218600-52-3

Basic information

• Product Name: (4aS,6aR,6bS,13aS,15aR,15bR)-Methyl 2,2,6a,6b,9,9,13a-heptaMethyl-15-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,13,13a,15,15a,15b-octadecahydropiceno[2,3-d]isoxazole-4a-carboxylate
• Synonyms: (4aS,6aR,6bS,13aS,15aR,15bR)-Methyl 2,2,6a,6b,9,9,13a-heptaMethyl-15-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,13,13a,15,15a,15b-octadecahydropiceno[2,3-d]isoxazole-4a-carboxylate;Oleana-2,9(11)-dieno[2,3-d]isoxazol-28-oic acid, 12-oxo-, methyl ester;(4aS,6aR,6bS,13aS,15aR,15bS)-methyl 2,2,6a,6b,9,9,13a-heptamethyl-15-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,13,13a,15,15a,15b-octadecahydropiceno[2,3-d]isoxazole-4a-carboxylate
• CAS NO: 218600-52-3
• Molecular Formula: C32H45NO4
• Molecular Weight: 507.7
• Mol File: 218600-52-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4aS,6aR,6bS,13aS,15aR,15bR)-Methyl 2,2,6a,6b,9,9,13a-heptaMethyl-15-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,13,13a,15,15a,15b-octadecahydropiceno[2,3-d]isoxazole-4a-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS,6aR,6bS,13aS,15aR,15bR)-Methyl 2,2,6a,6b,9,9,13a-heptaMethyl-15-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,13,13a,15,15a,15b-octadecahydropiceno[2,3-d]isoxazole-4a-carboxylate(218600-52-3)
• EPA Substance Registry System: (4aS,6aR,6bS,13aS,15aR,15bR)-Methyl 2,2,6a,6b,9,9,13a-heptaMethyl-15-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,13,13a,15,15a,15b-octadecahydropiceno[2,3-d]isoxazole-4a-carboxylate(218600-52-3)

Safety Data

• Hazardous Substances Data: 218600-52-3(Hazardous Substances Data)

Usage

General Description

The chemical "(4aS,6aR,6bS,13aS,15aR,15bR)-Methyl 2,2,6a,6b,9,9,13a-heptaMethyl-15-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,13,13a,15,15a,15b-octadecahydropiceno[2,3-d]isoxazole-4a-carboxylate" is a complex organic molecule with a long and specific name that describes its chemical structure. Despite its complicated name, it is essentially an ester composed of a picenoyl group, a methyl group, and a carbonyl group. It contains 18 carbon atoms and forms a unique isoxazole ring structure. This chemical's complex structure makes it suitable for use in various chemical and biological applications, including but not limited to organic synthesis, pharmaceutical research, and medicinal chemistry.

Upstream product

• 357953-28-7 benzyl 3β-acetoxy-12-oxoolean-28-oate 
• 357953-27-6 (4aS,6aS,6bR,10S,12aR)-benzyl 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 
• 303114-51-4 oleanolic acid benzyl ester 
• 508-02-1 Oleanolic acid 
• 1185309-11-8 12-oxo-isoxazolo[4,5-b]olean-9⁽¹¹⁾-en-28-oate 
• 74-88-4 methyl iodide 
• 1309236-59-6 benzyl 12-oxo-isoxazolo[4,5-b]olean-9⁽¹¹⁾-en-28-oate 
• 1309236-49-4 benzyl 3,12-dioxo-olean-9⁽¹¹⁾-en-28-oate 
• 1309236-46-1 benzyl 3β-hydroxy-12-oxo-olean-9(11)-en-28-oate 
• 218600-50-1 methyl 3,12-dioxoolean-9⁽¹¹⁾-en-28-oate 
• 65023-20-3 methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate 
• 65023-19-0 methyl 3β-hydroxy-12-oxoolean-9(11)-en-28-oate 
• 305818-39-7 methyl 2-hydroxymethylene-3,12-dioxoolean-9⁽¹¹⁾-en-28-oate 
• 218600-51-2 (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Formyl-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester 

Downstream Products

• 218600-53-4 bardoxolone methyl 
• 218600-44-3 bardoxolone 
• 305818-40-0 1,2-dihydro-2-cyano-3,12-dioxooleana-1,9⁽¹¹⁾-dien-28-oic acid methyl ester 

Relevant articles and documents

Oleanolic acid derivative with conjugated diene structure C ring and preparation method and application thereof

The invention belongs to the field of medicinal chemistry, and particularly relates to an oleanolic acid derivative with a conjugated diene structure C ring and a preparation method and application thereof. In particular, the invention also provides a pharmaceutical composition comprising an effective amount of the derivative or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier; moreover, the derivative or the pharmaceutically acceptable salt thereof can be used for treating inflammation-related diseases and has antitumor activity, and the safety of the compound is improved or equivalent.

Synthetic oleanane and ursane triterpenoids with modified rings A and C: A series of highly active inhibitors of nitric oxide production in mouse macrophages

We have designed and synthesized 16 new olean- and urs-1-en-3-one triterpenoids with various modified rings C as potential antiinflammatory and cancer chemopreventive agents and evaluated their inhibitory activities against production of nitric oxide induced by interferon-γ in mouse macrophages. This investigation revealed that 9(11)-en-12-one and 12-en-11-one functionalities in ring C increase the potency by about 2-10 times compared with the original 12-ene. Subsequently, we have designed and synthesized novel olean- and urs-1-en-3-one derivatives with nitrile and carboxyl groups at C-2 in ring A and with 9(11)-en-12-one and 12-en-11-one functionalities in ring C. Among them, we have found that methyl 2-cyano-3, 12-dioxooleana-1,9(11)-dien-28-oate (25), 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO) (26), and methyl 2-carboxy-3,12-dioxooleana-1,9(11)-dien-28-oate (29) have extremely high potency (IC50 = 0.1 nM level). Their potency is similar to that of dexamethasone although they do not act through the glucocorticoid receptor. Overall, the combination of modified rings A and C increases the potency by about 10 000 times compared with the lead compound, 3-oxooleana-1,12-dien-28-oic acid (8) (IC50 = 1 μM level). The selected oleanane triterpenoid, CDDO (26), was found to be a potent, multifunctional agent in various in vitro assays and to show antiinflammatory activity against thioglycollate-interferon-γ-induced mouse peritonitis.