Rose oxide
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Names | |
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IUPAC name
Tetrahydro-4-methyl-2-(2-methylpropenyl)-2H-pyran
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Identifiers | |
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3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.036.763 |
EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C10H18O | |
Molar mass | 154.25 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rose oxide[1] is a fragrance chemical found in roses and rose oil. It also contributes to the flavor of some fruits, such as lychee, and wines, such as Gewürztraminer.
Chemistry
Rose oxide is an organic compound of the pyran class of monoterpenes. The compound has 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.[2]
Production
Rose oxide can be 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.[3]
References
- ^ Ghodsi, Mohammadi Ziarani; Fatemeh, Mohajer; Seyedh, Mahboobeh Jamali; Nader, Ale Ebrahim (2020-11-30). "Quantitative and Qualitative Bibliometric Scope Toward the Synthesis of Rose Oxide as a Natural Product in Perfumery". Current Organic Synthesis. 17 (8): 610–624. doi:10.2174/1872208314666200722161044. PMID 32703138. S2CID 220731373.
- ^ 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.; Aubry, J. M. (2010). ""Dark" Singlet Oxygenation of β-Citronellol: A Key Step in the Manufacture of Rose Oxide". Organic Process Research & Development. 14: 259–262. doi:10.1021/op900076g.
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