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Merck

45199

Sigma-Aldrich

Enterolactone

~95% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C18H18O4
Número de CAS:
Peso molecular:
298.33
Beilstein/REAXYS Number:
4699604
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.77
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assay

~95% (HPLC)

Quality Level

form

solid

storage temp.

2-8°C

SMILES string

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

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

InChI key

HVDGDHBAMCBBLR-PBHICJAKSA-N

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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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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
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
Li-Quan Wang
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 777(1-2), 289-309 (2002-09-25)
The mammalian phytoestrogens enterodiol (END) and enterolactone (ENL) are produced in the colon by the action of bacteria on the plant precursors matairesinol (MAT), secoisolariciresinol (SECO), their glycosides, and other precursors in the diet. Both END and ENL have been
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
Julie Aarestrup et al.
The British journal of nutrition, 109(12), 2269-2275 (2012-11-02)
The phyto-oestrogen enterolactone has been hypothesised to protect against hormone-dependent cancers, probably through its antioestrogenic potential. We investigated whether a higher level of plasma enterolactone was associated with a lower incidence of endometrial cancer in a case-cohort study in the

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