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45199

Sigma-Aldrich

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:
78473-71-9
Molecular Weight:
298.33
Beilstein:
4699604
MDL number:
MFCD01861506
UNSPSC Code:
85151701
PubChem Substance ID:
57650263
NACRES:
NA.77

Assay

~95% (HPLC)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Barbara Michalak et al.
Frontiers in pharmacology, 9, 401-401 (2018-05-10)
Aim of the study: Taking into account that overactivated leukocytes are an important factor in the development of many chronic diseases, we investigated the activity of phytochemically characterized (HPLC-DAD-MSn) extracts from forsythia leaves and flowers on the pro- and anti-inflammatory
Pauliina Damdimopoulou et al.
The Journal of nutrition, 141(9), 1583-1589 (2011-07-15)
Enterolactone (EL) is an enterolignan produced by gut microbiota from dietary plant lignans. Epidemiological and experimental studies suggest that EL and plant lignans may reduce the risk of breast and prostate cancer as well as cardiovascular disease. These effects are
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