Record Information
Version1.0
Creation date2010-04-08 22:07:55 UTC
Update date2020-09-17 15:35:02 UTC
Primary IDFDB008104
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDiacetone alcohol
DescriptionDiacetone alcohol, sometimes referred to as DAA, 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. Diacetone alcohol is an organic compound with the chemical formula CH3C(O)CH2C(OH)(CH3)2. Diacetone alcohol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a colorless liquid, used as a solvent and a common synthetic intermediate used for the preparation of other compounds. Diacetone alcohol is found in the highest concentration in cow milk but it has also been detected, not quantified, in several different foods, such as fruits, mung beans, papaya, and soybeans. Diacetone alcohol is commercially used in cellulose ester lacquers, particularly of the brushing type, where it produces brilliant gloss and a hard film and where its lack of odor is desirable. It is used in lacquer thinners, dopes, wood stains, wood preservatives and printing pastes, in coating compositions for paper and textiles, permanent markers, in making artificial silk and leather, in imitation gold leaf, in celluloid cements, as a preservative for animal tissue, in metal cleaning compounds, in the manufacture of photographic film, and in hydraulic brake fluids, where it is usually mixed with an equal volume of castor oil.
CAS Number123-42-2
Structure
Thumb
Synonyms
SynonymSource
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
2-Pentanone, 4-hydroxy-4-methyl-biospider
4-Hydroxy-4-methyl-pentan-2-onbiospider
Diacetonalkohol(german)biospider
Diacetone alcohol [UN1148] [Flammable liquid]biospider
Pyranton Adb_source
Predicted 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
Chemical FormulaC6H12O2
IUPAC name4-hydroxy-4-methylpentan-2-one
InChI IdentifierInChI=1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3
InChI KeySWXVUIWOUIDPGS-UHFFFAOYSA-N
Isomeric SMILESCC(=O)CC(C)(C)O
Average Molecular Weight116.1583
Monoisotopic Molecular Weight116.083729628
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.04%; H 10.41%; O 27.55%DFC
Melting PointMp -44°DFC
Boiling PointBp11 63-64°DFC
Experimental Water Solubility1000 mg/mL at 25 oCLANDE,SS et al. (1976)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSDiacetone alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-8448b11a23b1992dae6dSpectrum
GC-MSDiacetone alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-8448b11a23b1992dae6dSpectrum
Predicted GC-MSDiacetone alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9000000000-d76ed4086dd090eb3564Spectrum
Predicted GC-MSDiacetone alcohol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-008c-9800000000-7f63674d7679f4e1ffdfSpectrum
Predicted GC-MSDiacetone alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDiacetone alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-3c88eab79df5c6518f022020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0002-9000000000-572e128698f79d45b0ee2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-1900000000-ee905ffae28bda8d89402020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-ce506b6d6b03fb57f31b2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9200000000-28461077d208c6f1dcdc2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-9100000000-7a7d9778efaa6f5729882016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-73e251e1e66b5c21ea3e2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4900000000-5c12de142cf98d10473d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-9800000000-99f2184179878c0cef4a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-357cee4d7e761ae814032016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-5900000000-d8f659fff4ba77520c792021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-9000000000-54862b15a43515a383ae2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-8218e01622fc7846c2622021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0535-9000000000-b03f6065de8ca3b84c542021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5c-9000000000-44d30b07046cd79b826f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-de6bdbea5fe400146c1f2021-09-24View Spectrum
NMRNot Available
ChemSpider ID13838151
ChEMBL IDCHEMBL3182048
KEGG Compound IDNot Available
Pubchem Compound ID31256
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31511
CRC / DFC (Dictionary of Food Compounds) IDDCB35-L:DCB35-L
EAFUS IDNot Available
Dr. Duke ID4-HYDROXY-4-METHYL-PENTAN-2-ONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).