Showing Compound Card for Diacetone alcohol (CDB000590)

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Record Information
Version1.0
Created at2020-03-19 00:45:26 UTC
Updated at2020-11-18 16:35:19 UTC
CannabisDB IDCDB000590
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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 has also been detected as a volatile component in cannabis plant samples (PMID: 26657499 ). 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.
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 Weight116.16
Monoisotopic Molecular Weight116.0837
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
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-44 °CNot Available
Boiling Point166 °CWikipedia
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0031511
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]