Enterolactone is a bioactive phenolic metabolite known as mammalian lignan, derived from dietary lignans. Enterolactone has estrogenic properties and anti-breast cancer activity. Enterolactone is a radiosensitizer of human breast cancer cell lines through damaged DNA repair and increased apoptosis.

Physicochemical Properties

Molecular Formula	C18H18O4
Molecular Weight	298.33
Exact Mass	298.12
CAS #	78473-71-9
Related CAS #	Enterolactone-d6;104411-11-2
PubChem CID	10685477
Appearance	Colorless to light yellow liquid
Density	1.3±0.1 g/cm3
Boiling Point	561.4±25.0 °C at 760 mmHg
Melting Point	141-143°C (lit.)
Flash Point	209.0±16.7 °C
Vapour Pressure	0.0±1.6 mmHg at 25°C
Index of Refraction	1.635
LogP	2.29
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Heavy Atom Count	22
Complexity	383
Defined Atom Stereocenter Count	2
SMILES	C1C(C(C(=O)O1)CC2=CC(=CC=C2)O)CC3=CC(=CC=C3)O
InChi Key	HVDGDHBAMCBBLR-WMLDXEAASA-N
InChi Code	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+/m0/s1
Chemical Name	(3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Entirelactone (25-75 μM; 48 hours) stops MDA-MB-231 breast cancer cells from growing in the 'S' phase[1]. Enterolactone (25-75 μM; 15 hours) activates caspase-3 to cause MDA-MB-231 breast cancer cells to undergo apoptosis[1]. The migration of MDA-MB-231 breast cancer cells triggered by TGF-β is inhibited by enterolactone. Through ECM, enterolactone prevents MDA-MB-231 breast cancer cells from undergoing TGF-β-induced invasion. In MDA-MB-231 breast cancer cells, enterolactone suppresses the EMT pathway that is triggered by TGF-β. Enterolactone inhibits the production of CD44 and MAPK-p38, which decreases the development of actin stress fibers. In MDA-MB-231 cells, enterolactone reverses TGF-β-induced EMT by blocking the ERK/NF-κB/Snail signaling pathway[1].
Cell Assay	Cell Viability Assay[1] Cell Types: MDA -MB-231 cells Tested Concentrations: 25, 50, 75 μM Incubation Duration: 48 hrs (hours) Experimental Results: There was a non-significant increase (~24%) in the S phase population following treatment with 25 μM EL, whereas there were significant increases (~34% and ~39%) following treatment with 50 and 75 μM EL, respectively.
ADME/Pharmacokinetics	Metabolism / Metabolites Enterolactone has known human metabolites that include Enterolactone O-glucuronide.
References	[1]. Enterolactone: A novel radiosensitizer for human breast cancer cell lines through impaired DNA repair and increased apoptosis. Toxicol Appl Pharmacol. 2016;313:180-194. [2]. Enterolactone modulates the ERK/NF-κB/Snail signaling pathway in triple-negative breast cancer cell line MDA-MB-231 to revert the TGF-β-induced epithelial-mesenchymal transition. Cancer Biol Med. 2018;15(2):137-156.
Additional Infomation	(3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one has been reported in Urtica dioica, Sesamum indicum, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.3520 mL	16.7600 mL	33.5199 mL
	5 mM	0.6704 mL	3.3520 mL	6.7040 mL
	10 mM	0.3352 mL	1.6760 mL	3.3520 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.