45199
Enterolactone
~95% (HPLC)
Synonym(s):
trans-α,β-Bis(3-hydroxybenzyl)butyrolactone
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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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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
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
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
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
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
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