844467-91-0Relevant academic research and scientific papers
Preparation method of phytol and intermediates thereof
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Paragraph 0064-0099, (2021/03/18)
The invention discloses a preparation method of phytol and intermediates thereof, which comprises the following steps: (1) carrying out esterification rearrangement reaction on isophytol and anhydrideunder the action of perchlorate to obtain phytol ester; and (2) carrying out transesterification on the phytol ester to obtain the phytol. According to the preparation method disclosed by the invention, the total molar yield of the phytol can be up to 88.1%, the generation of potassium acetate or sodium acetate waste solids caused by a potassium hydroxide or sodium hydroxide hydrolysis process isavoided by adopting an ester exchange process, three wastes are effectively controlled, and the method is green and environment-friendly.
Isolation, characterization and antioxidant, tyrosinase inhibitory activities of constituents from the flowers of cercis glabra ‘spring-1’
Shu, Penghua,Li, Yamin,Luo, Yuehui,Yu, Mengzhu,Fei, Yingying,Liu, Wanrong,Yang, Yuan,Wei, Xialan,Zhang, Yuhuan,Tu, Tieyao,Zhang, Lin
, p. 254 - 260 (2021/05/05)
A phytochemical study on the flowers of Cercis glabra ‘Spring-1’ led to the isolation and identification of twelve compounds, including one new compound named as 1-O-α-L-rhamnosyl-(E)-phytol (1) and eleven known compounds. Their structures were elucidated based on physical data analysis, including HR-ESI-MS, NMR, UV, IR, and acid hydrolysis. All compounds were screened for in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl method. Compounds 4 and 5 exhibited obvious DPPH radical scavenging activities. All the isolates were tested for their inhibitory effects on mushroom tyrosinase, and compounds 6, 7, 10 and 11 showed moderate tyrosinase inhibitory activities.
Full racemic phytol composition, and preparation method and application thereof
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, (2020/12/10)
The present invention provides a full racemic phytol composition with high E-configuration content, a preparation method of the full racemic phytol composition and applications of the full racemic phytol composition in preparation of vitamin K1. The full racemic phytol composition comprises Z-configuration full racemic phytol and E-configuration full racemic phytol, wherein a ratio of Z/(Z+E) is less than or equal to 15%. The preparation method comprises the following steps: with isophytol as a raw material, performing halogenation, esterification, ester group removal reaction and the like toobtain the full racemic phytol composition with high E-configuration content.
Synthesis method and method for synthesizing plant alcohol, isoplant alcohol and geranyl geraniol by using intermediate farnesylacetone (by machine translation)
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, (2020/07/21)
The invention relates to a synthesis method of intermediate farnesyl acetone and a method for synthesizing vitamin E, vitamin K1, vitamin K2 side chain isovegetable alcohol, plant alcohol and geranyl geraniol by using farnesyl acetone, and concretely relates to hydrogenation of 5 - farnesyl -2 - acetone and farnesyl acetone through three Grignard reaction to obtain plant ketone. The farnesyl acetone reacts with the vinyl chloride Grignard reagent to obtain geranyl linalool, the aromatic leaf-based geraniol is rearranged under acid catalysis, or farnesyl acetone is directly reacted with the hydroxyl-protected 2 - chloroethanol Grignard reagent to obtain geraniol. The plant alcohol is reacted with the vinyl chloride Grignard reagent to obtain the plant alcohol, and the plant alcohol is directly reacted with the hydroxyl-protected 2 - chloroethanol Grignard reagent to obtain the plant alcohol. The method has the advantages of cheap and easily available starting materials, short synthetic process steps, low product cost and the like. (by machine translation)
Enantioselective Synthesis and Activity of All Diastereoisomers of (E)-Phytal, a Pheromone Component of the Moroccan Locust, Dociostaurus maroccanus
Guerrero, Angel,Ramos, Victoria Elena,López, Sergio,Alvarez, José María,Domínguez, Aroa,Coca-Abia, María Milagro,Bosch, María Pilar,Quero, Carmen
, p. 72 - 80 (2019/01/15)
The Moroccan locust, Dociostaurus maroccanus (Thunberg, 1815) (Orthoptera: Acrididae), is a polyphagous pest capable of inflicting large losses in agriculture under favorable environmental and climatic conditions. Currently, control of the pest relies solely on the application of conventional insecticides that have negative effects on the environment and human safety. In the search for a more rational, environmentally acceptable approach for locust control, we have previously reported that (Z/E)-phytal (1) is a male-produced candidate sex pheromone of this acridid. This molecule, with two stereogenic centers at C-7 and C-11, has four different diastereomers along with the Z/E stereochemistry of the double bond at C-2. In this paper, we present for the first time the enantioselective synthesis of the four diastereomers of (E)-phytal and their electrophysiological and behavioral activity on males and females. Our results demonstrate that the (R,R)-phytal is the most active diastereomer in both assays, significantly attracting females in a double-choice Y olfactometer, and confirming the previous chromatographic assignment as component of the sex pheromone of the Moroccan locust.
New 29-nor-cycloartanes with a 3,4-seco- and a novel 2,3-seco-structure from the leaves of Sinocalycanthus chinensis
Kashiwada, Yoshiki,Nishimura, Kazuya,Kurimoto, Shin-Ichiro,Takaishi, Yoshihisa
experimental part, p. 2790 - 2796 (2011/06/19)
Eight new triterpenoids, including sinocalycanchinensins A-E (1-5) with a 3,4-seco-29-nor-cycloartane skeleton, sinocalycanchinensin F (6) possessing a novel 2,3-seco-29-nor-cycloartane skeleton, and 29-nor-cycloartanes, sinocalycanchinensins G and H (7 and 8), have been isolated from the leaves of Sinocalycanthus chinensis. Their structures were elucidated on the basis of spectroscopic examinations. The cytotoxicities of the isolated new triterpenes against a panel of human cancer cell lines, including multi-drug resistant (MDR) cancer cell lines, were also evaluated. Compound 5 demonstrated enhanced cytotoxicity against MDR KB cells in the presence of colchicine, although all the compounds showed moderate or no cytotoxicities.
Biosynthesis of chloroplastidic and extrachloroplastidic terpenoids in liverwort cultured cells: 13C serine as a probe of terpene biosynthesis via mevalonate and non-mevalonate pathways
Itoh, Daisuke,Kawano, Kyouhei,Nabeta, Kensuke
, p. 332 - 336 (2007/10/03)
Two terpenoid biosynthetic pathways, the mevalonate and non-mevalonate (glyceraldehyde phosphatepyruvate) routes, were examined by feeding 13C-labeled serines ([1-13C]- and [3-13C]-) to the cultured cells of the liverwort, Heteroscyphus planus. The labeling patterns observed in the isoprenoid unit of the biosynthetically 13C-labeled stigmasterol corresponded to those expected from the mevalonate pathway, while those of the phytyl side chain corresponded to those from the non-mevalonate pathway. Thus, serine is a potential probe to determine the origin of terpenoid biosynthesis, in either the mevalonate or non-mevalonate pathway.
Stereocontrol of 1,5-related stereocentres using an intermediate silyl group-the diastereoselectivity of nucleophilic attack on a double bond adjacent to a stereogenic carrying a silyl group
Fleming, Ian,Maiti, Pranab,Ramarao, Chandrashekar
, p. 3989 - 4004 (2007/10/03)
R-5-Methylcyclohex-2-enone 1 reacts successively with the phenyldimethylsilylzincate reagent and acetaldehyde to give with regiocontrol the aldols 7, dehydration of which creates the E-exocyclic double bond of the α-β-unsaturated ketone 2. Conjugate addition of the ethylcuprate reagent to this compound takes place with high (96 : 4) selectivity in favour of the R stereoisomer 12, hydrolysis of which gives (2R,3R,5S,2′ R)-2-(but-2′-yl)-3-dimethyl(phenyl)silyl-5-methylcyclohexanone 3. The oxime acetate of this ketone undergoes fragmentation in the presence of trimethylsilyl trifluoromethanesulfonate to give 3R,7R,5E-3,7-dimethylnon-5-enonitrile 4, in which an open-chain 1,5-stereo-chemical relationship is set up with a high level of stereocontrol. A similar sequence adding 4-methylpentylcuprate to the enone 2, and fragmentation gives 3R,7R,5E-3,7,11-trimethyldodec-5-enonitrile 20. Reduction and hydrogenation of this nitrile gives 3R,7R-3,7,11 -trimethyldodecanal 22, which can be converted into phytol 25. The ketoaldehyde 29 reacts with samarium iodide to give only the alcohol 30, in which the radical anion has attacked from the top surface, just like the cuprate reagents in their reactions with the ketone 2.
Development of synthetic routes to D,L-α-tocopherol (vitamin E) from biologically produced geranylgeraniol
Hyatt, John A.,Kottas, Gregg S.,Effler, Janet
, p. 782 - 787 (2013/09/06)
The use of the biologically derived diterpene alcohol geranylgeraniol was explored as an alternative to petrochemical-based isophytol as a side-chain synthon for producing D,L-α-tocopherol. Two routes were studied, both of which begin with allylic epoxidation followed by olefin hydrogenation to give epoxyphytol. Epoxyphytol can be reduced with Red-Al to provide phytan-1,3-diol which upon acid-catalyzed condensation with trimethylhydroquinone gives vitamin E in fair yield. In a higher-yielding process, epoxyphytol was deoxygenated with methylrhenium trioxide/triphenylphosphine to generate a mixture of phytol and isophytol (> 90% yield from geranylgeraniol). This mixture can serve as a "plug-in" replacement for isophytol in the final step of the currently practiced vitamin E chemistry. The use of methylrhenium trioxide to catalyse dehydration of vinyl dialkyl carbinols to 1,3-dienes was also demonstrated.
A convenient and asymmetric protocol for the synthesis of natural products containing chiral alkyl chains via Zr-catalyzed asymmetric carboalumination of alkenes. Synthesis of phytol and vitamins E and K.
Huo,Negishi
, p. 3253 - 3256 (2007/10/03)
[reaction: see text]. A convenient and asymmetric protocol for the synthesis of chiral oligoisoprenoids is described. Typically, a C14 vitamin E side chain 5 was synthesized in 47% yield over four steps. Isomeric purity of 5 was upgraded to >99% R at C-2 and 97% R at C-6 by the statistical formation of stereoisomeric p-phenylenebisurethanes and their diastereomeric separation. In addition, phytol and vitamin K were synthesized in 21% and 28% overall yields, respectively, over five steps from 1.
