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40043

Sigma-Aldrich

Matairesinol

≥85% (HPLC)

Synonym(s):

(αR,βR)-α,β-Bis(4-hydroxy-3-methoxybenzyl)butyrolactone

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About This Item

Empirical Formula (Hill Notation):
C20H22O6
CAS Number:
580-72-3
Molecular Weight:
358.39
Beilstein/REAXYS Number:
7826317
MDL number:
MFCD03453216
UNSPSC Code:
41116105
PubChem Substance ID:
329755924
NACRES:
NA.21

Quality Level

100

assay

≥85% (HPLC)

storage temp.

2-8°C

SMILES string

COc1cc(C[C@H]2COC(=O)[C@@H]2Cc3ccc(O)c(OC)c3)ccc1O

InChI

1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1

InChI key

MATGKVZWFZHCLI-LSDHHAIUSA-N

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Other Notes

Matairesinol, a phytoestrogen is employed as dietary supplement leading to metabolites with estrogenic properties[1]; HPLC determination of matairesinol[2]

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCB2725
BCBQ6689V
BCBW3093

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L.P. Meagher, G.R. Beecher
J. Food Compos. Anal., 13, 935-935 (2000)
Johanna W Lampe et al.
Journal of AOAC International, 89(4), 1174-1181 (2006-08-19)
Phytoestrogens occur naturally in plants and are structurally similar to mammalian estrogens. The lignans are a class of phytoestrogen and can be metabolized to the biologically active enterolignans, enterodiol, and enterolactone by a consortium of intestinal bacteria. Secoisolariciresinol diglucoside (SDG)
Barbara Raffaelli et al.
Organic & biomolecular chemistry, 6(14), 2619-2627 (2008-07-05)
Various conflicting data on the rearrangement and absolute stereochemistry of hydroxylignano-9,7'-lactones are resolved using 18O labeled compounds, also confirmed by an X-ray analysis of a pure lignano-9,7'-lactone enantiomer, obtained for the first time. Under NaH/DMF rearrangement conditions a silyl protected
Ivon E J Milder et al.
The American journal of clinical nutrition, 84(2), 400-405 (2006-08-10)
Plant lignans are converted to enterolignans that have antioxidant and weak estrogen-like activities, and therefore they may lower cardiovascular disease and cancer risks. We investigated whether the intakes of 4 plant lignans (lariciresinol, pinoresinol, secoisolariciresinol, and matairesinol) were inversely associated
Piero Frediani et al.
Journal of agricultural and food chemistry, 55(10), 3877-3883 (2007-04-24)
A general synthetic procedure leading to isotopomeric dihydro-2(3H)furanones (gamma-butyrolactones) containing two, four, or six deuterium atoms has been developed. The labeled dihydro-2(3H)furanones were synthesized in quantitative yield from the saturated diacid C4 (succinic) or unsaturated diacids C4 (fumaric, maleic, or
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