(+)-Secoisolariciresinol Chemical Properties

Melting point:

111-112 °C(Solv: chloroform (67-66-3); isopropyl ether (108-20-3))

Boiling point:

609.1±55.0 °C(Predicted)

Density 

1.251±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: Soluble

form 

Solid

pka

9.81±0.20(Predicted)

color 

White to off-white

Major Application

food and beverages

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-/m1/s1

InChIKey

PUETUDUXMCLALY-HZPDHXFCSA-N

SMILES

O(C)c1c(ccc(c1)C[C@@H]([C@@H](CO)Cc2cc(c(cc2)O)OC)CO)O

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

(+)-Secoisolariciresinol Usage And Synthesis

Uses

food and beverages

Definition

ChEBI: (+)-secoisolariciresinol is an enantiomer of secoisolariciresinol having (+)-(2S,3S)-configuration. It is an enantiomer of a (-)-secoisolariciresinol.

References

[1] CHRISTOPHE HANO . Flaxseed (Linum usitatissimum L.) extract as well as (+)-secoisolariciresinol diglucoside and its mammalian derivatives are potent inhibitors of α-amylase activity[J]. Bioorganic & Medicinal Chemistry Letters, 2013, 23 10: Pages 3007-3012. DOI: 10.1016/j.bmcl.2013.03.029
[2] SHIORI TOMINAGA. The Effect of Secoisolariciresinol on 3T3-L1 Adipocytes and the Relationship between Molecular Structure and Activity[J]. Bioscience, Biotechnology, and Biochemistry, 2009, 148 5 Suppl 1: 35-39. DOI: 10.1271/bbb.80393
[3] D D KITTS. Antioxidant activity of the flaxseed lignan secoisolariciresinol diglycoside and its mammalian lignan metabolites enterodiol and enterolactone.[J]. Molecular and Cellular Biochemistry, 1999, 202 1-2: 91-100. DOI: 10.1023/a:1007022329660