Revised structures of pipoxide and pipoxide chlorohydrin

✍ Scribed by B.S. Joshi; D.H. Gawad; H. Fuhrer

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 187 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)86310-3

✦ Synopsis

The etructures assigned earlier to pipoxlde and pipoxlde ohlorohydrin have been revised on the basis of 360 Liz PM2 spectral evidence and deooupllng experiments.

In the aourse of chemical investigation of Piper species, i-5 we have examined four plants viz., P. attenuatum, P. aaleatum, P. hookeri and PO niRrum* Hexane extraction of the whole plant of P. attenuatum, P. galeatum and P. hookeri afforded a orystalline compound m.p. 150°,CO]D 4 74' which was shown to be identical with arotepoxlde (I), known to possess signifiaant antitumour activity in Lewis lung carcinoma6.

Chromatographic separation of the hexane extracts of P. hookeri and 5 niarum afforded colourless plates, mop. 154°,&]D -49' (C 2; Cml3), c2iH18°6~ M+ at m/e 366; A,, (BtOH) 228, 274, 280 nm (log E, 4.46, 3.29, 3.19), dmax (nujol) 3440, 1722, 1680, 1600 am-', tic (sigel) Rf 0.24 (CHC13:2$ MeOH). This was found to be identical with pipoxide'.

Ae pipoxlde was reported to have a rotation[aii" + 24.5., the OHD curves of both compounds were determined which showed them to be superimposable. OHD (c 0.05, =3) IIp3600 -100; @I292 -