869788-74-9

Basic information

• Product Name: Oleanonic acid benzyl ester
• Synonyms: Oleanonic acid benzyl ester;3-Oxo-olean-12-en-28-oic acid phenylmethyl ester
• CAS NO: 869788-74-9
• Molecular Formula: C₃₇H₅₂O₃
• Molecular Weight: 544.81
• Product Categories: Pentacyclic triterpenes
• Mol File: 869788-74-9.mol
• Article Data: 23

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Oleanonic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Oleanonic acid benzyl ester(869788-74-9)
• EPA Substance Registry System: Oleanonic acid benzyl ester(869788-74-9)

Safety Data

• Hazardous Substances Data: 869788-74-9(Hazardous Substances Data)

Upstream product

• 303114-51-4 oleanolic acid benzyl ester 
• 508-02-1 Oleanolic acid 
• 100-44-7 benzyl chloride 
• 1034619-10-7 2β,3β-dihydroxyolean-12-en-28-oic acid benzyl ester 
• 17990-42-0 Oleanonsaeure 
• 100-39-0 benzyl bromide 
• 1272616-97-3 oleanolic acid benzyl ester 
• 25499-90-5 3-epioleanolic acid 

Downstream Products

• 869788-75-0 (4aS,6aS,6bR,8aR,12aR,12bR,14bS)-10-Acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14b-hexadecahydro-2H-picene-4a-carboxylic acid benzyl ester 
• 876723-81-8 2α-hydroxy-3-oxoolean-12-en-28-oic acid benzyl ester 
• 892869-52-2 (4aS,6aS,6bR,8aR,12aR,12bR,14bS)-11-[(E)-Hydroxyimino]-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid benzyl ester 
• 892869-60-2 C₃₈H₅₁NO₃ 
• 892869-54-4 C₃₇H₅₀N₂O₃ 
• 892869-55-5 (4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-10-Hydroxy-11-[(E)-hydroxyimino]-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 benzyl ester 
• 892869-53-3 (4aS,6aS,6bR,8aR,12aR,12bR,14bS)-11-[(E)-Hydroxyimino]-10-[(Z)-hydroxyimino]-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 benzyl ester 
• 130216-67-0 2-hydroximino-3-oxo-oleanolic acid 
• 130216-69-2 oleanolic acid <2,3-c>furazan 
• 218600-48-7 isoxazolo[4,5-b]olean-12-en-28-oic acid 
• 876724-09-3 2-hydroxyethyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate 
• 876723-91-0 benzyl-2-hydroxy-3-oxoolean-1,12-dien-28-oic acid 
• 876723-86-3 benzyl-2α,3α-dihydroxyolean-12-en-28-oic acid 
• 876724-30-0 (4aS,6aS,6bR,8aR,11R,12aR,12bR,14bS)-11-Acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid benzyl ester 

Relevant articles and documents

Pentacyclic triterpenoid TGR5 receptor stimulant, preparation method and application thereof

The invention discloses a pentacyclic triterpenoid TGR5 receptor stimulant, a preparation method and application of the pentacyclic triterpenoid TGR5 receptor stimulant. The structure of the pentacyclic triterpenoid TGR5 receptor stimulant is as shown in a formula I, and the definition of each substituent is as shown in the specification and claims. According to the pentacyclic triterpenoid compound, the solubility is increased, the permeability is improved, the TGR5 receptor agonist activity is remarkably improved, Caco-2 monolayer cells can be penetrated, and the in-vivo drug effect exertion of the compound after oral administration is guaranteed. The TGR5 receptor stimulant is expected to be further developed into a medicine for treating metabolic diseases represented by diabetes.

Oleanolic acid oxime derivatives and their conjugates with aspirin modulate the NF-κB-mediated transcription in HepG2 hepatoma cells

The aim of this study was to evaluate the effect of new oleanolic acid oxime (OAO) derivatives and their conjugates with aspirin (ASP) on the expression and activation of NF-κB in human hepatoma HepG2 cells. OAO derivatives showed a stronger cytotoxic effect against HepG2 cells compared with their conjugates with aspirin. Moreover, conjugation of OAO with ASP led to enhanced downregulation of NF-κB expression and activation. Among the hybrids with ASP, compounds: 19, 3-(2-acetoxy)benzoyloxyiminoolean-12-en-28-oic acid morpholide and 13, 3-(2-acetoxy)benzoyloxyiminoolean-12-en-28-oic acid methyl ester, differing, respectively, in morpholide and methyl ester groups at the C-17 position of oleanolic acid (OA) molecule were the most efficient. COX-2 transcript and protein levels were also diminished after treatment with these compounds. The results of this study indicate that the new derivatives of OAO and particularly their conjugates with ASP, downregulate the expression of COX-2 in HepG2 cells by modulating the NF-κB signaling pathway and suggest their potential application in the prevention of liver inflammation and cancer.

Synthesis and antitumor activity evaluation of novel oleanolic acid derivatives

Ten novel oleanolic acid (OA) derivatives were synthesized through modifications at positions of A ring and C-28. Inhibitory activities of the oleanolic acid derivatives against SGC7901 and A549 cell lines were evaluated and confirmed by the tetrazolium b