218600-50-1

Basic information

• Product Name: Olean-9(11)-en-28-oic acid, 3,12-dioxo-, methyl ester (9CI)
• Synonyms: Olean-9(11)-en-28-oic acid, 3,12-dioxo-, methyl ester (9CI);3,12-Dioxoolean-9(11)-en-28-oic acid methyl ester;(4aS,6aR,6bS,12aS,14aR,14bR)-Methyl 2,2,6a,6b,9,9,12a-heptaMethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate;Methyl 3,12-dioxoolean-9(11)-en-28-oate;Olean-9(11)-en-28-oic acid, 3,12-dioxo-, methyl ester
• CAS NO: 218600-50-1
• Molecular Formula: C31H46O4
• Molecular Weight: 482.69454
• Mol File: 218600-50-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 557.072°C at 760 mmHg
• Flash Point: 232.707°C
• Appearance: /
• Density: 1.10
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Olean-9(11)-en-28-oic acid, 3,12-dioxo-, methyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Olean-9(11)-en-28-oic acid, 3,12-dioxo-, methyl ester (9CI)(218600-50-1)
• EPA Substance Registry System: Olean-9(11)-en-28-oic acid, 3,12-dioxo-, methyl ester (9CI)(218600-50-1)

Safety Data

• Hazardous Substances Data: 218600-50-1(Hazardous Substances Data)

Usage

General Description

Olean-9(11)-en-28-oic acid, 3,12-dioxo-, methyl ester (9CI) is a specific chemical compound with an exact structure defined by its name. It is in the steroid family of organic molecules, which are naturally occurring compounds comprised of carbon atoms arranged in four ring-like formations. This specific compound has two oxygen atoms attached, making it a type of dioxo compound. It also contains a methyl ester group, which means it consists of a carbon atom double-bonded to an oxygen atom and single-bonded to another oxygen atom that is linked to a methyl group -CH3. The (9CI) in the name suggests that it is indexed in the Ninth Collective Index of the Chemical Abstracts Service. This chemical is complex and typically found in specialised scientific laboratory or industrial settings.

InChI:InChI=1/C31H46O4/c1-26(2)13-15-31(25(34)35-8)16-14-30(7)24(19(31)18-26)20(32)17-22-28(5)11-10-23(33)27(3,4)21(28)9-12-29(22,30)6/h17,19,21,24H,9-16,18H2,1-8H3/t19-,21-,24-,28-,29+,30+,31-/m0/s1

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 
• 4339-72-4 oleanolic acid 3-acetate 
• 508-02-1 Oleanolic acid 
• 1724-17-0 oleanolic acid methyl ester 
• 25493-94-1 methyl 3-O-β-acetyl-11-dehydro-12-oxo-18β-oleanolate 
• 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 

Downstream Products

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

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.