Record Information
Version1.0
Creation date2010-04-08 22:09:44 UTC
Update date2019-11-26 03:05:09 UTC
Primary IDFDB011629
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-Lariciresinol
Description(-)-lariciresinol 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 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-lariciresinol can be found in a number of food items such as cassava, acorn, celeriac, and banana, which makes (-)-lariciresinol a potential biomarker for the consumption of these food products.
CAS Number83327-19-9
Structure
Thumb
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP2.16ALOGPS
logP2.31ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.75ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area88.38 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.19 m³·mol⁻¹ChemAxon
Polarizability38.57 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H24O6
IUPAC name4-{4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl}-2-methoxyphenol
InChI IdentifierInChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3
InChI KeyMHXCIKYXNYCMHY-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(CC2COC(C2CO)C2=CC=C(O)C(OC)=C2)=CC=C1O
Average Molecular Weight360.401
Monoisotopic Molecular Weight360.1572885
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
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen 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 CompositionC 66.65%; H 6.71%; O 26.64%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -17.8 (Me2CO)DFC
Spectroscopic UV Data283 (e 10500) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(-)-Lariciresinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001r-1927000000-001aebbbc4190b3cd4d6Spectrum
Predicted GC-MS(-)-Lariciresinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Lariciresinol, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-0609000000-f7b88f3b846a43fa7e5d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-004i-0609000000-497ccc5bdc45a10d35162021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-0009000000-a75389de6f0f97063fff2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0900000000-dd554fba6f34415f2aad2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03fr-0900000000-718d40dc06914aa1fc692021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-08fr-0900000000-faa89b1aa0b3f4c77d4e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-0709000000-a6fb001327c41202d60b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-08fr-0900000000-494abb3f4b6c4c4e00b12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0bt9-0900000000-91baad059be3220ac9d72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03fr-0900000000-ccb216f23e4ecfd6f5f22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-0009000000-a8f1982bd91bba2f61ea2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-0609000000-6b93e74aba9c3378e7bd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-0009000000-fb84486be61c014aa09f2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0119000000-64f05aa45bb6e77829b32015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03du-0779000000-a8301760f53bcf9f12032015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1901000000-65f618ede698063b43d22015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0119000000-64f05aa45bb6e77829b32015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03du-0779000000-a8301760f53bcf9f12032015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1901000000-65f618ede698063b43d22015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-3ffeb6c4aaa793d3af6b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvl-0019000000-c2cca8faa0927f1ba6ee2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-1925000000-204c3f64a4b6834c4b0e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-3ffeb6c4aaa793d3af6b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvl-0019000000-c2cca8faa0927f1ba6ee2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-1925000000-204c3f64a4b6834c4b0e2015-05-27View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID134203
Pubchem Substance IDNot Available
ChEBI ID544854
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDLKK06-K:GVY27-F
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000603
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 ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.