3-Epioleanolic acid

Base Information

• Chemical Name: 3-Epioleanolic acid
• CAS No.: 25499-90-5
• Molecular Formula: C30H48 O3
• Molecular Weight: 456.70
• ChEMBL ID: CHEMBL486382
• DSSTox Substance ID: DTXSID201316135
• Metabolomics Workbench ID: 72175
• Nikkaji Number: J70.008H
• Wikidata: Q27136594
• Mol file: 25499-90-5.mol

Synonyms:3-Epioleanolic acid;25499-90-5;Epi-Oleanolic Acid;3-epi-Oleanolic Acid;CHEMBL486382;CHEBI:68103;(20R)-3alpha-Hydroxyolean-12-en-28-oic acid;(4aS,6aR,6aS,6bR,8aR,10R,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-carboxylic acid;SCHEMBL26940985;DTXSID201316135;BDBM50241532;3-alpha-Hydroxyolean-12-en-28-oate;AKOS037515061;LMPR0106150020;3alpha-Hydroxyolean-12-en-28-oic Acid;3-alpha-Hydroxyolean-12-en-28-oic acid;Q27136594;(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-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-carboxylic acid

Chemical Property of 3-Epioleanolic acid

Chemical Property:

• Melting Point: 297-299 °C(Solv: methanol (67-56-1))
• Boiling Point: 553.5±50.0 °C(Predicted)
• PKA: 4?+-.0.70(Predicted)
• PSA: 57.53000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 7.23360
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 456.36034539
• Heavy Atom Count: 33
• Complexity: 885

Purity/Quality:

98%min ^*data from raw suppliers

3-epi-OleanolicAcid ^*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(CCC(C5(C)C)O)C)C)C2C1)C)C(=O)O)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)O)C)C)(C)C)O
• Uses: 3-epi-Oleanolic Acid is a possible drug candidate for treating Alzheimer’s disease. It is an important reagent in preparation of 3-O-β-chacotriosyl oleanane-type triterpenoids which are potential H5N1 entry inhibitors.

Technology Process of 3-Epioleanolic acid

There total 44 articles about 3-Epioleanolic 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: 90.0%

(4aS,6aS,6bR,10R,12aR)-10-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodo-nonyl ester → 3-epi-oleanolic acid (508-02-1,6880-10-0,25499-90-5)

Guidance literature:

With ammonium chloride; zinc; In ethanol; for 0.25h; Heating;

DOI:10.1016/S0040-4039(98)00906-X

Reference yield: 31.0%

momordin Id → 28-desglucosylchikusetsusaponin IVa (26020-14-4,108322-31-2) + oleanolic acid (508-02-1,6880-10-0,25499-90-5) + momordin Ic

Guidance literature:

With sulfuric acid; at 80 ℃; for 20h;

DOI:10.1016/0031-9422(88)80773-8

Reference yield:

stipuleanosides R1 → β-D-glucose (492-61-5) + D-glucuronic acid (6556-12-3,489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) + α-L-arabinofuranoside (38029-69-5) + oleanolic acid (508-02-1,6880-10-0,25499-90-5)

Guidance literature:

With β-glucuronidase; acetate buffer; at 37 ℃; hydrolysis; other enzyme (glycyrrhizinic acid hydrolase);

upstream raw materials:

entada saponin II

3-O-α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranosyl-oleanolic acid 28-O-β-D-xylopyranosyl(1->6)-β-D-glucopyranosyl ester

saponin-C methylester

saponin-D methylester