| Common Name |
(-)-Matairesinol
| Description |
(-)-Matairesinol is found in asparagus. Matairesinol is a plant lignan. It occurs with secoisolariciresinol in numerous foods such as oil seeds, whole grains, vegetables, and fruits. (Wikipedia) (-)-Matairesinol belongs to the family of Dibenzylbutyrolactone Lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB35698 ((-)-Matairesinol)
| Synonyms |
| Value |
Source |
3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanoneChEBI
Artigenin congenerChEBI
MatairesinolChEBI
(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-resinolMeSH
| Chemical Formlia |
C20H22O6
| Average Molecliar Weight |
358.3851
| Monoisotopic Molecliar Weight |
358.141638436
| IUPAC Name |
(3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
| Traditional Name |
matairesinol
| CAS Registry Number |
580-72-3
| SMILES |
[H][C@]1(CC2=CC=C(O)C(OC)=C2)COC(=O)[C@]1([H])CC1=CC=C(O)C(OC)=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 Key |
MATGKVZWFZHCLI-LSDHHAIUSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lignans, neolignans and related compounds
| Sub Class |
Furanoid lignans
| Direct Parent |
Dibenzylbutyrolactone lignans
| Alternative Parents |
Lignan lactones
Methoxyphenols
Phenoxy compounds
Methoxybenzenes
Anisoles
Alkyl aryl ethers
1-hydroxy-2-unsubstituted benzenoids
Gamma butyrolactones
Oxolanes
Carboxylic acid esters
Oxacyclic compounds
Monocarboxylic acids and derivatives
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| 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
Oxolane
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
| Molecliar Framework |
Aromatic heteromonocyclic compounds
| External Descriptors |
polyphenol (CHEBI:6698 )
gamma-lactone (CHEBI:6698 )
lignan (CHEBI:6698 )
Lignans (C10682 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Food
| Biofunction |
Nutrient
| Application |
Nutrient
| Cellliar locations |
Membrane
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point119 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.012 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.63 m3·mol-1ChemAxon
Polarizability36.86 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Membrane
| Biofluid Locations |
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 595
8017326
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 595
10798213
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 595
10952094
details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 595
7722188
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
595
| Phenol Explorer Metabolite ID |
595
| FoodDB ID |
FDB014417
| KNApSAcK ID |
C00000606
| Chemspider ID |
106491
| KEGG Compound ID |
C10682
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Matairesinol
| NuGOwiki Link |
HMDB35698
| Metagene Link |
HMDB35698
| METLIN ID |
Not Available
| PubChem Compound |
119205
| PDB ID |
MAX
| ChEBI ID |
65005
Product: Biotin Hydrazide
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 12490620
