Showing metabocard for Diacetone alcohol (BMDB0031511)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:41:05 UTC
Update Date2020-06-04 19:22:34 UTC
BMDB IDBMDB0031511
Secondary Accession Numbers
  • BMDB31511
Metabolite Identification
Common NameDiacetone alcohol
DescriptionDiacetone alcohol, also known as pyranton, belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group. Thus, diacetone alcohol is considered to be an oxygenated hydrocarbon lipid molecule. Diacetone alcohol exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Methyl-2-pentanol-4-oneChEBI
4-Hydroxy-2-keto-4-methylpentaneChEBI
4-Hydroxy-4-methyl-2-pentanoneChEBI
4-Hydroxy-4-methylpentan-2-oneChEBI
AcetonyldimethylcarbinolChEBI
DiacetonalkoholChEBI
Diacetone-alcoolChEBI
Diacetonyl alcoholChEBI
Dimethyl acetonyl carbinolChEBI
(CH3)2C(OH)CH2C(O)CH3HMDB
2-Hydroxy-2-methyl-4-pentanoneHMDB
2-Methyl-3-pentanol-4-oneHMDB
4-Hydroxy-4-methyl pentan-2-oneHMDB
4-Hydroxy-4-methyl-pentan-2-ONHMDB
4-Hydroxy-4-methylpentanoneHMDB
4-Hydroxy-4-methylpentanone-2HMDB
4-Idrossi-4-metil-pentan-2-oneHMDB
4-Methyl-2-pentanon-4-olHMDB
4-Methyl-4-hydroxy-2-pentanoneHMDB
DiacetonalcoholHMDB
DiacetonalcoolHMDB
DiacetoneHMDB
DiacetonealcoolHMDB
Diketone alcoholHMDB
Hydroxy-4-methyl-2-pentanoneHMDB
PyrantonHMDB
Pyranton aHMDB
PyratonHMDB
TyrantonHMDB
Diacetone alcoholMeSH
Chemical FormulaC6H12O2
Average Molecular Weight116.1583
Monoisotopic Molecular Weight116.083729628
IUPAC Name4-hydroxy-4-methylpentan-2-one
Traditional Namediacetone alcohol
CAS Registry Number123-42-2
SMILES
CC(=O)CC(C)(C)O
InChI Identifier
InChI=1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3
InChI KeySWXVUIWOUIDPGS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentBeta-hydroxy ketones
Alternative Parents
Substituents
  • Beta-hydroxy ketone
  • Tertiary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-44 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.04ALOGPS
logP0.22ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)15.21ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity31.65 m³·mol⁻¹ChemAxon
Polarizability12.76 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-8448b11a23b1992dae6dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-8448b11a23b1992dae6dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-d76ed4086dd090eb3564View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-008c-9800000000-7f63674d7679f4e1ffdfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-3c88eab79df5c6518f02View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0002-9000000000-572e128698f79d45b0eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-1900000000-ee905ffae28bda8d8940View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-ce506b6d6b03fb57f31bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9200000000-28461077d208c6f1dcdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-9100000000-7a7d9778efaa6f572988View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-73e251e1e66b5c21ea3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4900000000-5c12de142cf98d10473dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-9800000000-99f2184179878c0cef4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-357cee4d7e761ae81403View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-5900000000-d8f659fff4ba77520c79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-9000000000-54862b15a43515a383aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-8218e01622fc7846c262View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0535-9000000000-b03f6065de8ca3b84c54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5c-9000000000-44d30b07046cd79b826fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-de6bdbea5fe400146c1fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified0.58 +/- 0.84 mg/100g dry matter contentNot SpecifiedNot Specified
Normal
    • Brigitta Gaspardo...
 details
MilkDetected and Quantified0.66 +/- 0.45 mg/100g dry matter contentNot SpecifiedNot Specified
Normal
    • Brigitta Gaspardo...
 details
MilkDetected and Quantified0.000887 +/- 0.00115 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.000443 +/- 0.000975 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.00133 +/- 0.00222 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0031511
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008104
KNApSAcK IDC00052715
Chemspider ID13838151
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiacetone_alcohol
METLIN IDNot Available
PubChem Compound31256
PDB IDNot Available
ChEBI ID55381
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77. [PubMed:12463694 ]
  2. Brigitta Gaspardo, Giuseppe Procida, Saša Volarič, Sandy Sgorlon & Bruno Stefanon (2009). Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009. Italian Journal of Animal Science .