moronic acid

Base Information

• Chemical Name: moronic acid
• CAS No.: 6713-27-5
• Molecular Formula: C30H46O3
• Molecular Weight: 454.693
• UNII: XW8W7HC4JK
• DSSTox Substance ID: DTXSID30891948
• Nikkaji Number: J15.954I
• Wikipedia: Moronic_acid
• Wikidata: Q6913266
• Metabolomics Workbench ID: 28741
• ChEMBL ID: CHEMBL472646
• Mol file: 6713-27-5.mol

Synonyms:(+)-Moronicacid;3-Oxoolean-18-en-28-oic acid;Ambronic acid;Moronic acid;

Chemical Property of moronic acid

Chemical Property:

• Vapor Pressure: 1.51E-13mmHg at 25°C
• Melting Point: 212 °C(dec.)
• Refractive Index: 1.551
• Boiling Point: 550 °C at 760 mmHg
• Flash Point: 300.5 °C
• PSA: 54.37000
• Density: 1.09 g/cm³
• LogP: 7.44180
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 454.34469533
• Heavy Atom Count: 33
• Complexity: 927

Purity/Quality:

98%,99%, ^*data from raw suppliers

Moronic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(C2=C1)CCC4C3(CCC5C4(CCC(=O)C5(C)C)C)C)C)C(=O)O)C
• Isomeric SMILES: C[C@@]12CC[C@]3(CCC(C=C3[C@H]1CC[C@H]4[C@]2(CC[C@@H]5[C@@]4(CCC(=O)C5(C)C)C)C)(C)C)C(=O)O
• Uses: Moronic Acid and its derivatives can have antidiabetic activity by inhibiting PTP-1B. Moronic Acid is also shown sustained antidiabetic and antihyperglycemic action possibly mediated by an insulin sensitization in rat models.

Technology Process of moronic acid

There total 2 articles about moronic 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: 85.0%

moronic aldehyde → Moronic acid (6713-27-5)

Guidance literature:

moronic aldehyde; With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; water; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 12.25h; Cooling with ice;

With ammonium chloride; In tetrahydrofuran; water; tert-butyl alcohol; at 20 ℃;

DOI:10.1016/j.tet.2009.03.100

Reference yield: 78.0%

3β,28-dihydroxyoleanan-18(19)-ene (568-49-0) → Moronic acid (6713-27-5)

Guidance literature:

With Jones reagent; In acetone; at 0 ℃; for 4h;

DOI:10.1134/S1068162009020125

Reference yield: 96.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Moronic acid (6713-27-5) → 3-oxo-olean-18-en-28-oic acid methyl ester (55887-94-0)

Guidance literature:

With potassium hydroxide; In diethyl ether; ethanol; water; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2016.02.082

upstream raw materials:

3β,28-dihydroxyoleanan-18(19)-ene

Downstream raw materials:

Morolic acid

N-(olean-3-oxo-18-en-28-oyl)-aminoundecanoic acid methyl ester

N-(olean-3-oxo-18-en-28-oyl)-L-leucine methyl ester

N-(olean-3β-hydroxy-18-en-28-oyl)-(1-hydroxymethyl-3-methyl)-butylamide

Refernces

• 1、 Flekhter,Medvedeva,Tolstikov,Galin,Yunusov,Mai, Huong Nguen Thi,Tien, Le Viet,Savinova,Boreko,Titov,Glukhov. "Synthesis of olean-18(19)-ene derivatives from betulin". . p. 233 - 239. Retrieved 2009.