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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:28:09 UTC
Update Date2019-07-23 06:23:16 UTC
HMDB IDHMDB0037227
Secondary Accession Numbers
  • HMDB37227
Metabolite Identification
Common NameCitronellyl butyrate
DescriptionCitronellyl butyrate, also known as E275 or fema 2312, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Citronellyl butyrate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862996
Synonyms
ValueSource
Citronellyl butyric acidGenerator
(1)-3,7-Dimethyloct-6-enyl butyrateHMDB
3,7-Dimethyl-6-octen-1-yl butyrateHMDB
3,7-Dimethyl-6-octenyl butanoateHMDB
Butanoic acid, 3,7-dimethyl-6-octen-1-yl esterHMDB
Butanoic acid, 3,7-dimethyl-6-octenyl esterHMDB
Butyric acid, 3,7-dimethyl-6-octenyl ester (8ci)HMDB
Butyric acid, ester with citronellolHMDB
e275HMDB
FEMA 2312HMDB
Chemical FormulaC14H26O2
Average Molecular Weight226.355
Monoisotopic Molecular Weight226.193280076
IUPAC Name3,7-dimethyloct-6-en-1-yl butanoate
Traditional Name3,7-dimethyloct-6-en-1-yl butanoate
CAS Registry Number141-16-2
SMILES
CCCC(=O)OCCC(C)CCC=C(C)C
InChI Identifier
InChI=1S/C14H26O2/c1-5-7-14(15)16-11-10-13(4)9-6-8-12(2)3/h8,13H,5-7,9-11H2,1-4H3
InChI KeyXQPZQXTWYZAXAK-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
  • Fatty acid ester
  • 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 DescriptorsNot Available
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 Solubility0.012 g/LALOGPS
logP4.93ALOGPS
logP4.34ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity68.87 m³·mol⁻¹ChemAxon
Polarizability28.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00rx-9100000000-adf929332f117b653cc7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-008a-9300000000-5190c6b3c8ba0a74d864Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00rx-9100000000-adf929332f117b653cc7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-008a-9300000000-5190c6b3c8ba0a74d864Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08ml-9700000000-7d5d14e3eb0c9f976b01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-6790000000-64129f846c392693a12fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9400000000-c87498cf8b86d83caebbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9100000000-d179c931bebfdf1013e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-8390000000-589cf0d48808257d7503Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-9210000000-ceef9b887d1536dede0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ko-9200000000-6b5f1d9d65f23e6a0218Spectrum
MSMass Spectrum (Electron Ionization)splash10-00rx-9100000000-a242f53795353291cf70Spectrum
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 IDFDB016234
KNApSAcK IDNot Available
Chemspider ID8503
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8835
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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.