(-)-Matairesinol (CHEM021941)

Record Information
Version1.0
Creation Date2016-05-25 18:16:14 UTC
Update Date2026-05-14 18:05:49 UTC
Accession NumberCHEM021941
Identification
Common Name(-)-Matairesinol
ClassSmall Molecule
Description
A 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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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
External Links
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.