Rose oxide
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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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Infobox references | |
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.
- ^ 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.
Categories:
- Alkene derivatives
- Tetrahydropyrans
- Monoterpenes