Augustic acid

Base Information

• Chemical Name: Augustic acid
• CAS No.: 26707-60-8
• Molecular Formula: C30 H48 O4
• Molecular Weight: 472.709
• ChEMBL ID: CHEMBL482673
• DSSTox Substance ID: DTXSID101317673
• Metabolomics Workbench ID: 138202
• Nikkaji Number: J88.450B
• Wikidata: Q105162062
• Mol file: 26707-60-8.mol

Synonyms:augustic acid

Chemical Property of Augustic acid

Chemical Property:

• Melting Point: 308-310 °C
• Boiling Point: 570.0±50.0 °C(Predicted)
• PKA: 4.63±0.70(Predicted)
• PSA: 77.76000
• Density: 1.14±0.1 g/cm3(Predicted)
• LogP: 6.20440
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 472.35526001
• Heavy Atom Count: 34
• Complexity: 919

Purity/Quality:

99%, ^*data from raw suppliers

(2BETA,3BETA)-2,3-DIHYDROXY-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: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)C)O)O)C)C)C2C1)C)C(=O)O)C
• Isomeric SMILES: C[C@@]12CC[C@@H]3[C@@]([C@H]1CC=C4[C@]2(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)(C[C@@H]([C@@H](C3(C)C)O)O)C

Technology Process of Augustic acid

There total 22 articles about Augustic 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: 100.0%

benzyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate (464876-77-5) → maslinic acid (4373-41-5,5957-40-4,26563-68-8,26707-60-8,120707-84-8,125137-38-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmcl.2005.10.014

Reference yield: 70.0%

methyl maslinate (22425-82-7) → maslinic acid (4373-41-5,5957-40-4,26563-68-8,26707-60-8,120707-84-8,125137-38-4)

Guidance literature:

With lithium; In ethylenediamine; for 4h; Heating;

Reference yield: 48.0%

(2α)-2-hydroxy-3-oxo-olean-12-en-28-oic acid (73584-62-0) + acetone (67-64-1) → maslinic acid (4373-41-5,5957-40-4,26563-68-8,26707-60-8,120707-84-8,125137-38-4) + (2α,3α)-(isopropylidenedioxy)olean-12-en-28-oic acid

Guidance literature:

(2α)-2-hydroxy-3-oxo-olean-12-en-28-oic acid; With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 1h;

acetone; With sulfuric acid; at 0 - 60 ℃; for 0.5h;

DOI:10.1016/j.tet.2015.09.037

upstream raw materials:

methyl maslinate

2α,3β-diacetoxyoleane 12-ene-28-carboxylic acid

3-acetylmaslinic acid (TARB-2)

benzyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate

Downstream raw materials:

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

2-hydroxyethyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate

benzyl (2α,3β)-2,3-di-acetoxy-olean-12-en-28-oate

C₄₀H₅₈O₅

Refernces

• 1、 Sommerwerk, Sven,Heller, Lucie,Serbian, Immo,Csuk, René. "Straightforward partial synthesis of four diastereomeric 2,3-dihydroxy-olean-12-en-28-oic acids from oleanolic acid". . p. 8528 - 8534. Retrieved 2016/02/03.
• 2、 Wang, Hong-Min,Liu, Qun-Fang,Zhao, Yi-Wu,Liu, Shuang-Zhu,Chen, Zhen-Hua,Zhang, Ru-Jun,Wang, Zhen-Zhong,Xiao, Wei,Zhao, Wei-Min. "Four new triterpenoids isolated from the resin of Garcinia hanburyi". . p. 20 - 28. Retrieved 2014/02/14.