Enterodiol

Names

[ Name ]:
Enterodiol

[Synonym ]:
3,3'-[2,3-Bis(hydroxymethyl)butane-1,4-diyl]diphenol
Enterodiol
Arbo 9

Biological Activity

[Description]:

Enterodiol is transformed by human intestinal bacteria from lignans contained in various whole-grain cereals, nuts, legumes, flaxseed, and vegetables. Enterodiol has an apoptotic effect in colorectal cancer (CRC) cells. Anti-cancer activities[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[Target]

Human Endogenous Metabolite

[In Vitro]

Enterodiol (0-100 μM; 24-72 hours) results in an apoptosis rate of up to 40% in CT26 cells. Enterodiol shows no cytotoxicity toward RAW264.7 macrophages[1]. Enterodiol (0-100 μM; 24-48 hours) also suppresses the migration of CRC cells in a concentration-dependent manner. The phosphorylation of ERK, JNK, and p38 is down-regulated with Enterodiol treatment. Enterodiol (0-100 μM; 48 hours) decreases the expression levels of anti-apoptotic proteins in CRC cells[1].

[In Vivo]

Enterodiol (1 mg/kg; intra-tumor injection method; once every other day until day 32) suppresses tumor markedly[2]. Animal Model: 4-8 weeks old female BALB/c nude mice[2] Dosage: 1 mg/kg Administration: Intra-tumor injection method; once every other day until day 32 Result: A significant reduction in the tumor volume in the experimental groups compared to the PBS group.

[References]

[1]. Shin MK, et al. Apoptotic effect of enterodiol, the final metabolite of edible lignans, in colorectal cancer cells. J Sci Food Agric. 2019;99(5):2411-2419.

[2]. Liu H, et al. Enterolactone has stronger effects than enterodiol on ovarian cancer. J Ovarian Res. 2017;10(1):49. Published 2017 Jul 24.

Chemical & Physical Properties

[ Density]:
1.251g/cm3

[ Boiling Point ]:
554.9ºC at 760 mmHg

[ Molecular Formula ]:
C₁₈H₂₂O₄

[ Molecular Weight ]:
302.36

[ Flash Point ]:
262.5ºC

[ Exact Mass ]:
302.15200

[ PSA ]:
80.92000

[ LogP ]:
2.10000

[ Index of Refraction ]:
1.626

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ WGK Germany ]:
3