Clove sesquiterpene alcohol

Caryophyllene nitrosochloride, (CjgHgJjN OoCL, is obtained when a mixture of the sesquiterpene, alcohol, ethyl acetate, and ethyl nitrite is cooled in a freezing mixture, and then treated with a saturated solution of hydrochloric acid in alcohol. The reaction mass is allowed to stand on ice for an hour and is then exposed to sunlight. Thus prepared it melts at about 158° to 163°, and can be separated into two compounds, one being that of a-caryophyllene and the other that of yS-caryophyllene Deussen s sesquiterpenes of natural caryophyllene from clove oil), a-caryophyllene nitrosochloride melts at 177", and /3-caryophyllene nitrosochloride at 159°. They can be separated by fractional crystallisation. The corresponding a-nitrolbenzylamine melts at 126° to 128°, and the /3-nitrolbenzylamine at 172° to 173°. The bimolecular formula given above is probable but not certain. 

Semmler and Mayer have isolated a sesquiterpene alcohol, from the high boiling fractions of oil of cloves.. It was probably not obtained in an absolutely pure condition, but had the following characters, which must be regarded as approximate only —... 

The oil from clove stems does not differ materially in characters firom that of ordinary cloves. The specific gravity, however, may fall as low as 1 040. The eugenol-content rarely falls below 85 per cent. The stem oil has. boen found to contain traces of naphthalene, a sesquiterpene alcohol, C jH O, and a crystalline body (C iHjjO) ( ), melting at 146. ... 

CHAiUNCt CaryophyUene (C15H24) is an unusual sesquiterpene familiar to you as a major cause of the odor of cloves. Determine its structure from the following information. (Caution The structure is totally different from that of a-caryophyllene alcohol in Problem 72.)... 

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