Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:11:28 UTC
Update date2018-05-29 01:14:54 UTC
Primary IDFDB014799
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNootkatone
DescriptionConstituent of grapefruit oil and juice. Flavouring ingredient. Nootkatone is found in many foods, some of which are citrus, sweet orange, lime, and lemon.
CAS Number4674-50-4
Structure
Thumb
Synonyms
SynonymSource
(+)-5,6-Dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-oneHMDB
4BetaH,5alpha-eremophila-1(10),11-dien-2-oneHMDB
4BetaH,5alpha-eremorphila-1(10)11-dien-2-oneHMDB
NootkataneHMDB
(+)-5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-onebiospider
(+)-Nootkatonebiospider
4βH,5α-Eremophila-1(10),11-dien-2-onebiospider
4βH,5α-Eremorphila-1(10)11-dien-2-onebiospider
4betaH,5alpha-Eremophila-1(10),11-dien-2-onebiospider
4betaH,5alpha-Eremorphila-1(10)11-dien-2-onebiospider
5,6-Dimethyl-8-isopropenylbicyclo(4.4.0)dec-1-en-3-onebiospider
FEMA 3166db_source
Nootkanonebiospider
Nootkatonedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
logP3.89ALOGPS
logP3.7ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)18.91ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.07 m³·mol⁻¹ChemAxon
Polarizability26.1 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H22O
IUPAC name4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one
InChI IdentifierInChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3
InChI KeyWTOYNNBCKUYIKC-UHFFFAOYSA-N
Isomeric SMILESCC1CC(=O)C=C2CCC(CC12C)C(C)=C
Average Molecular Weight218.3346
Monoisotopic Molecular Weight218.167065326
Classification
Description belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
Alternative Parents
Substituents
  • Eremophilane sesquiterpenoid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 82.52%; H 10.16%; O 7.33%DFC
Melting PointMp 36-37°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +195.5 (c, 1.5 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbi-1910000000-b45e411b466c6a4f701eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0190000000-c24752b1318a3a711643View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-017i-2930000000-22f4dc6376ca69ed6b2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9700000000-fc684e09e444485e471bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-985cf431add494d4b1caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-9295b5b0acc45864f5c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0930000000-b1395e8a051a4ce6d609View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID20797
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJVX45-L:JVX45-L
EAFUS ID2720
Dr. Duke IDNOOTKATONE
BIGG IDNot Available
KNApSAcK IDC00016987
HET IDNot Available
Flavornet ID4674-50-4
GoodScent IDrw1005641
SuperScent IDNot Available
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 ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
grapefruit
  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
grapefruit peel
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
citrus
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
gardenia
  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.
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).