Cineole 1.8- epoxy-p-menthane

FEMA No. 2465 1,8-Cineol 1,8 Epoxy-p-menthane 1 8 Oxido-p-menthane... 

Synonyms 1,8-Cineole 1,8-Epoxy-p-menthane Source Francisco, J. C. Sivik, B. J. Supercrit. Fluids 2002), 23(1), 11-19. 

Eucaliptol (1,8-cineol, 1,8-epoxy-p-menthane, l,3,3-trimethyl-2-oxabicyclo[2.2.21-octane) [470-82-6] M 154.2, m 1.3°, 1.5°, b 39-39.3°/4mm, 176-176.4°/760mm, df 0.9232, nf 1.4575. Purify 1,8-cineol by dilution with an equal volume of pet ether, then saturate with dry HBr. The precipitate is filtered off, washed with small volumes of pet ether, then cineole is regenerated by stirring the crystals with H2O. It can also be purified via its o-cresol or resorcinol addition compounds. Store it over Na until required. Purify it also by fractional distillation. It is insoluble in H2O but soluble in organic solvents. [IR Kome et al. Nippon Kagaku Zasshi [J Chem Soc Japan (Pure Chem Sect)] 80 66 1959, Chem Abstr 603 1961, Beilstein 17 II 32, 17/1 V 273.]... 

Eucalyptus essential oil contains 70 to 80% of the compound eucalyptol (also called 1,8-cineole or 1,8-epoxy-p-menthane) (Chennoufi et al. 1980 De Vincenzi et al. 2002 ... 

Cineoles l,4-C.=l-methyl-4-(l-methylethyl)-7-oxa-bicyclo[2.2.1]heptane, 1,4-epoxy-p-menthane 1,8-C.= l,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 1,8-epoxy-p-menthane). 

An example of terpenic 1,2-epoxides is -caryophyllene oxide, also known as (-)-epoxycaryophyllene (8-31), which occurs in many essential oils. An example of terpenic 1,4-epoxides is the so-called (-l-)-dill ether, (3J ,4S,8S)-3,9-epoxy-p-menth-l-ene (8-31), which is a typical component of the essential oil of caraway (30%) and dill. An example of unsaturated 1,4-epoxides is (-l-)-menthofuran (8-31), the metabolite of ketone (-l-)-pulegone. Both compounds are components of peppermint oil (see Table 8.32, later) and are hepatotoxic. Monoterpenoid compound (- -)-l,8-cineole (also known as limonene oxide, eucalyptol or 1,8-epoxy-p-menthane 8-31) is an example of more complex structures. It is present in essential oils of many types of spices, and higher quantities are found in the essential oil of trees of the genus Eucalyptus (Myrtaceae). Trivial and systematic names of selected ethers are given in Table 8.8. 

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