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Merck

45199

Enterolactone

~95% (HPLC)

Synonym(s):

trans-α,β-Bis(3-hydroxybenzyl)butyrolactone

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About This Item

Empirical Formula (Hill Notation):
C18H18O4
CAS Number:
78473-71-9
Molecular Weight:
298.33
UNSPSC Code:
85151701
NACRES:
NA.77
PubChem Substance ID:
57650263
MDL number:
MFCD01861506
Beilstein/REAXYS Number:
4699604

Key Documents

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Product Name

Enterolactone, ~95% (HPLC)

InChI

1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m1/s1

SMILES string

Oc1cccc(C[C@@H]2COC(=O)[C@H]2Cc3cccc(O)c3)c1

InChI key

HVDGDHBAMCBBLR-PBHICJAKSA-N

assay

~95% (HPLC)

form

solid

storage temp.

2-8°C

Quality Level

100

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Biochem/physiol Actions

Enterolactone is the major human metabolite of dietary sesamin (lignan from sesame seeds). A phytoestrogen, it shows an inverse correlation with risk of breast cancer in one study.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP0398
BCCN6171
BCCM5624
BCCL1264
BCCM1589

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Mark J McCann et al.
Molecular nutrition & food research, 57(2), 212-224 (2012-11-14)
There is evidence that a mammalian lignan, enterolactone (ENL), decreases the proliferation rate of prostate cancer cells, although previous studies have used concentrations difficult to achieve through dietary modification. We have therefore investigated the anti-proliferative effects of ENL in an
José L Peñalvo et al.
The Journal of nutrition, 142(4), 751-756 (2012-03-02)
Fiber-rich diets are associated with favorable lipid profiles, but the specific compounds and the mechanisms behind this effect are yet to be fully understood. Lignans are fiber-related polyphenols that have been associated with lower prevalence of cardiovascular disease. The objective
Anne Tuomisto et al.
Scientific reports, 9(1), 11209-11209 (2019-08-03)
The dietary lignan metabolite, enterolactone, has been suggested to have anti-cancer functions, and high serum enterolactone concentrations have been associated with decreased risk of breast and prostate cancers. We hypothesized that serum enterolactone concentrations as a marker of plant-based foods
Karin Preindl et al.
Analytical chemistry, 91(17), 11334-11342 (2019-08-10)
We are constantly exposed to a variety of environmental contaminants and hormones, including those mimicking endogenous estrogens. These highly heterogeneous molecules are collectively referred to as xenoestrogens and hold the potential to affect and alter the delicate hormonal balance of
Kirstine S Krogholm et al.
The British journal of nutrition, 108(10), 1904-1912 (2012-03-29)
Since collection of 24 h urine samples is very time consuming and difficult to obtain, epidemiological studies typically only obtain spot urine samples. The aim of the present study was to evaluate whether flavonoids and enterolactone in overnight urine could
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