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Showing metabocard for Citronellyl trans-2-methyl-2-butenoate (HMDB0032209)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:48:30 UTC
Update Date2019-07-23 06:10:32 UTC
HMDB IDHMDB0032209
Secondary Accession Numbers
  • HMDB32209
Metabolite Identification
Common NameCitronellyl trans-2-methyl-2-butenoate
DescriptionCitronellyl trans-2-methyl-2-butenoate, also known as citronellyl tiglate or 3,7-dimethyl-6-octenyl 2-methylcrotonate, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Citronellyl trans-2-methyl-2-butenoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862232
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Citronellyl trans-2-methyl-2-butenoic acidGenerator
3,7-Dimethyl-6-octenyl (2Z)-2-methyl-2-butenoateHMDB
3,7-Dimethyl-6-octenyl 2-methylcrotonateHMDB
Citronellyl tiglateHMDB
e-Citronellyl tiglateHMDB
Chemical FormulaC15H26O2
Average Molecular Weight238.3657
Monoisotopic Molecular Weight238.193280076
IUPAC Name3,7-dimethyloct-6-en-1-yl (2E)-2-methylbut-2-enoate
Traditional Name3,7-dimethyloct-6-en-1-yl (2E)-2-methylbut-2-enoate
CAS Registry Number24717-85-9
SMILES
C\C=C(/C)C(=O)OCCC(C)CCC=C(C)C
InChI Identifier
InChI=1S/C15H26O2/c1-6-14(5)15(16)17-11-10-13(4)9-7-8-12(2)3/h6,8,13H,7,9-11H2,1-5H3/b14-6+
InChI KeyUCFQYMKLDPWFHZ-MKMNVTDBSA-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
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate 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 Solubility0.018 g/LALOGPS
logP5.36ALOGPS
logP4.96ChemAxon
logS-4.1ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity74.32 m³·mol⁻¹ChemAxon
Polarizability29.83 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bu0-9710000000-6d99a21facc6a4c402e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-5690000000-413387ba49788a191622Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053i-9410000000-201d966e343c0afd10f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pw9-9000000000-01f55b7390bf35f02d55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3290000000-177c5ecfc428e7ae8bb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9110000000-78092628c059ad9ea1c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aba-9200000000-ac690f68d08cbae4e66eSpectrum
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 IDFDB009194
KNApSAcK IDNot Available
Chemspider ID4905187
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6386037
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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. (). EAFUS: Everything Added to Food in the United States.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.