25493-94-1

Basic information

• Product Name: (4aS,6aR,6bR,10S,12aR,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-docosahydropicene-4a-carboxylate
• Synonyms: (4aS,6aR,6bR,10S,12aR,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-docosahydropicene-4a-carboxylate
• CAS NO: 25493-94-1
• Molecular Formula: C₃₃H₅₂O₅
• Molecular Weight: 528.76298
• Mol File: 25493-94-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4aS,6aR,6bR,10S,12aR,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-docosahydropicene-4a-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS,6aR,6bR,10S,12aR,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-docosahydropicene-4a-carboxylate(25493-94-1)
• EPA Substance Registry System: (4aS,6aR,6bR,10S,12aR,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-docosahydropicene-4a-carboxylate(25493-94-1)

Safety Data

• Hazardous Substances Data: 25493-94-1(Hazardous Substances Data)

Usage

General Description

The chemical compound "(4aS,6aR,6bR,10S,12aR,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-docosahydropicene-4a-carboxylate" is a complex organic molecule with a long and specific structure. It is a ester compound, containing a carboxylate group and an acetate group, and it also has several methyl groups attached to the carbon backbone. The chemical name describes the exact arrangement of atoms and functional groups in the molecule. (4aS,6aR,6bR,10S,12aR,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-docosahydropicene-4a-carboxylate may have potential applications in the pharmaceutical, agricultural, or materials industries, but further research and analysis would be needed to fully understand its potential uses and effects.

Upstream product

• 25493-69-0 (4aS,6aS,6bR,10S,12aR)-methyl 10-acetoxy-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 
• 116227-28-2 3β-acetoxy-12α,13-epoxy-13α,18α-oleanan-28-oic acid methyl ester 
• 75-09-2 dichloromethane 
• 109-63-7 trifluoroborane diethyl ether 
• 508-02-1 Oleanolic acid 
• 116298-16-9 3β-hydroxy-12β,13β-epoxyolean-28-oic acid methyl ester 
• 1724-17-0 oleanolic acid methyl ester 
• 4339-72-4 oleanolic acid 3-acetate 
• 64-19-7 acetic acid 
• 7722-84-1 dihydrogen peroxide 
• 399033-01-3 methyl 3-O-β-acetyl-12α,13α-epoxy-18β-oleanolate 
• 116227-28-2 C₃₃H₅₂O₅ 
• 108776-85-8 3β-hydroxy-12-oxoolean-28-oic acid methyl ester 
• 108-24-7 acetic anhydride 

Downstream Products

• 65023-20-3 methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate 
• 218600-44-3 bardoxolone 
• 218600-53-4 bardoxolone methyl 
• 218600-50-1 methyl 3,12-dioxoolean-9⁽¹¹⁾-en-28-oate 
• 65023-19-0 methyl 3β-hydroxy-12-oxoolean-9(11)-en-28-oate 

Relevant articles and documents

Synthesis of erythrodiol C-ring derivatives and their activity against Chlamydia trachomatis

To develop new potential agents against Chlamydia trachomatis among oleanane type triterpenoids the synthesis, spectral and X-ray analysis as well as antimicrobial screening of C-12 oxygen and nitrogen derivatives of erythrodiol is presented. The reduction of methyl 3β-acetoxy-12-oxo-oleanoate with LiAlH4 led to isomeric erythrodiol 12β- and 12α-hydroxy-derivatives, their stereochemistry with respect to the position of hydroxyl-group at C-12 was determined based on the multiplets splitting patterns, the magnitude of the spin–spin interaction, and NOESY interactions. Methyl 3β-acetoxy-12-oxo-oleanoate was transformed to 12E-hydroxyimino- and 12E-methoxyimino-derivatives by the interaction with NH2OH?HCl or CH3ONH2?HCl, respectively. By Beckmann rearrangement with SOCl2 in dioxane 12E-oxime was converted to C-lactame and its following reduction with LiAlH4 in THF or dioxane led to erythrodiol C-azepanone or C-azepane derivatives. The structure 3-O,12-N-bis-acetyl-derivative of C-azepane-erythrodiol was confirmed by the single crystal X-ray analysis. Erythrodiol 12β-hydroxy- and C-azepane derivatives were found to be lead compounds with significant activity against C. trachomatis with MIC 1.56 and 3.125 μg/mL. Molecular docking was employed to suggest potential binding interaction, the tested compounds are likely to act as Cdu1 protein inhibitors while 12β-hydroxy-erythrodiol exhibited the highest affinity towards this respective target protein. These results indicated that C-ring oxygen and nitrogen erythrodiol derivatives might be considered for further research in the design of antibacterial agents against Chlamydia trachomatis.

Synthesis and anti-HIV activity of oleanolic acid derivatives

Thirteen oleanolic acid derivatives were prepared and evaluated for anti-HIV activity in H9 lymphocytes. Saturating the C12-C13 double bond and converting the C17-carboxyl group to an aminomethyl group led to compounds 13-15 and 19-20, respectively, which showed improved anti-HIV activity. Compound 15 was the most potent derivative with EC50=0.0039 μg/mL and TI=3570.

New enone derivatives of oleanolic acid and ursolic acid as inhibitors of nitric oxide production in mouse macrophages

New derivatives of 3-oxoolean-1-en-28-oic acid and 3-oxours-1-en-28-oic acid were synthesized. Nine of them showed significant inhibitory activity against interferon-γ-induced nitric oxide production in mouse macrophages when assayed at the 1 μM level. 3,12-Dioxoolean-1,9-dien-28-oic acid (3) had the highest activity (IC50, 0.9 μM).