alpha-Sinensal (CHEM031595)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:46:05 UTC
Update Date2016-11-09 01:19:17 UTC
Accession NumberCHEM031595
Identification
Common Namealpha-Sinensal
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass218.335 g/mol
Monoisotopic Mass218.167 g/mol
CAS Registry Number17909-77-2
IUPAC Name(2E,6E,9E)-2,6,10-trimethyldodeca-2,6,9,11-tetraenal
Traditional Nameα-sinensal
SMILESC\C(CC\C=C(\C)C=O)=C/C\C=C(\C)C=C
InChI IdentifierInChI=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-KVDYQJCMSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-9630000000-44fc0ab88fd372513051Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02u0-5910000000-948d6ab8a9b9a963d81aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9500000000-2527dc92fcb7c9f17055Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054o-9200000000-107c1c1b69f678dd2e4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0890000000-3a3db1e2c2c2b7999336Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bi-2930000000-b1d4d2bb9e84aac665faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-082i-3900000000-6d208aa38d4b4c1be98dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0038215
FooDB IDFDB097362
Phenol Explorer IDNot Available
KNApSAcK IDC00003188
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444866
ChEBI ID10332
PubChem Compound ID5281534
Kegg Compound IDC09729
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM