Matairesinol

Matairesinol[1]
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=
PubChem	119205
ChemSpider	106491 Y
DrugBank	DB04200
ChEMBL	CHEMBL425148 N
Jmol-3D images	Image 1
SMILES O=C2OC[C@H](Cc1cc(OC)c(O)cc1)[C@H]2Cc3ccc(O)c(OC)c3
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
Properties
Molecular formula	C20H22O6
Molar mass	358.39 g mol−1
Exact mass	358.141638 u
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Matairesinol is a plant lignan. It occurs with secoisolariciresinol in numerous foods such as oil seeds, whole grains, vegetables, and fruits.^[2]

The plant lignans are precursors of the enterolignans (mammalian lignans). 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.^[3]

Although there are studies which indicate the disease prevention (cardio-protective and hormone associated cancers like breast cancer) benefits of lignans, the results are not yet conclusive.^[4]

References

1. ^ Matairesinol at Sigma-Aldrich
2. ^ Niemeyer HB, Honig DM, Kulling SE, Metzler M (October 2003). "Studies on the metabolism of the plant lignans secoisolariciresinol and matairesinol". J. Agric. Food Chem. 51 (21): 6317–25. doi:10.1021/jf030263n. PMID 14518962. 
3. ^ Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC (March 2005). "Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol". Br. J. Nutr. 93 (3): 393–402. doi:10.1079/BJN20051371. PMID 15877880. http://journals.cambridge.org/abstract_S0007114505000504. 
4. ^ Linus Pauling Institute at Oregon State University