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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:40 UTC
Update Date2019-07-23 06:11:20 UTC
HMDB IDHMDB0032591
Secondary Accession Numbers
  • HMDB32591
Metabolite Identification
Common NameDehydrozingerone
DescriptionDehydrozingerone, also known as dehydro-[0]-paradol or fema 3738, belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. Dehydrozingerone is an extremely weak basic (essentially neutral) compound (based on its pKa). Dehydrozingerone is a sweet, balsam, and creamy tasting compound. Outside of the human body,.
Structure
Data?1563862279
Synonyms
ValueSource
3-Methoxy-4-hydroxybenzalacetoneHMDB
4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-oneHMDB
4-Hydroxy-3-methoxybenzalacetoneHMDB
4-Hydroxy-3-methoxybenzylideneacetoneHMDB
4-Hydroxy-3-methoxystyryl methyl ketoneHMDB
Dehydro-[0]-paradolHMDB
DehydrozingerolHMDB
FEMA 3738HMDB
FeruloylmethaneHMDB
Methyl-3-methoxy-4-hydroxy styryl ketoneHMDB
MHSKHMDB
VanillalacetoneHMDB
Vanillidene acetoneHMDB
VanillylidenacetoneHMDB
Vanillylidene acetoneHMDB
VanylidenacetoneHMDB
[0]-DehydroparadolHMDB
DehydrozingeroneMeSH
Methyl-3-methoxy-4-hydroxystyryl ketone, (e)-iosmerMeSH
MMHSKMeSH
Methyl-3-methoxy-4-hydroxystyryl ketoneMeSH
Chemical FormulaC11H12O3
Average Molecular Weight192.2112
Monoisotopic Molecular Weight192.07864425
IUPAC Name(3Z)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one
Traditional Name(3Z)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one
CAS Registry Number1080-12-2
SMILES
COC1=C(O)C=CC(\C=C/C(C)=O)=C1
InChI Identifier
InChI=1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3-
InChI KeyAFWKBSMFXWNGRE-ARJAWSKDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids and derivatives
Alternative Parents
Substituents
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Anisole
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Enone
  • Alpha,beta-unsaturated ketone
  • Acryloyl-group
  • Ketone
  • Ether
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point129 - 130 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.55 g/LALOGPS
logP2.17ALOGPS
logP2ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity55.06 m³·mol⁻¹ChemAxon
Polarizability19.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002e-1900000000-e01f45dfa4bcc8706ea0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dm-3390000000-db76e9295977c10858daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-325e7a918d5a6a14018eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002o-1900000000-3cb7bcf210d80b950f38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n0-8900000000-16af356cbeed6678316dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-dcd820e6fb07f8fabab0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-c9c0e048b4d9e5807536Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00nb-2900000000-7191f343bff36489dc9bSpectrum
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 IDFDB010528
KNApSAcK IDNot Available
Chemspider ID30654931
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound59039607
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Agarwal M, Walia S, Dhingra S, Khambay BP: Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes. Pest Manag Sci. 2001 Mar;57(3):289-300. [PubMed:11455660 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .