A lignan with diverse biological activities
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(+)-Secoisolariciresinol

Item No. 33155

Technical Information
Formal Name
2S,3S-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol
CAS Number
145265-02-7
Synonyms
  • (+)-SECO
Molecular Formula
C20H26O6
Formula Weight
Purity
≥98%
Formulation
A crystalline solid
SMILES
COC(C=C1C[C@H](CO)[C@@H](CO)CC2=CC(OC)=C(C=C2)O)=C(C=C1)O
InChi Code
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
InChi Key
PUETUDUXMCLALY-HZPDHXFCSA-N
Origin
Plant/Taxus chinensis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    (+)-Secoisolariciresinol ((+)-SECO) is a lignan that has been found in flaxseed and has diverse biological activities.1,2,3 It inhibits α-glucosidase and α-amylase in a cell-free assay when used at a concentration of 20 µM.1 (+)-SECO (0.3 mM) reduces adiponectin production by, and triglyceride accumulation in, 3T3-L1 adipocytes.2 It stimulates IgM production in HB4C5 hybridoma cells when used at concentrations ranging from 0.1 to 100 µM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hano, C., Renouard, S., Molinié, R., et alFlaxseed (Linum usitatissimum L.) extract as well as (+)-secoisolariciresinol diglucoside and its mammalian derivatives are potent inhibitors of α-amylase activity. Bioorg. Med. Chem. Lett. 23(10), 3007-3012 (2013).

    2. Tominaga, S., Sugahara, T., Nishimoto, S., et alThe effect of secoisolariciresinol on 3T3-L1 adipocytes and the relationship between molecular structure and activity. Biosci. Biotechnol. Biochem. 73(1), 35-39 (2009).

    3. Sugahara, T., Yamauchi, S., Nishimoto, S., et alThe structure-activity relationships of flaxseed lignan, secoisolariciresinol. Interdisciplinary Studies on Environmental Chemistry 263-268 (2008).