41670-48-8Relevant academic research and scientific papers
Deuterium-labeled phaseic acid and dihydrophaseic acids for internal standards.
Hirai, Nobuhiro,Kondo, Satoru,Ohigashi, Hajime
, p. 2408 - 2415 (2003)
The concentration of abscisic acid in plants is regulated not only by biosynthesis, but also by metabolism. Abscisic acid is metabolized to phaseic acid via 8'-hydroxyabscisic acid, and phaseic acid is then converted to dihydrophaseic acid and its epimer. A quantitative analysis of these metabolites is important as well as that of abscisic acid to understand changes in the concentration of abscisic acid in plants. However, no internal standards of the metabolites suitable for quantitative analysis have been reported. We prepared 7'-deuterium-labeled phaseic acid with a deuterium content of 86%, using the equilibrium reaction between phaseic acid and 8'-hydroxyabscisic acid. 7'-Deuterium-labeled dihydrophaseic acids were obtained by reducing 7'-deuterium-labeled phaseic acid. The levels of the metabolites in plant organs were determined by using the deuterated metabolites as internal standards.
Syntheses of (±)-methyl 6′ α-demethyl-6′ α-cyanoabscisate and (±)-methyl 6′ α-demethyl-6′ α-methoxycarbonylabscisate
Inoue, Takahiro,Oritani, Takayuki
, p. 1071 - 1074 (2007/10/03)
New abscisic acid analogs possessing a cyano or methoxycarbonyl group at the 6α-position of methyl abscisate were synthesized by regioselective hydrocyanation. These compounds had weak activity in the rice second leaf sheath elongation test.
A NOVEL ACYLATED FLAVONOID GLYCOSIDE FROM ASTRAGALUS COMPLANATUS
Cui, Baoliang,Kinjo, Junei,Nakamura, Motoyuki,Nohara, Toshihiro
, p. 6135 - 6138 (2007/10/02)
A novel flavonoid glycoside acylated with a sesquiterpene, dihydrophaseic acid, was obtained from the seeds of Astragalus complanatus R.BR.
Total synthesis of (±)-phaseic acid
Abrams, Garth D.,Abrams, Suzanne R.,Nelson, Lloyd A. K.,Gusta, Lawrence V.
, p. 5543 - 5554 (2007/10/02)
A highly stereoselective synthesis of (±)-phaseic acid is described. Photochemical reaction of the nitrite derived from trans-4-hydroxy-2,2,6-trimethylcyclohexanone functionalizes the methyl group of the geminal pair cis to the hydroxyl group of the start
STEREOCONTROLLED SYNTHESIS OF BOTH THE ENANTIOMERS OF PHASEIC ACID AND ITS METHYL ESTERS, A PIVOTAL METABOLITE OF ABSCISIC ACID.
Kitahara, Takeshi,Touhara, Kazushige,Watanabe, Hidenori,Mori, Kenji
, p. 6387 - 6400 (2007/10/02)
Both the enantiomers of phaseic acid 2a and its methyl ester 2b were synthesized in highly stereocontrolled manner starting from ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclohexanocarboxylate 5 of 98.4 percent e.e. 6-Oxabicyclooctenone 16 was empl
Glycinoeclepins, Natural Hatching Stimuli for the Soybean Cyst Nematode, Heterodera Glycines. I. Isolation
Masamune, Tadashi,Anetai, Masaki,Fukuzawa, Akio,Tagasuki, Mitsuo,Matsue, Hideki,et al.
, p. 981 - 1000 (2007/10/02)
Hatching stimuli, designated as glycinoeclepins, for the soybean cyst nematode (Heterodera glycines) have been isolated by repeated chromatography of the aqueous extracts of dried roots of kidney bean (Phaseolus vulgaris), one of the host plants of the nematode.One of these compounds, glycinoeclepin A, stimulates the hatching and emergence of larvae in vitro in highly diluted aqueous solutions.
Total Synthesis of (+/-)-Methyl Phaseates
Takahashi, Shunya,Oritani, Takayuki,Yamashita, Kyohei
, p. 1589 - 1596 (2007/10/02)
(+/-)-Methyl phaseates were synthesized from (+/-)-4-(6'-acetoxymethyl-2'-6'-dimethyl-1'-cyclohexen-1'-yl)-but-3-en-2-one (20), which was prepared from a useful terpenoid building block, (+/-)-2-hydroxymethyl-2,6-dimethyl-1-cyclohexanone (11a and 11b).Pho
