123-35-3Relevant academic research and scientific papers
Acid-catalyzed hydrolysis of alcohols and their β-D-glucopyranosides
Skouroumounis, George K.,Sefton, Mark A.
, p. 2033 - 2039 (2000)
The hydrolysis, in model wine at pH 3, of the allylic, homoallylic, and propargylic glycosides, geranylβ-D-glucopyranoside, [3'-(1'-cyclohexenyl)- 1'-methyl-2'-propynyl]-β-D-glucopyranoside, (3'RS,9'SR)(3'-hydroxy-5'- megastigmen-7-yn-9-yl)-β-D-glucopyranoside, (3',5',5'-trimethyl-3'- cyclohexenyl)-β-D-glucopyranoside, E-(7'-oxo-5',8'-megastigmadien-3'-yl)-β- D-glucopyranoside (3-hydroxy-β-damascone-β-D-glucopyranoside), and their corresponding aglycons has been studied. In general, aglycons were more rapidly converted to transformation products than were the corresponding glucosides. Glycoconjugation of geraniol in grapes is a process that reduces the flavor impact of this compound in wine, not only because geraniol is an important flavor component of some wines but also because the rate of formation of other flavor compounds from geraniol during bottle-aging is reduced. However, when flavor compounds such as β-damascenone are formed in competition with flavorless byproducts, such as 3-hydroxy-β-damascone, by acid-catalyzed hydrolytic reactions of polyols, then glycoconjugation is a process that could enhance as well as suppress the formation of flavor, depending on the position of glycosylation. (3'RS,9'SR)-(3'-Hydroxy-5'- megastigmen-7'-yn-9'-yl)-β-D-glucopyranoside hydrolyzed more slowly but gave a higher proportion of β-damascenone in the products than did the aglycon at 50 °C. Reaction temperature also effected the relative proportion of the hydrolysis products. Accelerated studies do not parallel natural processes precisely but only approximate them.
Molybdenum- and tungsten-catalyzed allylation of aromatic compounds with allylic esters and alcohols
Shimizu, Isao,Sakamoto, Toshiaki,Kawaragi, Saeko,Maruyama, Yooichiro,Yamamoto, Akio
, p. 137 - 138 (1997)
A novel method to substitute aromatic compounds with allylic groups using oxygen-containing allylic compounds in the presence of molybdenum or tungsten carbonyls under neutral conditions has been developed. The method is applicable to one step synthesis of methyl eugenol.
Preparation of 1-Alkenes by the Palladium-Catalyzed Hydrogenolysis of Terminal Allylic Carbonates and Acetates with Formic Acid-Triethylamine
Tsuji, Jiro,Minami, Ichiro,Shimizu, Isao
, p. 623 - 627 (1986)
A useful method for the preparation of 1-alkenes from terminal allylic carbonates and acetates by the palladium-catalyzed reaction with formates is described.Formic acid-triethylamine is a suitable reductant.As catalyst, Pd2(dba)3CHCl3-P(n-Bu)3 gave the best result, 0.05-0.2 molpercent being sufficient (turnover 500-2000).Using this method, various 1-alkenes were prepared in good yields with high selectivity.
Selective Synthesis of 1,3-Dienic Terpenes in a β-Form through Regioselective 1,4-Elimination of Allylic Ethers
Otera, Junzo,Niibo, Yoshihisa,Okuda, Kazuhiro
, p. 1829 - 1832 (1986)
γ-Methyl-substituted allylic ethers proved to be converted into β-substituted dienes exclusively on treatment with t-BuOK in refluxing THF or cyclohexane.
Thermal behaviour of selected C10H16 monoterpenes
Stolle, Achim,Brauns, Claudia,Nuechter, Matthias,Ondruschka, Bernd,Bonrath, Werner,Findeisen, Matthias
, p. 3317 - 3325 (2006)
The presented work investigates the thermal behaviour of selected monoterpenes under various reactor temperatures and residence times (carrier gas, reactor inserts). In addition to the analysis of the liquid products by capillary GC and GC-MS, chemical derivatisation techniques (Diels-Alder reaction, hydrogenation) were used to identify the liquid-phase products. A thermal conversion of β-pinene (1), myrcene (2) and limonene (4) in a reaction network is presented and the experimental evidence for the formation of pyrolysis products by a biradical pathway is discussed. The reaction network was modified based on the identification of additional C10H 16 terpene isomers. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Flash vacuum thermolysis of terpenic compounds in the pinane series
Lemee,Ratier,Duboudin,Delmond
, p. 1313 - 1318 (1995)
The flash pyrolysis of various derivatives (hydrocarbons and oxygenated compounds) in the pinane series has been studied. We observed a high degree of conversion and good selectivity.
Novel route to a fruitful mixture of terpene fragrances in particular phellandrene starting from natural feedstock geraniol using weak acidic boron based catalyst
Eisenacher, Matthias,Beschnitt, Stefan,H?lderich, Wolfgang
, p. 214 - 217 (2012)
Myrcene, ocimene and in particular phellandrene were selectively generated as products by dehydration of the natural feedstock geraniol over a weak acidic boron pentasil zeolite catalyst in a gas phase reaction. Additionally linalool was formed by rearrangement reaction. The total selectivity of these 4 terpenes is up to 99%.
Thermal behavior of pinan-2-ol and linalool
Leiner, Janne,Stolle, Achim,Ondruschka, Bernd,Netscher, Thomas,Bonrath, Werner
, p. 8358 - 8375 (2013)
Linalool is an important intermediate for syntheses of isoprenoid fragrance compounds and vitamins A and E. One process option for its production is the thermal gas-phase isomerization of cis- and trans-pinan-2-ol. Investigations of this reaction were performed in a flow-type apparatus in a temperature range from 350-600 °C and a residence time range of 0.6-0.8 s. Rearrangement of the bicyclic alcohol led to linalool, plinols arising from consecutive reactions of linalool and other side products. Effects of residence time, temperature, surface-to-volume-ratio, carrier gas, and the presence of additives on yield and selectivity were studied. Furthermore, the effects of such parameters on ene-cyclization of linalool affording plinols were investigated. Results indicate that manipulation of the reaction in order to affect selectivity is difficult due to the large free path length to other molecules in the gas phase. However, conditions have been identified allowing one to increase the selectivity and the yield of linalool throughout pyrolysis of pinan-2-ol.
Comparative thermolysis of β-and α-pinenes in supercritical ethanol: The reaction characterization and enantiomeric ratios of products
Chibiryaev,Yermakova,Kozhevnikov,Sal'nikova,Anikeev
, p. 1234 - 1238 (2007)
The thermolysis of β-pinene and the co-thermolysis of an equimolar mixture of β-and α-pinenes in supercritical ethanol were carried out. The reaction of β-pinene affords β-myrcene as the major product (>70%). Considerable differences in the temperature dependence of the reaction rate were revealed for the transformations of β-pinene into β-myrcene and of α-pinene into limonene. The pre-exponential factors and the activation energies were calculated. The enantiomeric ratios of the thermolysis products of β-and α-pinenes and limonene were estimated. The starting monoterpenes do not undergo racemization during thermolysis. The thermolysis of enantiomerically pure α-pinene affords racemic (±)-limonene, whereas (-)-β-pinene gives (-)-limonene. The enantiomeric ratio in the latter remains equal to the enantiomeric purity of the starting β-pinene.
Preparation method of myrcene
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Paragraph 0033-0034, (2021/11/19)
The method uses geraniol and/or nerol and/or linalool as a raw material, uses a palladium source and an organic phosphine as a catalyst to prepare myrcene, and realizes chemical synthesis of myrcene. The method has the advantages of high catalytic efficiency and high product selectivity.
