Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:39:13 UTC
Update Date2022-03-07 02:54:35 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
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point180.00 °C. @ 1.00 mm HgThe Good Scents Company Information System
Water Solubility0.49 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.624 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+164.11330932474
DeepCCS[M-H]-161.75530932474
DeepCCS[M-2H]-194.64130932474
DeepCCS[M+Na]+170.20630932474
AllCCS[M+H]+158.032859911
AllCCS[M+H-H2O]+154.432859911
AllCCS[M+NH4]+161.432859911
AllCCS[M+Na]+162.432859911
AllCCS[M-H]-155.132859911
AllCCS[M+Na-2H]-156.032859911
AllCCS[M+HCOO]-157.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-SinensalC\C(CC\C=C(/C)C=O)=C/CCC(=C)C=C2238.0Standard polar33892256
beta-SinensalC\C(CC\C=C(/C)C=O)=C/CCC(=C)C=C1643.2Standard non polar33892256
beta-SinensalC\C(CC\C=C(/C)C=O)=C/CCC(=C)C=C1688.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - beta-Sinensal GC-MS (Non-derivatized) - 70eV, Positivesplash10-0v4i-9720000000-3063da139361032080412017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Sinensal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sinensal 10V, Positive-QTOFsplash10-014i-3490000000-33f122d22f63dd620d692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sinensal 20V, Positive-QTOFsplash10-0159-9820000000-edcb7278d53f79d1de692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sinensal 40V, Positive-QTOFsplash10-0udi-9100000000-0facb41da0d98b774dec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sinensal 10V, Negative-QTOFsplash10-014i-0090000000-eb12bc38ac78dda6e6982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sinensal 20V, Negative-QTOFsplash10-014i-1290000000-53d6fb8a58a5ba180ff72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sinensal 40V, Negative-QTOFsplash10-0pbi-9820000000-9f1482668f17c500dab42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sinensal 10V, Negative-QTOFsplash10-014i-0890000000-5cf22b4f248740f722c62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sinensal 20V, Negative-QTOFsplash10-01bi-2930000000-e0f5a8034d4108fef1652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sinensal 40V, Negative-QTOFsplash10-07vi-3900000000-fff8b9311f58d26b3f6a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sinensal 10V, Positive-QTOFsplash10-030r-6910000000-ad60edf8298d563cc50e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sinensal 20V, Positive-QTOFsplash10-052f-9400000000-2e70007be9ae3daf67ae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sinensal 40V, Positive-QTOFsplash10-0006-9200000000-d9203176cd55062f58ff2021-09-22Wishart LabView Spectrum
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 IDFDB097363
KNApSAcK IDC00003189
Chemspider ID4444867
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
MarkerDB IDNot Available
Good Scents IDrw1050371
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.