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Merck
CN

04157

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
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329747890
MDL number:
MFCD03453216
Beilstein/REAXYS Number:
7826317

Key Documents

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SMILES string

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

InChI key

MATGKVZWFZHCLI-LSDHHAIUSA-N

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

grade

analytical standard

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

Quality Level

100

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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

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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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)
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)
E Peuhu et al.
Oncogene, 29(6), 898-908 (2009-11-26)
Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) has been shown to be selectively pro-apoptotic in cancer cells, with minimal toxicity to normal tissues. Although this feature makes TRAIL a promising anticancer agent, not all cancer cell types are sensitive to TRAIL-induced
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
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