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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:39:13 UTC
Update Date2019-07-23 06:19:10 UTC
HMDB IDHMDB0035643
Secondary Accession Numbers
  • HMDB35643
Metabolite Identification
Common Namebeta-Sinensal
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.
Structure
Data?1563862750
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 Weight218.34
Monoisotopic Molecular Weight218.167065328
IUPAC Name(2E,6E)-2,6-dimethyl-10-methylidenedodeca-2,6,11-trienal
Traditional Nameβ-sinensal
CAS Registry Number3779-62-2
SMILES
C\C(CC\C=C(/C)C=O)=C/CCC(=C)C=C
InChI Identifier
InChI=1S/C15H22O/c1-5-13(2)8-6-9-14(3)10-7-11-15(4)12-16/h5,9,11-12H,1-2,6-8,10H2,3-4H3/b14-9+,15-11+
InChI KeyNOPLRNXKHZRXHT-YFVJMOTDSA-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 Solubility0.0069 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
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, Positivesplash10-0v4i-9720000000-3063da13936103208041Spectrum
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
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 IDNot Available
KNApSAcK IDC00003189
Chemspider IDNot Available
KEGG Compound IDC09730
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281535
PDB IDNot Available
ChEBI ID10444
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.