(-)-Matairesinol (CHEM021941)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:16:14 UTC
Update Date2016-11-09 01:17:23 UTC
Accession NumberCHEM021941
Identification
Common Name(-)-Matairesinol
ClassSmall Molecule
DescriptionA lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanoneChEBI
Artigenin congenerChEBI
(-)-MatairesinolKegg
(3R,4R)-3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-oneKegg
(8R,8'r)-(-)-MatairesinolHMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-furanoneHMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-furanoneHMDB
Matai-resinolHMDB
(3R,4R)-Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanoneHMDB
(8R,8’R)-(-)-matairesinolHMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanoneHMDB
Dihydro-3,4-divanillyl-2(3H)-furanoneHMDB
MatairesinolChEBI
Chemical FormulaC20H22O6
Average Molecular Mass358.385 g/mol
Monoisotopic Mass358.142 g/mol
CAS Registry Number580-72-3
IUPAC Name(3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Traditional Namematairesinol
SMILES[H][C@]1(CC2=CC=C(O)C(OC)=C2)COC(=O)[C@]1([H])CC1=CC=C(O)C(OC)=C1
InChI IdentifierInChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1
InChI KeyMATGKVZWFZHCLI-LSDHHAIUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct ParentDibenzylbutyrolactone lignans
Alternative Parents
Substituents
  • Dibenzylbutyrolactone
  • Lignan lactone
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP2.79ALOGPS
logP3.29ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.64ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.63 m³·mol⁻¹ChemAxon
Polarizability36.86 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0912000000-7b4af0e03073d528f059Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-052o-1050900000-0801cdc5bc6f2e25f382Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-1910000000-191002f29f51f8e6746eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0079-1900000000-ad747afeebed0450284cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0910000000-d73fdf135ee1bbb9da5fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0910000000-13d87e9eff437c2a9d40Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0915000000-b1d73d4f3f39292146a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0900000000-09f594bc50d3bf31b0a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0009000000-6831b867bff98cf45ad0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0915000000-057c5e3fa08e00ed5af0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-1900000000-9c62c902e5e1ba7ce812Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0109000000-659f3b6afcb8605169afSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-1910000000-28e93dc2781ea1307a60Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0910000000-bd8df1e0e46ee7a489b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0009000000-fd38fb0f0d7d7af381a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0915000000-854075d816aefffb1afbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0915000000-b52be1df53fd1d7baa01Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-1900000000-6a7fe76ee0a12b4bfac3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0915000000-78d9cef4ae13070206f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-0910000000-f8a176428857ea61be78Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0abi-0948000000-33391728008094755667Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0229000000-da790a5b3ff80ab843dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ri-0978000000-407d81dd6dfadba216c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ims-1910000000-060bdfec7823f760bd09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-25c656431001e8e5785fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-0129000000-eefe04935cde889de64cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-0986000000-2b1737e1ecb9a7ee39f9Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04200
HMDB IDHMDB0035698
FooDB IDFDB014417
Phenol Explorer ID595
KNApSAcK IDC00000606
BiGG IDNot Available
BioCyc IDCPD-8912
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMatairesinol
Chemspider ID106491
ChEBI ID6698
PubChem Compound ID119205
Kegg Compound IDC10682
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15653677
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19935713
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20734328
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21315909
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21522091
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21597179
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21736835
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22037685
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22113872
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22396124
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22483751
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22646817
13. Muller U, Mrestani Y, Neubert R, Drager B: Chiral separation of the plant lignan matairesinol by capillary electrophoresis. Electrophoresis. 2008 Sep;29(17):3582-7. doi: 10.1002/elps.200700800.
14. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.