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Showing Compound Zingerone (FDB010527)

Record Information
Version1.0
Creation date2010-04-08 22:09:10 UTC
Update date2020-02-24 19:10:59 UTC
Primary IDFDB010527
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. Based on a literature review a significant number of articles have been published on Zingerone.
CAS Number122-48-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(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
2-Butanone, 4-(4-hydroxy-3-methoxyphenyl)-biospider
4-(4-hydroxy-3-methoxy-phenyl)-butan-2-onebiospider
4-(4-Hydroxy-3-methoxyphenyl)-2-butanone, 9CI, 8CIdb_source
Zingeronedb_source
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H14O3
IUPAC name4-(4-hydroxy-3-methoxyphenyl)butan-2-one
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
Isomeric SMILESCOC1=C(O)C=CC(CCC(C)=O)=C1
Average Molecular Weight194.2271
Monoisotopic Molecular Weight194.094294314
Classification
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.02%; H 7.26%; O 24.71%DFC
Melting PointMp 41°DFC
Boiling PointBp 185.5°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSZingerone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-5900000000-42ac2a1b364f92df5152Spectrum
Predicted GC-MSZingerone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9370000000-988fce303c33c65d61c8Spectrum
Predicted GC-MSZingerone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-4c68e7e311ed162223a52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004s-1900000000-e0ac7417df02644e07612016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9l-7900000000-2f6d6b18947145fb0dbf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-8f3da5e61712d1ffacb32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-53b85d6dc1005c5d4df02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-f12fadc90e8da514347f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-9700000000-885efff123d09c2298692021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9500000000-6b1a5bf42da790be18f42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059m-7900000000-fe627d4904dd2c51d3332021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-5d0af36deea574d177be2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-0900000000-f505f559b715ddb1b3252021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6900000000-251b2e68bd1f83dfb7142021-09-24View Spectrum
NMRNot Available
ChemSpider ID28952
ChEMBL IDCHEMBL25894
KEGG Compound IDC17497
Pubchem Compound ID31211
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32590
CRC / DFC (Dictionary of Food Compounds) IDFCC42-M:FCC43-N
EAFUS ID3911
Dr. Duke IDZINGERONE|ZINGIBERONE|GINGERONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1006231
SuperScent ID31211
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5-lipoxygenase inhibitor23924 An agent that blocks the activity of 5-lipoxygenase, an enzyme involved in leukotriene production, reducing inflammation and allergic responses. Therapeutically, it's used to treat asthma, allergies, and inflammatory disorders, such as arthritis, by inhibiting the synthesis of pro-inflammatory leukotrienes.DUKE
Adrenergic37962 An agent that stimulates the adrenergic nervous system, mimicking the effects of adrenaline. It plays a biological role in regulating heart rate, blood pressure, and energy. Therapeutically, adrenergic agents are used to treat conditions such as asthma, hypertension, and cardiac arrest, with key medical uses including bronchodilation, vasoconstriction, and increased cardiac output.DUKE
Anti-atherosclerotic38070 An agent that prevents or slows the formation of atherosclerosis, a condition characterized by plaque buildup in arteries. It reduces inflammation, improves lipid profiles, and inhibits platelet aggregation, commonly used to manage cardiovascular diseases, such as coronary artery disease, and prevent heart attacks and strokes.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti ulcer49201 An agent that reduces stomach acid and protects the mucous lining, preventing ulcer formation. It is used to treat conditions like gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome, promoting healing and relieving symptoms.DUKE
Cardiotonic38070 An agent that strengthens heart muscle contractions, enhancing cardiac output. It plays a biological role in regulating heart function and is therapeutically used to treat heart failure, improving symptoms and exercise tolerance. Key medical uses include managing cardiomyopathy, atrial fibrillation, and congestive heart failure.DUKE
Cyclooxygenase inhibitor35544 An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation.DUKE
Name48318 flavorDUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
ParalyticAn agent that induces temporary paralysis or muscle relaxation, used therapeutically to facilitate surgical procedures, manage muscle spasms, and treat conditions like tetanus and seizures, by blocking nerve transmission to muscles.DUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.DUKE
SecretogogueA substance that stimulates secretion, playing a biological role in regulating hormone and enzyme release. Therapeutically, it has applications in treating conditions like hyposecretion and is used to manage digestive issues, respiratory problems, and endocrine disorders, promoting healthy secretion in various bodily systems.DUKE
Vasodilator35620 An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
clove
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
animal
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
phenolic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ginger
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanilla
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).