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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:45 UTC
Update Date2023-02-21 17:20:42 UTC
HMDB IDHMDB0031511
Secondary Accession Numbers
  • HMDB31511
Metabolite Identification
Common NameDiacetone alcohol
DescriptionDiacetone alcohol 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. Diacetone alcohol is found, on average, in the highest concentration within milk (cow). Diacetone alcohol has also been detected, but not quantified in, several different foods, such as fruits, mung beans (Vigna radiata), papayas (Carica papaya), and soy beans (Glycine max). This could make diacetone alcohol a potential biomarker for the consumption of these foods. Diacetone alcohol 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 small amount of articles have been published on Diacetone alcohol.
Structure
Data?1677000042
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-44 °CNot Available
Boiling Point164.00 to 166.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mL at 25 °CNot Available
LogP0.026 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility145 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+125.47931661259
DarkChem[M-H]-120.09231661259
DeepCCS[M+H]+130.95330932474
DeepCCS[M-H]-128.46830932474
DeepCCS[M-2H]-164.8130932474
DeepCCS[M+Na]+139.93130932474
AllCCS[M+H]+126.632859911
AllCCS[M+H-H2O]+122.432859911
AllCCS[M+NH4]+130.532859911
AllCCS[M+Na]+131.732859911
AllCCS[M-H]-128.032859911
AllCCS[M+Na-2H]-131.432859911
AllCCS[M+HCOO]-135.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Diacetone alcoholCC(=O)CC(C)(C)O1322.1Standard polar33892256
Diacetone alcoholCC(=O)CC(C)(C)O823.4Standard non polar33892256
Diacetone alcoholCC(=O)CC(C)(C)O857.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Diacetone alcohol,1TMS,isomer #1CC(=O)CC(C)(C)O[Si](C)(C)C1036.9Semi standard non polar33892256
Diacetone alcohol,1TMS,isomer #2CC(=CC(C)(C)O)O[Si](C)(C)C1052.9Semi standard non polar33892256
Diacetone alcohol,1TMS,isomer #3C=C(CC(C)(C)O)O[Si](C)(C)C1045.8Semi standard non polar33892256
Diacetone alcohol,2TMS,isomer #1CC(=CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C1188.8Semi standard non polar33892256
Diacetone alcohol,2TMS,isomer #1CC(=CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C1146.3Standard non polar33892256
Diacetone alcohol,2TMS,isomer #2C=C(CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C1197.4Semi standard non polar33892256
Diacetone alcohol,2TMS,isomer #2C=C(CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C1198.4Standard non polar33892256
Diacetone alcohol,1TBDMS,isomer #1CC(=O)CC(C)(C)O[Si](C)(C)C(C)(C)C1264.8Semi standard non polar33892256
Diacetone alcohol,1TBDMS,isomer #2CC(=CC(C)(C)O)O[Si](C)(C)C(C)(C)C1269.9Semi standard non polar33892256
Diacetone alcohol,1TBDMS,isomer #3C=C(CC(C)(C)O)O[Si](C)(C)C(C)(C)C1253.9Semi standard non polar33892256
Diacetone alcohol,2TBDMS,isomer #1CC(=CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1626.1Semi standard non polar33892256
Diacetone alcohol,2TBDMS,isomer #1CC(=CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1617.8Standard non polar33892256
Diacetone alcohol,2TBDMS,isomer #2C=C(CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1632.7Semi standard non polar33892256
Diacetone alcohol,2TBDMS,isomer #2C=C(CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1642.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Diacetone alcohol EI-B (Non-derivatized)splash10-052f-9000000000-8448b11a23b1992dae6d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diacetone alcohol EI-B (Non-derivatized)splash10-052f-9000000000-8448b11a23b1992dae6d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diacetone alcohol GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-d76ed4086dd090eb35642017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diacetone alcohol GC-MS (1 TMS) - 70eV, Positivesplash10-008c-9800000000-7f63674d7679f4e1ffdf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diacetone alcohol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diacetone alcohol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Diacetone alcohol LC-ESI-QFT , positive-QTOFsplash10-014i-0900000000-3c88eab79df5c6518f022020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diacetone alcohol LC-ESI-QTOF 35V, positive-QTOFsplash10-0002-9000000000-572e128698f79d45b0ee2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diacetone alcohol LC-ESI-QFT , negative-QTOFsplash10-014i-1900000000-ee905ffae28bda8d89402020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Diacetone alcohol 35V, Positive-QTOFsplash10-0002-9000000000-ce506b6d6b03fb57f31b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetone alcohol 10V, Positive-QTOFsplash10-0002-9200000000-28461077d208c6f1dcdc2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetone alcohol 20V, Positive-QTOFsplash10-000t-9100000000-7a7d9778efaa6f5729882016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetone alcohol 40V, Positive-QTOFsplash10-001i-9000000000-73e251e1e66b5c21ea3e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetone alcohol 10V, Negative-QTOFsplash10-014i-4900000000-5c12de142cf98d10473d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetone alcohol 20V, Negative-QTOFsplash10-014j-9800000000-99f2184179878c0cef4a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetone alcohol 40V, Negative-QTOFsplash10-0002-9000000000-357cee4d7e761ae814032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetone alcohol 10V, Negative-QTOFsplash10-014j-5900000000-d8f659fff4ba77520c792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetone alcohol 20V, Negative-QTOFsplash10-0a4j-9000000000-54862b15a43515a383ae2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetone alcohol 40V, Negative-QTOFsplash10-0a4i-9000000000-8218e01622fc7846c2622021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetone alcohol 10V, Positive-QTOFsplash10-0535-9000000000-b03f6065de8ca3b84c542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetone alcohol 20V, Positive-QTOFsplash10-0a5c-9000000000-44d30b07046cd79b826f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diacetone alcohol 40V, Positive-QTOFsplash10-0006-9000000000-de6bdbea5fe400146c1f2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1203631
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .