Tirucallol

Base Information

• Chemical Name: Tirucallol
• CAS No.: 514-46-5
• Molecular Formula: C₃₀H₅₀O
• Molecular Weight: 426.726
• DSSTox Substance ID: DTXSID001317294
• Nikkaji Number: J13.991B
• Wikidata: Q104951328
• Metabolomics Workbench ID: 28731
• Mol file: 514-46-5.mol

Synonyms:lanostan-8,24-dien-3-ol;tirucallol

Chemical Property of Tirucallol

Chemical Property:

• Vapor Pressure: 4.83E-12mmHg at 25°C
• Boiling Point: 498.9°Cat760mmHg
• Flash Point: 221.1°C
• PSA: 20.23000
• Density: 0.98g/cm³
• LogP: 8.47910
• XLogP3: 8.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 426.386166214
• Heavy Atom Count: 31
• Complexity: 767

Purity/Quality:

≥98% ^*data from raw suppliers

Tirucallol(NewProduct) 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC=C(C)C)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C)C
• Isomeric SMILES: C[C@@H](CCC=C(C)C)[C@@H]1CC[C@]2([C@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C

Technology Process of Tirucallol

There total 11 articles about Tirucallol 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: 77.0%

5α-tirucalla-8,24-dien-3-one (54325-09-6) → tirucallol (514-46-5)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 3h; Heating;

Reference yield: 74.0%

d-3β-hydroxy-5α,13α,14β,17α,20αH-lanost-8-en-24-al (124816-97-3) + isopropyltriphenylphosphonium iodide (24470-78-8) → d-tirucallol (514-46-5)

Guidance literature:

With n-butyllithium; Tris(3,6-dioxaheptyl)amine; 1.) THF, 0 deg C, 10 min, 2.) 10 min, 0 deg C;

DOI:10.1021/jo00294a043

Reference yield: 65.0%

lanostenone-3 (5539-04-8,13879-13-5,54325-09-6) → epi-3α lanostenol (79-63-0,514-46-5,514-47-6,13879-06-6,19044-12-3,76582-59-7,82570-26-1,84924-98-1,107596-76-9,110269-67-5)

Guidance literature:

With L-Selectride;

upstream raw materials:

2,3-Oxidosqualene

ethanol

24-bromo-euphadien-(8.24)-ol-(3β)

5α-tirucalla-8,24-dien-3-one

Downstream raw materials:

euphol acetate

eupha-8,24-dien-3-one-(2,4-dinitro-phenylhydrazon); euphone-(2,4-dinitro-phenylhydrazone)

euphene-(8)-dione-(7.11)

Tirucall-8-enyl-acetat

Refernces

• 1、 Bartlett, William R.,Johnson, William S.,Plummer, Mark S.,Small, Vernon R.. "Cationic Cyclization of a Substrate Having an Internal Acetylenic Bond. Synthesis of Euphol and Tirucallol". . p. 2215 - 2224. Retrieved 2007/10/02.
• 2、 Boar, Robin B.,Couchman, Lorraine A.,Perkins, M. John. "Synthesis of Some 3-Oxygenated Tirucalla-7,24- and -8,24-dienes". . p. 1052 - 1063. Retrieved 2007/10/02.