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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:40 UTC
Update Date2023-02-21 17:22:25 UTC
HMDB IDHMDB0032591
Secondary Accession Numbers
  • HMDB32591
Metabolite Identification
Common NameDehydrozingerone
DescriptionDehydrozingerone, also known as vanillidene acetone or MMHSK, 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 a sweet, balsam, and creamy tasting compound. Based on a literature review very few articles have been published on Dehydrozingerone.
Structure
Data?1677000145
Synonyms
ValueSource
Vanillidene acetoneMeSH
4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-oneMeSH
DehydrozingerolMeSH
Methyl-3-methoxy-4-hydroxystyryl ketone, (e)-iosmerMeSH
4-Hydroxy-3-methoxybenzalacetoneMeSH
MMHSKMeSH
Methyl-3-methoxy-4-hydroxystyryl ketoneMeSH
3-Methoxy-4-hydroxybenzalacetoneHMDB
4-Hydroxy-3-methoxybenzylideneacetoneHMDB
4-Hydroxy-3-methoxystyryl methyl ketoneHMDB
dehydro-[0]-ParadolHMDB
FEMA 3738HMDB
FeruloylmethaneHMDB
Methyl-3-methoxy-4-hydroxy styryl ketoneHMDB
MHSKHMDB
VanillalacetoneHMDB
VanillylidenacetoneHMDB
Vanillylidene acetoneHMDB
VanylidenacetoneHMDB
[0]-DehydroparadolHMDB
DehydrozingeroneMeSH
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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point129 - 130 °CNot Available
Boiling Point344.00 to 345.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility3163 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.401 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+148.06330932474
DeepCCS[M-H]-145.70530932474
DeepCCS[M-2H]-179.93630932474
DeepCCS[M+Na]+154.61730932474
AllCCS[M+H]+141.732859911
AllCCS[M+H-H2O]+137.432859911
AllCCS[M+NH4]+145.732859911
AllCCS[M+Na]+146.832859911
AllCCS[M-H]-142.432859911
AllCCS[M+Na-2H]-143.032859911
AllCCS[M+HCOO]-143.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DehydrozingeroneCOC1=C(O)C=CC(\C=C/C(C)=O)=C13157.7Standard polar33892256
DehydrozingeroneCOC1=C(O)C=CC(\C=C/C(C)=O)=C11700.7Standard non polar33892256
DehydrozingeroneCOC1=C(O)C=CC(\C=C/C(C)=O)=C11838.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dehydrozingerone,1TMS,isomer #1COC1=CC(/C=C\C(C)=O)=CC=C1O[Si](C)(C)C1928.6Semi standard non polar33892256
Dehydrozingerone,1TMS,isomer #2C=C(/C=C\C1=CC=C(O)C(OC)=C1)O[Si](C)(C)C1985.3Semi standard non polar33892256
Dehydrozingerone,2TMS,isomer #1C=C(/C=C\C1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2003.6Semi standard non polar33892256
Dehydrozingerone,2TMS,isomer #1C=C(/C=C\C1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C1984.8Standard non polar33892256
Dehydrozingerone,1TBDMS,isomer #1COC1=CC(/C=C\C(C)=O)=CC=C1O[Si](C)(C)C(C)(C)C2191.1Semi standard non polar33892256
Dehydrozingerone,1TBDMS,isomer #2C=C(/C=C\C1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C2251.7Semi standard non polar33892256
Dehydrozingerone,2TBDMS,isomer #1C=C(/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C2534.0Semi standard non polar33892256
Dehydrozingerone,2TBDMS,isomer #1C=C(/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C2453.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dehydrozingerone GC-MS (Non-derivatized) - 70eV, Positivesplash10-002e-1900000000-e01f45dfa4bcc8706ea02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydrozingerone GC-MS (1 TMS) - 70eV, Positivesplash10-00dm-3390000000-db76e9295977c10858da2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydrozingerone 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 - Dehydrozingerone 10V, Positive-QTOFsplash10-002f-0900000000-325e7a918d5a6a14018e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrozingerone 20V, Positive-QTOFsplash10-002o-1900000000-3cb7bcf210d80b950f382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrozingerone 40V, Positive-QTOFsplash10-05n0-8900000000-16af356cbeed6678316d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrozingerone 10V, Negative-QTOFsplash10-0006-0900000000-dcd820e6fb07f8fabab02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrozingerone 20V, Negative-QTOFsplash10-0006-0900000000-c9c0e048b4d9e58075362017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrozingerone 40V, Negative-QTOFsplash10-00nb-2900000000-7191f343bff36489dc9b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrozingerone 10V, Negative-QTOFsplash10-0006-0900000000-3b8fc77e2c5dffca77652021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrozingerone 20V, Negative-QTOFsplash10-001i-0900000000-aada0d8b77e7f4fcd5c72021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrozingerone 40V, Negative-QTOFsplash10-0159-3900000000-f5aae80da5ac8fcbe0db2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrozingerone 10V, Positive-QTOFsplash10-0006-0900000000-c561edb0db1778f2c43f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrozingerone 20V, Positive-QTOFsplash10-0006-2900000000-c57b920512e4633fbb982021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrozingerone 40V, Positive-QTOFsplash10-004l-6900000000-c846b210bd5956e197032021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDFDB010528
KNApSAcK IDC00053959
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
MarkerDB IDNot Available
Good Scents IDrw1005791
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.. .