(+/-)-Enterodiol-13C3

Base Information

• Chemical Name: (+/-)-Enterodiol-13C3
• CAS No.: 918502-74-6
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 305.337
• Mol file: 918502-74-6.mol

Synonyms:

Chemical Property of (+/-)-Enterodiol-13C3

Chemical Property:

• Melting Point: 174-176 °C
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Acetone (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

racEnterodiol-13C3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A labelled compound closely related to Enterolactone (E558950). A metabolite of sesame lignans (sesamin, sesamolin). Inhibits colonic cancer cell growth by inducing cell cycle arrest and apoptosis. Possible relationship between exposure and reduced risk of breast cancer.

Technology Process of (+/-)-Enterodiol-13C3

There total 9 articles about (+/-)-Enterodiol-13C3 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 39.0%

3x 13C enterolactone (741283-63-6,918502-72-4) → 3x 13C enterodiol (741283-64-7,918502-74-6)

Guidance literature:

3x ¹³C enterolactone; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃;

With sulfuric acid; In tetrahydrofuran; water; at 0 ℃;

Reference yield: 39.0%

[7,7',9'-13C3]enterolactone (918502-72-4) → [7,7',9'-13C3]enterodiol (918502-74-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃;

DOI:10.1002/jlcr.1007

Reference yield:

3-methoxy[α-13C]benzyl iodide (741283-61-4) → [7,7',9'-13C3]enterodiol (918502-74-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LDA / hexane; tetrahydrofuran; ethylbenzene / 3 h / -78 °C

1.2: 55 percent / tetrahydrofuran; hexane; ethylbenzene / -78 - 20 °C

2.1: 68 percent / boron tribromide / CH₂Cl₂ / 2.5 h / 20 °C

3.1: 39 percent / lithium aluminium hyrdide / tetrahydrofuran / 20 °C

With lithium aluminium tetrahydride; boron tribromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; ethylbenzene;

DOI:10.1002/jlcr.1007

upstream raw materials:

[7,7',9'-13C₃]enterolactone

3-methoxy[α-13C]benzyl iodide

3-methoxy[α-13C]benzyl alcohol

3-methoxy[carboxy-13C]benzoic acid

Refernces

• 1、 -. "SYNTHESIS OF 13C-LABELLED ESTROGEN ANALOGUES". Page 49-50. . Retrieved 2010/02/08.