ZINGERONE (CHEM007870)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:31:11 UTC
Update Date2016-11-09 01:13:41 UTC
Accession NumberCHEM007870
Identification
Common NameZINGERONE
ClassSmall Molecule
DescriptionA methyl ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at positions 3 and 4 by methoxy and hydroxy groups respectively. The major pungent component in ginger.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(0)-ParadolChEBI
(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketoneChEBI
2-(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketoneChEBI
3-Methoxy-4-hydroxybenzylacetoneChEBI
4-(3-Methoxy-4-hydroxyphenyl)-2-butanoneChEBI
4-(3-Methoxy-4-hydroxyphenyl)butan-2-oneChEBI
4-(4-Hydroxy-3-methoxyphenyl)-2-butanoneChEBI
4-Hydroxy-3-methoxybenzylacetoneChEBI
[0]-ParadolChEBI
GingeroneChEBI
VanillylacetoneChEBI
ZingheroneChEBI
ZingiberoneChEBI
0 ParadolMeSH
4-(4-Hydroxy-3-methoxyphenyl)butan-2-oneMeSH
Vanillyl acetoneMeSH
4-(4-Hydroxy-3-methoxy-phenyl)-butan-2-oneHMDB
4-(4-Hydroxy-3-methoxyphenyl)-2-butanone, 9ci, 8ciHMDB
FEMA 3124HMDB
[0]ParadolHMDB
Chemical FormulaC11H14O3
Average Molecular Mass194.227 g/mol
Monoisotopic Mass194.094 g/mol
CAS Registry Number122-48-5
IUPAC Name4-(4-hydroxy-3-methoxyphenyl)butan-2-one
Traditional Namezingerone
SMILESCOC1=C(O)C=CC(CCC(C)=O)=C1
InChI IdentifierInChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3
InChI KeyOJYLAHXKWMRDGS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ketone
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.57 g/LALOGPS
logP2.02ALOGPS
logP1.92ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.96 m³·mol⁻¹ChemAxon
Polarizability20.95 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-5900000000-42ac2a1b364f92df5152Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9370000000-988fce303c33c65d61c8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-4c68e7e311ed162223a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004s-1900000000-e0ac7417df02644e0761Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9l-7900000000-2f6d6b18947145fb0dbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-8f3da5e61712d1ffacb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-53b85d6dc1005c5d4df0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-f12fadc90e8da514347fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-9700000000-885efff123d09c229869Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9500000000-6b1a5bf42da790be18f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059m-7900000000-fe627d4904dd2c51d333Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-5d0af36deea574d177beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-0900000000-f505f559b715ddb1b325Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6900000000-251b2e68bd1f83dfb714Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0032590
FooDB IDFDB010527
Phenol Explorer IDNot Available
KNApSAcK IDC00056662
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkZingerone
Chemspider ID28952
ChEBI ID68657
PubChem Compound ID31211
Kegg Compound IDC17497
YMDB IDYMDB01809
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18472135
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18670185
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19367122
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19459736
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19463966
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20211236
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20606379
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20713432
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=20799069
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21335001
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21551955
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21769642
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=21802408
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=21929329
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22173270
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22329630
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22596078
18. Morimoto Y, Shibata Y: Effects of various fragrant ingredients on desmopressin-induced fluid retention in mice. Yakugaku Zasshi. 2010 Jul;130(7):983-7.
19. Kabuto H, Nishizawa M, Tada M, Higashio C, Shishibori T, Kohno M: Zingerone [4-(4-hydroxy-3-methoxyphenyl)-2-butanone] prevents 6-hydroxydopamine-induced dopamine depression in mouse striatum and increases superoxide scavenging activity in serum. Neurochem Res. 2005 Mar;30(3):325-32.
20. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.