Showing Compound Card for p-Hydroxyacetophenone (CDB005786)

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Record Information
Version1.0
Created at2020-04-27 16:56:27 UTC
Updated at2022-12-13 19:31:28 UTC
CannabisDB IDCDB005786
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namep-Hydroxyacetophenone
Description4'-Hydroxyacetophenone or p-Hydroxyacetophenone, also known as 4-acetylphenol or piceol, 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. 4'-Hydroxyacetophenone exists as a white to beige crystalline powder and is very soluble in water. It has a a mild, sweet, floral, balsamic odor and a very bland taste. It is used in the cosmetic industry as a perfuming agent and as an antioxidant. Industrially, 4'-Hydroxyacetophenone is used in the synthesis of several pharmaceutical drugs including octopamine, sotalol, bamethan, and dyclonine. 4'-Hydroxyacetophenone occurs naturally in many plants and plant foods and has been detected in coffee, cloudberries, cranberries, mangos, sweet oranges, sherry and in the needles and in mycorrhizal roots of the Norway spruce (Picea abies) (PMID: 2364913 ; PMID: 24197010 ). 4'-Hydroxyacetophenone is a potent xanthine oxidase inhibitor (PMID: 24712453 ) that appears to be even more potent than allipurinol. It is also one of several phenolic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4-Hydroxyphenyl)ethan-1-oneChEBI
4-AcetylphenolChEBI
4-HydroxyacetophenoneChEBI
Methyl p-hydroxyphenyl ketoneChEBI
p-HydroxyacetophenoneChEBI
p-Hydroxyphenyl methyl ketoneChEBI
Para-hydroxyacetophenoneChEBI
1-(4-Hydroxyphenyl)ethanoneMeSH
PiceolMeSH
1-(4-Hydroxyphenyl)-1-ethanonePhytoBank
4-AcetophenolPhytoBank
4-Hydroxyphenyl methyl ketonePhytoBank
4-HydroxyphenylethanonePhytoBank
4'-HydroxyacetophenonePhytoBank
4’-HydroxyacetophenonePhytoBank
Methyl 4-hydroxyphenyl ketonePhytoBank
p-AcetophenolPhytoBank
p-AcetylphenolPhytoBank
Chemical FormulaC8H8O2
Average Molecular Weight136.15
Monoisotopic Molecular Weight136.0524
IUPAC Name1-(4-hydroxyphenyl)ethan-1-one
Traditional Name4-hydroxyacetophenone
CAS Registry Number99-93-4
SMILES
CC(=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O2/c1-6(9)7-2-4-8(10)5-3-7/h2-5,10H,1H3
InChI KeyTXFPEBPIARQUIG-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
  • Acetophenone
  • Aryl alkyl ketone
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.62ALOGPS
logP1.23ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.79ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.44 m³·mol⁻¹ChemAxon
Polarizability14.03 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-MSp-Hydroxyacetophenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00du-7900000000-d662d6422b3203ce6789Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-000i-0900000000-d0c8d0e2664443ed89872020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 9V, positivesplash10-0002-9000000000-b74cf4499a634c9ffb732020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-9e4c5c6c3c991ce66f112016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-2f9b3f426dd159391ac12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9500000000-45be089438cc4e1568752016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-41d0b95e36341e40ba732016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-ca421e03a2bcc4aa7b122016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9600000000-4735be11aa27c97b17402016-08-04View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Island HoneyDetected and Quantified0.00643 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.00603 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.00679 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0167830
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010503
KNApSAcK IDC00002698
Chemspider IDNot Available
KEGG Compound IDC10700
BioCyc IDCPD-10598
BiGG IDNot Available
Wikipedia LinkPiceol
METLIN IDNot Available
PubChem Compound7469
PDB IDNot Available
ChEBI ID28032
References
General References
  1. Lokke H: Picein and piceol concentrations in Norway spruce. Ecotoxicol Environ Saf. 1990 Jun;19(3):301-9. doi: 10.1016/0147-6513(90)90032-z. [PubMed:2364913 ]
  2. Munzenberger B, Heilemann J, Strack D, Kottke I, Oberwinkler F: Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce. Planta. 1990 Aug;182(1):142-8. doi: 10.1007/BF00239996. [PubMed:24197010 ]
  3. Chu YH, Chen CJ, Wu SH, Hsieh JF: Inhibition of xanthine oxidase by Rhodiola crenulata extracts and their phytochemicals. J Agric Food Chem. 2014 Apr 30;62(17):3742-9. doi: 10.1021/jf5004094. Epub 2014 Apr 18. [PubMed:24712453 ]