65023-19-0

Basic information

• Product Name: (4aS,6aR,6bS,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-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,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-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 (3α,5ξ,18α)-3-hydroxy-12-oxoolean-9(11)-en-28-oate
• CAS NO: 65023-19-0
• Molecular Formula: C31H48O4
• Molecular Weight: 484.71042
• Mol File: 65023-19-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4aS,6aR,6bS,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-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,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-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(65023-19-0)
• EPA Substance Registry System: (4aS,6aR,6bS,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-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(65023-19-0)

Safety Data

• Hazardous Substances Data: 65023-19-0(Hazardous Substances Data)

Usage

General Description

The chemical compound "(4aS,6aR,6bS,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-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 molecule with a long and specific chemical structure. It contains a methyl group, a hydroxy group, and a carboxylate group, as well as a series of fused cycloalkane rings and multiple methyl substituents. (4aS,6aR,6bS,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-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 highly hydrophobic and likely has a low water solubility due to its complex and bulky structure. It is likely to exhibit unique chemical and physical properties, and its synthesis and potential applications would be of interest to synthetic chemists and researchers in the field of organic chemistry.

Upstream product

• 65023-18-9 3β-hydroxy-12-oxoolean-9(11)-en-28-oic acid 
• 65023-20-3 methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate 
• 4339-72-4 oleanolic acid 3-acetate 
• 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 
• 508-02-1 Oleanolic acid 
• 35959-11-6 3β-acetoxy-13-hydroxy-12-oxo-oleanan-28-oic acid-lactone 
• 1724-17-0 oleanolic acid methyl ester 
• 25493-94-1 methyl 3-O-β-acetyl-11-dehydro-12-oxo-18β-oleanolate 

Downstream Products

• 218600-50-1 methyl 3,12-dioxoolean-9⁽¹¹⁾-en-28-oate 
• 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 

Relevant articles and documents

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Efficient and scalable synthesis of bardoxolone methyl (CDDO-methyl ester)

Bardoxolone methyl (2-cyano-3,12-dioxooleane-1,9(11)-dien-28-oic acid methyl ester; CDDO-Me) (1), a synthetic oleanane triterpenoid with highly potent anti-inflammatory activity (levels below 1 nM), has completed a successful phase I clinical trial for the treatment of cancer and a successful phase II trial for the treatment of chronic kidney disease in type 2 diabetes patients. Our synthesis of bardoxolone methyl (1) proceeds in ～50% overall yield in five steps from oleanolic acid (2), requires only one to two chromatographic purifications, and can provide gram quantities of 1.

Design and synthesis of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages

New derivatives with electron-withdrawing substituents at the C-2 position of 3-oxoolean-1-en-28-oic acid were synthesized. Among them, 2- cyano-3,12-dioxoleam-1,9-dien-28-oic acid (CDDO) was 400 times more potent than previous compounds we have made as an inhibitor of production of nitric oxide induced by interferon γ in mouse macrophages (IC50, 0.4 nM). The potency of CDDO was similar to that of dexamethasone, although CDDO does not act through the glucocorticoid receptor.