16509-46-9Relevant academic research and scientific papers
Biogenetic studies in Syringa vulgaris L.: Synthesis and bioconversion of deuterium-labeled precursors into lilac aldehydes and lilac alcohols
Kreck, Mirjam,Pueschel, Susen,Wuest, Matthias,Mosandl, Armin
, p. 463 - 469 (2003)
Syringa vulgaris L. inflorescences were fed with aqueous solutions of regioselectively deuterated compounds assumed to be precursors of lilac aldehyde and lilac alcohol, respectively. Volatiles were extracted by stir bar sorptive extraction (SBSE) and analyzed using enantioselective multidimensional gas chromatography/mass spectrometry (enantio-MDGC/MS); deuterium-labeled lilac aldehydes and lilac alcohols were separated from unlabeled stereoisomers on a fused silica capillary column, coated with heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin (DIME-β-CD) (30%) in SE 52 (70%), as the chiral stationary phase. Feeding experiments with [5,5-2H2]mevalonic acid lactone 22 and [5,5-2H2]deoxy-D-xylose 23 indicate that the novel mevalonate independent 1-deoxy-D-xylose 5-phosphate/2C-methyl-D-erythritol 4-phosphate pathway is the dominant metabolic route for biosynthesis in lilac flowers. Additionally, bioconversion of deuterium-labeled d5-(R/S)-linalool 3, d6-(R)-linalool 21, d5-(R/S)-8-hydroxylinalool 6, d5-(R/S)-8-oxolinalool 7, d5-lilac aldehydes 8-11 and d5-lilac alcohols 12-15 into lilac during in vivo feeding experiments was investigated and the metabolic pathway is discussed. Incubation of petals with an aqueous solution of deuterated d5-(R/S)-linalool 3 indicates an autonomic terpene biosynthesis of lilac flavor compounds in the flower petals of lilac.
Manganese-mediated acetylation of alcohols, phenols, thiols, and amines utilizing acetic anhydride
Jain, Isha,Sharma, Ramandeep,Malik, Payal
supporting information, p. 2952 - 2960 (2019/09/13)
Manganese(II) chloride-catalyzed acetylation of alcohols, phenols thiols and amines with acetic anhydride is reported. This method is environment-friendly and economically viable as it involves inexpensive, relatively benign catalyst, mild reaction condition, and simple workup. Acetylation is performed under the solvent-free condition at ambient temperature and acetylated products obtained in good to excellent yields. Primary, secondary heterocyclic amines, and phenols with various functional groups are smoothly acetylated in good yields. This method exhibits exquisite chemoselectivity, the amino group is preferentially acetylated in the presence of a hydroxyl/thiol group.
Characterization of a novel esterase isolated from intertidal flat metagenome and its tertiary alcohols synthesis
Oh, Ki-Hoon,Nguyen, Giang-Son,Kim, Eun-Young,Kourist, Robert,Bornscheuer, Uwe,Oh, Tae-Kwang,Yoon, Jung-Hoon
experimental part, p. 67 - 73 (2012/09/07)
A gene coding for an esterase (EstEH112) was isolated from metagenome originated from Korean intertidal flat sediment. The putative esterase gene encoded a 340 amino acids protein with characteristic residues of lipolytic enzymes such as a conserved pentapeptide (GXSXG), the typical catalytic S-D-H triad, and a GGG(A)X-motif in the oxyanion hole near the active site similar to the hormone sensitive lipase (HSL) family. p-Nitrophenyl butyrate was the best substrate for the enzyme among the other p-nitrophenyl esters investigated. The apparent optimal temperature and pH for EstEH112 was 35°C and at pH 8.0, respectively. EstEH112 efficiently catalyzed the hydrolysis of various large tertiary alcohol esters. These characteristics of EstEH112 make it a potential candidate for application in biocatalysis.
Enantioselective monoterpene alcohol acetylation in Origanum, Mentha and Salvia species
Larkov, Olga,Zaks, Alon,Bar, Einat,Lewinsohn, Efraim,Dudai, Nativ,Mayer, Alfred M.,Ravid, Uzi
experimental part, p. 2565 - 2571 (2009/04/06)
Selected plants within the Origanum, Mentha and Salvia genera, that contain significant amounts of chiral volatile alcohols and their related acetates, exhibit remarkable enantioselectivity of alcohol acetyl transferase (AAT) activity and particularly can discriminate between linalool enantiomers. Origanum dayi AAT produced almost enantiomerically pure (R)-linalyl acetate by enzymatic acetylation of racemic linalool, whereas the closely related O. majorana AAT produced a mixture of (R)- and (S)-linalyl acetate with a ratio of 6:4. Vmax of O. dayi acetylation activity was 30-fold higher for (R)-linalool, whereas in O. majorana no such differences were found.
Total partial synthesis of (3S, 6S)-(+)-3,7-dimethyl-6-hydroxy-3- acetoxyocta-1,7-diene and (3S, 6S)-(-)-3,7-dimethylocta-1,7-diene-3,6-diol from geraniol
Liu, Zuosheng,Lan, Jiong,Li, Yulin,Xing, Yacheng,Cen, Wen
, p. 324 - 325 (2007/10/03)
The synthesis of (3S, 6S)-(+)-3,7-dimethyl-6-hydroxy-3-acetoxyocta-1,7- diene and (3S, 6S)-(-)3,7-dimethylocta-1,7-diene-3,6-diol via the rearrangement of the chiral 2,3-epoxy alcohol, with the system Ph3P, pyridine, I2 and H2O, is described.
Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: The linalool route
Vidari, Giovanni,Rosa, Anna Di,Zanoni, Giuseppe,Bicchi, Carlo
, p. 3547 - 3557 (2007/10/03)
Each of the four enantiomerically pure tetrahydropyran linalool oxides was prepared by separate enantioselective Sharpless dihydroxylation of (R)- or (S)-linalyl acetate with AD-mix-α or AD-mix-β, followed by a completely stereoselective N-phenylselenophthalimide cyclization of an intermediate allylic alcohol.
Absolute stereochemistry of chinesin I and II
Aramaki, Yoshinori,Chiba, Kazuhiro,Tada, Masahiro
, p. 683 - 688 (2007/10/02)
The absolute stereochemistry of chinesin I and II has been elucidated by synthetic and spectroscopic experiments.Tetrahydrochinesin I was degraded with ozonolysis and converted into the cyclopentane derivative 5 whose absolute stereochemistry was elucidated by synthesis from (-)-linalool.Degradation of chinesin I with H2SO4 gave (S)-2-methylbutyric acid.Finally, the absolute configuration of chinesin I was established as 4R, 8S, 9R, 12R, 24S.
