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Showing Compound 3,5,8-Megastigmatrien-7-one (FDB015480)

Record Information
Version1.0
Creation date2010-04-08 22:11:52 UTC
Update date2019-11-26 03:11:39 UTC
Primary IDFDB015480
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3,5,8-Megastigmatrien-7-one
Descriptionbeta-Damascenone, also known as damascenone, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. Thus, beta-damascenone is considered to be an isoprenoid. beta-Damascenone exists in all eukaryotes, ranging from yeast to plants to humans. beta-Damascenone is a sweet, apple, and apple.rose tasting compound. beta-Damascenone is found, on average, in the highest concentration within red wine. beta-Damascenone has also been detected, but not quantified in, several different foods, such as lichees (Litchi chinensis), teas (Camellia sinensis), grape wine, pineapples (Ananas comosus), and herbs and spices. This could make beta-damascenone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on beta-Damascenone.
CAS Number23726-93-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-oneChEBI
(e)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-oneChEBI
(e)-beta-DamascenoneChEBI
beta-(e)-DamascenoneChEBI
DamascenoneChEBI
trans-beta-DamascenoneChEBI
trans-DamascenoneChEBI
(e)-b-DamascenoneGenerator
(e)-Β-damascenoneGenerator
b-(e)-DamascenoneGenerator
Β-(e)-damascenoneGenerator
trans-b-DamascenoneGenerator
trans-Β-damascenoneGenerator
b-DamascenoneGenerator
Β-damascenoneGenerator
1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-oneHMDB
(2e)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-oneChEBI
(e)-β-damascenonebiospider
(e)-beta -DamascenoneHMDB
(e)-β-damascenoneGenerator
β-(e)-damascenonebiospider
β-damascenonebiospider
2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-biospider
2,6,6-Trimethyl-1-trans-crotonoyl-1,3-cyclohexadienebiospider
4-(2,6,6-Trimethylcyclohexa-1,3-dienyl)but-2-en-4-onebiospider
beta -(e)-DamascenoneHMDB
beta -DamascenoneHMDB
beta-Damascenonebiospider
Damascenone, trans-biospider
Trans-β-damascenonebiospider
trans-beta -DamascenoneHMDB
trans-β-damascenoneGenerator
β-(e)-damascenoneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP4.02ALOGPS
logP3.68ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.02 m³·mol⁻¹ChemAxon
Polarizability22.61 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H18O
IUPAC name(2E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
InChI IdentifierInChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+
InChI KeyPOIARNZEYGURDG-FNORWQNLSA-N
Isomeric SMILESC\C=C\C(=O)C1=C(C)C=CCC1(C)C
Average Molecular Weight190.286
Monoisotopic Molecular Weight190.1357652
Classification
Description Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnones
Alternative Parents
Substituents
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 82.06%; H 9.53%; O 8.41%DFC
Melting PointNot Available
Boiling PointBp13 116-118°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-MS3,5,8-Megastigmatrien-7-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01dm-5900000000-4bcd624fdf9c5e42b887Spectrum
Predicted GC-MS3,5,8-Megastigmatrien-7-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,5,8-Megastigmatrien-7-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,5,8-Megastigmatrien-7-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,5,8-Megastigmatrien-7-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-8da6e151fea92abe412a2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kg-6900000000-2069d91b82e6511da0ae2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9200000000-6695f41d1b443f4da5982016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-3f94da9b260ed91041b82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-7afc8b9366085d67da732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007n-4900000000-d38de494cceadf7b6a172016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-797743ba698bddb677b12021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-d9210597b39735810ebf2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-2900000000-4ac82453126eb07d119f2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-022c-0900000000-3c6a17c1864038197fc52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-2900000000-7fc87120284ef620e86a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac0-7900000000-3e0424c46a79abc4667d2021-09-24View Spectrum
NMRNot Available
ChemSpider ID4517997
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5366074
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36572
CRC / DFC (Dictionary of Food Compounds) IDKCQ14-A:KCQ14-A
EAFUS ID3741
Dr. Duke IDDAMASCENONE|BETA-DAMASCENONE
BIGG IDNot Available
KNApSAcK IDC00035536
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID23726-93-4
GoodScent IDrw1441071
SuperScent ID5366074
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
anti edemicDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
rose
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
honey
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
apple
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
smoky
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
tobacco
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
apple.rose
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
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).