- Synthesis method of 3-methyl-2-butene-1-geranoil formate
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The invention belongs to the technical field of chemical synthesis and particularly relates to a synthesis method of 3-methyl-2-butene-1-geranoil formate. According to the synthesis method of the 3-methyl-2-butene-1-geranoil formate and on the basis of the existing technical process, sodium hydrogen sulfite serves as a catalyst, the yield of a 3-methyl-2-butene-1-geranoil formate product is further increased, more preferably, reaction is conducted under the existence of ionic liquid, the reaction time is effectively increased besides the yield of the products is effectively increased, and higher product yield can be obtained within shorter time.
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Paragraph 0043-0050
(2018/07/06)
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- Heteropoly acid catalyzed cyclization of nerolidol and farnesol: Synthesis of α-bisabolol
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Heteropoly acid H3PW12O40 is an active and environmentally friendly homogeneous catalyst for the synthesis of α-bisabolol, a high-priced and highly demanded ingredient for the fragrance, cosmetic and pharmaceutical industries, starting from more abundant biomass-based sesquiterpenic alcohols. The solvent nature remarkably affects the reaction pathways and product selectivity. In acetone solutions, α-bisabolol can be obtained in 55-60% GC yields from nerolidol and 60-70% GC yields from farnesol at complete substrate conversions, which are probably the best results ever reported for these reactions. α-Bisabolol synthesized by this method contains no farnesol, which is a potentially allergenic compound and should be avoided in the commercially used α-bisabolol. This advantage is especially important because the distillative separation of α-bisabolol and farnesol is a troublesome task. The catalyst shows high turnover numbers and operates under mild nearly ambient conditions.
- De Meireles, Augusto L.P.,Costa, Maíra Dos Santos,Da Silva Rocha, Kelly A.,Gusevskaya, Elena V.
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p. 271 - 275
(2015/07/07)
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- Enantioselective microbial synthesis of the indigenous natural product (-)-α-bisabolol by a sesquiterpene synthase from chamomile (Matricaria recutita)
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(-)-α-Bisabolol, a sesquiterpene alcohol, is a major ingredient in the essential oil of chamomile (Matricaria recutita) and is used in many health products. The current supply of (-)-α-bisabolol is mainly dependent on the Brazilian candeia tree (Eremanthus erythropappus) by distillation or by chemical synthesis. However, the distillation method using the candeia tree is not sustainable, and chemical synthesis suffers from impurities arising from undesirable α-bisabolol isomers. Therefore enzymatic synthesis of (-)-α-bisabolol is a viable alternative. In the present study, a cDNA encoding (-)-α-bisabolol synthase (MrBBS) was identified from chamomile and used for enantioselective (-)-α-bisabolol synthesis in yeast. Chamomile MrBBS was identified by Illumina and 454 sequencing, followed by activity screening in yeast. When MrBBS was expressed in yeast, 8mg of α-bisabolol was synthesized de novo per litre of culture. The structure of purified α-bisabolol was elucidated as (S,S)- α-bisabolol [or (-)-α-bisabolol]. Although MrBBS possesses a putative chloroplast-targeting peptide, it was localized in the cytosol, and a deletion of its N-terminal 23 amino acids significantly reduced its stability and activity. Recombinant MrBBS showed kinetic properties comparable with those of other sesquiterpene synthases. These data provide compelling evidence that chamomile MrBBS synthesizes enantiopure (-)-α-bisabolol as a single sesquiterpene product, opening a biotechnological opportunity to produce (-)-α-bisabolol.
- Son, Young-Jin,Kwon, Moonhyuk,Ro, Dae-Kyun,Kim, Soo-Un
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p. 239 - 248
(2015/03/03)
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- Method for Converting Farnesol to Nerolidol in the Presence of Alpha-Bisabolol
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A method for converting farnesol to nerolidol in the presence of alpha-bisabolol including providing or preparing a mixture of alpha-bisabolol, farnesol, and one or more catalysts for selective isomerization of farnesol to nerolidol in the presence of alpha-bisabolol, and converting at least a portion of the farnesol to nerolidol.
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- Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesvl diohosohate
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We report the structures and stereochemistry of seven bisabolyl-derived sesquiterpenes arising from an unprecedented 1,6-cyclization (cisoid pathway) efficiently catalyzed by tobacco 5-epi-aristolochene synthase (TEAS). The use of (2Z,6E)-farnesyl diphosphate as an alternate substrate for recombinant TEAS resulted in a robust enzymatic cyclization to an array of products derived exclusively (≥99.5%) from the cisoid pathway, whereas these same products account for ca. 2.5% of the total hydrocarbons obtained using (2E,6E)-farnesyl diphosphate. Chromatographic fractionations of extracts from preparative incubations with the 2Z,6E substrate afforded, in addition to the acyclic allylic alcohols (2Z,6E)-farnesol (6.7%) and nerolidol (3.6%), five cyclic sesquiterpene hydrocarbons and two cyclic sesquiterpene alcohols: (+)-2-epiprezizaene (44%), (-)-α-cedrene (21.5%), (R)-(-)-β-curcumene (15.5%), R-acoradiene (3.9%), 4-epi-α-acoradiene (1.3%), and equal amounts of α-bisabolol (1.8%) and epi-R-bisalolol (1.8%). The structures, stereochemistry, and enantiopurities were established by comprehensive spectroscopic analyses, optical rotations, chemical correlations with known sesquiterpenes, comparisons with literature data, and GC analyses. The major product, (+)-2-epi-prezizaene, is structurally related to the naturally occurring tricyclic alcohol, jinkohol (2-epi-prezizaan-7 β-ol). Cisoid cyclization pathways are proposed by which all five sesquiterpene hydrocarbons are derived from a common (7R)-β-bisabolyl+/pyrophosphate - ion pair intermediate. The implications of the cisoid catalytic activity of TEAS are discussed.
- Faraldos, Juan A.,O'Maille, Paul E.,Dellas, Nikki,Noel, Joseph P.,Coates, Robert M.
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experimental part
p. 4281 - 4289
(2010/05/15)
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- METHOD FOR PRODUCING BISABOLOL WHICH IS FARNESOL FREE OR IS LOW IN FARNESOL
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The present invention relates to a method of producing pure or enriched bisabolol by separating substance mixtures comprising bisabolol and farnesol by selective esterification of farnesol and subsequent distillative separation. The invention relates specifically to a method as specified above comprising the selective transesterification of mixtures comprising formyl-bisabolol and formyl-farnesol and subsequent distillative separation. The present invention furthermore relates to a method of producing farnesol esters.
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Page/Page column 7-8
(2010/09/07)
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- Method for Producing Alpha-Bisabolol from Farnesol
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The present invention relates to a process for preparing α-bisabolol, comprising the reaction of farnesol in the presence of a ketone, of a sulfonic acid and of a further strong acid.
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Page/Page column 3
(2008/12/04)
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- PROCESS FOR REMOVING FARNESOL FROM MIXTURES WITH ALPHA-BISABOLOL
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Process for esterification of farnesol in an initial mixture comprising alpha-bisabolol, farnesol and optionally other components, with the following steps: 1. Preparation or production of the initial mixture, 2. Adding (i) a transesterification catalyst and (ii) one or more compounds of formula (B) [in-line-formulae]R2YnCO2R1??(B) [/in-line-formulae] in which the following applies: R1 stands for an alkyl residue with 1 to 12 C atoms; R2 stands for hydrogen, an alkyl residue with 1 to 20 C atoms, a cycloalkyl residue with 5 to 20 C atoms, an aryl residue with 6 to 20 C atoms or a heteroaryl residue with 5 to 20 C atoms; and Y stands for CH2, CH(Me), CH(Et), C(Me)2, CH2—CH(Me), CH(Me)-CH2 or CH2—CH(Me)-CH2 and n stands for a whole number from 0 to 6; or R2 stands for a group CO2R3, R3 standing for an alkyl residue with 1 to 12 C atoms; and Y stands for CH2, CH(Me), CH(Et), C(Me)2, CH2—CH(Me), CH(Me)-CH2 or CH2—CH(Me)-CH2 and n stands for a whole number from 0 to 8, or Y stands for an optionally substituted phenyl or naphthyl ring with a total of at most four substituents on the ring, n=1 applying.
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Page/Page column 5
(2008/06/13)
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- METHOD FOR THE PRODUCTION OF ALPHA-BISABOLOL FROM NEROLIDOL
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The invention relates to a method for the production of alpha-bisabolol, consiting of the following step: nerolidol is reacted with a mixture of ketone, sulfonic acid and perchloric acid.
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Page/Page column 9
(2008/06/13)
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- Asymmetric epoxidation of homoallylic alcohols and application in a concise total synthesis of (-)-α-bisabolol and (-)-8-epi-α-bisabolol
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Vanadium triisopropoxide oxide and an α-amino acid-based hydroxamic acid (e.g. 1) form the catalyst for the asymmetric epoxidation of homoallylic alcohols presented here. 3-Substituted alcohols 2 were epoxidized to the corresponding epoxy alcohols 3 with good ee values. In addition, a concise total synthesis of (-)-αand (-)-8-epi-α-bisabolol was achieved.
- Makita, Naoya,Hoshino, Yujiro,Yamamoto, Hisashi
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p. 941 - 943
(2007/10/03)
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- A concise enantiocontrolled total synthesis of (-)-α-bisabolol and (+)-4-epi-α-bisabolol
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The regiocontrolled hydrogenation of the cyclohexadiene 6, synthesised from the chiral cyclobutanone 3 was effectively achieved with [1,4-bis(diphenylphosphino)butane](1,5-cyclooctadiene)rhodium (1) tetrafluoroborate as catalyst to give the olefins 7 and 8 which were converted into (-)-α-bisabolol la and (+)-4-epi-α-bisabolol 15 via 9 and 10, 11 and 12, and 13 and 14.
- Nemoto, Hideo,Shiraki, Motohiro,Nagamochi, Masatoshi,Fukumoto, Keiichiro
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p. 4939 - 4942
(2007/10/02)
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- CYCLIZATION OF SOME LINEAR TERPENOLS INITIATED BY "ACTIVATED" DMSO
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It was shown that the acylhydroxysulfonium salt generated in situ from DMSO and trifluoroacetic anhydride causes low-temperature cyclization of geraniol, linalool, and nerol in an aprotic medium to a mixture of p-menthane monoterpenoids, and the maximum yield is obtained in the case of the last two terpenols.A similar result was obtained for E-nerolidol.
- Surkova, A. A.,Lozanova, A. V.,Dragan, V. A.,Gur'yan, V. A.,Moiseenkov, A. M.
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p. 760 - 762
(2007/10/02)
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- STRUCTURE - ODOR CORRELATION - IX: FROM 1,8-CINEOL TO SESQUICINEOL - CHANGE OF ODOR WITH STRUCTURE
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Cu(I) catalyzed 1,4-Grignard reaction of the key compound 6 led to the bicyclic keto ethers 7-15 together with small amounts of the alcohols 16-25.Wolff-Kishner reduction of 8-15 gave the 1,8-cineol homologues 26-32 and sesquicineol (2). - The fresh and camphoraceous odor of 1 changes stepwise with increasing side chain to herbaceous and spicy notes, compounds with branched side chains show lavender undertones. 2 has a pleasant fruity, floral and sweet fragrance.
- Weyerstahl, Peter,Krohn, Kerstin
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p. 3503 - 3514
(2007/10/02)
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- Electroreductive Intermolecular Coupling of Ketones with Olefins
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Electroreductive coupling of ketones with a variety of olefins such as 1-olefins, dienes, and trienes afforded the corresponding tertiary alcohols in good yields and high regioselectivity.
- Shono, Tatsuya,Kashimura, Shigenori,Mori, Yasuo,Hayashi, Takashi,Soejima, Takeshi,Yamaguchi, Yoshihide
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p. 6001 - 6003
(2007/10/02)
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- ORGANOMANGANESE (II) REAGENTS XIV: A SHORT AND EFFICIENT SYNTHESIS OF DIASTEREOISOMERIC (+/-)-α-BISABOLOLS AND (+/-)-CHLORPHENOXAMINE
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Diastereomeric (+/-)-α-bisabolols (7), a sesquiterpenoid alcohol, and (+/-)-chlorphenoxamine (12), an antihistamine, have been prepared in excellent yields.Both these short and convenient syntheses involve as a key step the one-pot elaboration of a dissymetrical tertiary alcohol via an organomanganese reagent (5 to 7 and 9 to 10 respectively).
- Cahiez, Gerard,Rivas-Enterrios, Jose,Clery, Patrick
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p. 3659 - 3662
(2007/10/02)
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- AN ELECTROCHEMICAL METHOD SPECIFICALLY DIRECTED TO THE PREPARATION OF DL-BISABOLOL FROM DL-NEROLIDOL
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A product-selective electrosynthesis of dl-bisabolol from dl-nerolidol was accomplished by a constant current electrolysis in commercial acetone containing a small amount of LiClO4
- Uneyama, Kenji,Masatsugu, Yosinori,Ueda, Takesi,Torii, Sigeru
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p. 529 - 530
(2007/10/02)
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- CHEMISTRY OF THE ORGANOSILICON COMPOUNDS-165 2-TRIMETHYLSILYL-METHYL-1, 3-BUTADIENE-A VERSATILE BUILDING BLOCK FOR TERPENE SYNTHESIS
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Two types of synthetically useful reactions of 2-trimethylsilylmethyl-1,3-butadiene (7) are discussed.Reactions of 7 with acid chlorides, aldehydes, ketones and acetals activated by a Lewis acid give isoprenylated compounds, while 7 undergoes the Diels-Alder reaction whit dienophiles.High regiospecificity of the reaction qualifies 7 for a versatile building block of terpene synthesis.
- Sakurai, Hideki,Hosomi, Akira,Saito, Masaki,Sasaki, Koshi,Iguchi, Hirokazu,et al.
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p. 883 - 894
(2007/10/02)
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- α-BISABOLOL β-D-FUCOPYRANOSIDE FROM CARTHAMUS LANATUS
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A sesquiterpene glycoside has been isolated from the aerial parts of Carthamus lanatus and identified by its spectroscopic and chemical properties as α-bisabolol β-D-fucopyranoside.Key Word Index - Carthamus lanatus; Compositae; sesquiterpene glycoside; α-bisabolol β-D-fucopyranoside.
- Feliciano, Arturo San,Barrero, Alejandro F.,Miguel, Jose M.,Corral, Del,Gacimartin, Maria V.,Medarde, Manuel
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p. 2115 - 2117
(2007/10/02)
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- Sur la stereochimie de la cyclisation du nerolidol an α-bisabolol
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The cyclisation of linalyl to α-terpinyl derivatives is known to take place with efficient transfer of chirality.Information was needed about the analogous cyclisation of nerolidyl to bisabolyl derivatives.This was made possible through the recent determination of the absolute configuration of bisabolol and epibisabolol.Hydrolysis of (+)(S) nerolidyl paranitrobenzoate has been carried out under the experimental conditons used for (-)(R) linalyl paranitrobenzoate.Strong asymmetric induction was observed about C4 (in the ring) but very little, if any, about C8 (in the chain).The cyclisation of (+)(S) nerolidol has been brought about by 90/10 aqueous formic acid.Under these experimental conditions very little asymmetric induction is observed about C8 or C4.This is explained by rapid racemisation of the starting material under the cyclisation conditions.
- Fourneron, Jean-Dominique,Julia, Marc
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p. 387 - 392
(2007/10/02)
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- LES SESQUITERPENES BISABOLANIQUES PAR PRENYLATIONS ACIDES: UNE SYNTHESE FACILE DE LA DELOBANONE ET DE LA 8-EPI-DELOBANONE
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A convenient approach to bisabolane sesquiterpenoids by acid catalysed prenylation of readily available monoterpenes is described.
- Harwood, Laurence M.,Julia, Marc
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p. 1743 - 1746
(2007/10/02)
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