beta-Sinensal (CHEM029543)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:14:10 UTC
Update Date2016-11-09 01:18:54 UTC
Accession NumberCHEM029543
Identification
Common Namebeta-Sinensal
ClassSmall Molecule
Descriptionbeta-Sinensal, also known as FEMA 3141, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. beta-Sinensal is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). beta-Sinensal can be found in citrus, lemon, and sweet orange, which makes beta-sinensal a potential biomarker for the consumption of these food products. beta-Sinensal is used as a food additive (EAFUS: Everything Added to Food in the United States) and also 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
2,6-Dimethyl-10-methylene-2,6,11-dodecatrienalKegg
b-SinensalGenerator
Β-sinensalGenerator
(2E,6E)-2,6-Dimethyl-10-methylene-2,6,11-dodecatrienalHMDB
(e,e)-2,6-Dimethyl-10-methylene-2,6,11-dodecatrienalHMDB
TianchengquanHMDB
trans,trans-2,6-Dimethyl-10-methylene-2,6,11-dodecatrienalHMDB
trans-Β-sinensalHMDB
FEMA 3141HMDB
beta-SinensalHMDB
Chemical FormulaC15H22O
Average Molecular Mass218.335 g/mol
Monoisotopic Mass218.167 g/mol
CAS Registry Number3779-62-2
IUPAC Name(2E,6E)-2,6-dimethyl-10-methylidenedodeca-2,6,11-trienal
Traditional Nameβ-sinensal
SMILESC\C(CC\C=C(\C)C=O)=C/CCC(=C)C=C
InChI IdentifierInChI=1S/C15H22O/c1-5-13(2)8-6-9-14(3)10-7-11-15(4)12-16/h5,9,11-12H,1-2,6-8,10H2,3-4H3/b14-9+,15-11-
InChI KeyNOPLRNXKHZRXHT-PVMFERMNSA-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 Solubility0.0069 g/LALOGPS
logP4.81ALOGPS
logP4.23ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity72.97 m³·mol⁻¹ChemAxon
Polarizability26.94 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, Positivesplash10-0v4i-9720000000-3063da13936103208041Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3490000000-33f122d22f63dd620d69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-9820000000-edcb7278d53f79d1de69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9100000000-0facb41da0d98b774decSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-eb12bc38ac78dda6e698Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1290000000-53d6fb8a58a5ba180ff7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-9820000000-9f1482668f17c500dab4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0890000000-5cf22b4f248740f722c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bi-2930000000-e0f5a8034d4108fef165Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07vi-3900000000-fff8b9311f58d26b3f6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-030r-6910000000-ad60edf8298d563cc50eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9400000000-2e70007be9ae3daf67aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-d9203176cd55062f58ffSpectrum
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 IDHMDB0035643
FooDB IDFDB097363
Phenol Explorer IDNot Available
KNApSAcK IDC00003189
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444867
ChEBI ID10444
PubChem Compound ID5281535
Kegg Compound IDC09730
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