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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 20:42:38 UTC
Update Date2022-03-07 02:54:36 UTC
HMDB IDHMDB0035698
Secondary Accession Numbers
  • HMDB0035789
  • HMDB35698
  • HMDB35789
Metabolite Identification
Common NameMatairesinol
DescriptionMatairesinol belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Matairesinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, matairesinol is found, on average, in the highest concentration in a few different foods such as sesame, burdocks, and flaxseeds, and in a lower concentration in oats, asparagus, and poppies. Matairesinol has also been detected, but not quantified in, several different foods, such as silver lindens, tamarinds, cherry tomato, skunk currants, and fireweeds. This could make matairesinol a potential biomarker for the consumption of these foods. Matairesinol is composed of gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).
Structure
Data?1601223509
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 Weight358.3851
Monoisotopic Molecular Weight358.141638436
IUPAC Name(3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Traditional Namematairesinol
CAS Registry Number580-72-3
SMILES
COC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C1
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point119 °CNot Available
Boiling Point593.03 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility50.71 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.655 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.36231661259
DarkChem[M-H]-186.94131661259
DeepCCS[M+H]+188.02530932474
DeepCCS[M-H]-185.62930932474
DeepCCS[M-2H]-218.80330932474
DeepCCS[M+Na]+194.04930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MatairesinolCOC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C15024.8Standard polar33892256
MatairesinolCOC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C13124.7Standard non polar33892256
MatairesinolCOC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C13192.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Matairesinol,1TMS,isomer #1COC1=CC(C[C@H]2C(=O)OC[C@@H]2CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O3180.4Semi standard non polar33892256
Matairesinol,1TMS,isomer #2COC1=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O3181.7Semi standard non polar33892256
Matairesinol,2TMS,isomer #1COC1=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C3200.7Semi standard non polar33892256
Matairesinol,1TBDMS,isomer #1COC1=CC(C[C@H]2C(=O)OC[C@@H]2CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O3442.6Semi standard non polar33892256
Matairesinol,1TBDMS,isomer #2COC1=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O3443.4Semi standard non polar33892256
Matairesinol,2TBDMS,isomer #1COC1=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C3687.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Matairesinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0912000000-7b4af0e03073d528f0592017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Matairesinol GC-MS (2 TMS) - 70eV, Positivesplash10-052o-1050900000-0801cdc5bc6f2e25f3822017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Matairesinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOFsplash10-000i-1910000000-191002f29f51f8e6746e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOFsplash10-0079-1900000000-ad747afeebed0450284c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOFsplash10-000i-0910000000-d73fdf135ee1bbb9da5f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOFsplash10-000i-0910000000-13d87e9eff437c2a9d402021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOFsplash10-000i-0915000000-b1d73d4f3f39292146a12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 30V, Positive-QTOFsplash10-000i-0900000000-09f594bc50d3bf31b0a22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOFsplash10-0a4l-0009000000-6831b867bff98cf45ad02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOFsplash10-000i-0915000000-057c5e3fa08e00ed5af02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 50V, Positive-QTOFsplash10-000i-1900000000-9c62c902e5e1ba7ce8122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOFsplash10-0a4l-0109000000-659f3b6afcb8605169af2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 50V, Positive-QTOFsplash10-000i-1910000000-28e93dc2781ea1307a602021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 30V, Positive-QTOFsplash10-000i-0910000000-bd8df1e0e46ee7a489b72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOFsplash10-0a4l-0009000000-fd38fb0f0d7d7af381a52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOFsplash10-000i-0915000000-854075d816aefffb1afb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOFsplash10-000i-0915000000-b52be1df53fd1d7baa012021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOFsplash10-000i-1900000000-6a7fe76ee0a12b4bfac32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 6V, Positive-QTOFsplash10-000i-0915000000-78d9cef4ae13070206f12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 40V, Negative-QTOFsplash10-00di-0910000000-f8a176428857ea61be782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Matairesinol 20V, Negative-QTOFsplash10-0abi-0948000000-333917280080947556672021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Matairesinol 10V, Positive-QTOFsplash10-0a4i-0229000000-da790a5b3ff80ab843dc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Matairesinol 20V, Positive-QTOFsplash10-06ri-0978000000-407d81dd6dfadba216c42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Matairesinol 40V, Positive-QTOFsplash10-0ims-1910000000-060bdfec7823f760bd092016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Matairesinol 10V, Negative-QTOFsplash10-0a4i-0009000000-25c656431001e8e5785f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Matairesinol 20V, Negative-QTOFsplash10-0bt9-0129000000-eefe04935cde889de64c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Matairesinol 40V, Negative-QTOFsplash10-01ot-0986000000-2b1737e1ecb9a7ee39f92016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 595 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 595 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 595 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 595 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00467 +/- 0.00933 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.00400 +/- 0.00333 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0653 +/- 0.00867 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04200
Phenol Explorer Compound ID595
FooDB IDFDB014417
KNApSAcK IDC00000606
Chemspider ID106491
KEGG Compound IDC10682
BioCyc IDCPD-8912
BiGG IDNot Available
Wikipedia LinkMatairesinol
METLIN IDNot Available
PubChem Compound119205
PDB IDNot Available
ChEBI ID6698
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1486251
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:18803219 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .