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beta-Ionone (FDB015469)

Record Information
Version1.0
Creation date2010-04-08 22:11:51 UTC
Update date2020-09-17 15:30:10 UTC
Primary IDFDB015469
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namebeta-Ionone
DescriptionBeta-ionone, also known as (e)-b-ionone or trans-beta-ionone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Beta-ionone is a neutral compound. Beta-ionone has a dry, floral, and flower taste with a cedar wood-like scent. It is a naturally occurring organic compound found in a variety of essential oils, including rose oil, flowers from Boronia megastigma (brown boronia; doi: 10.21273/hortsci.30.4.876d) and coml oil. Beta-ionone is found in highest concentrations in corns, tea, and carrots and in lower concentrations in hyssops, peppermints, and safflowers. Beta-ionone has also been detected in common grapes, sour cherries, common wheats, garden tomato, and wakames making beta-ionone a potential biomarker for the consumption of these foods. Beta-ionone is used as to make Vitamins A, E and K1. It is used as a fragrance in perfumes, cosmetics and personal care products, and household cleaners and detergents. Beta-ionone is used as a food flavoring in beverages, ice-cream, baked goods and candies ( https://doi.org/10.1533/9780857095725.1.231).
CAS Number79-77-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP4.11ALOGPS
logP3.28ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)19.71ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.82 m³·mol⁻¹ChemAxon
Polarizability23.36 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H20O
IUPAC name(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one
InChI IdentifierInChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7+
InChI KeyPSQYTAPXSHCGMF-BQYQJAHWSA-N
Isomeric SMILESCC(=O)\C=C\C1=C(C)CCCC1(C)C
Average Molecular Weight192.2973
Monoisotopic Molecular Weight192.151415262
Classification
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Cyclofarsesane sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Sesquiterpenoid
  • Ionone derivative
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 81.20%; H 10.48%; O 8.32%DFC
Melting PointNot Available
Boiling PointBp24 150-151°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
EI-MSMass Spectrum (Electron Ionization)splash10-004l-6900000000-9288b23b92d86ede53362014-10-20View Spectrum
GC-MSbeta-Ionone, non-derivatized, GC-MS Spectrumsplash10-002f-8900000000-c13b694647d1f5e201bfSpectrum
GC-MSbeta-Ionone, non-derivatized, GC-MS Spectrumsplash10-004i-3900000000-b2fd6907056260485dd2Spectrum
GC-MSbeta-Ionone, non-derivatized, GC-MS Spectrumsplash10-004l-9800000000-3e2f914b8442dedd62d9Spectrum
GC-MSbeta-Ionone, non-derivatized, GC-MS Spectrumsplash10-004l-6900000000-a0ed0929b7cb7526955dSpectrum
GC-MSbeta-Ionone, non-derivatized, GC-MS Spectrumsplash10-004l-4900000000-3169016f24891f9035d6Spectrum
GC-MSbeta-Ionone, non-derivatized, GC-MS Spectrumsplash10-002f-8900000000-c13b694647d1f5e201bfSpectrum
GC-MSbeta-Ionone, non-derivatized, GC-MS Spectrumsplash10-004i-3900000000-b2fd6907056260485dd2Spectrum
GC-MSbeta-Ionone, non-derivatized, GC-MS Spectrumsplash10-004l-9800000000-3e2f914b8442dedd62d9Spectrum
GC-MSbeta-Ionone, non-derivatized, GC-MS Spectrumsplash10-004l-6900000000-a0ed0929b7cb7526955dSpectrum
GC-MSbeta-Ionone, non-derivatized, GC-MS Spectrumsplash10-004l-4900000000-3169016f24891f9035d6Spectrum
Predicted GC-MSbeta-Ionone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004j-2900000000-00c10c6b19261d08ffeaSpectrum
Predicted GC-MSbeta-Ionone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-0f7a122ff9743bcbf0772016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004u-4900000000-9dad39944d71a20a0f872016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9400000000-77a4b4a15731ccc833162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-b62117da7fb50997c0272016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-e7133a7253517651678a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05ed-3900000000-c1d86be9896bad6ad97e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-2dfc2141d793c1b81afc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05gl-7900000000-4e2d786c5425c33577a52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9500000000-66ef449f7e5f912217042021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-14436e4d9ff8d032db542021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-0900000000-85f77f47306d558369112021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1900000000-5f53d8abc51bbf1e4e992021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
ChemSpider ID553581
ChEMBL IDCHEMBL559945
KEGG Compound IDC12287
Pubchem Compound ID638014
Pubchem Substance IDNot Available
ChEBI ID32325
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36565
CRC / DFC (Dictionary of Food Compounds) IDKCN48-Y:KCN48-Y
EAFUS ID1806
Dr. Duke IDBETA-IONONE
BIGG IDNot Available
KNApSAcK IDC00029816
HET IDID3
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID79-77-6
GoodScent IDrw1131301
SuperScent ID638014
Wikipedia IDIonone
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
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cytochrome-p450 inducerDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hypocholesterolemicDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
trichomonicideDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
seaweed
  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
violet
  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
flower
  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
raspberry
  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
orange
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
jam
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
dry
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  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.
orris
  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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.