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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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
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
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
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
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