154905-69-8Relevant articles and documents
New sesquiterpenoids from Lycianthes marlipoensis
Guo, Fujiang,Li, Yuanchao
, p. 2364 - 2369 (2005)
Two new sesquiterpenoids and one derivative, lycifuranone A (= (4R)-4,5-dihydro-4-(3-hydroxy-2,6-dimethylbenzyl)-5,5-dimethylfuran-2(3H)-one; 1), lycifuranone B (= 4,5-dihydroxy-3-methyl-2-1{[(3R)-tetra-hydro-2,2-dimethyl- 5-oxofuran-3-yl]methyl} benzaldehyde; 2), and lycifuranone C (= (4R)-4-(3,4-dihydroxy-6-{(2S,4R,6S)-4-[2-(4-hydroxy-3-methoxyphenyl)ethyl] -6-pentyl[1,3]dioxan-2-yl}-2-methylbenzyl)-4,5-dihydro-5,5-dimethylfuran-2(3H) -one; 3), respectively, have been isolated from the roots of Lycianthes marlipoensis, and their structures were established by spectroscopic methods.
GINGEROL COMPOUNDS AND THEIR USE AS FLAVOR MODIFIERS
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Page/Page column 55, (2021/05/21)
The present disclosure relates to gingerol compounds, whether in their diol form or as a derivative, and their use to enhance the salty taste or the umami taste of a flavored article. The disclosure also provides compositions and flavored products contain
A chiral pool and cross metathesis based synthesis of gingerdiols
Wan, Zhi-Li,Zhang, Guo-Liang,Chen, Hui-Jun,Wu, Yikang,Li, Yan
, p. 2128 - 2139 (2014/04/17)
Both (3R,5S)- and (3R,5R)-gingerdiols were synthesized. Their 1,3-diol motifs were derived from enantiopure epoxy chiral building blocks that were readily accessible from D-gluconolactone. The effect of deuterating the OH groups of the natural isomer on its optical rotation was also examined. In the course of the syntheses of the targets, an unexplored cross-metathesis (CM) reaction of unprotected 5-substituted pent-1-ene-3,5-diols was investigated, in which the CM product readily underwent an allylic epimerization and oxidation, as the starting diols rearranged into ketones with unprecedented ease. These problems were eventually resolved by performing the CM reaction in toluene in the presence of phenol. The cause of these unexpected, yet very interesting phenomena, was determined to be the presence of the unprotected OH group at C-5 of the 5-substituted pent-1-ene-3,5-diol. A mechanistic rationale is also presented. Copyright
Synthesis of gingerol and diarylheptanoids
Sabitha, Gowravaram,Srinivas, Chitti,Reddy, Teega Rammohan,Yadagiri, Kurra,Yadav, Jhillu Singh
, p. 2124 - 2133 (2012/03/27)
The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds.
A new method for the demetallation of tricarbonyliron diene complexes by total hydrogenation with Raney nickel. Application to a very short synthesis of (+)-[6]-gingerdiol
Franck-Neumann, Michel,Geoffroy, Philippe,Bissinger, Paul,Adelaide, Sylvie
, p. 6401 - 6404 (2007/10/03)
Demetallation of tricarbonyliron diene complexes is rapidly achieved by treatment with freshly prepared Raney nickel. The ligands which are totally hydrogenated during the decomplexation are easily isolated in high yields, without racemization, if chiral.
GINGERDIOL RELATED COMPOUNDS FROM THE RHIZOMES OF ZINGIBER OFFICINALE
Kikuzaki, Hiroe,Tsai, Saiu-Mei,Nakatani, Nobuji
, p. 1783 - 1786 (2007/10/02)
-Gingerdiol and four analogues, (3R,5S)-5-acetoxy-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane, (3R,5S)-3-acetoxy-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane, (3R,5S)-3,5-diacetoxy-1-(4-hydroxy-3-methoxyphenyl)decane and (3R,5S)-3,5-diacetoxy-1-(3,4
