25499-90-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Epioleanolic acid is used as a drug candidate for the treatment of Alzheimer's disease. Its potential therapeutic effects are attributed to its ability to target and modulate specific pathways involved in the progression of the disease, offering a promising alternative for patients suffering from this neurodegenerative condition.
Additionally, 3-Epioleanolic acid serves as an important reagent in the preparation of 3-O-β-chacotriosyl oleanane-type triterpenoids. These compounds have been identified as potential inhibitors of the H5N1 virus entry, which could be crucial in the development of antiviral treatments and preventive measures against avian influenza.

Upstream product

• 76742-94-4 oleanolic acid 3-O-β-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-4)-β-D-xylopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 
• 26020-14-4 glycoside F 
• 75799-17-6 saponin V 
• 75799-17-6 hishoushi-saponin A 
• 75799-17-6 oleanolic acid 3-O-β-D-xylopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 
• 75799-17-6 oleanolic acid 3-O-β-D-ribopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 
• 58546-61-5 silphioside A 
• 72629-77-7 oleanolic acid 3-O-β-D-glucopyranosyl-(1-4)-β-D-xylopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 
• 99633-18-8 rotundinoside B 
• 99633-19-9 rotundinoside C 
• 90452-93-0 silphioside E 
• 80145-52-4 saponin-D 
• 80135-33-7 saponin-C 
• 29014-88-8 saponin-D methylester 

Downstream Products

• 1721-57-9 Oleanolsaeuremethylester-acetat 
• 17990-42-0 Oleanonsaeure 
• 1724-17-0 oleanolic acid, methyl ester 
• 1401414-17-2 C₃₇H₅₀ClNO₄ 
• 1449424-94-5 C₄₄H₅₆ClNO₄ 
• 1449424-96-7 C₄₄H₅₅Cl₂NO₄ 
• 1449424-98-9 C₄₄H₅₆ClNO₄ 
• 1449424-99-0 C₄₄H₅₆N₂O₆ 
• 1449425-01-7 C₄₉H₆₁NO₄ 
• 1449425-03-9 C₄₅H₅₈ClNO₅ 
• 1449425-05-1 C₄₄H₅₆FNO₄ 
• 1449425-07-3 C₄₄H₅₆BrNO₄ 
• 1449425-09-5 C₄₃H₅₆N₂O₄ 
• 1401414-18-3 C₃₇H₄₉Cl₂NO₄ 

Relevant academic research and scientific papers

TRITERPENE GLYCOSIDES OF Silphium perfoliatum. III. STRUCTURE OF SILPHIOSIDE E

A new triterpene glycoside - silphioside E - has been isolated from the epigeal part of Silphium perfoliatum L. and its structure has been established on the basis of chemical transformations and spectral characteristics as oleanolic acid 28-O-β-D-glycopyranoside 3-O-2)-β-D-glucopyranoside>.

TRITERPENE GLYCOSIDES OF Silphium perfoliatum. V. THE STRUCTURE OF SILPHIOSIDE A

From the epigeal part of Silphium perfoliatum L. we have isolated glycoside F, identified as oleanolic acid 3-O-β-D-glucopyranosiduronic acid and a new triterpene glycoside - silphioside A - for which the structure of oleanolic acid 28-O-β-D-glucopyranoside 3-O-(methyl β-D-glucopyranosiduronate) has been established.

A Novel Cleavage of Allyl Protection

A novel, efficient, and mild cleavage of allyl protection is developed employing perfluoroalkylation and subsequent elimination.

75. New Triterpenoid N-Acetylglycosides with Molluscicidal Activity from Tetrapleura tetraptera TAUB

Activity-guided fractionation of the MeOH extract of the fruits of Tetrapleura tetraptera TAUB. (Mimosaceae) afforded 4 saponins 1-4, which exhibited strong molluscicidal properties against the schistosomiasis-transmitting snails Biomphalaria glabrata.Chemical, enzymatic, and spectral methods (DCI-MS, 1H-NMR, 13C-NMR) showed that they were N-acetylglycosides of oleanolic acid and of echinocystic acid.Apart from saponin 1 (aridanin), previously isolated from this plant, glycosides 2-4 are new naturally occuring compounds.

SAPONINS FROM ROOTS OF MOMORDICA COCHINCHINENSIS

Ten minor saponins, momordins Ia-Ie and IIa-IIe, were isolated from the root of Momordica cochinchinensis, along with the known major saponins, momordins I and II.Their structures were established on the basis of chemical and spectroscopic analysis.The structures of the two new saponins were assigned as 3β-(((O-β-D-xylopyranosyl-(1-->2)-O-β-D-xylopyranosyl-(1-->3))O-β-D-glucopyranuronosyl)oxy)-olean-12-ene-28-oic acid for momordin Id and momordin Id-28-β-D-glucopyranosyl ester for momordin IId.It was confirmed that the genuine saponin present in the root was not the monodesmoside but the bisdesmoside, though the former is the major component in the dry root. Key word Index--Momordica cochinchinensis; Cucurbitaceae; saponin; momordin; oleanolic acid; monodesmoside; bisdesmoside; 13C NMR.

Substrate Specificity of Glycyrrhizinic Acid Hydrolase

Glycyrrhizinic acid hydrolase produced by Aspergillus niger selectively hydrolyzed the 3-O-β-D-glucuronide linkage of glycyrrhizinic acid.The substrate specificity of this enzyme was investigated for synthetic glucuronides of aliphatic alcohols as well as natural glucuronide saponins.It was revealed that the glucuronide linkage with low molecular weight alcohols was not cleaved by this enzyme, while the 3-O-β-D-glucuronide linkage saponins of oleanolic acid was selectively hydrolyzed.It was also disclosed that both the 4-hydroxyl and carboxyl groups of the glucuronide moiety must be unsubstituted for hydrolysis by this enzyme.

Entada Saponins (ES) II and IV from the Bark of Entada phaseoloides

The structures of entada saponins II and IV, isolated from the bark of Entada phaseoloides (L.) Merrill (Leguminosae), were elucidated as 3-O-2)-α-L-arabinopyranosyl-(1->6)>4)>-2-acetamido-2-deoxy-β-D-glucopyranosyl-28-O-3)-β-D-xylopyranosyl(1->2)>4)>-6-O-((6R)-6-hydroxy-2,6-dimethyl-(2E)-2,7-octadienoyl)-β-D-glucopyranosyl olenolic acid (1) and entagenic acid (3).Keywords - Entada phaseoloides; Leguminosae; triterpene saponin; 13C-NMR chemical shift; entada saponin II; entada saponin IV