Introduction：Basic information about CAS 78473-71-9|Enterolactone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Enterolactone |
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| CAS Number | 78473-71-9 | Molecular Weight | 298.33 |
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| Density | 1.3±0.1 g/cm3 | Boiling Point | 561.4±25.0 °C at 760 mmHg |
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| Molecular Formula | C18H18O4 | Melting Point | 141-143°C (lit.) |
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| MSDS | Chinese | Flash Point | 209.0±16.7 °C |
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| Symbol |
GHS07 | Signal Word | Warning |
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Names
| Name | enterolactone |
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| Synonym | More Synonyms |
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Enterolactone BiologicalActivity
| Description | Enterolactone is a bioactive phenolic metabolite known as a mammalian lignan derived from dietary lignans. Enterolactone has estrogenic properties and anti-breast cancer activity[1]. Enterolactone is a radiosensitizer for human breast cancer cell lines through impaired DNA repair and increased apoptosis[2]. |
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| Related Catalog | Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>Cancer |
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| In Vitro | Enterolactone (25-75 μM; 48 hours) arrests the growth of MDA-MB-231 breast cancer cells in the ‘S’ phase[1] Enterolactone (25-75 μM; 15 hours) triggers apoptosis in MDA-MB-231 breast cancer cells via caspase-3 activation[1]. Enterolactone inhibits TGF-β-induced migration of MDA-MB-231 breast cancer cells. Enterolactone inhibits TGF-β-induced invasion of MDA-MB-231 breast cancer cells through ECM. Enterolactone inhibits the TGF-β-induced EMT program in MDA-MB-231 breast cancer cells. Enterolactone reduces the formation of actin stress fibers by inhibiting the expression of CD44 and MAPK-p38. Enterolactone inhibits the ERK/NF-κB/Snail signaling pathway to revert TGF-β-induced EMT in MDA-MB-231 cells[1]. Cell Viability Assay[1] Cell Line: MDA-MB-231 cells Concentration: 25, 50, 75 μM Incubation Time: 48 hours Result: 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. |
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| References | [1]. Bigdeli B, et al. 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]. Mali AV, et al. 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. |
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Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
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| Boiling Point | 561.4±25.0 °C at 760 mmHg |
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| Melting Point | 141-143°C (lit.) |
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| Molecular Formula | C18H18O4 |
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| Molecular Weight | 298.33 |
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| Flash Point | 209.0±16.7 °C |
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| Exact Mass | 298.120514 |
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| PSA | 66.76000 |
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| LogP | 2.29 |
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| Vapour Pressure | 0.0±1.6 mmHg at 25°C |
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| Index of Refraction | 1.635 |
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| InChIKey | HVDGDHBAMCBBLR-PBHICJAKSA-N |
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| SMILES | O=C1OCC(Cc2cccc(O)c2)C1Cc1cccc(O)c1 |
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| Storage condition | 2-8°C |
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Safety Information
| Symbol |
GHS07 |
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| Signal Word | Warning |
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| Hazard Statements | H315-H319-H335 |
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| Precautionary Statements | P261-P305 + P351 + P338 |
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| Hazard Codes | Xi: Irritant; |
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| Risk Phrases | R36/37/38 |
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| Safety Phrases | 26-36 |
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| RIDADR | NONH for all modes of transport |
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Synonyms
| HPMF |
| HBBL |
| (3R,4R)-3,4-Bis(3-hydroxybenzyl)dihydrofuran-2(3H)-one |
| trans-Dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-2(3H)-furanone |
| Enterolaktone |
| 2(3H)-Furanone, dihydro-3,4-bis((3-hydroxyphenyl)methyl)-, (3R,4R)-rel- |
| 2(3H)-Furanone, dihydro-3,4-bis((3-hydroxyphenyl)methyl)-, trans- |
| Enterolakton |
| 2(3H)-Furanone, dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-, (3R,4R)- |
| ENTEROLACTON |
| rac Enterolactone |
| (3R,4R)-3,4-Bis(3-hydroxybenzyl)dihydro-2(3H)-furanone |
| Compound 180/442 |
