305818-39-7

Basic information

• Product Name: (4aS,6aR,6bS,12aS,14aR,14bR,Z)-Methyl 11-(hydroxyMethylene)-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
• Synonyms: (4aS,6aR,6bS,12aS,14aR,14bR,Z)-Methyl 11-(hydroxyMethylene)-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
• CAS NO: 305818-39-7
• Molecular Formula: C32H46O5
• Molecular Weight: 510.70464
• Mol File: 305818-39-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 599.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: (4aS,6aR,6bS,12aS,14aR,14bR,Z)-Methyl 11-(hydroxyMethylene)-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(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS,6aR,6bS,12aS,14aR,14bR,Z)-Methyl 11-(hydroxyMethylene)-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(305818-39-7)
• EPA Substance Registry System: (4aS,6aR,6bS,12aS,14aR,14bR,Z)-Methyl 11-(hydroxyMethylene)-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(305818-39-7)

Safety Data

• Hazardous Substances Data: 305818-39-7(Hazardous Substances Data)

Usage

General Description

The chemical "(4aS,6aR,6bS,12aS,14aR,14bR,Z)-Methyl 11-(hydroxyMethylene)-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" is a complex organic compound. Its molecular formula and structure indicate a long chain of carbon atoms with several methyl and carbonyl (C=O) functional groups, as well as a hydroxyMethylene (-CH2OH) group. It is likely a derivative of picene, a hydrocarbon compound, and contains a carboxylate group. Due to its lengthy and complex structure, the chemical is likely to have various potential applications in organic chemistry, pharmaceuticals, and materials science.

Upstream product

• 218600-50-1 methyl 3,12-dioxoolean-9⁽¹¹⁾-en-28-oate 
• 109-94-4 formic acid ethyl ester 
• 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 

Relevant articles and documents

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.