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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:29:41 UTC
Update Date2019-07-23 06:25:58 UTC
HMDB IDHMDB0038215
Secondary Accession Numbers
  • HMDB0013693
  • HMDB13693
  • HMDB38215
Metabolite Identification
Common Namealpha-Sinensal
Descriptionalpha-Sinensal, also known as α-sinensal or (2E,6E,9E)-2,6,10-trimethyl-2,6,9,11-dodecatetraenal, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. alpha-Sinensal is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). alpha-Sinensal is a constituent of orange oil. It plays an important role in the overall flavour and aroma of orange fruit.
Structure
Data?1563863158
Synonyms
ValueSource
a-SinensalGenerator
Α-sinensalGenerator
(2E,6E,9E)-2,6,10-Trimethyl-2,6,9,11-dodecatetraenalHMDB
(e,e,e)-2,6,10-Trimethyldodeca-2,6,9,11-tetraen-1-alHMDB
2,6,10-Trimethyl-(2E,6E,9E)-2,6,9,11-dodecatetraenalHMDB
2,6,10-Trimethyl-(e,e,e)-2,6,9,11-dodecatetraenalHMDB
2,6,10-Trimethyl-2,6,9,11-dodecatetraenalHMDB
alpha-SinensalHMDB
Chemical FormulaC15H22O
Average Molecular Weight218.34
Monoisotopic Molecular Weight218.167065328
IUPAC Name(2E,6E,9E)-2,6,10-trimethyldodeca-2,6,9,11-tetraenal
Traditional Nameα-sinensal
CAS Registry Number17909-77-2
SMILES
C\C(CC\C=C(/C)C=O)=C/C\C=C(/C)C=C
InChI Identifier
InChI=1S/C15H22O/c1-5-13(2)8-6-9-14(3)10-7-11-15(4)12-16/h5,8-9,11-12H,1,6-7,10H2,2-4H3/b13-8+,14-9+,15-11+
InChI KeyPFSTYGCNVAVZBK-JQGMZEBDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Medium-chain aldehyde
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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 Solubility0.016 g/LALOGPS
logP5.06ALOGPS
logP4.17ChemAxon
logS-4.1ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity74.05 m³·mol⁻¹ChemAxon
Polarizability27.11 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, Positivesplash10-0udl-9630000000-44fc0ab88fd372513051Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3590000000-5eff757743c8c1ad43caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gc0-9720000000-4c5c846303f21f30b570Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9100000000-a33955da910d70157f2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-70cf9ab627666ef51adfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1290000000-ef81e35e2dea73f32699Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-9820000000-f920da939dd7d7f44d51Spectrum
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 IDFDB017457
KNApSAcK IDC00003188
Chemspider ID4444866
KEGG Compound IDC09729
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281534
PDB IDNot Available
ChEBI ID10332
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. (). 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.