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
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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
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
Katharina Buck et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 29(28), 3730-3738 (2011-09-09)
Lignans--plant-derived compounds with estrogen-dependent and -independent anticarcinogenic properties--have been associated with postmenopausal breast cancer risk, but data are limited regarding their effect on survival. Dietary lignans are metabolized to enterolignans, which are subsequently absorbed and become bioavailable. We assessed the
Riina A Kekkonen et al.
The Journal of nutrition, 141(5), 870-876 (2011-03-18)
A high serum concentration of enterolactone, an enterolignan produced by colonic microbiota from precursors in cereals, vegetables, and fruits, is associated with reduced risk of acute coronary events. Probiotics and prebiotics modify colonic metabolism and may affect the serum enterolactone
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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