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Key Documents

60372

Sigma-Aldrich

Secoisolariciresinol

≥95.0% (HPLC)

Synonym(s):

(2R,3R)-2,3-Bis(4-hydroxy-3-methoxybenzyl)-1,4-butanediol

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About This Item

Empirical Formula (Hill Notation):
C20H26O6
Molecular Weight:
362.42
Beilstein:
6611290
EC Number:
MDL number:
UNSPSC Code:
41116105
PubChem Substance ID:
NACRES:
NA.21

Quality Level

Assay

≥95.0% (HPLC)

form

solid

SMILES string

OC[C@@H]([C@H](CO)CC1=CC=C(O)C(OC)=C1)CC2=CC(OC)=C(O)C=C2

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

InChI key

PUETUDUXMCLALY-HOTGVXAUSA-N

Application

Secoisolariciresinol is a metabolite of secoisolariciresinol diglucoside (SDG), an antioxidant present in flaxseed.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Physical form

mixture of enantiomers of the (R*,R*)-diastereoisomer

Other Notes

Component of functional food. Flaxseed lignan with antioxidant activity

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Cheng-Zhi Wang et al.
BMC microbiology, 10, 115-115 (2010-04-20)
The effects of enterolignans, e.g., enterodiol (END) and particularly its oxidation product, enterolactone (ENL), on prevention of hormone-dependent diseases, such as osteoporosis, cardiovascular diseases, hyperlipemia, breast cancer, colon cancer, prostate cancer and menopausal syndrome, have attracted much attention. To date
D D Kitts et al.
Molecular and cellular biochemistry, 202(1-2), 91-100 (2000-03-08)
The antioxidant activities of the flaxseed lignan secoisolariciresinol diglycoside (SDG) and its mammalian lignan metabolites, enterodiol (ED) and enterolactone (EL), were evaluated in both lipid and aqueous in vitro model systems. All three lignans significantly (p < or = 0.05)
Shiori Tominaga et al.
Food & function, 3(1), 76-82 (2011-10-28)
Flaxseed lignan, secoisolariciresinol has been reported to possess health benefits. We previously synthesized each stereoisomer of secoisolariciresinol and found that (-)-secoisolariciresinol reduces lipid accumulation and induces adiponectin production in 3T3-L1 adipocytes. Here we show the effects of (-)-secoisolariciresinol on high-fat
K Struijs et al.
Journal of applied microbiology, 107(1), 308-317 (2009-03-24)
It has been investigated whether secoisolariciresinol (SECO) and anhydrosecoisolariciresinol (AHS), an acid degradation product of SECO, could be fermented in a similar way, and to a similar extent, by members of the intestinal microbiota. AHS and SECO were demethylated by
Sandra M Sacco et al.
Journal of medicinal food, 14(10), 1208-1214 (2011-06-15)
Flaxseed, rich in the phytoestrogen lignan secoisolariciresinol diglycoside (SDG), provides protection against bone loss at the lumbar vertebrae primarily when combined with low-dose estrogen therapy in the ovariectomized rat model of postmenopausal osteoporosis. Whether SDG metabolites are accessible to skeletal

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