T he rose is called "the queen of flowers". The reasons for this popular honorary name are its shape, color, and fragrance; the latter being the motive for the cultivation of many species of this flower, for example, the one shown in Figure 1. In poetry, the scent of roses has often been highly praised. 1 An early example is the famous oriental fairy-tale "Thousand and One Nights". 2 William Shakespeare mentioned the scent of roses; 3 in sonnet 54 he wrote Oh how much more doth beauty beautious seem by that sweet ornament which truth doth give. The rose looks fair, but fairer we it deem for that sweet odor which doth in it live. In this article, some of the major chemical components of rose blossoms and a few additional odorous substances are chosen to engage the reader's attention and to arouse interest in the molecular structures involved. The content of this article is not new; besides recent research-and application-oriented reviews, 4À7 there are other publications 8À11 that are helpful for teaching, including a book 12 that describes the chemistry of fragrance compounds (6 chapters) and the theoretical background required (9 chapters). The present article, however, combines the topic of some fragrance materials with the isomerism of organic molecules.To benefit from this article, the student should be familiar with the basic structure 13a,14a of alkane, alkene, alcohol, ether, and ketone molecules. In addition, the principles 8,12,15 of distillation and chromatography should be known. This contribution is recommended as a lesson on the relationship between molecular structure and odor for chemistry students in their second year at university.The first sections of the article are dedicated to the isolation of odorous compounds from rose petals and to the different types of structural isomerism. The next sections describe gas chromatographyÀmass spectrometry, types of separable isomers, and the composition of the materials isolated. Besides the constituents of many rose species, examples of other odorant molecules occurring as isomers are briefly described. Finally, applications and origins of fragrance materials are mentioned.
' ISOLATION OF ODOROUS COMPOUNDS FROM ROSE PETALS
Rose OilA traditional method for isolating volatile constituents of roses is heating the blossoms with water in the flask of a distillation apparatus or blowing steam through the flask. 8,15 Under these conditions, a so-called azeotropic mixture of lipophilic components and water is formed that possesses a boiling point somewhat below 100°C, 12a,16 although the separated chemicals without water show much higher boiling points, for example, about 230°C in the case of the odorous compounds present in roses. The addition of water generally enables the distillation of high boiling or sensitive lipophilic compounds at a temperature that makes decomposition reactions less likely. Upon cooling the vapor phase, an aqueous liquid and a lipophilic layer are obtained. The aqueous phase from this distillation contains small quantities of partially ...