Record Information
Version1.0
Creation date2010-04-08 22:13:41 UTC
Update date2019-11-26 03:16:06 UTC
Primary IDFDB018395
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLirioresinol A
DescriptionLirioresinol A, also known as syringa-resinol or S(8-8)S, belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. Lirioresinol A is an extremely weak basic (essentially neutral) compound (based on its pKa). Lirioresinol A has been detected, but not quantified in, alcoholic beverages and herbs and spices. This could make lirioresinol a a potential biomarker for the consumption of these foods.
CAS Number21453-71-4
Structure
Thumb
Synonyms
SynonymSource
4,4'-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol)ChEBI
S(8-8)SChEBI
(+)-EpisyringaresinolHMDB
SymplicosigenolHMDB
SyringaresinolHMDB
Syringa-resinolHMDB
Syringaresinol, (1R-(1alpha, 3aalpha,4alpha,6aalpha))-isomerHMDB
Syringaresinol, (1alpha,3aalpha, 4alpha,6aalpha)-(+-)-isomerHMDB
Lirioresinol Adb_source
Predicted Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
logP2.23ALOGPS
logP1.96ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.84 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity108.03 m³·mol⁻¹ChemAxon
Polarizability43 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H26O8
IUPAC name4-[4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenol
InChI IdentifierInChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3
InChI KeyKOWMJRJXZMEZLD-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(=CC(OC)=C1O)C1OCC2C1COC2C1=CC(OC)=C(O)C(OC)=C1
Average Molecular Weight418.437
Monoisotopic Molecular Weight418.162767808
Classification
Description belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassNot Available
Direct ParentFuranoid lignans
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointMp 210-211°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +127 (CHCl3)DFC
Spectroscopic UV Data273 (e 2090) (MeOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00li-1982000000-33ff9b96f717a6cbdd51JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-052b-2096070000-90aaa198754bac5787a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-c2fea9ac570d65fb16a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0075900000-e62697a54d5f8d4b5ac6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5900000000-c07121ca65cff3f586c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-c2fea9ac570d65fb16a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0075900000-e62697a54d5f8d4b5ac6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5900000000-c07121ca65cff3f586c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-c2fea9ac570d65fb16a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0075900000-e62697a54d5f8d4b5ac6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5900000000-c07121ca65cff3f586c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-58a345c7e13bfd692354JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0034900000-287f53100d59888eb2e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-2936000000-63cd67d7185fea1cc098JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-58a345c7e13bfd692354JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0034900000-287f53100d59888eb2e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-2936000000-63cd67d7185fea1cc098JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-58a345c7e13bfd692354JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0034900000-287f53100d59888eb2e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-2936000000-63cd67d7185fea1cc098JSpectraViewer
ChemSpider ID90423
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID100067
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID598
DrugBank IDNot Available
HMDB IDHMDB38928
CRC / DFC (Dictionary of Food Compounds) IDHQG59-G:LKK17-O
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 ReferenceNot Available
Content Reference