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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:57:19 UTC
Update Date2019-07-23 06:15:20 UTC
HMDB IDHMDB0034160
Secondary Accession Numbers
  • HMDB34160
Metabolite Identification
Common Name(±)-Citronellyl acetate
Description(±)-Citronellyl acetate is found in alcoholic beverages. (±)-Citronellyl acetate is a flavouring ingredient. (±)-Citronellyl acetate is a constituent of citronella oil, orange juice, lemon juice and peel, grapefruit peel, swangi (Citrus hystrix), ginger, tarragon, myrtle leaf, West Indian lemongrass oil and beer.
Structure
Data?1563862520
Synonyms
ValueSource
3,7-Dimethyl-6-octen-1-yl acetateKegg
3,7-Dimethyl-6-octen-1-yl acetic acidGenerator
(±)-citronellyl acetic acidGenerator
(+/-)-citronellyl acetateHMDB
1-Acetoxy-3,7-dimethyloct-6-eneHMDB
2-Octen-8-ol, 2,6-dimethyl-, acetateHMDB
3,7-Dimethyl-6-octen-1-ol acetateHMDB
3,7-Dimethyl-6-octen-1-yl ethanoateHMDB
6-Octen-1-ol, 3,7-dimethyl-, 1-acetateHMDB
6-Octen-1-ol, 3,7-dimethyl-, acetateHMDB
6-Octen-L-ol, 3,7-dimethyl-, acetateHMDB
Acetic acid, 3,7-dimethyl-6-octen-1-yl esterHMDB
Acetic acid, citronellyl esterHMDB
beta-Citronellol acetateHMDB
beta-Citronellyl acetateHMDB
Cephrol acetateHMDB
DL-Citronellol acetateHMDB
FEMA 2311HMDB
Chemical FormulaC12H22O2
Average Molecular Weight198.306
Monoisotopic Molecular Weight198.161979948
IUPAC Name3,7-dimethyloct-6-en-1-yl acetate
Traditional Namecitronellyl acetate
CAS Registry Number150-84-5
SMILES
CC(CCOC(C)=O)CCC=C(C)C
InChI Identifier
InChI=1S/C12H22O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,11H,5,7-9H2,1-4H3
InChI KeyJOZKFWLRHCDGJA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohol esters
Direct ParentFatty alcohol esters
Alternative Parents
Substituents
  • Fatty alcohol ester
  • Monoterpenoid
  • Acyclic monoterpenoid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • 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:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP4.13ALOGPS
logP3.19ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity59.64 m³·mol⁻¹ChemAxon
Polarizability24.4 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00l6-9100000000-045f190926c18eb95193JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05o1-9200000000-6c549e192c218d0f0609JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00l6-9100000000-045f190926c18eb95193JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05o1-9200000000-6c549e192c218d0f0609JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-9400000000-647ee7273b1211245f77JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-d62f4d3daa7625d42573JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5900000000-1250db2a0c197578fb4eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9100000000-30796815da6d847bc888JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3900000000-12566dcfe874c1015c5cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9400000000-a8164e301b87ef9a7180JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-7ef7e7467b8fd8b4411dJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-00l6-9100000000-51cdcd6bcfa29c08c98fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012446
KNApSAcK IDC00035564
Chemspider ID8667
KEGG Compound IDC12298
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9017
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.