Alepterolic acid

Base Information

• Chemical Name: Alepterolic acid
• CAS No.: 63399-38-2
• Molecular Formula: C20H32O3
• Molecular Weight: 320.46600
• DSSTox Substance ID: DTXSID601019953
• Nikkaji Number: J3.410.486G
• Wikidata: Q105154547
• Mol file: 63399-38-2.mol

Synonyms:(E)-5-((1S,4aR,6S,8aR)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)-3-methylpent-2-enoic acid;alepterolic acid

Chemical Property of Alepterolic acid

Chemical Property:

• PSA: 57.53000
• LogP: 4.56710
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 320.23514488
• Heavy Atom Count: 23
• Complexity: 517

Purity/Quality:

98%min ^*data from raw suppliers

Alepterolicacid ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(=O)O)CCC1C(=C)CCC2C1(CCC(C2(C)C)O)C
• Isomeric SMILES: C/C(=C\C(=O)O)/CC[C@H]1C(=C)CC[C@@H]2[C@@]1(CC[C@@H](C2(C)C)O)C

Technology Process of Alepterolic acid

There total 7 articles about Alepterolic 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:

methyl 3β-acetoxyanticopalate (37886-51-4,86341-41-5,124819-82-5) → 3β-hydroxyanticopalic acid (37886-47-8,63399-38-2,74559-97-0,84711-18-2,86363-30-6,103190-27-8)

Guidance literature:

With sodium hydroxide; In ethanol; at 80 ℃; for 0.5h;

DOI:10.1007/BF00580548

Reference yield:

methyl(E)-3-methyl-5-(trans-decahydro-5',5',8a'β-trimethyl-2'-methylene-6'β-hydroxy-1'β-naphthalenyl)-2-pentenoate (37886-50-3,63399-41-7,74559-98-1,86363-31-7,103190-26-7,124819-85-8,142434-52-4) → (E)-3-methyl-5-(trans-decahydro-5',5',8a'β-trimethyl-2'-methylene-6'β-hydroxy-1'β-naphthalenyl)-2-pentenoic acid (37886-47-8,63399-38-2,74559-97-0,84711-18-2,86363-30-6,103190-27-8)

Guidance literature:

With potassium hydroxide; In methanol; for 30h; Yield given; Ambient temperature;

Reference yield:

methyl 5--5',5',8a'β-trimethyl-2'-methylene-1'β-naphthalenyl>-3-oxo-pentanoate (103142-86-5) → (E)-3-methyl-5-(trans-decahydro-5',5',8a'β-trimethyl-2'-methylene-6'β-hydroxy-1'β-naphthalenyl)-2-pentenoic acid (37886-47-8,63399-38-2,74559-97-0,84711-18-2,86363-30-6,103190-27-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / sodium hydride

2: 99 percent / HF / acetonitrile; H₂O / 2 h / 0 °C

3: aq.KOH / methanol / 30 h / Ambient temperature

With potassium hydroxide; hydrogen fluoride; sodium hydride; In methanol; water; acetonitrile;

upstream raw materials:

methyl(E)-3-methyl-5-(trans-decahydro-5',5',8a'β-trimethyl-2'-methylene-6'β-hydroxy-1'β-naphthalenyl)-2-pentenoate

methyl 5--5',5',8a'β-trimethyl-2'-methylene-1'β-naphthalenyl>-3-oxo-pentanoate

Trifluoro-methanesulfonic acid (1S,4aR,6S,8aS)-6-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester

(Z)-5-[(1S,4aR,6S,8aR)-6-(tert-Butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl]-3-(diethoxy-phosphoryloxy)-pent-2-enoic acid methyl ester

Refernces

• 1、 Raldugin, V. A.,Pentegova, V. A.. "DERIVATIVES OF ANTICOPALIC ACID AND OTHER NEW COMPOUNDS FROM THE OLEORESIN OF Pinus pumila". . p. 149 - 154. Retrieved 2007/10/02.