(5beta)-12-methoxypodocarpa-8,11,13-trien-16-oic acid

Base Information

• Chemical Name: (5beta)-12-methoxypodocarpa-8,11,13-trien-16-oic acid
• CAS No.: 10037-26-0
• Molecular Formula: C18H24 O3
• Molecular Weight: 288.387
• NSC Number: 115716
• DSSTox Substance ID: DTXSID00905445
• Mol file: 10037-26-0.mol

Synonyms:1-Phenanthrenecarboxylicacid, 1,2,3,4,4a,9,10,10a-octahydro-6-methoxy-1,4a-dimethyl-, [1S-(1a,4aa,10ab)]-; Podocarpa-8,11,13-trien-16-oic acid, 12-methoxy- (8CI);(+)-O-Methylpodocarpic acid; (+)-Podocarpic acid methyl ether;12-Methoxypodocarpa-8,11,13-trien-15-oic acid;12-Methoxypodocarpa-8,11,13-trien-19-oic acid; NSC 115716; O-Methylpodocarpicacid

Chemical Property of (5beta)-12-methoxypodocarpa-8,11,13-trien-16-oic acid

Chemical Property:

• Vapor Pressure: 3.18E-08mmHg at 25°C
• Boiling Point: 431.8°C at 760 mmHg
• Flash Point: 153°C
• Density: 1.119g/cm³
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 288.17254462
• Heavy Atom Count: 21
• Complexity: 421

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(C1CCC3=C2C=C(C=C3)OC)(C)C(=O)O

Technology Process of (5beta)-12-methoxypodocarpa-8,11,13-trien-16-oic acid

There total 29 articles about (5beta)-12-methoxypodocarpa-8,11,13-trien-16-oic acid 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: 95.0%

methyl O-methylpodocarpate (1231-74-9) → O-methylpodocarpic acid (10037-26-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In o-xylene; at 165 ℃; for 48h;

Reference yield: 41.0%

podocarpic acid (5947-49-9) + dimethyl sulfate (77-78-1) → methyl O-methylpodocarpate (1231-74-9) + O-methylpodocarpic acid (10037-26-0)

Guidance literature:

With sodium hydroxide; In methanol; for 24h; Ambient temperature;

Reference yield: 32.0%

chloro-trimethyl-silane (75-77-4) + methyl O-methylpodocarpate (1231-74-9) → O-methylpodocarpic acid (10037-26-0) + 12-methoxy-19-trimethylsilylpodocarpa-8,11,13-trien-19-ol + 12-methoxy-19-trimethylsilyloxypodocarpa-8,11,13-triene

Guidance literature:

With lithium; In tetrahydrofuran; for 96h; Ambient temperature;

DOI:10.1071/C98015

upstream raw materials:

methyl O-methylpodocarpate

12-O-methylpodocarpal

podocarpic acid

dimethyl sulfate

Downstream raw materials:

4,10-Dimethylphenanthren

12-methoxy-8,11,13-podocarpatriene-19-amide

12-O-methylpodocarpal

methyl O-methylpodocarpate

Refernces

• 1、 Manchand. "". . p. 667. Retrieved 1971.
• 2、 Cui, Yong-Mei,Yasutomi, Eriko,Otani, Yuko,Yoshinaga, Takashi,Ido, Katsutoshi,Sawada, Kohei,Ohwada, Tomohiko. "Design, synthesis and characterization of podocarpate derivatives as openers of BK channels". scheme or table. p. 5197 - 5200. Retrieved 2009/05/07.
• 3、 Zhang, Qingwei,Mohan, Raju M.,Cook, Laura,Kazanis, Sophia,Peisach, Daniel,et al.. "Asymmetric Induction in Mn(III)-Based Oxidative Free-Radical Cyclizations of Phenylmenthyl Acetoacetates and 2,5-Dimethylpyrrolidine Acetoacetamides". . p. 7640 - 7651. Retrieved 2007/10/02.