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Showing Compound (-)-3-Isothujone (FDB014962)

Record Information
Version1.0
Creation date2010-04-08 22:11:34 UTC
Update date2019-11-26 03:11:02 UTC
Primary IDFDB014962
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-3-Isothujone
DescriptionIngredient of absinthe. Presence in food and beverages regulated by legislation Thujone is a ketone and a monoterpene that occurs naturally in two diastereomeric forms: (-)-alpha-thujone and (+)-beta-thujone. It has a menthol odor. In addition to (-)-alpha-thujone and (+)-beta-thujone, there are their enantiomeric forms, (+)-alpha-thujone and (-)-beta-thujone. (-)-3-Isothujone is found in many foods, some of which are mugwort, pepper (c. frutescens), common oregano, and cornmint.
CAS Number546-80-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-3-ThujanoneChEBI
(1S,4R,5R)-(-)-3-ThujanoneChEBI
(1S,4R,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-oneChEBI
[1S-(1alpha,4alpha,5alpha)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-oneChEBI
alpha-ThujoneChEBI
L-ThujoneChEBI
ThujonChEBI
ThujoneChEBI
[1S-(1a,4a,5a)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-oneGenerator
[1S-(1Α,4α,5α)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-oneGenerator
a-ThujoneGenerator
Α-thujoneGenerator
(-)-a-ThujoneHMDB
(-)-alpha-ThujoneHMDB
(-)-IsothujoneHMDB
(-)-ThujoneHMDB, MeSH
(-)-trans-ThujoneHMDB
(1S,4R,5R)-Thujan-3-oneHMDB
alpha-(-)-ThujoneHMDB
L-alpha-ThujoneHMDB
3-IsothujoneMeSH, HMDB
3-ThujanoneMeSH, HMDB
beta-Thujone, 1S-(1alpha,4beta,5alpha)-isomerMeSH, HMDB
beta-ThujoneMeSH, HMDB
beta-Thujone, (1S-(1alpha,4alpha,5alpha))-isomerMeSH, HMDB
beta-Thujone, (1alpha,4alpha,5alpha)-isomerMeSH, HMDB
(-)-3-IsothujoneKEGG
(+)-ThujoneMeSH
cis-ThujoneMeSH
alpha, beta-ThujoneMeSH
(1S,4R,5R)-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-onePhytoBank
(-)-α-ThujonePhytoBank
AbsintholPhytoBank
[1S-(1α,4α,5α)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-oneGenerator
α-Thujonebiospider
3-Thujanone, (-)-biospider
3-Thujanone, (1S,4R,5R)-(-)-biospider
Isothujone, (-)-biospider
α-thujoneGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.44 g/LALOGPS
logP1.74ALOGPS
logP2.28ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.54 m³·mol⁻¹ChemAxon
Polarizability17.94 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16O
IUPAC name(1S,4R,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
InChI IdentifierInChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1
InChI KeyUSMNOWBWPHYOEA-MRTMQBJTSA-N
Isomeric SMILESCC(C)[C@@]12C[C@@H]1[C@@H](C)C(=O)C2
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
Classification
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Thujane monoterpenoid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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 78.90%; H 10.59%; O 10.51%DFC
Melting Point< 25 oC
Boiling PointBp12 78°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D -20.5 (c, 2 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS(-)-3-Isothujone, non-derivatized, GC-MS Spectrumsplash10-0159-9100000000-9e3f8c13550e0c33d603Spectrum
GC-MS(-)-3-Isothujone, non-derivatized, GC-MS Spectrumsplash10-0159-9100000000-9e3f8c13550e0c33d603Spectrum
Predicted GC-MS(-)-3-Isothujone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ou-9300000000-5ac67463cc6dff4e26c5Spectrum
Predicted GC-MS(-)-3-Isothujone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e5a1ab6ee8fcd2e7222d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-7900000000-e4ab468ffb3afaf161292016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pe9-9000000000-960a6c7d4901afec92332016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-07a82b9f8d15764ed9042016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-65761ceb0d88aa809b6a2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-4023ebf09d9995d371112016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-e8b89c21a7958e1852782021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pdl-7900000000-5c5ad8968d995b2431ac2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-8900000000-a32be7e7fd99fd0b8b232021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-9300000000-eac02498908e1d67934a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-22a79a891aa2c60d074e2021-09-25View Spectrum
NMRNot Available
ChemSpider ID229574
ChEMBL IDCHEMBL1444078
KEGG Compound IDC09906
Pubchem Compound ID261491
Pubchem Substance IDNot Available
ChEBI ID9577
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36115
CRC / DFC (Dictionary of Food Compounds) IDJXM68-F:JXM66-D
EAFUS IDNot Available
Dr. Duke IDALPHA-THUJONE|(-)-THUJONE|THUJONE
BIGG IDNot Available
KNApSAcK IDC00034795
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1048021
SuperScent IDNot Available
Wikipedia IDThujone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
abortifacient50691 A chemical substance that interrupts pregnancy after implantation.DUKE
anti helmintic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cerebrodepressantDUKE
convulsantDUKE
counterirritantDUKE
emmenagogueDUKE
epileptigenicDUKE
hallucinogenicDUKE
herbicide24527 A substance used to destroy plant pests.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
larvicideDUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.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
respira inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
toxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
cedarleaf
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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.