(2alpha,3beta)-2,3-Bis(acetyloxy)-olean-12-en-28-oic acid

Base Information

• Chemical Name: (2alpha,3beta)-2,3-Bis(acetyloxy)-olean-12-en-28-oic acid
• CAS No.: 6089-92-5
• Molecular Formula: C34H52O6
• Molecular Weight: 556.783
• ChEMBL ID: CHEMBL508614
• DSSTox Substance ID: DTXSID501233588
• Nikkaji Number: J1.310.378J
• Wikidata: Q104950384
• Mol file: 6089-92-5.mol

Synonyms:6089-92-5;CHEMBL508614;DTXSID501233588;(2alpha,3beta)- 2,3-Bis(acetyloxy)-olean- 12-en-28-oic acid;BDBM50346699;(2alpha,3beta)-2,3-Bis(acetyloxy)olean-12-en-28-oic acid;(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-diacetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Chemical Property of (2alpha,3beta)-2,3-Bis(acetyloxy)-olean-12-en-28-oic acid

Chemical Property:

• PSA: 89.90000
• LogP: 7.34600
• XLogP3: 7.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 556.37638937
• Heavy Atom Count: 40
• Complexity: 1140

Purity/Quality:

99% ^*data from raw suppliers

(2ALPHA,3BETA)-2,3-BIS-(ACETYLOXY)-OLEAN-12-EN-28-OIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC2(C(CCC3(C2CC=C4C3(CCC5(C4CC(CC5)(C)C)C(=O)O)C)C)C(C1OC(=O)C)(C)C)C
• Isomeric SMILES: CC(=O)O[C@@H]1C[C@]2([C@@H](CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)C([C@H]1OC(=O)C)(C)C)C

Technology Process of (2alpha,3beta)-2,3-Bis(acetyloxy)-olean-12-en-28-oic acid

There total 12 articles about (2alpha,3beta)-2,3-Bis(acetyloxy)-olean-12-en-28-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%

maslinic acid (4373-41-5,5957-40-4,26563-68-8,26707-60-8,120707-84-8,125137-38-4) + acetic anhydride (108-24-7) → 2α,3β-diacetoxyoleane 12-ene-28-carboxylic acid (6089-92-5)

Guidance literature:

With pyridine; In dichloromethane; for 1h; Heating;

Reference yield: 80.8%

maslinic acid (4373-41-5,5957-40-4,26563-68-8,26707-60-8,120707-84-8,125137-38-4) + acetic anhydride (108-24-7) → 2α-acetoxy-3β-hydroxy-olean-12-en-28-oic acid + 2α,3β-diacetoxyoleane 12-ene-28-carboxylic acid (6089-92-5)

Guidance literature:

With pyridine; at 20 ℃; for 24h;

DOI:10.1016/j.ejmech.2013.12.049

Reference yield: 74.0%

maslinic acid (4373-41-5,5957-40-4,26563-68-8,26707-60-8,120707-84-8,125137-38-4) + acetyl chloride (75-36-5) → 2α-acetoxy-3β-hydroxy-olean-12-en-28-oic acid + 2α,3β-diacetoxyoleane 12-ene-28-carboxylic acid (6089-92-5)

Guidance literature:

With pyridine; at 5 ℃; for 24h;

DOI:10.1016/j.ejmech.2019.07.049

upstream raw materials:

maslinic acid

acetic anhydride

3-acetylmaslinic acid (TARB-2)

acetyl chloride

Downstream raw materials:

(2α,3β) methyl 2,3-diacetyl-olean-12-en-28-oate

maslinic acid

(E)-(3-phenyl)prop-2-enyl oxy-olean-12-en-28-oate

(2α,3β)-bisacetyloxy-N-benzyl-olean-12-en-28-oic amide