Euphadienol

Base Information

• Chemical Name: Euphadienol
• CAS No.: 514-47-6
• Molecular Formula: C₃₀H₅₀O
• Molecular Weight: 426.726
• Mol file: 514-47-6.mol

Synonyms:Eupha-8,24-dienol;(3S,5R,10S,13S,14S)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol;5alpha-Eupha-8,24-dien-3beta-ol;NSC 36571;BRN 3596105;13alpha,14beta,17betaH-Lanosta-8,24-dien-3beta-ol;Lanosta-8,24-dien-3-ol, (3beta,13alpha,14beta,17alpha)-;Lanosta-8,24-dien-3-ol, (3-beta,13-alpha,14-beta,17-alpha)-;13-alpha,14-beta,17-beta-H-Lanosta-8,24-dien-3-beta-ol

Chemical Property of Euphadienol

Chemical Property:

• Vapor Pressure: 4.83E-12mmHg at 25°C
• Melting Point: 116-117ºC
• Boiling Point: 498.9°Cat760mmHg
• PKA: 15.16±0.70(Predicted)
• 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:

99%, ^*data from raw suppliers

Euphadienol ^*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)C1CC[C@]2([C@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C
• Uses: antineoplastic, antiproliferative, antiinflammatory, antinociceptive Euphadienol is an alcohol tetracyclic triterpene which is considered to have anti-inflammatory action. Oral administration of euphadienol consistently reduces and limits the severity and development of experimental autoimmune encephalomyelitis (EAE) which is an established model of Multiple sclerosis (MS). Euphadienol has been found to inhibit various autonomic pressor and depressor responses in dogs and rats.

Technology Process of Euphadienol

There total 8 articles about Euphadienol 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: 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;

Reference yield: 41.9%

2,3-Oxidosqualene (14050-42-1,54910-48-4,54910-49-5,54910-50-8,55058-26-9,55058-27-0,132199-42-9,138809-21-9,147731-51-9,7200-26-2,54274-53-2,71606-52-5) → Lanosterol (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 bakers' yeast; In water; at 37 ℃; for 12h; Product distribution; 0.10 M phosphate buffer (pH 7.4), Triton X-100;

DOI:10.1021/ja00210a052

Reference yield:

eupha-8,24-diene-3β-ol-7-one → euphol (79-63-0,514-46-5,13879-06-6,19044-12-3,76582-59-7,82570-26-1,84924-98-1,107596-76-9,110269-67-5,514-47-6)

Guidance literature:

With methanol; sodium tetrahydroborate; Reflux;

upstream raw materials:

2,3-Oxidosqualene

ethanol

24-bromo-euphadien-(8.24)-ol-(3β)

lanostenone-3

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、 Bujons, Jorge,Guajardo, Richard,Kyler, Keith S.. "Enantioselective Enzymatic Sterol Synthesis by Ultrasonically Stimulated Bakers' Yeast". . p. 604 - 606. Retrieved 2007/10/02.