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Identification
YMDB IDYMDB01415
Name4-Mercapto-4-methylpentan-2-one
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description4-Mercapto-4-methylpentan-2-one is a volatile thiol and a major varietal aroma found in Sauvignon blanc wine and produced during fermentation. It is responsible for gooseberry-like aromas in Sauvignon blanc wines.
Structure
Thumb
Synonyms
  • 4-mercapto-4-methyl-2-pentanone
  • 4-methyl-4-mercapto-2-pentanone
  • 4-Methyl-4-sulfanyl-2-pentanone
  • 4-Methyl-4-thiolpentan-2-one
  • 4-sulfanyl-4-methylpentan-2-one
  • 4-Sulphanyl-4-methylpentan-2-one
  • 4-Methyl-4-mercaptopentan-2-one
  • 4-Methyl-4-sulphanyl-2-pentanone
  • 4-mercapto-4-Methyl-pentan-2-one
  • 4-mercapto-4-Methylpentan-2-one
  • 4-Methyl-4-mercapto-pentan-2-one
CAS number19872-52-7
WeightAverage: 132.224
Monoisotopic: 132.060885696
InChI KeyQRNZMFDCKKEPSX-UHFFFAOYSA-N
InChIInChI=1S/C6H12OS/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3
IUPAC Name4-methyl-4-sulfanylpentan-2-one
Traditional IUPAC Name4-methyl-4-sulfanylpentan-2-one
Chemical FormulaC6H12OS
SMILESCC(=O)CC(C)(C)S
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Alkylthiol
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.22 mg/mLALOGPS
logP2.01ALOGPS
logP1.27ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)9.92ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.78 m3·mol-1ChemAxon
Polarizability14.61 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
BlackcurrantFDB008119
Box treeFDB008119
Cat-urineFDB008119
MeatyFDB008119
SulfurousFDB008119
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-002f-9100000000-8e9ff8d3dd57a941e176View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-3900000000-f7c166c594ab2f5bd9e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-7900000000-415b660e2464f89dc70eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9100000000-cf87bb56a906d8284051View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001j-7900000000-67facb7cefc788001bd4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-9600000000-5a2f4ae474d4a47b0bebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9100000000-7653612fbae5886b1570View in MoNA
References
References:
  • Masneuf-Pomarede, I., Mansour, C., Murat, M. L., Tominaga, T., Dubourdieu, D. (2006). "Influence of fermentation temperature on volatile thiols concentrations in Sauvignon blanc wines." Int J Food Microbiol 108:385-390.16524635
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID77856
HMDB IDHMDB31519
Pubchem Compound ID88290
Kegg IDNot Available
ChemSpider ID79650
FOODB IDFDB008119
Wikipedia4-Mercapto-4-methylpentan-2-one
BioCyc IDNot Available