4674-50-4Relevant articles and documents
Preparation of (-)-aristolochene from (+)-valencene: Absolute configuration of (+)-aristolochene from Aspergillus terreus
Cane,Salaski,Prabhakaran
, p. 1943 - 1944 (1990)
The absolute configuration of (+)-aristolochene (1a), isolated from Aspergillus terreus, has been established by direct comparison with a sample of (-)-aristolochene (1b) prepared from (+)-valencene (2).
Highly efficient production of nootkatone, the grapefruit aroma from valencene, by biotransformation
Furusawa, Mai,Hashimoto, Toshihiro,Noma, Yoshiaki,Asakawa, Yoshinori
, p. 1513 - 1514 (2005)
Nootkatone (2), the most important and expensive aromatic of grapefruit, decreases the somatic fat ratio, and thus its demand is increasing in the cosmetic and fiber sectors. A sesquiterpene hydrocarbon, (+)-valencene (1), which is cheaply obtained from Valencia orange, was biotransformed by the green algae Chlorella species and fungi such as Mucor species, Botryosphaeria dothidea, and Botryodiplodia theobromae to afford nootkatone (2) in high yield.
Dastur
, p. 6509 (1973)
Manganese complex catalyst for valencene oxidation: The first use of metalloporphyrins for the selective production of nootkatone
DeFreitas-Silva, Gilson,Moreira Meireles, Alexandre,Robles-Azocar, Patrícia,da Silva, Vinicius Santos,de Melo, Carla Nunes
, (2021)
This work describes the oxidation of valencene, a sesquiterpene easily obtained from citrus fruits, and responsible for the fresh odor of oranges. The reactions were catalyzed by manganese porphyrins derived from 5,10,15,20-tetrakis(3,5-dimethoxyphenyl)porphyrin (H2T3,5DMPP): [MnIII(T3,5DMPP)Cl] (MnP1) and [MnIII(Br12T3,5DMPP)Cl] (MnP2), using iodosylbenzene (PhIO), iodobenzene diacetate [PhI(OAc)2], and molecular oxygen as oxidants. The systems MnP1/O2/acetonitrile and MnP1/O2/diethyl carbonate led to higher yields of valencene oxidation products (44% and 48%, respectively) as compared with MnP2 (9% and 7%, respectively), with nootkatone being the major product. The addition of a small amount of imidazole (molar MnP1: imidazole ratio of 1:5) to the MnP1/O2/diethyl carbonate led to superior yields (64%) as compared with systems without the additive. A mechanism for the formation of the two products obtained was also proposed.
METHOD FOR THE MANUFACTURE OF α,β-UNSATURATED KETONES
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Page/Page column 13, (2021/10/30)
A method for the manufacture of an α,β-unsaturated ketone, which method comprises oxidizing an alkene having -CH2- adjacent a carbon-carbon double bond to α,β-unsaturated ketone by passing air or oxygen through a solution of the hydrocarbon containing a catalyst consisting of N-hydroxyphthalimide (NHPI) and cobalt diacetate tetrahydrate at standard temperature and pressure during a period of at least 12 hours.
Pd-Catalyzed aerobic oxidation of the sesquiterpene isolongifolene: A green and heterogeneous process
Nunes de Melo, Carla,Robles-Azocar, Patrícia Alejandra,Rodrigues, Yuri Blanc
, (2020/12/25)
The oxidation of the sesquiterpene isolongifolene, catalyzed by Pd/SiO2 prepared through a conventional sol–gel method, resulted mainly in isolongifolen-9-one (65% selectivity), a compound which occupies a prominent place in perfume industry. In addition to the product obtained from the allylic oxidation of isolongifolene, the formation of other oxygenated products with potential industrial application (both total yield of 94%) was also observed. The system can be used for oxidation of other sesquiterpene, valencene. In this case, it was possible to obtain oxygenated products with up to 66% yield. The reactions occurred under mild conditions in a green and heterogeneous oxidation catalytic system. Pd (II) was used as a solo catalyst in the absence of co-oxidants. The catalyst can be easily recovered and re-used maintaining activity and selectivity.