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60372

Sigma-Aldrich

Secoisolariciresinol

≥95.0% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C20H26O6
Peso molecular:
362.42
Beilstein/REAXYS Number:
6611290
EC Number:
249-599-2
MDL number:
MFCD01075136
UNSPSC Code:
41116105
PubChem Substance ID:
329758917
NACRES:
NA.21

Quality Level

100

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
BCCH0033
BCCB5794
BCBR1232V
BCBH3105V
BCBL3009V

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PHL89525

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Eudesmine ≥95% (LC/MS-ELSD)

Sigma-Aldrich

SMB00182

Eudesmine

(−)-Arctigenin ≥95% (LC/MS-ELSD)

Sigma-Aldrich

SMB00075

(−)-Arctigenin

(−)-Syringaresinol 4-O-β-D-glucoside phyproof® Reference Substance

PHL83914

(−)-Syringaresinol 4-O-β-D-glucoside

Niina M Saarinen et al.
The British journal of nutrition, 104(6), 833-841 (2010-04-15)
Limited information is available on lignan metabolism and tissue distribution between sexes and the effects of prolonged lignan exposure on tissue concentrations. In the present study, excretion and tissue distribution of lignans were compared after 1 d and 7 d
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
M R O'Neil et al.
Domestic animal endocrinology, 37(3), 148-158 (2009-06-30)
To evaluate the estrogenic potential of secoisolariciresinol diglycoside (SDG) found in linseed meal (LSM) on visceral organ mass, IGF-I, and thyroid hormone (T(3) and T(4)) concentrations, 48 multiparous, ovariectomized ewes (54.6 +/- 1.1 kg) were used in a 3 x
Anni Woting et al.
FEMS microbiology ecology, 72(3), 507-514 (2010-04-08)
The bioactivity of lignans depends on their transformation by gut bacteria. The intestinal bacteria Clostridium saccharogumia, Eggerthella lenta, Blautia producta and Lactonifactor longoviformis convert the plant lignan secoisolariciresinol diglucoside via secoisolariciresinol (SECO) into the bioactive enterolignans enterodiol (ED) and enterolactone
Hisashi Nishiwaki et al.
Bioscience, biotechnology, and biochemistry, 75(9), 1735-1739 (2011-09-08)
The larvicidal activity against Culex pipiens of all stereoisomers of dihydroguaiaretic acid (DGA) and secoisolariciresinol was measured, and these DGAs were found to be potent. Sixteen (-)-DGA derivatives were then newly synthesized to analyze their structure-activity relationship. Two derivatives monohydroxylated
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