Summary
Reaction of menthols and cineoles withm-chloroperbenzoic acid afforded tertiary, secondary, and primary alcohols, some of which were natural products having potent plant growth regulatory activity or were mammlianm metabolies.
Literature
Ishida, T., Asakawa, Y., Okano, M., and Aratani, T., J. Pharm. Sci.68 (1979) 928; Ishida, T., Asakawa, Y., Takemoto, T., and Aratani, T., J. pharm. Sci.70 (1981) 406; Asakawa, Y., Taira, Z., Takemoto, T., Ishida, T., Kido, M., and Ichikawa, Y., J. pharm. Sci.70 (1981) 710; Ishida, T., Asakawa, Y., and Takemoto, T., J. pharm. Sci.71 (1982) 965.
Mazur, Y., Pure appl. Chem.41 (1975) 145.
Takeda, K., Pure appl. Chem.21 (1970) 181.
Breslow, R., Chem. Soc. Rev.1 (1972) 553.
Müller, W., and Schneider, H.-J., Angew. Chem., int. Ed. Engl.8 (1979) 407; Takaishi, N., Fujikura, Y., and Inamoto, Y., Synthesis1983, 293.
Nishimura, H., Kaku, K., Nakamura, T., Fukazawa, Y., and Mizutani, J., Agric. Biol. Chem.46 (1982) 319.
Yields refer to isolated yields based on consumed starting material.
Takagi, W., and Mitsui, T., J. org. Chem.25 (1960) 1476.
As the nomenclature suggested by IUPAC is somewhat complex, we have used simple names: e.g. 4β-hydroxy-1-menthol (7) rather than (1R, 2R, 4R)-1-isopropyl-4-methylcyclohexane-1,2-diol.
Nagasawa, T., Umemoto, K., Tsuneya, T., and Shiga, M., Agric. Biol. Chem.39 (1975) 2083.
All new compounds reported here showed satisfactory spectral data including high resolution mass spectra.1H-NMR spectra were measured on a JEOL JNM GX-400 (400 MHz) spectrometer.
This compound was one of the metabolites of rabbits (unpublished results).
Nishimura, H., Noma, Y., and Mizutani, J., Agric. Biol. Chem.46 (1982) 2601.
MacRae, I.C., Alberts, V., Carman, R.M., and Shaw, I.M., Aust. J. Chem.32 (1979) 917.
Author information
Authors and Affiliations
Additional information
We thank Nippon Terpene Co. Ltd for their generous gift of the compounds used in this work and Drs M. Kido and Y. Fukuyama, Otsuka Pharmaceutical Co. Ltd, for measurement of high resolution mass spectra. The present work was supported in part by a Grant-in-Aid for Cancer Research from the Ministry of Health and Welfare.
Rights and permissions
About this article
Cite this article
Asakawa, Y., Matsuda, R. & Tori, M. Hydroxylation of menthols and cineoles withm-chloroperbenzoic acid. Experientia 42, 201–203 (1986). https://doi.org/10.1007/BF01952469
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF01952469