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Key Documents

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:
Molecular Weight:
358.39
Beilstein:
7826317
MDL number:
UNSPSC Code:
41116105
PubChem Substance ID:
NACRES:
NA.21

Quality Level

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; HPLC determination of matairesinol

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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L.P. Meagher, G.R. Beecher
J. Food Compos. Anal., 13, 935-935 (2000)
Tanja Kraushofer et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 777(1-2), 61-66 (2002-09-25)
A HPLC method coupled with coulometric electrode array detection for the determination of matairesinol in flax seed is described. The defatted sample was spiked with bisphenol A (internal standard), refluxed for 75 min in a mixture of ethanol-bidistilled water-12 M
Ulrike Müller et al.
Electrophoresis, 29(17), 3582-3587 (2008-09-23)
Lignans are dimeric phenylpropanoid compounds in plants that enjoy increasing medicinal interest because of their phytoestrogen activity. Lignans are chiral compounds and for most natural occurring lignans, chirality is not known. Separation of racemic matairesinol by CE in a non-coated
Rong-Jyh Lin et al.
Natural product research, 22(9), 747-753 (2008-06-24)
(+)-(8R,8'S)-thujaplicatin methyl ether (1), arctigenin (2), matairesinol (3), trans-2,3-dibenzylbutyrolactone (4), vanillic acid (5), p-hydroxybenzoic acid (6), methoxybenzoic acid (7), methylparaben (8), stearic acid (9), palmitic acid (10), olenic acid (11), friedelinol (12), and a mixture of beta-sitosterol (13) and stigmasterol
Saya Kawahara et al.
Bioscience, biotechnology, and biochemistry, 74(9), 1878-1883 (2010-09-14)
The IgE-suppressive activity of (-)-matairesinol is demonstrated, and the structure-activity relationship of (-)-matairesinol clarified. 3',4-Dihydroxy-3,4'-dimethoxylignano-9,9'-lactone showed higher IgE-suppressive activity than (-)-matairesinol without any cytotoxic activity. Some derivatives bearing a longer and more bulky alkoxy group at the 3 or 4

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