Showing Compound Card for 2-Hydroxyacetophenon (CDB000508)

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Record Information
Version1.0
Created at2020-03-19 00:40:51 UTC
Updated at2020-11-18 16:35:13 UTC
CannabisDB IDCDB000508
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Hydroxyacetophenon
Description2-hydroxyacetophenone, also known as benzoylcarbinol or glycolophenone, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 2-hydroxyacetophenone is a neutral, hydrohpobic compound that is largely insoluble in water. 2-hydroxyacetophenone has a sweet, honey, tropical, almond or herbal odor and a cinnamon, cherry or tobacco-like taste. It occurs naturally in a number of foods including roasted almonds, coffee, papaya, rum, sherry and tomatoes. 2-hydroxyacetophenone has also been reported to be found in Cannabis sativa (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha-HydroxyacetophenoneChEBI
BenzoylcarbinolChEBI
GlycolophenoneChEBI
Hydroxymethyl phenyl ketoneChEBI
Omega-hydroxyacetophenoneChEBI
Phenacyl alcoholChEBI
a-HydroxyacetophenoneGenerator
Α-hydroxyacetophenoneGenerator
1-Phenyl-2-hydroxyethanoneMeSH
Chemical FormulaC8H8O2
Average Molecular Weight136.15
Monoisotopic Molecular Weight136.0524
IUPAC Name2-hydroxy-1-phenylethan-1-one
Traditional Namehydroxyacetophenone
CAS Registry Number582-24-1
SMILES
OCC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,9H,6H2
InChI KeyZWVHTXAYIKBMEE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Aryl alkyl ketone
  • Benzoyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha-hydroxy ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.74ALOGPS
logP0.71ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)13.79ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.16 m³·mol⁻¹ChemAxon
Polarizability14.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-Hydroxyacetophenon, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxyacetophenon, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxyacetophenon, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Hydroxyacetophenon, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-2900000000-60bcee901b07601d67a22020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-00di-2900000000-96e8da4e6b6475313e9f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 9V, positivesplash10-014i-0900000000-ce4486dc6a681e0ac4fd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-2900000000-7187c0bc010adbe32f8c2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-8c990636d1cc216496442019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-1900000000-3b00133362e3d5def7f12019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kdj-9400000000-403673898c31e86ad1c72019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-93880b12f41b109543df2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0550-4900000000-bd9324de0ada6091ef742019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3759365e51eaca7c97262019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-1900000000-34822d496c43ef3dc0d72021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-7900000000-c37439bf6f96ad724dbb2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fbc-9000000000-6f418f58c2faf645c8782021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-6569497ba1e79dbeb1b22021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-5900000000-915c0c810fb84e9bae392021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-effd11e920260e48536d2021-10-12View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0245150
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID61765
KEGG Compound IDC07189
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHydroxyacetophenone
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID28341
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. 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 ]