Seocalcitol

Base Information

• Chemical Name: Seocalcitol
• CAS No.: 134404-52-7
• Molecular Formula: C₃₀H₄₆O₃
• Molecular Weight: 454.693
• UNII: Q0OZ0D9223
• DSSTox Substance ID: DTXSID601025740
• Wikidata: Q27088781
• NCI Thesaurus Code: C26669
• Pharos Ligand ID: 2VFCDS6QDMRF
• Metabolomics Workbench ID: 35992
• ChEMBL ID: CHEMBL1908376
• Mol file: 134404-52-7.mol

Synonyms:1(S),3(R)-dihydroxy-20(R)-(5'-ethyl-5'-hydroxyhepta-1'(E),3'(E)-dien-1'-yl)-9,10-secopregna-5(Z),7(E),10(19)-triene;EB 1089;EB-1089;EB1089;seocalcitol

Chemical Property of Seocalcitol

Chemical Property:

• Vapor Pressure: 2.4E-17mmHg at 25°C
• Melting Point: 123-125°
• Refractive Index: 1.56
• Boiling Point: 608.5 °C at 760 mmHg
• PKA: 14.29±0.29(Predicted)
• Flash Point: 252.3 °C
• PSA: 60.69000
• Density: 1.06 g/cm³
• LogP: 6.42700
• Storage Temp.: Store at -20°C
• Solubility.: Soluble in DMSO
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 454.34469533
• Heavy Atom Count: 33
• Complexity: 812

Purity/Quality:

99% ^*data from raw suppliers

EB1089 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CC)(C=CC=CC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C)O
• Isomeric SMILES: CCC(CC)(/C=C/C=C/[C@@H](C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)C)O
• Recent ClinicalTrials: Seocalcitol Versus Placebo in Advanced Hepatocellular Carcinoma
• Description: EB 1089 is a synthetic vitamin D analog that is 50-200 times more potent than calcitriol at inhibiting cell proliferation and differentiation, yet displays reduced calcemic activity compared to that of calcitriol. It has been shown to promote tumor regression in vitro by inducing apoptosis.
• Uses: EB 1089 is an analogue of Calcitriol (C144500), which is a biologically active form of Vitamin D3 (1). It can be used in androgen receptor-targeted therapy research for breast cancer (2). EB 1089 exhibits anti-cancer properties.

Technology Process of Seocalcitol

There total 5 articles about Seocalcitol 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:

C42H74O3Si2 → seocalcitol (134404-52-7)

Guidance literature:

With tetrabutylammomium bromide; In tetrahydrofuran; at 20 ℃; for 12h;

Reference yield:

(2S)-2-((1R,3aR,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)propanal → seocalcitol (134404-52-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: phenyllithium / tetrahydrofuran / 1 h / -78 °C

1.2: Wittig Rearrangement / 5 h

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C

3.1: pyridinium chlorochromate / dichloromethane / 10 h / 20 °C

4.1: phenyllithium / tetrahydrofuran / 1 h / -78 °C

4.2: Wittig Rearrangement / 3 h

5.1: tetrabutylammomium bromide / tetrahydrofuran / 12 h / 20 °C

With tetrabutyl ammonium fluoride; tetrabutylammomium bromide; phenyllithium; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 1.1: |Wittig Olefination / 4.1: |Wittig Rearrangement;

Reference yield:

C27H50O2Si → seocalcitol (134404-52-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C

2.1: pyridinium chlorochromate / dichloromethane / 10 h / 20 °C

3.1: phenyllithium / tetrahydrofuran / 1 h / -78 °C

3.2: Wittig Rearrangement / 3 h

4.1: tetrabutylammomium bromide / tetrahydrofuran / 12 h / 20 °C

With tetrabutyl ammonium fluoride; tetrabutylammomium bromide; phenyllithium; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 3.1: |Wittig Rearrangement;

Refernces