Rose oxide
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| Rose oxide | ||
|---|---|---|
 | ||
| IUPAC name Tetrahydro-4-methyl-2-(2-methylpropenyl)-2H-pyran | ||
| Identifiers | ||
| CAS number | 16409-43-1, 876-17-5 (−)-cis 876-18-6 (−)-trans | |
| Properties | ||
| Molecular formula | C10H18O | |
| Molar mass | 154.25 g/mol | |
 (verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
Rose oxide is an organic compound of the pyran class and the monoterpene class and a fragrance found in roses and rose oil. The compound has both a cis- and a trans-isomer, each with a (+)- and (−)-stereoisomer, but only the (−)-cis isomer (odor threshold 0.5 ppb) is responsible for the typical rose (floral green) fragrance.[1] Rose oxide also contributes to the flavor of some fruits such as lychee and Gewürztraminer.
Rose oxide is produced industrially beginning with photooxygenation of citronellol to give the allyl hydroperoxide which is then reduced with sodium sulfite to provide the diol. Ring-closure with sulfuric acid forms both the cis- and trans-isomers in equal amounts.[2]
References
- ↑ Dieter Martinetz und Roland Hartwig: Taschenlehrbuch der Riechstoffe: ein Lexikon von A–Z. Verlag Harri Deutsch 1998; ISBN 3-8171-1539-3; S. 330ff.
- ↑ Alsters, P. L.; Jary, W. .; Nardello-Rataj, V. �R.; Aubry, J. M. (2010). ""Dark" Singlet Oxygenation of β-Citronellol: A Key Step in the Manufacture of Rose Oxide". Organic Process Research & Development 14: 259. doi:10.1021/op900076g.
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