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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:57:19 UTC
Update Date2021-10-13 06:39:12 UTC
HMDB IDHMDB0034160
Secondary Accession Numbers
  • HMDB34160
Metabolite Identification
Common Name(±)-Citronellyl acetate
Description(±)-Citronellyl acetate, also known as b-citronellol acetic acid or cephrol acetate, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. (±)-Citronellol acetate is a monoterpenoid that is the acetate ester of citronellol. It has been isolated from Citrus hystrix. (±)-Citronellyl acetate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1563862520
Synonyms
ValueSource
beta-Citronellol acetateChEBI
beta-Citronellyl acetateChEBI
3,7-Dimethyl-6-octen-1-yl acetateKegg
b-Citronellol acetateGenerator
b-Citronellol acetic acidGenerator
beta-Citronellol acetic acidGenerator
Β-citronellol acetateGenerator
Β-citronellol acetic acidGenerator
b-Citronellyl acetateGenerator
b-Citronellyl acetic acidGenerator
beta-Citronellyl acetic acidGenerator
Β-citronellyl acetateGenerator
Β-citronellyl acetic acidGenerator
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
Cephrol acetateHMDB
DL-Citronellol acetateHMDB
FEMA 2311HMDB
Citronellyl acetic acidGenerator
Citronellyl acetate, (S)-isomerMeSH
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
Description 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

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point229.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility5.69 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.220The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP10(4.13) g/LALOGPS
logP10(3.19) g/LChemAxon
logS10(-3.5) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.34931661259
DarkChem[M-H]-146.09231661259
DeepCCS[M+H]+149.58730932474
DeepCCS[M-H]-147.17930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(??)-Citronellyl acetateCC(CCOC(C)=O)CCC=C(C)C1687.7Standard polar33892256
(??)-Citronellyl acetateCC(CCOC(C)=O)CCC=C(C)C1346.8Standard non polar33892256
(??)-Citronellyl acetateCC(CCOC(C)=O)CCC=C(C)C1361.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (±)-Citronellyl acetate EI-B (Non-derivatized)splash10-00l6-9100000000-045f190926c18eb951932017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (±)-Citronellyl acetate EI-B (Non-derivatized)splash10-05o1-9200000000-6c549e192c218d0f06092017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (±)-Citronellyl acetate EI-B (Non-derivatized)splash10-00l6-9100000000-045f190926c18eb951932018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (±)-Citronellyl acetate EI-B (Non-derivatized)splash10-05o1-9200000000-6c549e192c218d0f06092018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Citronellyl acetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-9400000000-647ee7273b1211245f772016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Citronellyl acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-Citronellyl acetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00l6-9100000000-51cdcd6bcfa29c08c98f2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Citronellyl acetate 10V, Positive-QTOFsplash10-0002-1900000000-d62f4d3daa7625d425732016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Citronellyl acetate 20V, Positive-QTOFsplash10-000i-5900000000-1250db2a0c197578fb4e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Citronellyl acetate 40V, Positive-QTOFsplash10-066u-9100000000-30796815da6d847bc8882016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Citronellyl acetate 10V, Negative-QTOFsplash10-0002-3900000000-12566dcfe874c1015c5c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Citronellyl acetate 20V, Negative-QTOFsplash10-0a4i-9400000000-a8164e301b87ef9a71802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Citronellyl acetate 40V, Negative-QTOFsplash10-0a4l-9200000000-7ef7e7467b8fd8b4411d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Citronellyl acetate 10V, Positive-QTOFsplash10-053r-9400000000-7ea1d82e221a84d56f032021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Citronellyl acetate 20V, Positive-QTOFsplash10-00lr-9000000000-cf56e8724981e47b9ed72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Citronellyl acetate 40V, Positive-QTOFsplash10-05nf-9000000000-732bfb819967673653cf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Citronellyl acetate 10V, Negative-QTOFsplash10-0a4i-9200000000-03a8e205d6a049356fe12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Citronellyl acetate 20V, Negative-QTOFsplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-Citronellyl acetate 40V, Negative-QTOFsplash10-0a4i-9000000000-995316cfd01233c462442021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
FooDB 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 ID70478
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1012172
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.