50763-66-1Relevant articles and documents
+-Nootkatone derivative
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, (2017/08/27)
The invention discloses a preparation method for +-nootkatone derivative. The present invention uses the +-nootkatone derivative extracted from cedar leaves as the main material, a chemical compound II is obtained after the restoration through sodium borohydride, the chemical compound II reacts to obtain a chemical compound III and a chemical compound IV through the decomposition of enzymatic dynamics, or decomposes through dynamic kinetics to obtain a chemical compound III with more than 90% yield, a chemical compound V is obtained after hydrolyzing the chemical compound III. The present invention turns the latent chiral ketone group in +-nootkatone into a chirality hydroxy center, and splits further; the present invention has the characteristics of being simple in operation, being high in product yield and with good optics purity.
Highly efficient production of nootkatone, the grapefruit aroma from valencene, by biotransformation
Furusawa, Mai,Hashimoto, Toshihiro,Noma, Yoshiaki,Asakawa, Yoshinori
, p. 1513 - 1514 (2007/10/03)
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.
Biotransformation of citrus aromatics nootkatone and valencene by microorganisms
Furusawa, Mai,Hashimoto, Toshihiro,Noma, Yoshiaki,Asakawa, Yoshinori
, p. 1423 - 1429 (2007/10/03)
Biotransformations of the sesquiterpene ketone nootkatone (1) from the crude drug Alpiniae Fructus and grapefruit oil, and the sesquiterpene hydrocarbon valencene (2) from Valencia orange oil were carried out with microorganisms such as Aspergillus niger, Botryosphaeria dothidea, and Fusarium culmorum to afford structurally interesting metabolites. Their stereostructures were established by a combination of high-resolution NMR spectral and X-ray crystallographic analysis and chemical reaction. Metabolic pathways of compounds 1 and 2 by A. niger are proposed.
Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3
Sowden, Rebecca J.,Yasmin, Samina,Rees, Nicholas H.,Bell, Stephen G.,Wong, Luet-Lok
, p. 57 - 64 (2007/10/03)
The sesquiterpenoids are a large class of naturally occurring compounds with biological functions and desirable properties. Oxidation of the sesquiterpene (+)-valencene by wild type and mutants of P450cam from Pseudomonas putida, and of P450BM-3 from Bacillus megaterium, have been investigated as a potential route to (+)-nootkatone, a fine fragrance. Wild type P450cam did not oxidise (+)-valencene but the mutants showed activities up to 9.8 nmol (nmol P450)-1 min-1, with (+)-trans-nootkatol and (+)-nootkatone constituting >85% of the products. Wild type P450BM-3 and mutants had higher activities (up to 43 min-1) than P450cam but were much less selective. Of the many products, cis- and trans-(+)-nootkatol, (+)-nootkatone, cis-(+)-valencene-1,10-epoxide, trans-(+)-nootkaton-9-ol, and (+)-nootkatone-13S,14-epoxide were isolated from whole-cell reactions and characterised. The selectivity patterns suggest that (+)-valencene has one binding orientation in P450cam but multiple orientations in P450 BM-3.
The Preparation and Microbiological Hydroxylation of the Sesquiterpenoid Nootkatone
Arantes, Simone F.,Farooq, Afgan,Hanson, James R.
, p. 801 - 812 (2007/10/03)
The sesquiterpenoid nootkatone has been prepared from valencene by copper(I) iodide catalysed oxidation with t-butylhydroperoxide and hydroxylated at C-9 by Mucor plumbeus and Cephalosporium aphidicola.
The Rearrangement of Allylic Hydroperoxides Derived from (+)-Valencene
Davies, Alwyn G.,Davison, Ian G. E.
, p. 825 - 830 (2007/10/02)
(+)-Valencene (I) reacts with triplet oxygen to give 84 percent of the secondary β-hydroperoxyde (II) and 15 percent of the α-hydroperoxide (III); reaction with singlet oxygen gives principally (ca. 80 percent) the tertiary β-hydroperoxide (IV).This undergoes a Schenck rearrangement to give suprafacially the β-hydroperoxide (II) by a non-dissociative mechanism which does not involve exchange of oxygen in an atmosphere of 18O2.The hydroperoxide (II) then undergoes a slower Smith epimerization to the α-hydroperoxide (III) by a dissociative mechanism which involves a substantial (> 55 percent) exchange.
