65023-20-3

Basic information

• Product Name: (4aS,6aR,6bS,10S,12aS,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate
• Synonyms: (4aS,6aR,6bS,10S,12aS,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate;Methyl (3β,5ξ,18α)-3-acetoxy-12-oxoolean-9(11)-en-28-oate;Acetyl methyl epithelanthate
• CAS NO: 65023-20-3
• Molecular Formula: C33H50O5
• Molecular Weight: 526.7471
• Mol File: 65023-20-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 570.3±50.0 °C(Predicted)
• Appearance: /
• Density: 1.11±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (4aS,6aR,6bS,10S,12aS,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS,6aR,6bS,10S,12aS,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate(65023-20-3)
• EPA Substance Registry System: (4aS,6aR,6bS,10S,12aS,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate(65023-20-3)

Safety Data

• Hazardous Substances Data: 65023-20-3(Hazardous Substances Data)

Usage

General Description

The chemical (4aS,6aR,6bS,10S,12aS,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate is a complex organic compound with a long and specific chemical structure. It is a derivative of picene, a polycyclic aromatic hydrocarbon, and contains numerous methyl groups and an acetoxy group. (4aS,6aR,6bS,10S,12aS,14aR,14bR)-Methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate is a carboxylate ester, and its chemical properties are likely to be influenced by the presence of the acetoxy and carboxylate groups, as well as the specific arrangement of the methyl groups. The exact uses and potential applications of this chemical are not specified in the name, but its complex structure and functional groups indicate that it may have some relevance in organic synthesis or pharmaceutical research.

Upstream product

• 25493-94-1 methyl 3-O-β-acetyl-11-dehydro-12-oxo-18β-oleanolate 
• 10035-10-6 hydrogen bromide 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 508-02-1 Oleanolic acid 
• 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 
• 4339-72-4 oleanolic acid 3-acetate 
• 35959-11-6 3β-acetoxy-13-hydroxy-12-oxo-oleanan-28-oic acid-lactone 
• 1724-17-0 oleanolic acid methyl ester 
• 108-24-7 acetic anhydride 

Downstream Products

• 305818-40-0 1,2-dihydro-2-cyano-3,12-dioxooleana-1,9⁽¹¹⁾-dien-28-oic acid methyl ester 
• 305818-39-7 methyl 2-hydroxymethylene-3,12-dioxoolean-9⁽¹¹⁾-en-28-oate 
• 218600-53-4 bardoxolone methyl 
• 218600-44-3 bardoxolone 
• 218600-52-3 methyl 12-oxoisoxazolo[4,5-b]olean-9⁽¹¹⁾-en-28-oate 
• 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

Design and Synthesis of Irreversible Analogues of Bardoxolone Methyl for the Identification of Pharmacologically Relevant Targets and Interaction Sites

Semisynthetic triterpenoids such as bardoxolone methyl (methyl-2-cyano 3,12-dioxooleano-1,9-dien-28-oate; CDDO-Me) (4) are potent inducers of antioxidant and anti-inflammatory signaling pathways, including those regulated by the transcription factor Nrf2. However, the reversible nature of the interaction between triterpenoids and thiols has hindered attempts to identify pharmacologically relevant targets and characterize the sites of interaction. Here, we report a shortened synthesis and SAR profiling of 4, enabling the design of analogues that react irreversibly with model thiols, as well as the model protein glutathione S-transferase P1, in vitro. We show that one of these analogues, CDDO-epoxide (13), is comparable to 4 in terms of cytotoxicity and potency toward Nrf2 in rat hepatoma cells and stably modifies specific cysteine residues (namely, Cys-257, -273, -288, -434, -489, and -613) within Keap1, the major repressor of Nrf2, both in vitro and in living cells. Supported by molecular modeling, these data demonstrate the value of 13 for identifying site(s) of interaction with pharmacologically relevant targets and informing the continuing development of triterpenoids as novel drug candidates.