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Merck
CN

04157

Supelco

Matairesinol

analytical standard

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:
85151701
PubChem Substance ID:
329747890
NACRES:
NA.24

Key Documents

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grade

analytical standard

Quality Level

100

Assay

≥95.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

impurities

≤5.0% water

application(s)

food and beverages

format

neat

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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General description

Matairesinol, an enterolignan precursor and a naturally occurring dibenzylbutyrolactone lignan, is widely found in several plant-based foods, including oilseeds, whole grains, vegetables, and fruits. It is reported to have antioxidant, anti-estrogenic and anti-tumor properties.

Application

Matairesinol may be used as an analytical standard for the determination of the analyte in flax seeds, food products, transformed hairy root culture of Linum usitatissimum and human serum by chromatography based techniques.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG7200
BCCC7942
BCCC7019
BCCC3294
BCCB1891

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Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol
Milder IEJ, et al.
The British Journal of Nutrition, 93(3), 393-402 (2005)
Determination of lignans, phenolic acids and antioxidant capacity in transformed hairy root culture of Linum usitatissimum
Gabr AMM, et al.
Natural product research, 32(15), 1867-1871 (2018)
Determination of plant and enterolignans in human serum by high-performance liquid chromatography with tandem mass spectrometric detection
Smeds AI, et al.
Journal of Pharmaceutical and Biomedical Analysis, 41(3), 898-905 (2006)
Determination of matairesinol in flax seed by HPLC with coulometric electrode array detection
Kraushofer T and Sontag G
Journal of Chromatography. B, Biomedical Sciences and Applications, 777(1-2), 61-66 (2002)
Thomas Sandberg et al.
Journal of computational chemistry, 30(16), 2666-2673 (2009-04-28)
Molecular dynamics simulations were performed on the naturally occuring lignan hydroxymatairesinol (HMR) using the GROMACS software. The aim of this study was to explore the conformational behavior of HMR in aqueous solution adopting the TIP4P model. The topology of HMR
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