Secoisolariciresinol

Secoisolariciresinol 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 matairesinol has attracted much attention for its beneficial nutritional effects.^[1]

Secoisolariciresinol

Chemical structure of secoisolariciresinol
Names
IUPAC name (8R,8′R)-3,3′-Dimethoxylignane-4,4′,9,9′-tetrol
Systematic IUPAC name (2R,3R)-2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol
Other names (−)-Secoisolariciresinol
Identifiers
CAS Number	29388-59-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:65004 N
ChEMBL	ChEMBL368347 N
ChemSpider	58845 N
ECHA InfoCard	100.045.076
EC Number	249-599-2
KEGG	C18167 Y
PubChem CID	65373
UNII	M8QRJ7JEJH Y
CompTox Dashboard (EPA)	DTXSID50183615
InChI InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1 N Key: PUETUDUXMCLALY-HOTGVXAUSA-N N
SMILES COC1=C(C=CC(=C1)CC(CO)C(CC2=CC(=C(C=C2)O)OC)CO)O
Properties
Chemical formula	C20H26O6
Molar mass	362.422 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

Occurrence

The water extract of silver fir wood contains more than 5% of secoisolariciresinol.^[2] It is also present in nettle brew.^[3] Its content in flaxseed (Linum usitatissimum) was found to be 0.3%,^[4] which is the highest known content in food.

Biomedical aspects

In the intestine the gut microflora can form secoisolariciresinol from the secoisolariciresinol diglucoside and it can then be further transformed into the enterolignan enterodiol. Epidemiological studies showed associations between secoisolariciresinol intake and decreased risk of cardiovascular disease are promising, but they are yet not well established, perhaps due to low lignan intakes in habitual Western diets. At the higher doses used in intervention studies, associations were more evident.^[5][6]

Glycosides

• Secoisolariciresinol diglucoside