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Showing Compound Nerylacetone (FDB008523)

Record Information
Version1.0
Creation date2010-04-08 22:08:07 UTC
Update date2025-11-18 23:11:06 UTC
Primary IDFDB008523
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNerylacetone
DescriptionGeranylacetone or (5Z)-6,10-Dimethylundeca-5,9-dien-2-one, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Geranylacetone is neutral compound with . a citrus, earthy, and fatty taste. Geranylacetone is found in highest concentrations in wild carrots, carrots, and tortilla and in lower concentrations in corns. Geranylacetone has also been detected in figs, lemon grass, garden tomato (var.), tortilla chips, and papaya. This could make geranylacetone a potential biomarker for the consumption of these foods. Geranylacetone is an industrial intermediate in the vitamin E synthesis (https://doi.org/10.1002%2F14356007.a26_205).
CAS Number3879-26-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(e)-6,10-Dimethyl-5,9-undecadien-2-oneChEBI
(e)-6,10-Dimethylundeca-5,9-dien-2-oneChEBI
trans-GeranylacetoneChEBI
Geranylacetone, (e)-isomerMeSH
Geranyl acetoneMeSH
(5E)-6,10-Dimethyl-5,9-undecadien-2-oneHMDB
(5E)-6,10-Dimethylundeca-5,9-dien-2-oneHMDB
(e)-6,10-Dimethyl-5,9- undecadien-2-oneHMDB
(e)-Geranyl acetoneHMDB
(e)-GeranylacetoneHMDB
6,10-Dimethyl-(5E)-5,9-undecadien-2-oneHMDB
6,10-Dimethyl-(e)-5,9-undecadien-2-oneHMDB
6,10-Dimethyl-5,9-undecadien-2-oneHMDB
6,10-Dimethyl-5,9-undecadien-2-one, (e)HMDB
6,10-Dimethyl-5,9-undecadiene-2-oneHMDB
6,10-Dimethyl-undecadien-2-oneHMDB
6,10-Dimethylundecadien-2-oneHMDB
DihydropseudoiononeHMDB
FEMA 3542HMDB
Geranyl-acetoneHMDB
GeranylacetonHMDB
GeranylgeranylacetoneHMDB
TeprenoneHMDB
trans-2,6-Dimethyl-2,6-undecadien-2-oneHMDB
trans-6,10-Dimethyl-5,9-undecadien-2-oneHMDB
NerylacetoneMeSH
(5Z)-6,10-Dimethyl-5,9-undecadien-2-onebiospider
Allocorbiospider
Cedilanidbiospider
Ceglunatbiospider
Ceglunatebiospider
Celadigalbiospider
Celanidbiospider
Celanidebiospider
Celanidumbiospider
Cetosanolbiospider
cis-Geranyl acetonebiospider
Cis-geranylacetonebiospider
Desacetyllanatosidebiospider
Digilanid cbiospider
Digilanide cbiospider
Glycoside obtained from the leaves of digitalis lanata ehrhbiospider
Isolanidbiospider
Isolanidebiospider
Lanatigen cbiospider
Lanatosid cbiospider
Lanatosidebiospider
Lanatoside abiospider
Lanatoside cbiospider
Lanatoside c [inn:ban:DCF:jan]biospider
Lanatosido cbiospider
Lanatosidum cbiospider
Lanimerckbiospider
Lanocide-cbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.094 g/LALOGPS
logP4.59ALOGPS
logP3.68ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)19.6ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity63.83 m³·mol⁻¹ChemAxon
Polarizability24.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H22O
IUPAC name(5Z)-6,10-dimethylundeca-5,9-dien-2-one
InChI IdentifierInChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9-
InChI KeyHNZUNIKWNYHEJJ-XFXZXTDPSA-N
Isomeric SMILESCC(C)=CCC\C(C)=C/CCC(C)=O
Average Molecular Weight194.3132
Monoisotopic Molecular Weight194.167065326
Classification
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 80.36%; H 11.41%; O 8.23%DFC
Melting PointNot Available
Boiling PointNot Available
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-MSNerylacetone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9500000000-c7325d4dbb4acd6664adSpectrum
Predicted GC-MSNerylacetone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-22aaf2de71220d323f8c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05y1-5900000000-b9793a3c456efd9db5432016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9200000000-0ccb71b516f62ccb19822016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-49a606374f47e6c4e1432016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-37d60e4771277898dc212016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9600000000-52911be4f91a2692f60a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-25f17943b8774c03383e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9500000000-dd9588cb1a45fcad5a572021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9800000000-3d775ed45a51f2d2e1d12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lv-8900000000-d76105910cff9afee1a62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05o3-9100000000-f55f74cdbd28a20984b22021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9000000000-7f74fb997a0002677d592021-09-24View Spectrum
NMRNot Available
ChemSpider ID1362229
ChEMBL IDNot Available
KEGG Compound IDC13297
Pubchem Compound ID3879
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0031846
CRC / DFC (Dictionary of Food Compounds) IDDNB00-W:DMZ64-B
EAFUS IDNot Available
Dr. Duke IDCIS-GERANYL-ACETONE|NERYL-ACETONE
BIGG IDNot Available
KNApSAcK IDC00035563
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1057181
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
metallic
  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).