You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:39 UTC
Update Date2019-07-23 06:11:19 UTC
HMDB IDHMDB0032590
Secondary Accession Numbers
  • HMDB32590
Metabolite Identification
Common NameZingerone
DescriptionZingerone is found in fruits. Reputed pungent principle of ginger (Zingiber officinale). Flavour material used in imitation fruit flavours, ginger beer, ginger ale etc. Also present in cranberry, raspberry and mang
Structure
Data?1563862279
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
4-(4-Hydroxy-3-methoxy-phenyl)-butan-2-oneHMDB
4-(4-Hydroxy-3-methoxyphenyl)-2-butanone, 9ci, 8ciHMDB
4-(4-Hydroxy-3-methoxyphenyl)butan-2-oneHMDB
FEMA 3124HMDB
Vanillyl acetoneHMDB
[0]ParadolHMDB
Chemical FormulaC11H14O3
Average Molecular Weight194.2271
Monoisotopic Molecular Weight194.094294314
IUPAC Name4-(4-hydroxy-3-methoxyphenyl)butan-2-one
Traditional Namezingerone
CAS Registry Number122-48-5
SMILES
COC1=C(O)C=CC(CCC(C)=O)=C1
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point41 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-5900000000-42ac2a1b364f92df5152JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9370000000-988fce303c33c65d61c8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-4c68e7e311ed162223a5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004s-1900000000-e0ac7417df02644e0761JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9l-7900000000-2f6d6b18947145fb0dbfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-8f3da5e61712d1ffacb3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-53b85d6dc1005c5d4df0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-f12fadc90e8da514347fJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010527
KNApSAcK IDNot Available
Chemspider ID28952
KEGG Compound IDC17497
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkZingerone
METLIN IDNot Available
PubChem Compound31211
PDB IDNot Available
ChEBI ID68657
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Morimoto Y, Shibata Y: Effects of various fragrant ingredients on desmopressin-induced fluid retention in mice. Yakugaku Zasshi. 2010 Jul;130(7):983-7. [PubMed:20606379 ]
  2. 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. [PubMed:16018576 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Zingerone → 3,4,5-trihydroxy-6-[2-methoxy-4-(3-oxobutyl)phenoxy]oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Zingerone → [2-methoxy-4-(3-oxobutyl)phenyl]oxidanesulfonic aciddetails