Chloroform-soluble residues isolated

Figure 13. Structures of chloroform-soluble residues isolated from peanut roots treated with [ C] PCNB. Chloroform-soluble accounted for 59.2% of the in peanut roots.

Figure 14. Methylene chloride- or chloroform-soluble residues were isolated from plant tissues treated with V C] PCNB. All tissues were treated for 3 days except lake water which is rich in blue green algae (9 h), peanut plants (2-day treatment/2-day post-treatment), and peanut cell cultures (1 day).

Methylene chloride-soluble residues. Methylene chloride-or chloroform-soluble C-labeled products were major residues in all of the plant tissues examined except peanut cell ciiltures (Figure 3). Chloroform-soluble C accounted for 59.2 of the radioactivity isolated from peanut roots 48 hr after treatment with [ C]PCNB. The radioactivity was in the form of PCNB (28.7 ), pentachloroaniline (22.5 ), pentachlorothiophenol (2.6 ) pentachlorothloanlsole (3.1 ) pentachlorothloanlsole sulfoxide (0.5 ) S-(pentachlorophenyl)-2-thioaoetic acid [(S-(PCP)ThioAcetate] (0.5 ) and S-(pentachlorophenyl)-3-thio-2-hydroxypropionic acid [S-(PCP)ThioLactate] (0.2 ) and S-(PCP)Cys (trace) (J), The structures of these compounds are shown in Figure 13. Based on TLC, the last three compounds in this list were classified as polar chloroform- or methylene chloride-soluble residues and the remaining compounds were classified as nonpolar residues. 

The estimation of thebaine in the analysis of opium is described by Klyachkina [55] and Anneler [56], The alkaloid has been estimated in opium residues by condensation with benzoquinone, isolation of the very sparingly soluble adduct, and iodimetric titration of this in chloroform solution. This method is reported to be accurate to 0-5 per cent., provided resins, dyeing substances, and phenolic alkaloids are first removed [57]. Thebaine can also be estimated as its silicotungstate [53] or salicylate [54]. 

The isolation of narcotine from opium is simplified by the fact that most of it remains in the water-insoluble residue when opium is processed for the manufacture of morphine. The narcotine is then extractable from this residue with dilute acids, and after regeneration from the extract it may be purified by recrystallization from ethanol (107). The acid oxalate, m.p. 174°, has also been used to separate it from its chief contaminant, namely, papaverine (92,108, 109). Its salt with camphorsulfonic acid is practically insoluble in water whereas that of the other opium salts are quite soluble (110). The free base may be quickly purified by passing a chloroform or benzene solution through a column of calcium hydroxide, most of the impurities being absorbed (HI). 

ISOLATION. Rubijervine was first obtained by Wright and Luff from the rhizomes of V. album (69). Subsequently, Jacobs and Craig (32) gave a more exact description of its isolation. The benzene-extractable alkaloid mixture first deposited the sparingly soluble proto-veratrine and other crystalline bases. The amorphous residue was digested with methanolic sodium hydroxide at 60°. The hydrolyzate on fractional crystallization from chloroform-ethanol yielded rubijervine, isorubijervine, and germine in pure form. 

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