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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

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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Eudesmine ≥95% (LC/MS-ELSD)

Sigma-Aldrich

SMB00182

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(−)-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

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
Carol J Fabian et al.
Cancer prevention research (Philadelphia, Pa.), 3(10), 1342-1350 (2010-08-21)
Preclinical and correlative studies suggest reduced breast cancer with higher lignan intake or blood levels. We conducted a pilot study of modulation of risk biomarkers for breast cancer in premenopausal women after administration of the plant lignan secoisolariciresinol given as
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
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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