86391-07-3

Basic information

• Product Name: zerumbone epoxide
• CAS NO: 86391-07-3
• Molecular Weight: 234.338
• Mol File: 86391-07-3.mol

Chemical Properties

• CAS DataBase Reference: zerumbone epoxide(CAS DataBase Reference)
• NIST Chemistry Reference: zerumbone epoxide(86391-07-3)
• EPA Substance Registry System: zerumbone epoxide(86391-07-3)

Safety Data

• Hazardous Substances Data: 86391-07-3(Hazardous Substances Data)

Upstream product

• 74383-69-0 (E)-8-Methoxy-3,3,7,11-tetramethyl-12-oxa-bicyclo[9.1.0]dodec-4-en-6-one 
• 14790-72-8 zerumbone 
• 74383-70-3 (2E,9E)-6-methoxy-2,9-humuradien-8-one 
• 22471-70-1 (+/-)-(6R,7R)-epoxy-2,6,9,9-tetramethyl-2,10-cycloundecadien-1-one 
• 124-41-4 sodium methylate 

Downstream Products

• 22471-70-1 (4Z,7E)-1,5,9,9-Tetramethyl-12-oxa-bicyclo[9.1.0]dodeca-4,7-dien-6-one 

Relevant articles and documents

The thia-Michael reactivity of zerumbone and related cross-conjugated dienones: Disentangling stoichiometry, regiochemistry, and addition mode with an NMR-spectroscopy-based cysteamine assay

The cross-conjugated and electrophilic dienone system of the humulane sesquiterpene zerumbone (1a) was modified by E/Z photochemical isomerization and/or by removal of homoconjugation with the isolated endocyclic double bond of the medium-sized ring. The site (C-6/C-9), mode (transient or irreversible), stoichiometry (single or twofold), and comparative rates of thiol addition were evaluated using an NMR-spectroscopy-based cysteamine assay. Dramatic effects were seen, and this highlights the subtleties of the reaction and the limitations of our predictive power in this field. For biological endpoints sensitive to thiol trapping, a substantial separation between Michael reactivity and biological activity was found for 1a and its analogues. This supports the view that shape complementarity plays a critical role in the covalent binding of Michael acceptors to their macromolecular target(s). Using the NMR-spectroscopy-based cysteamine assay, the thia-Michael reactivity of the cross-conjugated dienone zerumbone and its photoisomers and epoxides was investigated, and marked differences were found. For biological endpoints sensitive to Michael acceptors, a substantial separation between reactivity and biological activity was observed.

Accessing Polycyclic Terpenoids from Zerumbone via Lewis Acid Catalyzed Synthetic Strategies

We herein disclose an effective strategy for the synthesis of [5.3.0] and [6.3.0] fused polycyclic terpenoids, which are important structural elements of natural products and biologically active compounds. The method comprises of Lewis acid catalyzed interrupted Nazarov cyclization of zerumbone derivatives such as zerumbone epoxide, triazole-appended zerumbone, zerumbal, and zerumbenone with a wide substrate scope with different indoles. Zerumbone epoxide furnished [5.3.0] and [6.3.0] fused structurally diverse sesquiterpenoids and all other zerumbone derivatives furnished the [6.3.0] fused motifs.

Cytotoxicity against cholangiocarcinoma cell lines of zerumbone derivatives

Cholangiocarcinoma (CCA) is an aggressive malignancy with a very high morbidity and mortality for which an effective treatment is lacking. In this study, seventeen zerumbone derivatives were synthesized and evaluated for in vitro cytotoxicity against chol

The chemistry of zerumbone. Part 5: Structural transformation of the dimethylamine derivatives

Zerumbone (1) and its 6,7-epoxide (2) react with ammonia and dimethylamine regio- and stereospecifically, affording monoamines 3, 4, 7 and 8. All adducts have the same relative configuration at C2 and C3. The conjugate amination is thermodynamically controlled to arrive at a single diastereomer. At 15°C 7 reacts with cyanide to give aminonitrile 10 as the single product, while at 30°C, acyclic aminonitrile 11 is also formed. The reaction with 8 affords at 0°C bicyclic aminonitrile 12 of the asteriscane skeleton, while at 30°C or higher temperature, mixtures of 12 and tricyclic nitriles 13 and 13′ are obtained. Refluxing of 7, 8 and 10 in aqueous acetonitrile promotes scission of the zerumbone ring by retro-Mannich reaction to provide acyclic aldehydes 16-18, respectively. The dimethylamino group of 7, 8 and 10 is eliminated stereospecifically by Cope- and base-catalyzed eliminations to regenerate the zerumbone skeleton in the products 1, 2 and 21. Cope elimination of 12 results in a mixture of 13 and 13′ by deaminative transannular etherification.

Chemistry of zerumbone. 2. Regulation of ring bond cleavage and unique antibacterial activities of zerumbone derivatives.

Further investigation of the chemistry of the eleven-membered cyclic sesquiterpene, zerumbone, the major component of the wild ginger, Zingiber zerumbet Smith, has revealed a new selective epoxidation process, a further example of a novel Favorskii-initiated double ring contraction, and a regiospecific fragmentation of zerumbone dibromide derivatives. Several zerumbone derivatives were found to be selective inhibitors of the growth of gram-positive bacteria.

TRANSANNULAR CYCLIZATIONS OF ZERUMBONE EPOXIDE

Formic acid catalyzed rearrangement of zerumbone epoxide 3 gives three major bicyclic products, 4-6.The most important rearrangement is a conrotatory electrocyclic Nazarow reaction.The structures were deduced from spectral and chemical evidence. 13C NMR data are presented.An X-ray study has independently confirmed the proposed structures.

Reaction of Zerumbone with Alkaline Hydrogen Peroxide and Sodium Methoxide

Zerumbone affords several interesting compounds on reaction with alkaline hydrogen peroxide and sodium methoxide.Structures of some of these compounds have been assigned on the basis of spectral data and chemical correlation.