data?1563862136
Synonyms
ValueSource
4-Methyl-4-mercapto-2-pentanoneChEBI
4-Methyl-4-mercaptopentan-2-oneChEBI
4-Methyl-4-sulfanyl-2-pentanoneChEBI
4-Methyl-4-thiolpentan-2-oneChEBI
4-Sulfanyl-4-methylpentan-2-oneChEBI
4-Sulphanyl-4-methylpentan-2-oneChEBI
4-Methyl-4-sulphanyl-2-pentanoneGenerator
4-mercapto-4-Methyl-pentan-2-oneHMDB
4-mercapto-4-Methylpentan-2-oneHMDB
4-Methyl-4-mercapto-pentan-2-oneHMDB
4-Mercapto-4-methyl-2-pentanoneChEBI
Chemical FormulaC6H12OS
Average Molecular Weight132.224
Monoisotopic Molecular Weight132.060885696
IUPAC Name4-methyl-4-sulfanylpentan-2-one
Traditional Name4-methyl-4-sulfanylpentan-2-one
CAS Registry Number19872-52-7
SMILES
CC(=O)CC(C)(C)S
InChI Identifier
InChI=1S/C6H12OS/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3
InChI KeyQRNZMFDCKKEPSX-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Alkylthiol
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point181.65 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility10970 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.432 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.22 g/LALOGPS
logP10(2.01) g/LALOGPS
logP10(1.27) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Acidic)9.92ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.78 m³·mol⁻¹ChemAxon
Polarizability14.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.18831661259
DarkChem[M-H]-124.02431661259
DeepCCS[M+H]+133.70530932474
DeepCCS[M-H]-131.25630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Mercapto-4-methyl-2-pentanoneCC(=O)CC(C)(C)S1437.8Standard polar33892256
4-Mercapto-4-methyl-2-pentanoneCC(=O)CC(C)(C)S934.4Standard non polar33892256
4-Mercapto-4-methyl-2-pentanoneCC(=O)CC(C)(C)S942.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Mercapto-4-methyl-2-pentanone,1TMS,isomer #1CC(=O)CC(C)(C)S[Si](C)(C)C1168.6Semi standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,1TMS,isomer #1CC(=O)CC(C)(C)S[Si](C)(C)C1198.1Standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,1TMS,isomer #2CC(=CC(C)(C)S)O[Si](C)(C)C1123.4Semi standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,1TMS,isomer #2CC(=CC(C)(C)S)O[Si](C)(C)C1212.0Standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,1TMS,isomer #3C=C(CC(C)(C)S)O[Si](C)(C)C1139.4Semi standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,1TMS,isomer #3C=C(CC(C)(C)S)O[Si](C)(C)C1178.7Standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,2TMS,isomer #1CC(=CC(C)(C)S[Si](C)(C)C)O[Si](C)(C)C1337.8Semi standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,2TMS,isomer #1CC(=CC(C)(C)S[Si](C)(C)C)O[Si](C)(C)C1391.3Standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,2TMS,isomer #2C=C(CC(C)(C)S[Si](C)(C)C)O[Si](C)(C)C1356.1Semi standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,2TMS,isomer #2C=C(CC(C)(C)S[Si](C)(C)C)O[Si](C)(C)C1409.9Standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,1TBDMS,isomer #1CC(=O)CC(C)(C)S[Si](C)(C)C(C)(C)C1410.7Semi standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,1TBDMS,isomer #1CC(=O)CC(C)(C)S[Si](C)(C)C(C)(C)C1435.2Standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,1TBDMS,isomer #2CC(=CC(C)(C)S)O[Si](C)(C)C(C)(C)C1332.6Semi standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,1TBDMS,isomer #2CC(=CC(C)(C)S)O[Si](C)(C)C(C)(C)C1433.2Standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,1TBDMS,isomer #3C=C(CC(C)(C)S)O[Si](C)(C)C(C)(C)C1357.8Semi standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,1TBDMS,isomer #3C=C(CC(C)(C)S)O[Si](C)(C)C(C)(C)C1378.2Standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,2TBDMS,isomer #1CC(=CC(C)(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1825.9Semi standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,2TBDMS,isomer #1CC(=CC(C)(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1843.5Standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,2TBDMS,isomer #2C=C(CC(C)(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1829.4Semi standard non polar33892256
4-Mercapto-4-methyl-2-pentanone,2TBDMS,isomer #2C=C(CC(C)(C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1836.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Mercapto-4-methyl-2-pentanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9100000000-8e9ff8d3dd57a941e1762016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Mercapto-4-methyl-2-pentanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 10V, Positive-QTOFsplash10-00lr-3900000000-f7c166c594ab2f5bd9e62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 20V, Positive-QTOFsplash10-00lr-7900000000-415b660e2464f89dc70e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 40V, Positive-QTOFsplash10-001i-9100000000-cf87bb56a906d82840512016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 10V, Negative-QTOFsplash10-001j-7900000000-67facb7cefc788001bd42016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 20V, Negative-QTOFsplash10-001j-9600000000-5a2f4ae474d4a47b0beb2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 40V, Negative-QTOFsplash10-001i-9100000000-7653612fbae5886b15702016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 10V, Negative-QTOFsplash10-0002-9100000000-5b554632046f18361f552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 20V, Negative-QTOFsplash10-001i-9000000000-942ac689538269d6ca7b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 40V, Negative-QTOFsplash10-0089-9000000000-e5eeba93e8d05760b98b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 10V, Positive-QTOFsplash10-004m-9000000000-3a7dea1da5a4cd9270372021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 20V, Positive-QTOFsplash10-004l-9000000000-99d12173b922c0f09a402021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Mercapto-4-methyl-2-pentanone 40V, Positive-QTOFsplash10-002f-9000000000-53764c8f862c3e9527d92021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008119
KNApSAcK IDNot Available
Chemspider ID79650
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Mercapto-4-methyl-2-pentanone
METLIN IDNot Available
PubChem Compound88290
PDB IDNot Available
ChEBI ID77856
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1038251
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .