Isopimarinol

Base Information

• Chemical Name: Isopimarinol
• CAS No.: 1686-64-2
• Molecular Formula: C₂₀H₃₂O
• Molecular Weight: 288.473
• DSSTox Substance ID: DTXSID601034979
• Metabolomics Workbench ID: 28530,132754
• Nikkaji Number: J428.792D
• Wikidata: Q27123466
• Mol file: 1686-64-2.mol

Synonyms:isopimarinol;Isopimarol;isopimara-7,15-dienol;1686-64-2;18-Hydroxy-isopimaradien;7,15-Isopimaradien-18-ol;Isopimara-7,15-dien-19-ol;(13S)-pimara-7,15-dien-18-ol;isopimaradienol;[(1R,4aR,4bS,7S,10aR)-1,4a,7-trimethyl-7-ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthren-1-yl]methanol;1-Phenanthrenemethanol, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-1,4a,7-trimethyl-, (1R,4aR,4bS,7S,10aR)-;CHEBI:52484;DUEINKIQNGZKPL-VYJAJWGXSA-N;DTXSID601034979;LMPR0104080008;(13alpha)-Pimara-7,15-dien-18-ol;C18221;Q27123466;[(1R,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthren-1-yl]methanol

Chemical Property of Isopimarinol

Chemical Property:

• PSA: 20.23000
• LogP: 5.11390
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 288.245315640
• Heavy Atom Count: 21
• Complexity: 465

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CCC2C(=CCC3C2(CCCC3(C)CO)C)C1)C=C
• Isomeric SMILES: C[C@@]1(CC[C@H]2C(=CC[C@@H]3[C@@]2(CCC[C@@]3(C)CO)C)C1)C=C

Technology Process of Isopimarinol

There total 4 articles about Isopimarinol 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: 79.0%

isopimaric acid (5835-26-7) → pimara-7,15-dien-18-ol (1686-64-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1007/s10600-022-03596-y

Reference yield:

isopimaric acid methyl ester (1686-62-0) → pimara-7,15-dien-18-ol (1686-64-2)

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1021/jo01036a003 DOI:10.1016/0031-9422(79)83064-2

Reference yield:

(1R,4aS,4bS,5R,7R,10aR)-1,4a,7-Trimethyl-5-(toluene-4-sulfonyloxy)-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-phenanthrene-1-carboxylic acid methyl ester → pimara-7,15-dien-18-ol (1686-64-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1016/0031-9422(79)83064-2

upstream raw materials:

isopimaric acid

isopimaric acid methyl ester

Downstream raw materials:

(2S,4aS,4bR,8R,8aR)-2,4b,8-Trimethyl-8-phenylsulfanylmethyl-2-vinyl-1,2,3,4,4a,4b,5,6,7,8,8a,9-dodecahydro-phenanthrene

isopimara-7,15-diene

Refernces

• 1、 Garcia-Alvarez,M.C. et al.. "-". . p. 1835 - 1837. Retrieved 1979.
• 2、 Chu, Min,Coates, Robert M.. "Partial Synthesis of 9,10-Syn Diterpenes via Tosylhydrazone Reduction: (-)-(9β)-Pimara-7,15-diene and (-)-(9β)-Isopimaradiene". . p. 4590 - 4597. Retrieved 2007/10/02.