Hydroxymatairesinol

Hydroxymatairesinol

Names
IUPAC name (3R,4R)-4-[(S)-Hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxybenzyl)dihydro-2(3H)-furanone
Systematic IUPAC name (3R,4R)-4-[(S)-Hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-3-(4-hydroxy-3-methoxybenzyl)dihydro-2(3H)-furanone
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	9123982
PubChem CID	10948757
InChI InChI=1S/C20H22O7/c1-25-17-8-11(3-5-15(17)21)7-13-14(10-27-20(13)24)19(23)12-4-6-16(22)18(9-12)26-2/h3-6,8-9,13-14,19,21-23H,7,10H2,1-2H3/t13-,14+,19-/m1/s1 Key: UKHWOLNMBQSCLJ-BIENJYKASA-N InChI=1/C20H22O7/c1-25-17-8-11(3-5-15(17)21)7-13-14(10-27-20(13)24)19(23)12-4-6-16(22)18(9-12)26-2/h3-6,8-9,13-14,19,21-23H,7,10H2,1-2H3/t13-,14+,19-/m1/s1 Key: UKHWOLNMBQSCLJ-BIENJYKABV
SMILES COC1=C(C=CC(=C1)C[C@@H]2[C@H](COC2=O)[C@@H](C3=CC(=C(C=C3)O)OC)O)O
Properties
Chemical formula	C20H22O7
Molar mass	374.384
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Hydroxymatairesinol (HMR) is a lignan found in Norway spruce (Picea abies). It is an enterolactone precursor with anticancer activities. In rats, HMR decreased the volume of induced tumours and stabilised established tumours, as well as preventing the development of new tumours. It has also shown anti-oxidant properties in vitro.

HMR's chemical structure is similar to matairesinol. At high concentrations, HMR has estrogenic properties, which are considerably weaker than those of estradiol.