60372
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
UNSPSC Code:
41116105
NACRES:
NA.21
PubChem Substance ID:
EC Number:
249-599-2
Beilstein/REAXYS Number:
6611290
MDL number:
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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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
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
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