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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:39 UTC
Update Date2022-03-07 02:53:23 UTC
HMDB IDHMDB0032590
Secondary Accession Numbers
  • HMDB32590
Metabolite Identification
Common NameZingerone
DescriptionZingerone, also known as vanillylacetone or [0]-paradol, 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. Zingerone is a sweet, animal, and clove tasting compound. Zingerone is found, on average, in the highest concentration within pot marjorams (Origanum onites) and gingers (Zingiber officinale). Zingerone has also been detected, but not quantified in, fruits and herbs and spices. This could make zingerone a potential biomarker for the consumption of these foods. Zingerone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Zingerone.
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
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 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
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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point41 °CNot Available
Boiling Point141.00 to 0.50 °C. @ 0.00 mm HgThe Good Scents Company Information System
Water Solubility3571 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.168 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.95831661259
DarkChem[M-H]-144.79831661259
DeepCCS[M+H]+146.35330932474
DeepCCS[M-H]-143.45530932474
DeepCCS[M-2H]-179.9230932474
DeepCCS[M+Na]+155.45830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ZingeroneCOC1=C(O)C=CC(CCC(C)=O)=C12838.4Standard polar33892256
ZingeroneCOC1=C(O)C=CC(CCC(C)=O)=C11599.4Standard non polar33892256
ZingeroneCOC1=C(O)C=CC(CCC(C)=O)=C11641.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Zingerone,1TMS,isomer #1COC1=CC(CCC(C)=O)=CC=C1O[Si](C)(C)C1769.5Semi standard non polar33892256
Zingerone,1TMS,isomer #2COC1=CC(CC=C(C)O[Si](C)(C)C)=CC=C1O1865.0Semi standard non polar33892256
Zingerone,1TMS,isomer #3C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C1809.7Semi standard non polar33892256
Zingerone,2TMS,isomer #1COC1=CC(CC=C(C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1915.7Semi standard non polar33892256
Zingerone,2TMS,isomer #1COC1=CC(CC=C(C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1870.9Standard non polar33892256
Zingerone,2TMS,isomer #2C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C1837.0Semi standard non polar33892256
Zingerone,2TMS,isomer #2C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C1829.9Standard non polar33892256
Zingerone,1TBDMS,isomer #1COC1=CC(CCC(C)=O)=CC=C1O[Si](C)(C)C(C)(C)C2009.5Semi standard non polar33892256
Zingerone,1TBDMS,isomer #2COC1=CC(CC=C(C)O[Si](C)(C)C(C)(C)C)=CC=C1O2116.3Semi standard non polar33892256
Zingerone,1TBDMS,isomer #3C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C2044.6Semi standard non polar33892256
Zingerone,2TBDMS,isomer #1COC1=CC(CC=C(C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2412.3Semi standard non polar33892256
Zingerone,2TBDMS,isomer #1COC1=CC(CC=C(C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2358.9Standard non polar33892256
Zingerone,2TBDMS,isomer #2C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C2300.6Semi standard non polar33892256
Zingerone,2TBDMS,isomer #2C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C2291.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Zingerone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-5900000000-42ac2a1b364f92df51522016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zingerone GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9370000000-988fce303c33c65d61c82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zingerone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zingerone 10V, Positive-QTOFsplash10-002b-0900000000-4c68e7e311ed162223a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zingerone 20V, Positive-QTOFsplash10-004s-1900000000-e0ac7417df02644e07612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zingerone 40V, Positive-QTOFsplash10-0f9l-7900000000-2f6d6b18947145fb0dbf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zingerone 10V, Negative-QTOFsplash10-0006-0900000000-8f3da5e61712d1ffacb32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zingerone 20V, Negative-QTOFsplash10-0006-2900000000-53b85d6dc1005c5d4df02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zingerone 40V, Negative-QTOFsplash10-0a4i-5900000000-f12fadc90e8da514347f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zingerone 10V, Negative-QTOFsplash10-0a4l-9700000000-885efff123d09c2298692021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zingerone 20V, Negative-QTOFsplash10-0a4i-9500000000-6b1a5bf42da790be18f42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zingerone 40V, Negative-QTOFsplash10-059m-7900000000-fe627d4904dd2c51d3332021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zingerone 10V, Positive-QTOFsplash10-000i-0900000000-5d0af36deea574d177be2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zingerone 20V, Positive-QTOFsplash10-0a4s-0900000000-f505f559b715ddb1b3252021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zingerone 40V, Positive-QTOFsplash10-0a4i-6900000000-251b2e68bd1f83dfb7142021-09-24Wishart LabView Spectrum
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
FooDB IDFDB010527
KNApSAcK IDC00056662
Chemspider ID28952
KEGG Compound IDC17497
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkZingerone
METLIN IDNot Available
PubChem Compound31211
PDB IDNot Available
ChEBI ID68657
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006231
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