(+)-Cuparene - CAS 56324-31-3
Category:
Main Product
Product Name:
(+)-Cuparene
Catalog Number:
56324-31-3
Synonyms:
(+)-CUPARENE; CUPARENE, (+); (R)-1-(P-TOLYL)-1,2,2-TRIMETHYLCYCLOPENTANE; (-)-1-Methyl-4-[(S)-1,2,2-trimethylcyclopentyl]benzene; (S)-(-)-Cuparene; (S)-Cuparene; 4-[(S)-1,2,2-Trimethylcyclopentane-1α-yl]toluene
CAS Number:
56324-31-3
Molecular Weight:
202.34
Molecular Formula:
C15H22
Quantity:
Data not available, please inquire.
COA:
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MSDS:
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Chemical Structure
CAS 56324-31-3 (+)-Cuparene

Reference Reading


1.Phytochemical analysis and cytotoxicity towards multidrug-resistant leukemia cells of essential oils derived from Lebanese medicinal plants.
Saab AM1, Guerrini A, Sacchetti G, Maietti S, Zeino M, Arend J, Gambari R, Bernardi F, Efferth T. Planta Med. 2012 Dec;78(18):1927-31. doi: 10.1055/s-0032-1327896. Epub 2012 Nov 15.
Juniperus excelsa fruit essential oil as well as J. oxycedrus, Cedrus libani, and Pinus pinea wood essential oils have been obtained with yields between 2.2 ± 0.3 % to 3.4 ± 0.5 % and analyzed by gas chromatography. Sesquiterpenes mainly characterized C. libani and J. oxycedrus essential oils, while in P. pinea and J. excelsa, monoterpenes were the most abundant compounds. In J. oxycedrus, cis-calamenene (7.8 %), cuparene (3.8 %), and cis-thujopsenal (2.0 %) have been detected for the first time. The cytotoxic activity of these essential oils against drug-sensitive CCRF-CEM and multidrug-resistant P-glycoprotein-expressing CEM/ADR5000 leukemia cells has been investigated (IC₅₀ values: 29.46 to 61.54 µg/mL). Remarkably, multidrug-resistant CEM/ADR5000 cells did not reveal cross-resistance, indicating that these essential oils might be useful to treat otherwise drug-resistant and refractory tumors.
2.Terpenoids Preserved in Fossils from Miocene-aged Japanese Conifer Wood.
Ludwiczuk A, Asakawa Y. Nat Prod Commun. 2015 Jun;10(6):1051-3.
The compositions of terpenoids from the solvent extracts of two silicified wood samples were analyzed using a GC/MS method. Chromatographic analysis showed that several biomolecules were preserved unaltered in the Miocene-aged Japanese wood. These were α-terpineol, α-cedrene, thujopsene, widdrol and ferruginol, among others. In addition to the bioterpenoids, the fossil woods contained a series of geoterpenoids that were generated from their biological precursors before and after burial. These were cadalene, daucalene, pseudowiddrene and cuparene. The chemical composition of both analyzed fossil samples suggest that the silicified woods collected in the Noto Peninsula belong to the Cupressaceae family; this was confirmed by morphological analysis. Both samples were identified as Taxodioxylon cunninghamioides, which is the most common Miocene wood in Japan.
3.Essential oils of Cupressus funebris, Juniperus communis, and J. chinensis (Cupressaceae) as repellents against ticks (Acari: Ixodidae) and mosquitoes (Diptera: Culicidae) and as toxicants against mosquitoes.
Carroll JF1, Tabanca N, Kramer M, Elejalde NM, Wedge DE, Bernier UR, Coy M, Becnel JJ, Demirci B, Başer KH, Zhang J, Zhang S. J Vector Ecol. 2011 Dec;36(2):258-68. doi: 10.1111/j.1948-7134.2011.00166.x.
Juniperus communis leaf oil, J. chinensis wood oil, and Cupressus funebris wood oil (Cupressaceae) from China were analyzed by gas chromatography and gas chromatography-mass spectrometry. We identified 104 compounds, representing 66.8-95.5% of the oils. The major components were: α-pinene (27.0%), α-terpinene (14.0%), and linalool (10.9%) for J. communis; cuparene (11.3%) and δ-cadinene (7.8%) for J. chinensis; and α-cedrene (16.9%), cedrol (7.6%), and β-cedrene (5.7%) for C. funebris. The essential oils of C. funebris, J. chinensis, and J. communis were evaluated for repellency against adult yellow fever mosquitoes, Aedes aegypti (L.), host-seeking nymphs of the lone star tick, Amblyomma americanum (L.), and the blacklegged tick, Ixodes scapularis Say, and for toxicity against Ae. aegypti larvae and adults, all in laboratory bioassays. All the oils were repellent to both species of ticks. The EC(95) values of C. funebris, J. communis, and J.
4.Use of P450 cytochrome inhibitors in studies of enokipodin biosynthesis.
Ishikawa NK1, Tahara S2, Namatame T2, Farooq A2, Fukushi Y2. Braz J Microbiol. 2014 Mar 10;44(4):1285-90. eCollection 2013.
Enokipodins A, B, C, and D are antimicrobial sesquiterpenes isolated from the mycelial culture medium of Flammulina velutipes, an edible mushroom. The presence of a quaternary carbon stereocenter on the cyclopentane ring makes enokipodins A-D attractive synthetic targets. In this study, nine different cytochrome P450 inhibitors were used to trap the biosynthetic intermediates of highly oxygenated cuparene-type sesquiterpenes of F. velutipes. Of these, 1-aminobenzotriazole produced three less-highly oxygenated biosynthetic intermediates of enokipodins A-D; these were identified as (S)-(-)-cuparene-1,4-quinone and epimers at C-3 of 6-hydroxy-6-methyl-3-(1,2,2-trimethylcyclopentyl)-2-cyclohexen-1-one. One of the epimers was found to be a new compound.