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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:
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; 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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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)
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
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
Boram Lee et al.
Biochemical and biophysical research communications, 421(1), 76-80 (2012-04-10)
Mitochondrial reactive oxygen species (mROS) are involved in cancer initiation and progression and function as signaling molecules in many aspects of hypoxia and growth factor-mediated signaling. Here we report that matairesinol, a natural small molecule identified from the cell-based screening
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
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