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:
Molecular Weight:
298.33
Beilstein:
4699604
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.
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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 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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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
Anja Olsen et al.
Breast cancer research and treatment, 128(3), 883-889 (2011-02-23)
Experimental and epidemiological studies have suggested that the phytoestrogen enterolactone is associated to biological mechanisms that may have positive effects on breast cancer development. In a recent study based on American breast cancer patients, high intakes of lignans, the precursor
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
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