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.
PROCESS FOR THE PREPARATION OF NOOTKATONE BY USING A IRON (III) PORPHYRIN COMPLEX CATALYST
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Page/Page column 5-7, (2020/12/29)
An allylic oxidation process comprising: forming a mixture containing valencene and an iron (lll)-X porphyrin complex catalyst in a sustainable solvent, introducing molecular oxygen into the mixture, and effecting allylic oxidation to produce nootkatone.