Record Information
Version1.0
Creation date2010-04-08 22:04:31 UTC
Update date2019-11-26 02:54:38 UTC
Primary IDFDB000333
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLariciresinol-sesquilignan
DescriptionLariciresinol-sesquilignan is a member of the class of compounds known as 7,9'-epoxylignans. 7,9'-epoxylignans are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. Lariciresinol-sesquilignan is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Lariciresinol-sesquilignan can be found in sesame, which makes lariciresinol-sesquilignan a potential biomarker for the consumption of this food product.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP2.46ALOGPS
logP2.45ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.75ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area147.3 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity146.66 m³·mol⁻¹ChemAxon
Polarizability58.99 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H36O10
IUPAC name1-(4-hydroxy-3-methoxyphenyl)-2-(4-{4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl}-2-methoxyphenoxy)propane-1,3-diol
InChI IdentifierInChI=1S/C30H36O10/c1-36-25-11-17(4-7-22(25)33)10-20-16-39-30(21(20)14-31)19-6-9-24(27(13-19)38-3)40-28(15-32)29(35)18-5-8-23(34)26(12-18)37-2/h4-9,11-13,20-21,28-35H,10,14-16H2,1-3H3
InChI KeyMWGNJVCCJCKLGJ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(CC2COC(C2CO)C2=CC=C(OC(CO)C(O)C3=CC=C(O)C(OC)=C3)C(OC)=C2)=CC=C1O
Average Molecular Weight556.6008
Monoisotopic Molecular Weight556.230847372
Classification
Description Belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct Parent7,9'-epoxylignans
Alternative Parents
Substituents
  • 7,9p-epoxylignan
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Oxacycle
  • Alcohol
  • Aromatic alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0301090000-d6cee158ca21ac034150Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0816190000-c2234582627476e6308cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-34023b7305c94afe1e92Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0101090000-18bad752e3811f6b8648Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0409140000-d2ee3dfa1c71d0113cfbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056u-0319000000-cbe22e2388d83b4fa2e3Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID623
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Smeds AI, Eklund PC, Sjoholm RE, Willfor SM, Nishibe S, Deyama T, Holmbom BR: Quantification of a broad spectrum of lignans in cereals, oilseeds, and nuts. J Agric Food Chem. 2007 Feb 21;55(4):1337-46. Epub 2007 Jan 30. Pubmed [Structure]
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.