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Rose oxide

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Rose oxide
Names
IUPAC name
Tetrahydro-4-methyl-2-(2-methylpropenyl)-2H-pyran
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.036.763 Edit this at Wikidata
EC Number
  • 240-457-5
UNII
  • InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3
    Key: CZCBTSFUTPZVKJ-UHFFFAOYSA-N
  • (−)-cis: InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10-/m1/s1
    Key: CZCBTSFUTPZVKJ-NXEZZACHSA-N
  • (−)-trans: InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10+/m1/s1
    Key: CZCBTSFUTPZVKJ-ZJUUUORDSA-N
  • (+)-cis: InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10-/m0/s1
    Key: CZCBTSFUTPZVKJ-UWVGGRQHSA-N
  • (+)-trans: InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10+/m0/s1
    Key: CZCBTSFUTPZVKJ-VHSXEESVSA-N
  • CC1CCOC(C1)C=C(C)C
  • (−)-cis: C[C@@H]1CCO[C@@H](C1)C=C(C)C
  • (−)-trans: C[C@@H]1CCO[C@H](C1)C=C(C)C
  • (+)-cis: C[C@H]1CCO[C@H](C1)C=C(C)C
  • (+)-trans: C[C@H]1CCO[C@@H](C1)C=C(C)C
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

[edit]

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]

Rose oxide isomers

Production

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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]

Rose oxide synthesis

References

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  1. ^ 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.
  2. ^ Dieter Martinetz und Roland Hartwig: Taschenlehrbuch der Riechstoffe: ein Lexikon von A–Z. Verlag Harri Deutsch 1998; ISBN 3-8171-1539-3; S. 330ff.
  3. ^ 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.