Matairesinol

Matairesinol^[1]

Names
IUPAC name (8β,8′α)-4,4′-Dihydroxy-3,3′-dimethoxylignano-9,9′-lactone
Systematic IUPAC name (3R,4R)-3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Other names (αR,βR)-α,β-Bis(4-hydroxy-3-methoxybenzyl)butyrolactone
Identifiers
CAS Number	580-72-3 Y
3D model ( JSmol )	Interactive image
ChEBI	CHEBI:6698 N
ChEMBL	ChEMBL425148 Y
ChemSpider	106491 Y
DrugBank	DB04200 Y
KEGG	C10682 Y
PubChem CID	119205
UNII	XLW63P8WUA Y
CompTox Dashboard (EPA)	DTXSID40920490
InChI 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 Y Key: MATGKVZWFZHCLI-LSDHHAIUSA-N Y 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 Key: MATGKVZWFZHCLI-LSDHHAIUBP Key: MATGKVZWFZHCLI-LSDHHAIUSA-N
SMILES O=C2OC[C@H](Cc1cc(OC)c(O)cc1)[C@H]2Cc3ccc(O)c(OC)c3
Properties
Chemical formula	C20H22O6
Molar mass	358.390 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Matairesinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, such as rye, and together with secoisolariciresinol has attracted much attention for its beneficial nutritional effects.^[2]

Metabolism

The plant lignans are precursors of the enterolignans (mammalian lignans).^[3] A number of plant lignans are metabolized to the enterolignans (enterodiol and enterolactone) that can potentially reduce the risk of certain cancers and cardiovascular diseases.^[4]

Biomedical considerations

Although some studies attribute disease preventative (cardio-protective and hormone associated cancers like breast cancer) benefits of lignans, the results are inconclusive.^[5] Matairesinol has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1).^[6]

References