Chemically, the cadinenes are bicyclicsesquiterpenes. The term cadinene has sometimes also been used in a broad sense to refer to any sesquiterpene with the so-called cadalane (4-isopropyl-1,6-dimethyldecahydronaphthalene) carbon skeleton. Because of the large number of known double-bond and stereochemical isomers, this class of compounds has been subdivided into four subclasses based on the relative stereochemistry at the isopropyl group and the two bridgehead carbon atoms.[1] The name cadinene is now properly used only for the first subclass below, which includes the compounds originally isolated from cade oil. Only one enantiomer of each subclass is depicted, with the understanding that the other enantiomer bears the same subclass name.
Cadalane skeleton
Cadinane stereochemistry
Muurolane stereochemistry
Amorphane stereochemistry
Bulgarane stereochemistry
Referencesedit
^ A.-K. Borg-Karlson, T. Norin and A. Talvitie (1981). "Configurations and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol". Tetrahedron. 37 (2): 425–430. doi:10.1016/s0040-4020(01)92031-9.
February 16, 2024
cadinenes, group, isomeric, hydrocarbons, that, occur, wide, variety, essential, producing, plants, name, derived, from, that, cade, juniper, juniperus, oxycedrus, wood, which, yields, from, which, cadinene, isomers, were, first, isolated, cadineneα, cadinene,. Cadinenes are a group of isomeric hydrocarbons that occur in a wide variety of essential oil producing plants The name is derived from that of the Cade juniper Juniperus oxycedrus L the wood of which yields an oil from which cadinene isomers were first isolated Cadinenes a Cadinenea Cadinene b Cadineneg Cadinene d CadineneNamesIUPAC names 1S 4aR 8aR 4 7 dimethyl 1 propan 2 yl 1 2 4a 5 6 8a hexahydronaphthalene a cadinene 1S 4aR 8aR 7 methyl 4 methylidene 1 propan 2 yl 1 2 3 4 4a 5 6 8a octahydronaphthalene g cadinene 1S 8aR 4 7 dimethyl 1 propan 2 yl 1 2 3 5 6 8a hexahydronaphthalene d cadinene IdentifiersCAS Number a 24406 05 1 Yb 11044 40 9 Yg 39029 41 9 Yd 1460 97 5 YChEBI a CHEBI 80749b CHEBI 27723g CHEBI 63203d CHEBI 15385ChEMBL b ChEMBL3120653d ChEMBL445759KEGG a C16815b C09625g C19738d C06394PubChem CID a 12306048b 10657g 92313d 441005UNII a X650G04I0A Yb Z07LA0GY4J Yg 2GHT32E0JU Yd 7848KI47OS YPropertiesChemical formula C 15H 24Molar mass 204 357 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Chemically the cadinenes are bicyclic sesquiterpenes The term cadinene has sometimes also been used in a broad sense to refer to any sesquiterpene with the so called cadalane 4 isopropyl 1 6 dimethyldecahydronaphthalene carbon skeleton Because of the large number of known double bond and stereochemical isomers this class of compounds has been subdivided into four subclasses based on the relative stereochemistry at the isopropyl group and the two bridgehead carbon atoms 1 The name cadinene is now properly used only for the first subclass below which includes the compounds originally isolated from cade oil Only one enantiomer of each subclass is depicted with the understanding that the other enantiomer bears the same subclass name Cadalane skeleton Cadinane stereochemistry Muurolane stereochemistry Amorphane stereochemistry Bulgarane stereochemistryReferences edit A K Borg Karlson T Norin and A Talvitie 1981 Configurations and conformations of torreyol d cadinol a cadinol T muurolol and T cadinol Tetrahedron 37 2 425 430 doi 10 1016 s0040 4020 01 92031 9 Retrieved from https en wikipedia org w index php title Cadinenes amp oldid 1053696737, wikipedia, wiki, book, books, library,
