24-Ethylidenecholesterol

Base Information

• Chemical Name: 24-Ethylidenecholesterol
• CAS No.: 18472-36-1
• Molecular Formula: C₂₉H₄₈O
• Molecular Weight: 412.7
• UNII: CS4PB4FQQ7
• Wikidata: Q105198828
• Mol file: 18472-36-1.mol

Synonyms:24-Ethylidenecholesterol;delta5-Avenosterol;CS4PB4FQQ7;Delta5-Avenasterin;(3beta)-stigmasta-5,24(28)-dien-3-ol;Stigmasta-5,24(28)-dien-3-ol, (3beta)-

Chemical Property of 24-Ethylidenecholesterol

Chemical Property:

• Vapor Pressure: 2.8E-12mmHg at 25°C
• Melting Point: 123 - 124 °C (petroleum ether)
• Boiling Point: 504.2°Cat760mmHg
• PKA: 15.03±0.70(Predicted)
• Flash Point: 220.3°C
• PSA: 20.23000
• Density: 0.98g/cm³
• LogP: 7.94490
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 8.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 412.370516150
• Heavy Atom Count: 30
• Complexity: 687

Purity/Quality:

99% ^*data from raw suppliers

Δ5-Avenasterol(E/Zmixture) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C
• Isomeric SMILES: CC=C(CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
• Uses: Δ5-Avenasterol is an analog of Stigmasterol (S686750); a plant sterol that is used as a precursor in the synthesis of progesterone.

Technology Process of 24-Ethylidenecholesterol

There total 16 articles about 24-Ethylidenecholesterol 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:

fucosterol acetate (51297-12-2) → 28-Isofucosterol (481-14-1,6793-19-7,17605-67-3,18472-36-1,83997-22-2,109062-46-6)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1002/cber.19701030902

Reference yield:

C34(13)CH62OSi → 28-Isofucosterol (481-14-1,6793-19-7,17605-67-3,18472-36-1,83997-22-2,109062-46-6) + C28(13)CH48O + C28(13)CH48O + C28(13)CH48O

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 2.5h; Title compound not separated from byproducts;

DOI:10.1016/S0031-9422(00)00122-9

Reference yield:

24-oxocholesterol (17752-16-8) → 28-Isofucosterol (481-14-1,6793-19-7,17605-67-3,18472-36-1,83997-22-2,109062-46-6)

Guidance literature:

Multi-step reaction with 2 steps

2: aq. K₂CO₃ / methanol

With potassium carbonate; In methanol;

DOI:10.1002/cber.19701030902

upstream raw materials:

3β-acetoxy-20β_FH,24ξH-stigmast-5-en-24-ol

3β-acetoxy-24ξH-stigmast-5-en-24-ol

fucosterol acetate

24-methylene cholesterol

Downstream raw materials:

3.5-dinitro-benzoic acid-(5α-stigmastanyl-(3β)-ester)

(24R)-5α-stigmastan-3β-ol benzoate

stigmastan-3-one

acetaldehyde

Refernces

• 1、 Nes, W. David,McCourt, Brian S.,Marshall, Julie A.,Ma, Jianzhong,Dennis, Allen L.,Lopez, Monica,Li, Haoxia,He, Ling. "Site-directed mutagenesis of the sterol methyl transferase active site from Saccharomyces cerevisiae results in formation of novel 24-ethyl sterols". . p. 1535 - 1542. Retrieved 2007/10/03.
• 2、 Sucrow,Radüchel. "The synthesis of (24(28)e)-stigmasta-5, 24(28)-die-3 beta-ol and (24(28)e)-alpha-stigmasta-7,24(28)-dien-3 beta-ol". . p. 2711 - 2717. Retrieved 2007/10/19.