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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:28:18 UTC
Update Date2022-03-07 02:55:14 UTC
HMDB IDHMDB0037230
Secondary Accession Numbers
  • HMDB37230
Metabolite Identification
Common NameCitronellyl alpha-toluate
DescriptionCitronellyl alpha-toluate, also known as citronellyl a-toluic acid, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Based on a literature review a small amount of articles have been published on Citronellyl alpha-toluate.
Structure
Data?1563862997
Synonyms
ValueSource
Citronellyl a-toluateGenerator
Citronellyl a-toluic acidGenerator
Citronellyl alpha-toluic acidGenerator
Citronellyl α-toluateGenerator
Citronellyl α-toluic acidGenerator
3,7-Dimethyl-6-octen-1-yl phenylacetateHMDB
3,7-Dimethyl-6-octenyl benzeneacetateHMDB
3,7-Dimethyl-6-octenyl phenylacetateHMDB
Acetic acid, phenyl-, 3,7-dimethyl-6-octenyl esterHMDB
Benzeneacetic acid, 3,7-dimethyl-6-octen-1-yl esterHMDB
Benzeneacetic acid, 3,7-dimethyl-6-octenyl esterHMDB
Citronellyl phenylacetateHMDB
e 2157HMDB
FEMA 2315HMDB
Chemical FormulaC18H26O2
Average Molecular Weight274.3978
Monoisotopic Molecular Weight274.193280076
IUPAC Name3,7-dimethyloct-6-en-1-yl 2-phenylacetate
Traditional Name3,7-dimethyloct-6-en-1-yl 2-phenylacetate
CAS Registry Number139-70-8
SMILES
CC(CCOC(=O)CC1=CC=CC=C1)CCC=C(C)C
InChI Identifier
InChI=1S/C18H26O2/c1-15(2)8-7-9-16(3)12-13-20-18(19)14-17-10-5-4-6-11-17/h4-6,8,10-11,16H,7,9,12-14H2,1-3H3
InChI KeyCVJBFMVLVJZZMM-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
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point342.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.076 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.840 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0019 g/LALOGPS
logP5.76ALOGPS
logP5.03ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity84.36 m³·mol⁻¹ChemAxon
Polarizability33.36 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.9731661259
DarkChem[M-H]-166.70231661259
DeepCCS[M+H]+168.85630932474
DeepCCS[M-H]-166.49830932474
DeepCCS[M-2H]-199.38430932474
DeepCCS[M+Na]+174.94930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Citronellyl alpha-toluateCC(CCOC(=O)CC1=CC=CC=C1)CCC=C(C)C2466.6Standard polar33892256
Citronellyl alpha-toluateCC(CCOC(=O)CC1=CC=CC=C1)CCC=C(C)C1867.6Standard non polar33892256
Citronellyl alpha-toluateCC(CCOC(=O)CC1=CC=CC=C1)CCC=C(C)C1990.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citronellyl alpha-toluate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-073702b258e1adfe291b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citronellyl alpha-toluate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 10V, Positive-QTOFsplash10-004i-2790000000-b80b9ebf5d1e9988ae872016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 20V, Positive-QTOFsplash10-014r-5910000000-59459f13b0171cad74f22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 40V, Positive-QTOFsplash10-014l-9200000000-d3285050c4c3bcf49baf2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 10V, Negative-QTOFsplash10-00xr-1960000000-3cc848e5dff32cce07612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 20V, Negative-QTOFsplash10-00kr-1910000000-91f60ec045db0c03d31e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 40V, Negative-QTOFsplash10-014u-5900000000-dbca8249a000b0f9eecc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 10V, Negative-QTOFsplash10-00di-0190000000-f2c2f8f406e6a5f923022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 20V, Negative-QTOFsplash10-006x-9650000000-e1f54325e46d4d3553682021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 40V, Negative-QTOFsplash10-0006-9300000000-088064f5b4177c2b53fc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 10V, Positive-QTOFsplash10-00o9-9740000000-a67826ffcf76a87579332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 20V, Positive-QTOFsplash10-014l-9500000000-29d93ea0e54c4efc5f292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 40V, Positive-QTOFsplash10-0006-9200000000-f9e0b64e0f46a9afadfd2021-09-22Wishart LabView Spectrum
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 IDFDB016237
KNApSAcK IDNot Available
Chemspider ID8437
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8767
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1020951
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.