Benzoate revised

Name of Substance Formula Wt/Formula/ Physical Form/ Solubility1/ Solubility 

FEMA No. 2665 3-p-Menthanol (NOTE /-Menthol is obtained from natural sources or by synthetic processes t/Z-Menthol is produced synthetically) 

IR Peroxide Value—5.0 (M-12) Melting Range (/-menthol)—between 41° and 44° (App. IIB) Nonvol. Res.—0.05% (M-17) Readily Ox. Subs. u//-inenthol 1 passes test (M-14) Spec. Rotat. (/-menthol)—between -45° and -51° (App. IIB) Spec. Rotat. (dZ-menthol)—between -2° and +2° (App. IIB) 

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These revised structures for neoline and chasmanine, (47 and 49, respectively) were also supported by a recent 13C NMR study of 26 diterpenoid alkaloids and their derivatives (66, 80). Finally, the structure of chasmanine as 49 was confirmed by an X-ray crystallographic analysis (73a, 81) of chasmanine 14a-benzoate hydrochloride. With the structure of chasmanine now definitely established, attention was directed to the reported chemical correlation of chasmanine and browniine. This supposed correlation was found to be in error by a 13C NMR study of browniine (57), lycoctonine (58), and certain of their derivatives. All but two 13C chemical shifts for browniine and lycoctonine, those of C-14 and C-18, are essentially identical. The 13CNMR study indicated identical stereochemistry of ring A in browniine and lycoctonine. This analysis provided evidence that the reaction sequence used in the reported correlation of browniine and chasmanine did not proceed as expected. 

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