Methyl oleanolate

Base Information

• Chemical Name: Methyl oleanolate
• CAS No.: 1724-17-0
• Molecular Formula: C₃₁H₅₀O₃
• Molecular Weight: 470.736
• European Community (EC) Number: 217-029-1
• DSSTox Substance ID: DTXSID50938142
• Nikkaji Number: J203.120E
• Wikidata: Q72493943
• Metabolomics Workbench ID: 138612
• ChEMBL ID: CHEMBL487412
• Mol file: 1724-17-0.mol

Synonyms:Methyl oleanolate;1724-17-0;oleanolic acid methyl ester;methyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate;(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-Methyl 10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate;CHEMBL487412;EINECS 217-029-1;Methyl (3beta)-3-hydroxyolean-12-en-28-oate;Oleanolic acid, methyl ester;MFCD00017382;Oleanolic acid methyl ester;Virgaureagenin B methyl ester;SCHEMBL2871108;DTXSID50938142;CS-M3610;BDBM50242287;AKOS016036260;methyl 3-hydroxyolean-12-en-28-oate;CS-14414;OLEANOLIC ACID METHYLESTER with HPLC;A811413;Olean-12-en-28-oic acid, 3-hydroxy-, methyl ester, (3b)-;Olean-12-en-28-oic acid, 3-hydroxy-, methyl ester, (3.beta.)-;Olean-12-en-28-oic acid, 3-hydroxy-, methyl ester, (3beta)-;(2R,5S,8R,9S,10S,13R,14S,17R)-2-bromo-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one;(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-Methyl10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Chemical Property of Methyl oleanolate

Chemical Property:

• Melting Point: 200-205oC
• Boiling Point: 526.1oCat760mmHg
• PKA: 15.15±0.70(Predicted)
• Flash Point: 190.7oC
• PSA: 46.53000
• Density: 1.07g/cm³
• LogP: 7.32200
• XLogP3: 7.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 470.37599545
• Heavy Atom Count: 34
• Complexity: 900

Purity/Quality:

98%min ^*data from raw suppliers

MethylOleanolate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 22-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C(=O)OC)C
• Isomeric SMILES: C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)OC)C)C)(C)C)O

Technology Process of Methyl oleanolate

There total 76 articles about Methyl oleanolate 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%

Oleanolic acid (508-02-1) + methyl iodide (74-88-4) → oleanolic acid methyl ester (1724-17-0,73584-64-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Oleanolic acid (508-02-1) → oleanolic acid methyl ester (1724-17-0,73584-64-2)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 ℃;

DOI:10.1016/j.bioorg.2019.103054

Reference yield: 100.0%

Oleanolic acid (508-02-1) + diazomethyl-trimethyl-silane (18107-18-1) → oleanolic acid methyl ester (1724-17-0,73584-64-2)

Guidance literature:

In methanol; benzene;

DOI:10.1248/cpb.47.141

upstream raw materials:

oleanolic acid

methyl iodide

methanol

methyl 3-oxooleanolate

Downstream raw materials:

3β-benzoyloxy-oleanen-(12)-oic acid-(28)-methyl ester

Oleanolic acid

hedaragenin

(3aR,5aR,5bS,7aS,11aS,13aR,13bR)-5a,5b,10,10,13b-Pentamethyl-3-oxo-1,2,3,3a,4,5,5a,5b,6,7,8,9,10,11,11a,13,13a,13b-octadecahydro-cyclopenta[a]chrysene-7a-carboxylic acid methyl ester

Refernces

• 1、 Na, MinKyun,Cui, Long,Min, Byung Sun,Bae, KiHwan,Yoo, Jae Kuk,Kim, Bo Yeon,Oh, Won Keun,Ahn, Jong Seog. "Protein tyrosine phosphatase 1B inhibitory activity of triterpenes isolated from Astilbe koreana". . p. 3273 - 3276. Retrieved 2006.
• 2、 Fu, Liangfeng,Gribble, Gordon W.. "Efficient and scalable synthesis of bardoxolone methyl (CDDO-methyl ester)". . p. 1622 - 1625. Retrieved 2013.
• 3、 Caglioti,L.,Cainelli,G.. "". . p. 1061 - 1062. Retrieved 1962.
• 4、 Bukharov,V.G. et al.. "". . . Retrieved 1969.
• 5、 Hariharan,V.,Rangaswami,S.. "-". . p. 621 - 624. Retrieved 1971.
• 6、 Gambaro, Vicente,Chamy, Maria C.,Garbarino, Juan A.,San-Martin, Aurelio,Castillo, Mariano. "NEO-CLERODANE DITERPENOIDS FROM BACCHARIS MACRAEI". . p. 2175 - 2178. Retrieved 1986.
• 7、 Martinez, Antonio,Perojil, Alberto,Rivas, Francisco,Parra, Andres,Garcia-Granados, Andres,Fernandez-Vivas, Antonia. "Biotransformation of oleanolic and maslinic methyl esters by Rhizomucor miehei CECT 2749". . p. 500 - 508. Retrieved 2015.
• 8、 Elsbaey, Marwa,Mwakalukwa, Rogers,Shimizu, Kuniyoshi,Miyamoto, Tomofumi. "Pentacylic triterpenes from Lavandula coronopifolia: structure related inhibitory activity on α-glucosidase". . p. 1436 - 1444. Retrieved 2019/08/26.
• 9、 -. "Application of methylsulfonyl 12-ketone oleanolic acid methyl ester in preparation of medicine for resisting viral hepatitis B". Paragraph 0029-0030; 0034-0035. . Retrieved 2020/10/30.