ZINGERONE (CED0006351)

Record Information
Version1.0
Creation Date2016-05-19 02:31:11 UTC
Update Date2026-05-14 19:52:02 UTC
Accession NumberCHEM007870
Identification
Common NameZINGERONE
ClassSmall Molecule
Description
Zingerone is an organic compound with the chemical formula C11H14O3 and an average molecular weight of 194.23 g/mol. ZINGERONE belongs to the methoxyphenols, a subclass of phenols within the organic compounds. Industrially, the substance is utilized as a fragrance, as well as a flavouring and nutrient. The compound is found in or released from eleven recorded sources across various sectors. Within the category of food, food processing and cookware, it is associated with the processing of fish and the preparation of vinegar, wine, sparkling wine, and fermentation processes for beer. In the realm of electrical and electronic equipment, it is linked to fixed capacitors and their manufacture, as well as electrically stimulated smoking devices. Additionally, it is identified in household cleaning and consumer products, specifically including bleaching agents, tobacco product cases, pipe accessories, cigar cigarettes, and other smoking requisites.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-5900000000-42ac2a1b364f92df5152Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-006x-9370000000-988fce303c33c65d61c8Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002b-0900000000-4c68e7e311ed162223a5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004s-1900000000-e0ac7417df02644e0761Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f9l-7900000000-2f6d6b18947145fb0dbfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-8f3da5e61712d1ffacb3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-2900000000-53b85d6dc1005c5d4df0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-5900000000-f12fadc90e8da514347fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9700000000-885efff123d09c229869Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9500000000-6b1a5bf42da790be18f4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-059m-7900000000-fe627d4904dd2c51d333Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-5d0af36deea574d177beNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4s-0900000000-f505f559b715ddb1b325Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-6900000000-251b2e68bd1f83dfb714Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2176.0Log mg/kg[1200:3900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
490Personal care & cosmeticsNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
605Pest RepellantsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
643HeadwearTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)16.2705
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)2.56902
Cytochrome P450 2C8 structureClick to view 3D structureCytochrome P450 2C8P10632HumansPredicted (SEA)5.29375
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)16.2705
Cytochrome P450 2B6 structureClick to view 3D structureCytochrome P450 2B6P20813HumansPredicted (SEA)1.32344
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)29.1156
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)83.9215
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)30.2833
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)22.4984
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)11.2103
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)35.8106
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)4.5931
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)6.07224
Click to view 3D structurePROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)P96878Mycobacterium tuberculosisPredicted (SEA)7.47353
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)18.6838
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)16.1926
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)11.0546
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)24.1333
Click to view 3D structureBeta-carbonic anhydrase 1P9WPJ7Mycobacterium tuberculosisPredicted (SEA)11.0546
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)68.5852
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)61.1116
Click to view 3D structurePolyunsaturated fatty acid lipoxygenase ALOX15P16050HumansPredicted (SEA)2.10193
Dual specificity protein kinase CLK4 structureClick to view 3D structureDual specificity protein kinase CLK4Q9HAZ1HumansPredicted (SEA)122.379
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)30.984
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)320.505
Concentrations
Not Available
External Links
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.